Winter Park Florida Condominiums for Sale

Winter Park Florida Condominiums for Sale

100 S Interlachen Avenue Unit 401, Winter Park
$850,000
3 Beds ⋅ 2 Baths ⋅ O6443942 MLS ⋅ Cloisters BLDG.
Opportunity knocks at The Cloisters! This rarely available fourth-floor corner residence offers an exceptional opportunity to create a truly personalized home, with windows on four sides filling the interiors with abundant natural light and capturing desirable eastern exposures, perfect for viewing the sunrise and rocket launches. Also, enjoy tree top and lake views. Held by the same family since 1979, this residence offers more than 1,600 square feet of living space, this 3 bedroom - 2 bath unit is ready for its next chapter. While the interiors await updating, the generous floor plan provides a wonderful blank canvas with endless possibilities to reimagine the space and make it your own. Additional features include in-unit washer and dryer hookups, an assigned parking and storage closet and the unique privacy afforded by its corner location. Nestled along the shores of beautiful Lake Osceola, The Cloisters offers an exceptional lifestyle with an array of desirable amenities, including a sparkling swimming pool, boat slips, a private dock, two fitness rooms, a clubhouse, internet and cable, an on-site manager, and an outdoor grilling area. Ideally situated in the heart of Winter Park, this sought-after community is just a short stroll from The Alfond Inn, SunRail, and the charm of Park Avenue, where you can enjoy an inviting collection of sidewalk cafés, fine dining, boutique shopping, and the picturesque beauty of Central Park. Experience the best of Winter Park living in this exceptional lakefront community. Bring your designer, your vision, and your personal style to transform this special Cloisters residence into something extraordinary. Call today for your private viewing of this wonderful unit.

100 S Interlachen Avenue Unit 401, Winter Park

Listing courtesy of FANNIE HILLMAN & ASSOCIATES. 407-644-1234
2500 Lee Road Unit 123, Winter Park
$169,900
1 Beds ⋅ 1 Baths ⋅ O6445068 MLS ⋅ Na BLDG.
LIVE THE WINTER PARK LAKEFRONT LIFESTYLE WITHOUT THE LAKEFRONT PRICE TAG! This UPDATED, GROUND-FLOOR 1-bedroom, 1-bath condo offers 645 SF of move-in-ready living in desirable Lakeside Manor on beautiful Lake Killarney. Enjoy easy first-floor access, peaceful park-like grounds, a sparkling lakefront pool, clubhouse, community boat access and docks—all just steps from your door. The location is exceptional—minutes from Winter Park Village, Park Avenue, Rollins College, shopping, dining and entertainment, with quick access to I-4 and Downtown Orlando. Perfect as a primary residence, second home or low-maintenance getaway. UPDATED. GROUND FLOOR. LAKEFRONT COMMUNITY. PRIME WINTER PARK LOCATION. Come see why Lakeside Manor remains one of Winter Park’s best-kept secrets!

2500 Lee Road Unit 123, Winter Park

Listing courtesy of HOME WISE REALTY GROUP, INC.. 407-712-2000
188 Sandlewood Unit 1, Winter Park
$290,000
2 Beds ⋅ 3 Baths ⋅ O6445407 MLS ⋅ 1 BLDG.
Welcome home to 188 Sandelwood Trail, a beautifully updated 2-bedroom, 2-full-bath residence in the heart of Winter Park. Thoughtfully refreshed and move-in ready, this home blends modern comfort with the charm and convenience that make Winter Park one of Central Florida's most sought-after addresses. Stylish wood-look flooring flows throughout the inviting living room, where a wood-burning fireplace creates a warm, welcoming focal point for relaxing evenings or entertaining friends. The updated kitchen shines with granite countertops and stainless steel appliances, combining function and style for everyday cooking. The primary suite is a true retreat, with serene views overlooking the sparkling pool and a private en-suite bath. The second bedroom and full bath adds flexibility for guests, a home office, or hobby space. Enjoy an unbeatable location just minutes from Park Avenue's boutique shopping and dining, lakes, parks, and cultural attractions, with easy access to major roadways for a convenient commute throughout the Orlando metro. Whether you're a first-time buyer, downsizing, or seeking a low-maintenance lifestyle, this Winter Park gem checks every box. Schedule your private showing today!

188 Sandlewood Unit 1, Winter Park

Listing courtesy of NOELKE REALTY. 407-607-7166
200 Saint Andrews Boulevard Unit 704, Winter Park
$159,000
1 Beds ⋅ 1 Baths ⋅ O6445691 MLS ⋅ 200 BLDG.
LOCATION, LIFESTYLE & OPPORTUNITY IN THE HEART OF WINTER PARK! Welcome to 200 Saint Andrews Boulevard #704, a charming top-floor, 1-bedroom, 1-bath condominium in the established Four Seasons Condominiums of Winter Park. Whether you’re searching for a primary residence, low-maintenance Winter Park retreat, or investment property, this condo offers an incredible opportunity just minutes from Rollins College, Park Avenue, and Downtown Winter Park. Located on the second and top floor, the residence offers a comfortable and functional layout with beautiful wood flooring throughout the living room and bedroom. The spacious living area flows into the dining space and kitchen, while the primary bedroom features a generous walk-in closet. Two separate entrances add convenience, and the oversized screened-in balcony provides the perfect place to enjoy morning coffee, unwind at the end of the day, or enjoy Florida’s year-round outdoor lifestyle. A private storage closet on the balcony provides additional space, and abundant community parking makes everyday living easy. Four Seasons is an established approximately 20-acre condominium community located within the City of Winter Park. Residents enjoy three community swimming pools, tennis courts, shuffleboard, a clubhouse with library, community laundry facilities, and more. COA INCLUDES WATER, TRASH, SEWER, PEST CONTROL, EXTERIOR AND GROUNDS MAINTENANCE. For buyers who value LOCATION, this one is hard to beat. Rollins College, iconic Park Avenue, and Downtown Winter Park are just minutes away, providing easy access to some of Central Florida’s best restaurants, boutiques, coffee shops, museums, community events, and entertainment. Enjoy nearby outdoor recreation at Cady Way Trail, Ward Park, Showalter Field, and the YMCA, plus convenient access to AdventHealth Winter Park, Baldwin Park, Winter Park Village, Downtown Orlando, I-4, and major Central Florida roadways. For investors, the combination of a Winter Park address, proximity to Rollins College and major employment, healthcare, shopping, dining, and recreation destinations makes this property an option worth considering for a long-term real estate investment. For an owner-occupant, it offers the opportunity to enjoy the Winter Park lifestyle in a low-maintenance condominium setting. Enjoy the convenience of being close to everything while coming home to an established community in one of Central Florida’s most recognized locations. Schedule your private showing and discover the possibilities at Four Seasons Winter Park!

200 Saint Andrews Boulevard Unit 704, Winter Park

Listing courtesy of EXP REALTY LLC. 888-883-8509
1695 Lee Road Unit C206, Winter Park
$140,000
2 Beds ⋅ 1 Baths ⋅ TB8551269 MLS ⋅ C BLDG.
Welcome to this bright and beautifully updated second-floor condo located in one of Winter Park's most desirable communities! This 2-bedroom, 1-bathroom residence offers the perfect blend of comfort, modern upgrades, and an unbeatable location. Updated Kitchen: Features dark wood cabinetry, light quartz counter tops, black and stainless-steel appliances, a modern commercial-style faucet, and an in-unit washer/dryer set. Spacious Living & Bedroom Areas: Enjoy durable luxury vinyl plank flooring throughout the main areas, bright natural light, and modern finishes. Renovated Bathroom: Outfitted with a updated vanity, chic black hardware, and stylish lighting fixtures. Private Balcony: Relax outdoors on your private covered balcony with peaceful views of the lush green courtyard and community grounds. Resort-style sparkling swimming pool with expansive sun deck. Well-maintained grounds with mature landscaping and tropical palm trees. Quiet, well-kept building entrance and grounds. Situated right off Lee Road, you are just minutes away from top dining, shopping, and entertainment spots. Enjoy close proximity to Park Avenue in Downtown Winter Park, Rollins College, I-4 access for an easy commute to Downtown Orlando or major attractions. Local parks, lakes, and grocery stores. Whether you are looking for a primary residence or a strong investment opportunity in the booming Central Florida market, this move-in-ready condo is a must-see! Schedule your private tour today!

1695 Lee Road Unit C206, Winter Park

Listing courtesy of INVESTMENT REALTY. 813-466-3430
173 Scottsdale Square Unit 173, Winter Park
$100,000
1 Beds ⋅ 1 Baths ⋅ S5158339 MLS ⋅ 173 BLDG.
INVESTMENT OPPORTUNITY! Add this well-maintained condo to your investment portfolio or make it your next income-producing property. Featuring a functional layout, neutral finishes, easy-care flooring, stainless-steel appliances, and plenty of natural light, this unit offers an attractive and low-maintenance option for investors. The comfortable living area flows to the outdoor space through sliding glass doors, creating a bright and inviting atmosphere. Conveniently located near shopping, dining, major roadways, and everyday necessities. Whether you're expanding your rental portfolio or looking for your next investment opportunity, this condo is worth a look. Schedule your showing today!

173 Scottsdale Square Unit 173, Winter Park

Listing courtesy of AXEN REALTY, LLC. 818-932-8800
1250 S Denning Drive Unit 119, Winter Park
$265,000
2 Beds ⋅ 2 Baths ⋅ O6444618 MLS ⋅ D BLDG.
Virtually Staged. Welcome to easy, low-maintenance living in the heart of Winter Park! This beautifully updated 2-bedroom, 2-full-bath, first-floor corner residence at Mead Garden Condominiums offers a fresh, move-in-ready interior paired with an exceptional location just minutes from some of Winter Park’s most desirable destinations. Recent updates include new luxury vinyl flooring throughout the kitchen and great room, new carpeting in both bedrooms, fresh interior paint, and a recently redone screened-in porch with a refreshed frame and new screening. The thoughtfully updated kitchen features shaker-style cabinetry, granite countertops with breakfast bar, and stainless steel appliances. Additional features include remodeled bathrooms, low-Emissivity windows and sliding glass door, crown molding, updated baseboards and light fixtures, Nest thermostat, A/C replaced in 2018, and water heater replaced in 2019. Enjoy Florida living from the screened-in porch with convenient direct access to the community pool, onsite laundry facility, and mailroom. The first-floor corner location offers added privacy, comfortable single-level living, and a designated parking space.

1250 S Denning Drive Unit 119, Winter Park

Listing courtesy of FANNIE HILLMAN & ASSOCIATES. 407-644-1234
100 S Interlachen Avenue Unit 101, Winter Park
$1,299,000
3 Beds ⋅ 2 Baths ⋅ O6438038 MLS ⋅ 100 BLDG.
Under contract-accepting backup offers. On the first floor within The Cloisters, this three-bedroom, two-bath residence offers 1,734 square feet of renovated living space in one of Winter Park’s accessible lakefront communities. An oversized tiled patio, partially covered and ideal for outdoor dining or morning coffee, extends the living space and enhances everyday functionality. Renovated in 2021 by Charles Clayton Construction, an award-winning luxury homebuilder, the residence features updated flooring, kitchen, baths, lighting and laundry. Wood flooring flows through the foyer, dining and living areas, while ceramic tile is installed in the bedrooms, and decorative tile in the baths. The kitchen is appointed with high-end appliances and custom solid wood cabinetry, designed for daily living and entertaining. The primary suite offers abundant natural light, a built-in closet and an en-suite bath with dual sinks, walk-in shower and a window providing natural illumination. A hall bath includes a tub-shower combination and additional storage. A sunroom off the third bedroom provides flexible space for a private office, den or reading room. The residence includes one assigned covered carport space and a dedicated climate-controlled storage unit on site. Two blocks from Park Avenue, residents enjoy convenient access to dining, shopping and cultural amenities in a lakefront community setting. The property presents an opportunity for full-time living, luxury downsizing or lock-and-leave lifestyle in the heart of Winter Park.

100 S Interlachen Avenue Unit 101, Winter Park

Listing courtesy of PREMIER SOTHEBY'S INTL. REALTY. 407-644-3295
192 Balfour Drive Unit 2, Winter Park
$319,000
2 Beds ⋅ 2 Baths ⋅ O6443731 MLS ⋅ 1 BLDG.
This ONE STORY Villa-Style condo is in a nice, quiet, Winter Park community close to everything! The open layout has a formal dining room and living room with a brick fireplace! The vaulted ceilings give it a large airy feeling especially with two atriums full of natural light! Sliding glass doors lead to a rear screened in porch from the Living Room. A perfect place to enjoy your morning coffee! The primary suite has large glass doors, going out to the private open air patio and garden area! The Kitchen atrium allows even more sun light and a place for your favorite plants! The kitchen cabinets and the movable coffee bar give plenty of storage space! Or you may want a two seater table and chair instead!! The beautiful granite speaks for itself. The best part is yet to come!! This condo has a 2 car Garage with a wall of storage cabinets. Plenty of room for your vehicle w added storage! Tile Roof new (2025). Membrane Roof new (2020). Re-piped (2013). AC new inside/out (2018). Electrical checked at move in (2013). You are minutes from Ward Park, Cady Way Trail and Pool, Crosby Wellness Center and Advent Health Winter Park Hospital, plus numerous stores and restaurants! This is a VERY QUIET 55+ community which allows no leasing through their BYLAWS !

192 Balfour Drive Unit 2, Winter Park

Listing courtesy of BHHS FLORIDA REALTY. 407-406-5300
100 S Virginia Avenue Unit 201, Winter Park
$1,450,000
3 Beds ⋅ 3 Baths ⋅ O6442678 MLS ⋅ The Douglas Grand BLDG.
Discover luxury and effortless living in this exquisite single-story, second-floor residence at the highly sought-after Douglas Grand in the heart of Winter Park. This spacious three-bedroom, three-bath condominium beautifully balances sophisticated entertaining with everyday comfort, offering an inviting open floor plan filled with natural light, elegant crown molding, and stunning French Oak hardwood flooring. The gourmet kitchen is a true chef’s retreat, featuring a generous island with stunning quartz countertops, custom wood cabinetry, top-of-the-line Sub-Zero, Wolf, and Bosch appliances, and a spacious walk-in pantry. The serene primary suite offers a luxurious escape with an indulgent soaking tub, dual vanities with granite countertops, and two expansive walk-in closets. The second bedroom features a private ensuite bath and generous walk-in closet, while the third bedroom offers excellent flexibility and convenient access to a full bath. Thoughtful updates and amenities include a spacious utility room with a LG washer and dryer, updated light fixtures throughout, Roman shade window treatments, color-changing recessed lighting, Google smart carbon monoxide/fire detectors, Nest thermostats, and a 81-gallon water heater installed in December 2023. One of the residence’s most desirable features is the private entry directly from the secure, gated garage, with two reserved parking spaces conveniently located just outside your front door. Ideally situated in the heart of Winter Park, Douglas Grand places you moments from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, the Winter Park 9-hole golf course, Winter Park Tennis Center, and Winter Park Village. Experience the best of Winter Park with the comfort, privacy, and convenience of elevated condominium living at Douglas Grand.

100 S Virginia Avenue Unit 201, Winter Park

Listing courtesy of KELLY PRICE & COMPANY LLC. 407-645-4321
602 Trinidad Court Unit 602, Winter Park
$227,000
2 Beds ⋅ 2 Baths ⋅ O6443577 MLS ⋅ 602 BLDG.
Virtually Staged. Beautiful Winter Park Condo with Vaulted Ceilings & Private Fenced Patio! Come home to this beautiful and spacious condo featuring vaulted ceilings, abundant natural light, and an open split floor plan designed for comfortable Florida living. The home features 18" tile flooring, neutral paint, ceiling fans, recessed lighting, blinds, a dry bar, and decorative glass-tile accents throughout. The centrally located kitchen comes fully equipped with a smooth-top range, refrigerator, dishwasher, and built-in microwave, making it perfect for everyday living and entertaining. The spacious upstairs primary bedroom offers privacy and includes a walk-in closet, ceiling fan, and private bathroom with attractive decorative details. Step outside and enjoy your own private fenced patio oasis, complete with tile flooring and additional storage—an ideal space for relaxing or entertaining. One of the highlights of this home is the abundance of storage space throughout. The community offers excellent amenities, including a swimming pool, clubhouse, tennis court, and basketball court. Conveniently located near Full Sail University, shopping, restaurants, golf, and everything Winter Park is. Schedule your showing today and make this beautiful Winter Park condo your next home!

602 Trinidad Court Unit 602, Winter Park

Listing courtesy of CLARA HERRERA REALTY. 407-921-1200
1306 S Pennsylvania Avenue Unit 5, Winter Park
$359,000
2 Beds ⋅ 1 Baths ⋅ O6443013 MLS ⋅ 1306 BLDG.
Charming Winter Park 2BR/1BA Condo with Lake Virginia Access! Beautifully renovated and ideally located near Park Avenue, Rollins College, Hannibal Square, and Mead Botanical Garden, this spacious second-floor condo combines architectural character with an unbeatable Winter Park lifestyle. Soaring cathedral/vaulted ceilings, hardwood floors, plantation shutters, custom built-ins, and French doors create a warm, cosmopolitan feel. The renovated kitchen features granite countertops, stainless-steel appliances, an induction range, bay window, and cozy dining nook. Spacious primary bedroom offers vaulted ceilings and French doors opening to a private screened outdoor space. Flexible second bedroom is ideal as a home office or guest room. Enjoy a private community dock with Lake Virginia access for kayaking, paddleboarding, or relaxing by the water. Expansive private deck overlooks picturesque Mead Gardens. Includes storage and garage space plus convenient in-unit laundry. Walk or bike to Park Avenue shops, restaurants, Rollins College, and everything that makes Winter Park so desirable!

1306 S Pennsylvania Avenue Unit 5, Winter Park

Listing courtesy of KELLER WILLIAMS WINTER PARK. 407-545-6430
7453 Daniel Webster Drive Unit A5, Winter Park
$150,000
2 Beds ⋅ 2 Baths ⋅ O6442597 MLS ⋅ A BLDG.
Welcome to this beautifully updated 2-bedroom, 2-bathroom condo in Winter Park. The home features a newer HVAC system installed in 2021, repiped plumbing completed in 2021, and a new electrical panel installed in 2021. One bedroom provides direct access to the patio, offering convenient outdoor space. The property is conveniently located near UCF, shopping, dining, major roadways, Downtown Orlando, and Orlando International Airport. An excellent opportunity to own a well-maintained condo in a convenient Central Florida location.

7453 Daniel Webster Drive Unit A5, Winter Park

Listing courtesy of LA ROSA REALTY PREMIER LLC. 407-401-9076
2463 Grand Teton Circle Unit 2463, Winter Park
$249,000
3 Beds ⋅ 3 Baths ⋅ O6443154 MLS ⋅ 2463 BLDG.
Virtually Staged. Don't miss this incredible opportunity in one of Winter Park's most desirable locations! This spacious 2-story condo offers over 1,700 square feet of living space, featuring an open floor plan that's perfect for everyday living and entertaining. A dedicated office space adds flexibility for remote work or a home study a rare find at this price point. While the home could use some updating, the bones and layout make this a fantastic canvas to add your personal touch and build instant equity. Currently occupied by a great tenant, this property is a perfect turnkey opportunity for investors looking to add a cash-flowing asset to their portfolio, or for buyers ready to move in once the lease ends on June 2027. With its unbeatable location near Winter Parks shopping, dining, and entertainment, this is the kind of opportunity that won't last long at $249,000. Don't miss this and make your appointment today!

2463 Grand Teton Circle Unit 2463, Winter Park

Listing courtesy of MAINFRAME REAL ESTATE. 407-513-4257
250 Carolina Avenue Unit 202, Winter Park
$699,000
3 Beds ⋅ 2 Baths ⋅ O6442686 MLS ⋅ Park West Building B BLDG.
Welcome to Park West, an exclusive gated community ideally located just moments from the heart of downtown Winter Park. This impeccably maintained 3-bedroom, 2-bath residence offers a spacious and thoughtfully designed floor plan. The inviting living and dining areas feature an open-concept layout anchored by a traditional decorative fireplace, creating a warm and comfortable setting for both everyday living and entertaining. The generous primary suite offers a private en-suite bath with a walk-in shower and an expansive walk-in closet. The second bedroom is conveniently positioned near the hall bath, which features a tub/shower combination. A dedicated laundry room with built-in shelving and abundant storage adds a level of convenience rarely found in condominium living. Residents of Park West enjoy an array of amenities, including a clubhouse, resort-style swimming pool, and tennis court which also has lines for pickleball, all within a beautifully maintained gated setting. Perhaps the greatest luxury is the location. From Park West, it’s an easy stroll to the boutiques, restaurants, and cultural attractions of Park Avenue, as well as Central Park, world-class museums, the SunRail station, and the Winter Park Golf Course. Offering space, comfort, amenities, and an unbeatable location, this is a wonderful opportunity to own a residence in one of Winter Park’s most desirable communities.

250 Carolina Avenue Unit 202, Winter Park

Listing courtesy of FANNIE HILLMAN & ASSOCIATES. 407-644-1234
7302 Swallow Run Unit 7302, Winter Park
$134,900
2 Beds ⋅ 2 Baths ⋅ O6442345 MLS ⋅ 5 BLDG.
Welcome to 7302 Swallow Run! This beautiful, move-in ready 2-bedroom, 2-bathroom condo offers the highly sought-after first-floor location and a prime setting directly across from both community pools. Nestled within the desirable Whisperwood community in Winter Park, this single-story condo features a wonderful split-bedroom floor plan and an open living concept with plenty of space to relax and entertain. Enjoy the convenience of NO CARPET throughout the home, along with a spacious living area that opens to a private balcony—perfect for enjoying your morning coffee or unwinding at the end of the day. The beautiful kitchen features gorgeous cabinetry, ample counter space, plenty of storage, and a full suite of appliances, all overlooking the open living area. A convenient breakfast bar provides additional seating, making everyday living and entertaining a breeze. The unit also includes a stackable washer and dryer for added convenience. Whisperwood is a quiet, welcoming condominium community with friendly neighbors and plenty to enjoy. Residents can take advantage of the community amenities and beautifully maintained grounds, all included in the affordable HOA fee. This particular unit enjoys an especially desirable location directly across from both community pools, a beautiful pond, and the community mailboxes. Beyond the community, you’ll enjoy all that the charming city of Winter Park has to offer. Located just three miles north of downtown Orlando, Winter Park is celebrated for its strong sense of community, beautiful parks, scenic chain of lakes, elegant homes, brick-lined streets, and mature tree canopy. The city offers an exceptional blend of historic charm and modern conveniences, with an array of shopping and dining destinations, museums, cultural attractions, and the renowned Rollins College. Conveniently located near Full Sail University and just a few miles from Rollins College, this home also provides easy access to major roadways including SR 408, SR 417, and SR 436. Come see 7302 Swallow Run and experience the convenience, charm, and lifestyle that make Winter Park such a wonderful place to call home!

7302 Swallow Run Unit 7302, Winter Park

Listing courtesy of THE NAVY HOUSE. 321-438-1318
2383 Sun Valley Circle Unit 2383, Winter Park
$234,900
2 Beds ⋅ 2 Baths ⋅ O6440965 MLS ⋅ 15 BLDG.
Don't miss your opportunity on this super clean 2 bed 2 bath Winter Park condo! Updated kitchen with White shaker cabinets, granite counters complete with all the appliances including washer and dryer. Formal dining room and family room with vaulted ceilings, skylights, along with a wet bar and cabinetry complimented by a centerpiece wood burning fireplace. Master bedroom features hardwood flooring along with updated vanity with granite counters along with a separate tub and shower. Secondary bedroom has laminate flooring along with updated vanity and granite countertops. Ceramic tile throughout the rest of the home as there is no carpet. French doors leading out to the oversized screen enclosed covered patio overlooking lush landscaping with no direct rear neighbor.  2 assigned parking spaces directly in front of the unit.There is also a small courtyard just outside the kitchen. Community features a recently remodeled pool, clubhouse and tennis courts. Winter Park location benefits include easy access to Full Sail University, UCF, Valencia College, Park Avenue filled with famous restaurants and boutique shopping.

2383 Sun Valley Circle Unit 2383, Winter Park

Listing courtesy of RE/MAX PRIME PROPERTIES. 407-347-4512
311 E Morse Boulevard Unit 1-5, Winter Park
$2,475,000
3 Beds ⋅ 3 Baths ⋅ O6441437 MLS ⋅ Bldg. Number 1 BLDG.
Quintessential Winter Park Lakefront Living with your own covered boatslip! You must see this Stunning Lakefront Penthouse Residence overlooking Lake Osceola and just two blocks from Park Avenue. Residence 1-5 is located on the quiet, private NE corner of the Whispering Water complex, and it offers the largest floor plan within Whispering Waters at 2,316 sq. ft. under A/C (plus two step-out balconies). This light-filled residence offers an open floor plan and raised ceiling heights. From the moment you enter, you are drawn to the breathtaking lake views and understated elegance of this spacious home. The lakefront great room includes a large living area with adjacent bar and dining areas. The living area opens to the kitchen allowing the lake view to be enjoyed in all main living areas. The kitchen has been updated with white wood cabinetry, a built-in stainless Bosch oven, Bosch glass induction cooktop, Bosch microwave, Subzero refrigerator with two freezer drawers and two additional built-in refrigerator drawers. The custom mirrored backsplash adds a luxury feel, and the flexible center console provides additional work space. The primary suite offers a large walk-in closet and en-suite bathroom with a large walk-in shower, custom floating vanity and elegant fixtures. Bedroom #2 includes two closets and is directly across the hall from a large full bathroom with tub/shower. The 3rd bedroom is currently configured as a large Family Room and includes built-in cabinetry, a private door to the South hallway, two closets and an adjacent alcove ideal for office space. In the photos you'll see a floor plan virtually depicting bedroom #3 with a wall and doorway to the main hallway and living areas. Bathroom #3 is just across the hall and features a large walk-in shower. Wait, there's more! Residence 1-5 includes your own covered boat slip (#1). The entire residence features new seagrass floor covering in all the main living areas. This neutral, organic flooring makes for the perfect contemporary, elegant foundation for your furnishings and for showing off your own custom carpets and rugs. Additional features include plantation shutters throughout, additional storage closet in the garage, and a designated parking space in the gated under-building garage. Residents enjoy a community pool, gated underground parking with elevator access, and an unbeatable location just steps from Park Avenue’s shops, restaurants, museums, and seasonal events. Residence 1-5 is the jewel of Whispering Waters. This home provides the very finest of Lakefront "lock and Leave" living in the heart of Winter Park. All measurements are approximate and Buyer to verify all dimensions. Please see attached Disclosures and Governing Documents.

311 E Morse Boulevard Unit 1-5, Winter Park

Listing courtesy of COLLADO REAL ESTATE. 386-427-0002
7476 Woodburn Court Unit 38, Winter Park
$170,000
2 Beds ⋅ 3 Baths ⋅ O6434437 MLS ⋅ 38 BLDG.
Terrific townhome in the Hidden Oaks community featuring an updated interior and its own private, fenced patio! Step inside to a bright and spacious living/dining area with beautiful wood laminate flooring and a convenient wet bar. The galley-style kitchen includes a breakfast area, along with a laundry closet equipped with a full-size washer and dryer. Upstairs, you'll find two spacious bedrooms, including one with an oversized walk-in closet. Additional storage is available under the stairs and in the A/C closet. The monthly condo fee includes water, sewer, trash, exterior maintenance, grounds maintenance, and community amenities! Enjoy community amenities, including a refreshing pool! Conveniently located just off Goldenrod Rd, with easy access to E Colonial, 408, and 417 for a quick commute and nearby everyday conveniences. Full Sail University is just 1.8 miles away, Valencia College is 4.5 miles away, and UCF is only 6.2 miles away!

7476 Woodburn Court Unit 38, Winter Park

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211
3651 N Goldenrod Road Unit C109, Winter Park
$165,000
2 Beds ⋅ 2 Baths ⋅ O6439897 MLS ⋅ C BLDG.
This is exactly what you are looking for! Adorable 2/2 close to Full Sail and UCF. Tons of shopping and restaurants and convenient to the 417 and the 408. Location makes this perfect for a primary residence or investment property. Split floor plan ideal for roommates. Walk to Full Sail. 15 minutes to downtown Orlando and approximately 30 minutes to most attractions. Exceptionally well taken care of and only needs your personal touches to make it a really cute home. Seller will offer an appliance package and a 1 year home warranty with the right contract. What are you waiting for come and get it!!

3651 N Goldenrod Road Unit C109, Winter Park

Listing courtesy of REAL ESTATE PROFESSIONALS SE. 407-331-7600
200 S Interlachen Avenue Unit 350, Winter Park
$2,350,000
3 Beds ⋅ 4 Baths ⋅ O6438596 MLS ⋅ Versailles Of Winter Park BLDG.
Welcome to The Versailles of Winter Park, an extraordinary opportunity to own one of only seven exclusive private residences in one of Winter Park's most coveted luxury communities, nestled just steps from the world-renowned Park Avenue and adjacent to the prestigious Alfond Inn & Spa. This magnificent third-floor residence offers 3,110 square feet of impeccably designed one-level living, oak hardwood floors throughout, elegant crown molding, and an abundance of natural light pouring through French doors set the tone for refined sophistication. Entertain effortlessly in the grand living area with a sprawling balcony adorned with Chicago brick and stone railing. Kitchen includes wood cabinet, granite, Monogram refrigerator, convection oven and microwave. The versatile split-bedroom floor plan ensures ultimate privacy, with the lavish primary suite accessed through double doors, walk-in closet, private balcony access, and an opulent spa bath featuring dual vanities, a soaking tub, walk-in shower. A designated office with wall-to-wall built-ins, a formal dining room accommodating up to twelve guests, a private two-car garage, and meticulously maintained landscaping. The Versailles of Winter Park is the ultimate expression of luxury living offering an unparalleled lifestyle just moments from the finest dining, boutique shopping, art festivals, and cultural events that makes Winter Park one of Florida's most desirable destinations.

200 S Interlachen Avenue Unit 350, Winter Park

Listing courtesy of KELLY PRICE & COMPANY LLC. 407-645-4321
1250 S Denning Drive Unit 127, Winter Park
$245,000
2 Beds ⋅ 2 Baths ⋅ O6439854 MLS ⋅ F BLDG.
Virtually Staged. Updated two-bedroom, two-bath residence offering 908 square feet and a first-floor, pool-facing location in Mead Garden Condominium. The move-in-ready interior features luxury vinyl plank flooring throughout the living areas and bedrooms, tile flooring in the baths and defined living and dining spaces. The kitchen is appointed with white transitional cabinetry, granite countertops, a white subway tile backsplash and stainless steel appliances, including a refrigerator, range, microwave and dishwasher. A pass-through to the dining area incorporates built-in cabinetry, glass-front display storage and additional counter space. The dining area flows into the living room, where sliding glass doors open to an enclosed sunroom overlooking the community pool and landscaped grounds. The primary bedroom features natural light from a pool-facing window, built-in closet storage and an en-suite bath with a walk-in shower and white tile surround. A second bedroom provides flexible space for a variety of uses, while the second full bath offers a tub and shower combination. Additional features include a newer water heater, updated plumbing fixtures and convenient access to the community laundry room just outside the residence. From 1250 South Denning Drive, Residence 127 offers proximity to Mead Botanical Garden, Rollins College, Park Avenue, Azalea Park, Seven Oaks Park and Winter Park dining and retail.

1250 S Denning Drive Unit 127, Winter Park

Listing courtesy of PREMIER SOTHEBY'S INTL. REALTY. 407-644-3295
500 N Pennsylvania Avenue Unit G, Winter Park
$349,500
2 Beds ⋅ 1 Baths ⋅ G5117377 MLS ⋅ Village Condominiums Of Winter BLDG.
Under contract-accepting backup offers. Virtually Staged. **Rare opportunity to own in the highly desired Downtown of Winter Park for under $350,000!** Enjoy the highly desired downtown Winter Park lifestyle with Park Avenue’s boutiques, restaurants, cafés, arts and culture, Rollins College, the Winter Park Train station, Casa Feliz, seasonal festivals and community events all just a short walk from your front door. This charming 2-bedroom, 1-bath condo offers an inviting open-concept living and dining area, along with a kitchen featuring granite countertops and convenient counter seating. Condo is highlighted with beautiful plantation shutters. Located within a charming, intimate condominium community, it offers a wonderful combination of comfort, location and low-maintenance living, all within an area known for its highly regarded Winter Park-area schools. Whether you’re searching for a primary residence, a second home, a great option for downsizing, or an investment property, this is your opportunity to own a piece of one of Central Florida’s most desirable cities. Imagine strolling to dinner on Park Avenue, meeting friends for coffee, walking to Rollins College, enjoying the beauty and history of Casa Feliz, browsing the shops, attending an art festival or catching the train — all without worrying about finding a parking space. Simply walk out your front door and enjoy the incredible lifestyle that makes Winter Park such a special place to call home. **Opportunities to own downtown Winter Park real estate at this price point are rare. Don’t miss your chance — schedule your private showing today before this one is sold. A location and lifestyle like this won’t last long!**

500 N Pennsylvania Avenue Unit G, Winter Park

Listing courtesy of OLYMPUS EXECUTIVE REALTY INC. mls@oerfl.com
3020 Antique Oaks Circle Unit 129, Winter Park
$135,000
2 Beds ⋅ 2 Baths ⋅ O6438679 MLS ⋅ 129 BLDG.
VALUE OPPORTUNITY IN WINTER PARK! Welcome to 3020 Antique Oaks Circle #129, a spacious 2-bedroom, 2-bath FIRST-FLOOR CONDO offering approximately 1,018 square feet in the conveniently located Parkview Village community in Winter Park, FL 32792. If you have been searching for an affordable Winter Park condo, investment property, renovation opportunity, first-floor condo or 2-bedroom condo in Winter Park, this property deserves your attention. The functional floor plan offers generous living space, two full bathrooms, an interior laundry area and the convenience of first-floor living. Parkview Village offers desirable community amenities including a COMMUNITY POOL, SPA, TENNIS COURTS and recreational areas, creating an appealing combination of location, convenience and value. LOCATION IS A MAJOR HIGHLIGHT! Enjoy easy access to Semoran Boulevard/436, Aloma Avenue, University Boulevard, Downtown Winter Park, Park Avenue, Rollins College, UCF and major Central Florida roadways. Shopping, restaurants, grocery stores and everyday conveniences are close by, making this an excellent option for buyers looking for a Winter Park condo close to dining, shopping, entertainment and employment centers. The property is currently served by Aloma Elementary School, Glenridge Middle School and Winter Park High School. Buyers are encouraged to independently verify current school zoning and assignments with Orange County Public Schools. IMPORTANT VALUE OPPORTUNITY: The property has known mold present in the kitchen area that requires professional remediation, and the asking price has been positioned to reflect the property's current condition and the work needed. This creates an opportunity for a buyer who is prepared to complete the necessary remediation and customize the property to their own style. Buyers are encouraged to perform their own inspections, obtain professional remediation evaluations and verify all property and association information. With a Winter Park address, first-floor location, 2 bedrooms, 2 full bathrooms, community amenities and convenient access to shopping, dining and major roadways, this condo offers significant potential for the buyer willing to address the existing condition. Bring your vision and take advantage of this affordable Winter Park condo opportunity!

3020 Antique Oaks Circle Unit 129, Winter Park

Listing courtesy of KELLER WILLIAMS CLASSIC. murraycoleman@kw.com
2500 Lee Road Unit 143, Winter Park
$130,000
1 Beds ⋅ 1 Baths ⋅ O6438724 MLS ⋅ Lakeside Manor BLDG.
It doesn't get much better than this: Living in a Lakefront and Winter Park community, that is convenient to I-4 providing easy access to points north and south, downtown Winter Park, shopping, fine dining, and the price can't be beat. The HOA dues includes water, trash pickup, a full package from Spectrum including internet. Lakeside Manor is situated on the north side of Lake Killarney, a 239 acre lake that is perfect for sailing, motor boating and skiing. The lush courtyard, lakeside pool, clubhouse and gazebo, updated dock and private boat ramp make this a serene place to enjoy the best of Central Florida in a noisy world. This one bedroom condo is in original condition, with 3 year old A/C unit, and is ready for your personal touches to make it your own.

2500 Lee Road Unit 143, Winter Park

Listing courtesy of PALMANO GROUP RE BROKERAGE LLC. 321-214-1211
3651 N Goldenrod Road Unit C205, Winter Park
$159,900
2 Beds ⋅ 2 Baths ⋅ O6438227 MLS ⋅ Building C BLDG.
Just Reduced $10k!! Priced to sell, already rented, perfect for investor buyer. This 2nd floor end unit boasts of an open floor plan with the kitchen being open to the living room/dining area and features a breakfast bar. Stainless Appliances, including Refrigerator, Microwave, Flat top Range/oven, Dishwasher, full size front load washer and Dryer in Laundry Closet. Community features a pool/clubhouse. Excellent school zone which includes desirable Winter Park School High School, Glenridge Middle School, Aloma Elementary School. An ideal location that makes a Great Rental Investment property, already leased. Location, Location, Location... with only a few minutes to downtown Orlando, UCF, Valencia, Full Sail, Rollins College, theme parks, beaches, airport, highways 417 & 408, entertainment, dining & shopping. Call now for your private showing, will not last.

3651 N Goldenrod Road Unit C205, Winter Park

Listing courtesy of CFRP REALTY LLC. 407-682-8686
5108 Lazy Oaks Drive Unit 5108, Winter Park
$269,000
2 Beds ⋅ 2 Baths ⋅ O6437795 MLS ⋅ 5108 BLDG.
Welcome to 5108 Lazy Oaks Drive, a 2-bedroom, 2-bathroom condo in a desirable Winter Park location. This light-filled home has approximately 1,008 square feet of comfortable living space with a functional floor plan, abundant windows, skylight and sliding glass doors that bring in plenty of natural light. The spacious living room features a beautiful brick fireplace and sliding glass door access to the screened-in back patio. The patio can also be accessed directly from the primary bedroom, creating a wonderful private outdoor space to enjoy your morning coffee, relax, or entertain. The primary suite features an en-suite bathroom with a walk-in shower, spacious two-sink vanity, and plenty of closet space. The guest bedroom is conveniently located just two steps from the second full bathroom, providing an ideal setup for family, guests, or a home office. The well-maintained original kitchen includes an electric range and oven, refrigerator, dishwasher, and two-basin stainless steel sink. Well-maintained tile flooring runs throughout the home, offering durability and easy maintenance. The spacious one-car garage has more than just parking, with a washer and dryer and plenty of additional storage space. The HOA fee is $277 per month and includes lawn maintenance and responsibility for the entire exterior of the condo, including the roof, providing added convenience and peace of mind for the homeowner. With its fresh interior, abundant natural light, brick fireplace, screened-in patio, private primary suite, attached garage, and low-maintenance lifestyle, 5108 Lazy Oaks Drive is a wonderful opportunity to own a comfortable home in Winter Park.

5108 Lazy Oaks Drive Unit 5108, Winter Park

Listing courtesy of BEYCOME OF FLORIDA LLC. 844-239-2663
151 N Orlando Avenue Unit 242, Winter Park
$269,000
2 Beds ⋅ 1 Baths ⋅ O6437574 MLS ⋅ Lake Killarney Condominiums BLDG.
Virtually Staged. Experience lakefront living at its finest in this exceptional Winter Park Condominium Community overlooking beautiful Lake Killarney. Hidden gem complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers unparalleled walkability. Stroll to Park Avenue's renowned boutiques, restaurants, and nightlife, catch a movie at Regal Cinemas, or conveniently shop at Publix and Trader Joe's. With countless restaurants, bars, and everyday amenities just steps away, you'll enjoy the perfect blend of tranquil waterfront living and vibrant urban convenience. Whether you're boating on the lake, lounging by the pool, or taking in the spectacular evening sunsets, this is a rare opportunity to enjoy one of Winter Park's most desirable waterfront lifestyles.

151 N Orlando Avenue Unit 242, Winter Park

Listing courtesy of COLONIALTOWN REALTY. 407-896-7300
222 Lewfield Circle, Winter Park
$189,900
2 Beds ⋅ 2 Baths ⋅ O6436344 MLS ⋅ 10 BLDG.
One or more photos was virtually staged. This 2 Bedroom, 2 Bath, 953 SF Winter Park condo in the amazing Stratford community offers a comfortable, functional floor plan complemented by fresh interior paint, updated flooring, and a 2026 HVAC system. The spacious living area features a ceiling fan and sliding glass doors that bring in natural light and open to a covered balcony, creating an easy extension of the indoor living space. The adjacent dining area provides flexibility for everyday meals or additional living space. The kitchen features wood cabinetry, generous counter space, tile flooring, and stainless steel refrigerator, while an in-unit laundry closet adds everyday convenience. Bedrooms feature updated flooring, neutral finishes, ceiling fans, and ample natural light. A large walk-in closet with extensive shelving and storage helps keep everything organized, while the bathroom includes a tiled walk-in shower and vanity storage. Freshly touched up throughout and offering a practical layout with comfortable living spaces, this Winter Park condo is ready for its next chapter.

222 Lewfield Circle, Winter Park

Listing courtesy of MARKET CONNECT REALTY LLC. 407-250-4708
285 Lewfield Circle Unit 285, Winter Park
$147,000
1 Beds ⋅ 1 Baths ⋅ O6435396 MLS ⋅ Lewfield 285 BLDG.
Virtually Staged. LOCATION, CONVENIENCE, AND EASY LIVING IN WINTER PARK! This move-in-ready first-floor, 1-bedroom, 1-bath condo features an open living and dining area, wood flooring throughout the main living areas, tile flooring in the primary bedroom, a private screened-in balcony, a fully equipped kitchen, and a stackable washer and dryer. Conveniently located near UCF, Rollins College, Valencia College, Park Avenue, and Downtown Orlando, with easy access to shopping, dining, and major highways. Community amenities include two pools, a tennis court, fitness center, and clubhouse. HOA includes water, trash, internet, pest control, exterior maintenance, and grounds care. A great opportunity to enjoy a low-maintenance lifestyle in a highly convenient Winter Park location.

285 Lewfield Circle Unit 285, Winter Park

Listing courtesy of COLDWELL BANKER REALTY. 407-352-1040
623 Grenadine Court Unit 623, Winter Park
$194,900
2 Beds ⋅ 2 Baths ⋅ O6434195 MLS ⋅ 623 BLDG.
PRICE ADJUSTMENT! Welcome to this Desirable Winter Park Villas Condo FIRST FLOOR 2 BEDROOM, 2 FULL BATH, 1037 square feet, featuring NEW AIR CONDITIONING SYSTEM and BRAND NEW CARPET freshly installed! EXCELLENT LOCATION walking or bike riding distance to FULL SAIL UNIVERSITY and easy access to UCF! Ideally located in rear of community with ample open parking. Your spacious Kitchen features ample counter space and abundant cabinetry, kitchen sink window with view of front door entry and parking area. Kitchen has a closet pantry and there is an opening to Dining Room with Bar Seating area. Dining Room has views to backyard and a Wet Bar with unique Sink Closet feature. Family Room has a fireplace and views of outside greenery. In hallway off entry is your Washer/Dryer closet and they are both included in the sale. The Primary Bedroom is large with walk in closet, full bathroom with tub shower combo and two vanities. The Secondary Bedroom features back yard views and built in closet and easy access to hallway full second bath. Outside you'll love the covered patio and lawn area for lounging or gardening outside. Off the patio is a storage closet for the Water Heater. Winter Park Villas amenities include community pool, fitness center and tennis courts. Seller is offering a One Year Assurant Home Warranty covering all the appliances included. Located in Winter Park School District and easy access to Orlando International Airport! Call for to see it today, priced under $200,000 location can't be beat! Property may be under audio/visual surveillance.

623 Grenadine Court Unit 623, Winter Park

Listing courtesy of COLDWELL BANKER REALTY. 407-333-8088
3019 Antique Oaks Circle Unit 127, Winter Park
$143,500
1 Beds ⋅ 1 Baths ⋅ O6434819 MLS ⋅ N/A BLDG.
Beautifully renovated first-floor 1-bedroom, 1-bath condominium in the highly desirable Parkview Village community, conveniently located directly across from Full Sail University on Semoran Blvd. This move-in-ready home features a spacious open-concept layout, an oversized bedroom with a walk-in closet, a dedicated laundry closet with a washer and dryer, and a private screened-in patio overlooking a beautiful mature tree for added privacy and relaxation. The home has been extensively updated with a newer A/C system, a fully renovated kitchen and bathroom, and a complete suite of stainless steel appliances-including the refrigerator, range, microwave, dishwasher, washer, and dryer-all replaced in 2022. Modern features include a preinstalled Nest Wi-fi thermostat, Eufy doorbell/lock, and wall-mounted TV brackets in both the living room and bedroom. Residents enjoy resort-style amenities including a community pool, hot tub, picnic and BBQ area, and a newly built fenced dog park. The location has easy access to Lake Baldwin, Downtown Winter Park, the University of Central Florida, Downtown Orlando, and Orlando International Airport. Major roadways including SR 436, SR 408, and East Colonial Drive are just minutes away, making commuting throughout Central Florida quick and convenient. Whether you're looking for a comfortable primary residence or an investment property, this exceptional condominium is the perfect combination of location, modern updates, and everyday convenience.

3019 Antique Oaks Circle Unit 127, Winter Park

Listing courtesy of BEYCOME OF FLORIDA LLC. 844-239-2663
1278 S Pennsylvania Avenue Unit 13, Winter Park
$799,000
3 Beds ⋅ 3 Baths ⋅ O6417455 MLS ⋅ Casa Jardin BLDG.
In the heart of Winter Park’s coveted Virginia Heights neighborhood, just moments from the boutiques, dining, and charm of Park Avenue and the green spaces of Seven Oaks Park, this exceptional Mediterranean-inspired end-unit condominium offers an unparalleled blend of elegance, comfort and accessible convenience. Encompassing nearly 2,000 square feet, the residence features three bedrooms, two-and-a-half baths and a thoughtfully designed floor plan that lives like a private home. Bathed in natural light, the interiors are framed by expansive window walls and floor-to-ceiling glass doors that create a bright, airy ambiance throughout. Architectural details including graceful arched passageways, column-lined hallways, and a custom wrought-iron spiral staircase add timeless character and sophistication. Beautifully updated and meticulously maintained, every room reflects a sense of warmth and refinement. The spacious primary retreat is a sanctuary, featuring soaring cathedral ceilings, dual walk-in closets and a spa-inspired bath designed for relaxation. Two additional bedrooms offer versatility for guests, family or a home office. The open-concept living and dining areas are enhanced by travertine and luxury vinyl plank flooring, coffered ceilings, designer lighting, and a beautifully appointed chef’s kitchen complete with solid wood cabinetry, granite countertops, a center island and generous walk-in pantry. French doors open to a freshly painted screened courtyard, creating a private outdoor escape ideal for entertaining or quiet evenings at home. Above, the freshly painted rooftop terrace provides a spectacular setting for alfresco dining, sunset gatherings or simply enjoying Florida’s year-round sunshine. Additional features include a powder bath, plantation shutters, ceiling fans throughout, an oversized two-car garage, and a third-floor walk-in attic offering abundant storage and exciting future expansion possibilities. Residents of Casa Jardin enjoy a beautifully refreshed community, recently enhanced with a new roof, exterior paint and professional landscaping. Ownership also includes exclusive access to Lake Virginia and renowned Winter Park Chain of Lakes through College Point, featuring a private lakefront gathering area along with kayak and paddleboard storage. Ideally near Azalea Lane Recreation Center, the Winter Park Tennis Center, Orange Avenue’s popular restaurants and shops, and top-rated schools, this remarkable residence offers a rare opportunity to enjoy one of Central Florida’s desirable lifestyles.

1278 S Pennsylvania Avenue Unit 13, Winter Park

Listing courtesy of PREMIER SOTHEBY'S INTL. REALTY. 407-644-3295
311 E Morse Boulevard Unit 4-5, Winter Park
$925,000
2 Beds ⋅ 2 Baths ⋅ O6432808 MLS ⋅ Building 4 BLDG.
Experience effortless Winter Park living in Whispering Waters, a premier 55+ lakefront community beautifully situated along the shores of Lake Osceola & just a short stroll from Park Avenue. Priced below appraised value, this rare third-floor mid-century modern condo offers exceptional value and a truly turnkey lifestyle. Filled with natural light, the thoughtfully designed floor plan features spacious living and dining areas overlooking tranquil waterfall ponds and lush, beautifully maintained grounds. A versatile bonus space provides the perfect setting for a home office, den, or creative retreat. The expansive owners suite is designed for relaxation, featuring a private sitting area, dual closets, direct access to the pool, and a spa-inspired bath complete with a jetted tub. The generously sized secondary bedroom offers a cozy reading nook and dual closets, providing comfort and flexibility for guests. Enjoy effortless, worry-free living with secure underground parking, a deeded parking space, and convenient elevator access. Even better, monthly association dues include electricity, air conditioning, heat, water, sewer, and trash—making everyday living remarkably simple. Step outside your door and enjoy everything that makes Winter Park so special, from the acclaimed shops and restaurants of Park Avenue to Rollins College and Winter Parks historic golf course. With its prime lakefront setting, exceptional location, and low-maintenance lifestyle, this is a rare opportunity to own a piece of one of Central Florida’s most desirable communities. Discover the best of Winter Park living at Whispering Waters—schedule your private showing today.

311 E Morse Boulevard Unit 4-5, Winter Park

Listing courtesy of KELLER WILLIAMS ADVANTAGE REALTY. murraycoleman@kw.com
250 Carolina Avenue Unit 205, Winter Park
$739,000
2 Beds ⋅ 2 Baths ⋅ O6433913 MLS ⋅ 250 BLDG.
Discover the ease of Winter Park living in the highly desirable gated community of Park West, ideally located just steps from Park Avenue. From this exceptional location, charming boutiques, sidewalk cafés, award-winning restaurants, and the popular weekly farmers market are all within easy reach—giving you the freedom to leave the car behind and enjoy everything Park Avenue has to offer. This beautifully remodeled second-floor corner residence offers the privacy, comfort, and convenience you've been looking for. The thoughtfully updated kitchen features wood cabinetry and granite countertops, while both bathrooms have been tastefully remodeled. Spacious bedrooms, generous storage, and a comfortable flow throughout the home provide plenty of room for everyday living or welcoming guests. Enjoy the simplicity of a well-maintained community with beautifully landscaped grounds, a sparkling swimming pool, and tennis courts. As a corner unit, this residence also offers enhanced privacy and convenient access into and out of the building—perfect for those seeking a low-maintenance lifestyle or an easy lock-and-leave retreat. With Rollins College and Full Sail University nearby and Park Avenue just moments away, this condo puts the best of Winter Park right at your doorstep. Whether you're looking for a full-time residence, a seasonal escape, or simply a home that allows you to spend less time on maintenance and more time enjoying life, Park West offers an exceptional combination of location, comfort, and convenience.

250 Carolina Avenue Unit 205, Winter Park

Listing courtesy of BHHS FLORIDA REALTY. 407-406-5300
7468 Canford Court Unit 24, Winter Park
$184,900
2 Beds ⋅ 2 Baths ⋅ O6433680 MLS ⋅ 24 BLDG.
This charming 2-bedroom, 1.5-bath condo offers a desirable townhome-style layout with spacious living areas and thoughtful storage throughout. The community features deluxe vinyl fencing installed by the HOA, along with a clubhouse and a community pool, providing great amenities for residents to enjoy. Inside, you’ll find the convenience of an in-unit washer and dryer combo, ample storage under the stairs, and a large carport with an attached storage shed. The spacious primary bedroom opens directly to a generous private balcony—perfect for relaxing or unwinding after a long day. Ideally located just 15 minutes or less from UCF, Rollins College, Valencia East, and Full Sail University, and only 20 minutes from Orlando International Airport. Whether you’re a first-time homebuyer, student, investor, or looking to make your move into Winter Park, this home delivers affordability, convenience, and excellent potential.

7468 Canford Court Unit 24, Winter Park

Listing courtesy of EMPIRE NETWORK REALTY. 407-440-3798
1250 S Denning Dr Unit Unit 233, Winter Park
$245,000
2 Beds ⋅ 2 Baths ⋅ O6430611 MLS ⋅ Mead Gardens Condominiums BLDG.
Located just minutes from Winter Park's famed Park Avenue, this charming 2 bed, 2 bathroom corner condominium features a light and bright open floor plan, updated finishes, views of Mead Gardens, and one of Central Florida's most sought after locations! As you enter the front door, you are immediately welcomed by views of Mead Botanical Gardens, Khaki oak wood-look luxury vinyl floors, an open living/dining room combo, a private balcony with garden views and kitchen with freshly painted cabinets and stainless steel appliances. Off of the family room, 2 spacious bedrooms including a master suite with a renovated bathroom, and a second bedroom with private access. Everyday is a vacation when you can start your day off with a coffee on the private balcony, cool off on a warm summer's day in the pool and end it with a walk through the 48 acre natural enclave just next door as the sun sets. Zoned for A rated schools including Audobon Park and Winter Park High school and located just minutes from world class shopping, dining and entertainment in historic downtown Winter Park, Downtown Orlando, and College Park. Schedule your showing Today!

1250 S Denning Dr Unit Unit 233, Winter Park

Listing courtesy of STOCKWORTH REALTY GROUP. 407-909-5900
2477 Tahoe Circle Unit 2477, Winter Park
$254,000
2 Beds ⋅ 2 Baths ⋅ O6432904 MLS ⋅ 2477 BLDG.
Virtually Staged. LIVE THE WINTER PARK LIFESTYLE! STYLE, SPACE & LOCATION—THIS ONE HAS IT ALL! Welcome to Cedarwood Village, where easy living meets one of Winter Park’s most desirable locations, just minutes from the charm, dining, shopping, and entertainment of Downtown Winter Park and Park Avenue. This beautifully maintained 2-bedroom, 2-bath residence with an enclosed bonus room offers a spacious, light-filled floor plan designed for both comfortable everyday living and entertaining. Vaulted ceilings enhance the open living and dining areas, while the generously sized kitchen features newer appliances, abundant cabinet and counter space, plus room for a cozy breakfast table. Retreat to the oversized primary suite, complete with two large closets and sliding glass doors opening to the bonus room. The renovated primary bath adds a touch of luxury with an updated vanity and impressive custom walk-in shower. The guest bedroom offers its own sliding glass doors leading to the front patio, creating a bright and inviting space for family or overnight guests. The updated guest bath adds convenience with a washer and dryer neatly tucked away in the closet. One of the home's best features is the enclosed bonus room, offering valuable additional living space that's perfect for a home office, den, reading retreat, hobby room, or simply a relaxing place to unwind. Enjoy the Florida lifestyle without leaving the neighborhood! Cedarwood Village offers a sparkling community pool, two tennis courts, and clubhouse for residents to enjoy. And then there’s the LOCATION! Shopping, restaurants, medical facilities, and everyday conveniences are all close by, with easy access to major roadways and the boutiques, sidewalk cafés, restaurants, parks, and unmistakable charm of Park Avenue and Downtown Winter Park just minutes away. More than a home—it’s a Winter Park lifestyle. Come see why Cedarwood Village is such a special place to call home!

2477 Tahoe Circle Unit 2477, Winter Park

Listing courtesy of RE/MAX TOWN & COUNTRY REALTY. 407-695-2066
283 Sandlewood Trail Unit 3, Winter Park
$285,000
2 Beds ⋅ 3 Baths ⋅ O6431475 MLS ⋅ 2 BLDG.
Virtually Staged. MOVE IN READY in Winter Park with nearly $30,000 in recent upgrades and improvements! This beautifully updated 2 bedroom, 2.5 bathroom condo in Sandlewood Creek offers a bright, open layout, conservation views and a quiet community setting in an incredibly convenient location. The main level features a spacious open living and dining area with plenty of room to create separate gathering and dining spaces while maintaining an easy flow throughout the home. The updated kitchen features white cabinetry, granite countertops, stainless steel appliances and a breakfast bar overlooking the living and dining space. A convenient half bath, interior laundry, washer and dryer included, and an additional downstairs storage closet complete the first floor. Step outside to the screened rear porch overlooking conservation, creating a peaceful outdoor space with added privacy. Upstairs, the primary bedroom features a private en suite bathroom, while the second bedroom is located near the additional full bath. A small landing separates the two bedrooms and includes an additional upstairs storage closet, providing valuable extra space for linens, seasonal items or everyday storage. Nearly $30,000 in recent upgrades and improvements include vinyl flooring and baseboards upstairs completed in September 2023, an updated kitchen with cabinetry, countertops and stainless steel appliances in 2023, AC installed in January 2024, roof is 2021, washing machine replaced in 2024, fresh interior paint and new downstairs baseboards completed in July 2026, plus a 2018 water heater. Sandlewood Creek is an established community with a community pool and one assigned parking space. Maitland Community Park is located directly behind the community and connects to additional park space, offering convenient access to trails and outdoor recreation. Park Avenue and Downtown Winter Park are approximately 10 minutes away, putting shopping, dining and entertainment within easy reach. With its extensive recent improvements, conservation setting, screened porch, multiple storage areas and convenient Winter Park location, this home is truly move in ready.

283 Sandlewood Trail Unit 3, Winter Park

Listing courtesy of RE/MAX INNOVATION. 407-281-1053
1695 Lee Road Unit D107, Winter Park
$180,000
1 Beds ⋅ 1 Baths ⋅ O6425124 MLS ⋅ Building D BLDG.
Don't miss out the great opportunity to own a unit in the heart of Winter Park Area. A perfect primary or secondary residence or investment home. Waterfall Cove is a great community with spacious pool, playground and lots of lush landscaping. Easy access to Major Highways a minute from I-4, bike away from Downtown Winter Park, close to major theme parks, major shopping area, restaurant, movie theater and a short drive to Cocoa Beach.

1695 Lee Road Unit D107, Winter Park

Listing courtesy of PRIMESTATE REALTY, INC.. 407-850-9494
7413 Belle River Court Unit 3, Winter Park
$214,900
3 Beds ⋅ 3 Baths ⋅ O6430667 MLS ⋅ 7413 BLDG.
MOTIVATED SELLER...Welcome To This Beautifully 3 Bedroom, 2.5 Bathroom Condominium Located in the Desirable Hidden Oaks Community. Offering Updated Living Space, This Home Combines Comfort, Style, and an Unbeatable Location. Step Inside to a Spacious and Inviting Family Room Featuring Beautiful Laminate Flooring, Abundant Natural Light, and an Open, Welcoming Atmosphere. The Updated Kitchen Is Sure to Impress with Quartz Countertops, Stainless Steel Appliances, and A Sliding Glass Door That Opens to a Private Patio—Perfect for Relaxing or Entertaining. Upstairs, You'll Find All Three Bedrooms and Two Full Bathrooms, including a Generously Sized Primary Suite with a Walk-In Closet and Large Front-Facing Windows That Fill the Room with Natural Light. Residents of Hidden Oaks Enjoy a Peaceful Setting with Access to a Community Swimming Pool, Assigned Parking, And Plenty of Guest Parking. Ideally Located Just Minutes from Major Highways 408 And 417, This Home Is Only 4 Minutes from Full Sail University, Minutes from the University of Central Florida (UCF), Downtown Orlando, and Conveniently Close to Valencia College, Rollins College, Winter Park Shopping and Dining, Restaurants, and Everyday Conveniences. The Property Is Also Zoned for Highly Desirable Winter Park Schools, Making It an Excellent Choice for Homeowners and Investors Alike. Don't Miss This Move-In-Ready Opportunity in One of the Area's Most Convenient Locations!

7413 Belle River Court Unit 3, Winter Park

Listing courtesy of OUTLET REALTY. 407-308-0600
5210 Lazy Oaks Drive, Winter Park
$279,900
2 Beds ⋅ 3 Baths ⋅ O6430356 MLS ⋅ 5210 BLDG.
Virtually Staged. DISCOVER THE SERENE BEAUTY OF THIS WINTER PARK TWO-STORY TOWNHOME! Located in the SOUGHT-AFTER Lazy Oaks community. Blending contemporary style with everyday convenience, GORGEOUS 2-BEDROOM, 2.5-BATHROOM, 1-CAR GARAGE HOME. From the moment you step inside, you’ll be greeted by an OPEN-CONCEPT LIVING AREA filled with NATURAL LIGHT, creating a warm and inviting atmosphere. Cook like a pro in the BRAND NEW KITCHEN featuring NEW QUARTZ COUNTERTOPS and SLEEK STAINLESS STEEL APPLIANCES—perfect for culinary enthusiasts. This home is LOADED WITH UPGRADES, including: Newer Roof with 30-Year Shingles, New Laminate Flooring Throughout, Renovated Bathrooms with New vanities, Fresh Interior & Exterior Paint, New Light Fixtures, Faucets, Toilets, Water Heater from 2020, HVAC System from 2015. With affordable condo fees, this home offers both comfort and peace of mind. Located in a wonderful community, you'll enjoy easy access to shopping, major roads, and just minutes away from the vibrant Park Avenue. This move-in-ready home truly has it all! All measurements are approximate and should be verified by the buyer. Virtual Staging was added to some of the pictures.

5210 Lazy Oaks Drive, Winter Park

Listing courtesy of IHOME REALTY FL LLC. 407-730-9971
1695 Lee Road Unit A101, Winter Park
$154,900
3 Beds ⋅ 2 Baths ⋅ O6429942 MLS ⋅ A BLDG.
Vacant! Great location! Must See! New paintinf interior, and new carpet. The best area at Winter Park, close to major shoppiing center,

1695 Lee Road Unit A101, Winter Park

Listing courtesy of CINO INTERNATIONAL INC. 407-354-3318
1000 S Semoran Boulevard Unit 302, Winter Park
$105,000
1 Beds ⋅ 1 Baths ⋅ O6428713 MLS ⋅ 302 BLDG.
Virtually Staged. 2018 AC, ROOF REPLACED BY HOA WITHIN THE LAST 3 YEARS ***Welcome to this exceptionally well-maintained 1-bedroom, 1-bathroom condominium ideally located in Winter Park! Lovingly cared for by its longtime owner, this home offers a wonderful combination of comfort, functionality, and convenience. *WASHER AND DRYER LOCATED IN UNIT* Inside, you'll find a spacious, thoughtfully designed layout featuring a generous living area, an oversized bedroom, and a large bathroom. The charming kitchen offers ample cabinet and counter space, creating an inviting space for both everyday living and entertaining. Step outside to your private balcony, the perfect place to enjoy your morning coffee or relax at the end of the day. The home's separate exterior entrance adds an extra level of convenience and privacy. Enjoy low-maintenance living with HOA dues that cover water, trash, exterior maintenance, and roof replacement. The community recently completed a roof replacement, providing added peace of mind for the new owner. Residents also enjoy access to the community pool, perfect for cooling off on warm Florida days. Conveniently located near UCF, Valencia College, Waterford Lakes Town Center, Orlando International Airport, major highways including SR 408 and SR 417, shopping, dining, and entertainment, this home is also zoned for highly desirable schools. Whether you're a first-time homebuyer, someone looking to downsize, or an investor seeking a well-maintained property in a prime East Orlando location, this condominium offers an outstanding opportunity. Schedule your private showing today!

1000 S Semoran Boulevard Unit 302, Winter Park

Listing courtesy of KELLER WILLIAMS ADVANTAGE III. murraycoleman@kw.com
1061 Aragon Avenue Unit 1061, Winter Park
$510,000
3 Beds ⋅ 3 Baths ⋅ S5152353 MLS ⋅ 1061 BLDG.
Excellent Winter Park location! This 3 bedroom 2.5 bath quad-condo LIVES LIKE A PRIVATE 2-STORY HOME, with attached oversized 2 car garage, private patio and back fenced area. (The unit is attached to another only by a common garage wall.) Priced below market value and LOWEST PRICE PER SQ FT in the area, to be sold AS-IS for the seller's convenience and TLC needed. ** ONE YEAR AHS Home Warranty included.** Nestled between Denning Dr and Orlando Ave, this home is an easy walk to the vibrant charm of Park Avenue, and close to the Winter Park Library, SunRail, and Rollins College. Publix and restaurants are just down the street! The first floor is tiled, with foyer entry, and comfortable family/dining/kitchen living area complete with fireplace. Sliding doors lead to a private patio. Upstairs, the large primary suite is a nice retreat with high ceilings, double walk in closets, double vanity and ample sized shower. Two more bedrooms and another bath complete the 2nd floor. High end washer and dryer are included in the attached garage, and a full wall workshop is in the garage too. Call to see it today!

1061 Aragon Avenue Unit 1061, Winter Park

Listing courtesy of WATSON REALTY CORP. 407-298-8800
2475 Tahoe Circle, Winter Park
$268,000
2 Beds ⋅ 2 Baths ⋅ O6428082 MLS ⋅ Na BLDG.
Turnkey Living in the Heart of Winter Park! Welcome to this beautifully maintained 2-bedroom, 2-bath townhome offering the perfect blend of comfort, convenience, and low-maintenance living. Vacant and move-in ready, this home has been freshly painted and features a recently replaced air conditioning system, providing peace of mind for its next owner. Inside, you'll find a thoughtfully designed floor plan with spacious living and dining areas, a well-appointed kitchen, and two generously sized bedrooms and bathrooms designed for comfort and functionality. Whether you're relaxing at home or entertaining friends and family, this inviting layout makes everyday living effortless. Step outside and enjoy the exceptional community amenities, including a sparkling swimming pool and tennis courts, perfect for enjoying Florida's year-round sunshine. Whether you're a first-time homebuyer, downsizing, seeking a second home, or looking for an investment opportunity, this property offers incredible versatility. Ideally located in desirable Winter Park, you'll be just minutes from shopping, dining, entertainment, major highways, UCF, Full Sail University, Downtown Winter Park, and Downtown Orlando, making commuting and enjoying Central Florida's best attractions a breeze. Don't miss your opportunity to own this beautifully updated, turnkey home in one of Central Florida's most sought-after communities! All room measurements, HOA information, square footage, and property details are deemed reliable but not guaranteed and should be independently verified by the buyer and buyer's agent.

2475 Tahoe Circle, Winter Park

Listing courtesy of COLDWELL BANKER REALTY. 407-352-1040
1000 S Semoran Boulevard Unit 305, Winter Park
$115,000
1 Beds ⋅ 1 Baths ⋅ O6428044 MLS ⋅ 1000 BLDG.
Freshly Updated 1-Bedroom Condo – Perfect for Homeowners or Investors! Whether you're looking for your first home, downsizing, or adding to your investment portfolio, this move-in-ready 1-bedroom, 1-bath condominium is an excellent opportunity. Featuring brand-new luxury vinyl plank flooring and a freshly painted interior, this home offers a clean, modern feel throughout. The open-concept floor plan seamlessly connects the kitchen, dining, and living areas, creating a bright and inviting space for everyday living and entertaining. A set of French doors leads to the screened-in porch, providing the perfect spot to enjoy your morning coffee or unwind after a long day. The spacious bedroom features a large walk-in closet, offering plenty of storage. This condo also includes one assigned parking space, along with additional guest parking for visitors. Residents enjoy access to a community pool and onsite laundry facilities, adding to the convenience of low-maintenance living. Ideally located just minutes from SR 408, the University of Central Florida (UCF), shopping, dining, restaurants, and entertainment, this condo offers an unbeatable combination of comfort, convenience, and value. Whether you're searching for a primary residence or a smart investment opportunity in a high-demand area, this Central Florida gem is one you won't want to miss!

1000 S Semoran Boulevard Unit 305, Winter Park

Listing courtesy of MAINFRAME REAL ESTATE. 407-513-4257
2526 Passamonte Drive Unit 10F, Winter Park
$335,000
3 Beds ⋅ 3 Baths ⋅ O6418710 MLS ⋅ 2526 BLDG.
Great investment opportunity, tenant occupied/income producing Winter Park property in gated community.

2526 Passamonte Drive Unit 10F, Winter Park

Listing courtesy of LEGACY CORNERSTONE INC. 407-674-5601
7450 Wynnewood Square Unit 189, Winter Park
$170,000
2 Beds ⋅ 3 Baths ⋅ O6425486 MLS ⋅ Na BLDG.
***Price Improvement*** This charming 2-bedroom, 2.5-bathroom townhome style condo offers the perfect blend of comfort and convenience. Enjoy the peace of mind that comes with a new AC (2025), a new roof (2021), newer water heater (2019) and new refrigerator and dishwasher ensuring your home is both energy-efficient and well-maintained. The entire first floor features ceramic tile, while the upstairs boasts beautiful laminate wood flooring—no carpet here! Both bedrooms are located upstairs, each with its own ensuite bathroom and additional storage above the mirrors. Downstairs, you'll find ample space for entertaining or simply relaxing, enhanced by the convenience of a wet bar. Located just minutes from UCF and Full Sail University, this condo is perfect for anyone looking to enjoy the vibrant local community without the long commute! With shopping, dining, and recreational activities nearby, you'll have everything you need right at your fingertips. Don’t miss out on this fantastic opportunity—schedule a showing today!

7450 Wynnewood Square Unit 189, Winter Park

Listing courtesy of REAL ESTATE PROFESSIONALS SE. 407-331-7600
1500 Gay Road Unit 4D, Winter Park
$164,500
1 Beds ⋅ 1 Baths ⋅ O6425078 MLS ⋅ 4 BLDG.
ANOTHER PRICE ADJUSTMENT! Lakefront Community! Enjoy Glorious Sunsets, Cocktails on the Deck and the Peace of Water and the Amazing Joy of Nature! All this near the heart of Winter Park and walking distance to all kinds of Shopping! One of few 1 Bedrooms and an Upstairs End Unit! Enjoy Spacious Room Sizes for easy Furniture Placement, Compact Kitchen, Bright Master Bedroom with additional Built-in Closets, Vanity and Mirrored Closets and updated Bath, accessible for Guests and close to Master! Updated Windows! Private Balcony! Owner is providing a One-Year Home Warranty. Make this affordable Unit your own!

1500 Gay Road Unit 4D, Winter Park

Listing courtesy of REALCOM REAL ESTATE SERVICES INC. 407-740-5300
2450 Grand Teton Circle Unit 2450, Winter Park
$250,000
3 Beds ⋅ 2 Baths ⋅ O6418973 MLS ⋅ 2450 BLDG.
Rare end units like this don't come around often! Welcome to 2450 Grand Teton Circle, tucked away in the well-maintained, established community of Cedarwood Village in Winter Park. This 3-bedroom, 2-bath home is filled with natural light thanks to its end-unit location, and the open layout makes it easy to relax, entertain and enjoy everyday living. The spacious living and dining areas flow together nicely, while the kitchen offers plenty of room to cook, gather, and stay connected with family and friends. Over the past several years, this home has been thoughtfully updated, giving the next owner peace of mind. Major improvements include a new roof, skylights, HVAC system, water heater, kitchen appliances, washer and dryer, updated LED lighting, and fresh interior paint. Both bathrooms have been beautifully remodeled, the home has been replumbed by the HOA, and the primary closet has been enhanced with custom shelving. Additional updates include new flooring in the secondary bedrooms, updated window blinds, and thoughtful finishing touches throughout. The private screened lanai has been transformed into a cozy outdoor retreat with fresh paint, a ceiling fan, new screens and screen door, string lighting, and decorative greenery—making it the perfect place to enjoy your morning coffee or unwind after a long day. Life here is easy. Cedarwood Village is a beautifully maintained, established community featuring a community pool and Clubhouse for your special events, tennis courts, and pickleball courts. The HOA has also recently repainted the exterior of the buildings, helping keep the neighborhood looking fresh and inviting. Best of all, this home is value priced, giving you an incredible opportunity to own in desirable Winter Park without the premium price tag. You're just minutes from Winter Park's shopping and dining, Full Sail University, UCF, major employers, and convenient access to SR-417 and downtown Orlando. If you've been looking for a move-in-ready home in a fantastic location with years of thoughtful updates already completed, this rare end unit is definitely worth a look!

2450 Grand Teton Circle Unit 2450, Winter Park

Listing courtesy of CHARLES RUTENBERG REALTY ORLANDO. 407-622-2122
5184 Lazy Oaks Drive, Winter Park
$275,000
2 Beds ⋅ 2 Baths ⋅ O6422366 MLS ⋅ Na BLDG.
Charming two-bedroom, two-bath condominium available in Winter Park. The reserve is fully funded, and monthly condominium fees are low. A comfortable foyer welcomes you inside, leading down the hallway to the second bedroom at the front of the home, where a large window overlooks the front green space. The kitchen opens to a bright, inviting space with skylights that bring natural light into the combined living and dining area. A fireplace adds warmth to the room, while sliding glass doors lead to a private screened enclosure overlooking additional green space at the rear of the property. Ideally positioned within the home, the kitchen features all-new appliances and an oversized pantry with spice shelving for easy organization. The primary bedroom offers an inviting entrance with closet space upon entry. Sliding glass doors fill the room with soft natural light, creating a calm and peaceful atmosphere. The primary bath includes a double vanity and additional deep closet space. From the bedroom, step out to the screened enclosure and enjoy quiet moments in the Florida breeze. Lazy Oaks Condominium is a charming, peaceful community in Winter Park. Conveniently located near shopping, restaurants, schools, and universities, it offers an inviting place to relax and call home.

5184 Lazy Oaks Drive, Winter Park

Listing courtesy of PAINE-ANDERSON PROPERTIES, INC. 407-695-7898
2305 Sun Valley Cir, Winter Park, Fl 32792, Winter Park
$279,900
2 Beds ⋅ 2 Baths ⋅ O6421422 MLS ⋅ 19 BLDG.
Beautifully renovated 2 bedroom, 2 bathroom condo at 2305 Sun Valley in Winter Park, offering a fresh modern design and thoughtful updates throughout. The fully redesigned kitchen features sleek cabinetry, quartz countertops, GE stainless steel appliances, a marble tile backsplash, abundant storage, recessed lighting, and a clean open feel that connects seamlessly to the main living areas. Wood-look porcelain tile flooring runs throughout the home, creating a cohesive, attractive, and low-maintenance finish. The spacious living area features vaulted ceilings, skylights, updated ceiling fans, and sliding glass doors that fill the space with natural light and lead to a covered screened patio overlooking green space. The primary suite includes an updated double vanity and a beautifully redesigned bathroom with a separate tub and newly installed shower. The second bathroom also offers an updated vanity and clean neutral finishes. Additional highlights include a 2021 AC, 2021 water heater, updated fixtures, generous natural light, and a screened outdoor living space ideal for relaxing and enjoying Florida’s indoor-outdoor lifestyle. This move-in ready Winter Park condo combines modern style, comfort, and everyday functionality. Residents enjoy access to a sparkling community pool, clubhouse, tennis and pickleball, and a pet walk with waste stations. Monthly fees also include roof and exterior building maintenance, exterior pest control, and landscaping, adding convenience and long-term value.The location is hard to beat, just minutes from Park Avenue, UCF, Rollins College, Full Sail University, shopping, dining, entertainment, and nearby medical facilities.

2305 Sun Valley Cir, Winter Park, Fl 32792, Winter Park

Listing courtesy of MARKET CONNECT REALTY LLC. 407-250-4708
2372 Sun Valley Circle Unit 2372, Winter Park
$285,000
2 Beds ⋅ 2 Baths ⋅ O6421135 MLS ⋅ Bldg 16 BLDG.
Welcome to this beautifully updated condo, ideally nestled between Winter Park and Maitland and perfect for a Seasonal or Year -round residence. Do you work from home and need a home office? This floor plan features a versatile upstairs loft overlooking the living and dining areas—perfect for your home office, fitness space, craft room, or additional guest accommodations. The bright, cheerful eat-in kitchen is both stylish and functional, showcasing quartz countertops, a glass tile backsplash, abundant cabinetry, a pull-out spice rack, trash/recycling cabinet, and a built-in storage unit. Sliding glass doors open to the private front courtyard, filling the space with natural light. Conveniently located laundry area, complete with washer and dryer, is tucked within the kitchen. The spacious living room features a cozy wood-burning fireplace and flows seamlessly into the dining area beneath soaring vaulted ceilings accented by skylights. Sliding glass doors lead to a screened lanai with a slate tile floor and a storage closet—an ideal spot to relax and enjoy Florida living. The primary suite also opens directly to the lanai and offers a beautifully renovated en-suite bath with a luxurious walk-in shower, updated vanity, linen cabinet, and a custom walk-in closet with built-in organizers. The front bedroom also includes a generous walk-in closet. Enjoy added privacy with a picturesque, tree-lined green space across the street rather than neighboring condos directly in front. Two dedicated parking spaces are conveniently located just outside your door. Cedarwood Village offers an exceptional location directly across from Casselberry Commons Shopping Plaza and is just minutes from Full Sail University, UCF, and Rollins College. Residents enjoy a community swimming pool, tennis courts with pickleball lines, and designated dog-walking areas. Additional highlights include a new roof and skylights installed in 2020. Monthly HOA fees cover exterior maintenance, lawn care, and community amenities, making this the perfect opportunity to enjoy carefree living in one of the area's most desirable communities.

2372 Sun Valley Circle Unit 2372, Winter Park

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211
1695 Lee Road Unit A116, Winter Park
$135,000
3 Beds ⋅ 2 Baths ⋅ O6420863 MLS ⋅ . BLDG.
Under contract-accepting backup offers. Welcome to this charming first-floor 3-bedroom, 2-bath condominium located in the beautiful city of Winter Park! Featuring laminate flooring throughout the main living areas, this inviting home offers an open-concept layout with a combined living and dining room that overlooks the kitchen, creating the perfect space for everyday living and entertaining. Each bedroom is equipped with a ceiling fan for added comfort, while the private rear patio provides a peaceful outdoor retreat complete with a bench—ideal for relaxing and enjoying Florida's beautiful weather. Whether you're searching for a primary residence, a seasonal getaway, or an investment opportunity, this condo offers exceptional value. HOA dues include pest control, basic cable, basic internet, exterior maintenance, and additional storage, providing convenience and peace of mind. Residents also enjoy access to community amenities including a swimming pool, playground, and clubhouse, all in a desirable Winter Park location close to shopping, dining, parks, and major roadways. Don't miss the opportunity to make this wonderful property your own!

1695 Lee Road Unit A116, Winter Park

Listing courtesy of REAL BROKER, LLC. 407-922-8986
1000 S Semoran Boulevard Unit 408, Winter Park
$138,000
1 Beds ⋅ 1 Baths ⋅ R4911527 MLS ⋅ 4 BLDG.
Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool and other amenities. Water and sewer is though HOA fees , nice bonus for tenants. This condo home is investment property with a long term tenant but can be ready for an owner occupant Current tenant is under market rent… opportunity to make some changes here. Schedule a showing today!

1000 S Semoran Boulevard Unit 408, Winter Park

Listing courtesy of KIMBRIDGE REALTY, LLC. 407-755-7367
1000 S Semoran Boulevard Unit 404, Winter Park
$138,000
1 Beds ⋅ 1 Baths ⋅ R4911526 MLS ⋅ 3 BLDG.
Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool and other amenities. Water and sewer is though HOA fees , nice bonus for tenants. This condo home is investment property with a long term tenant but can be ready for an owner occupant Current tenant is under market rent… opportunity to make some changes here. Schedule a showing today!

1000 S Semoran Boulevard Unit 404, Winter Park

Listing courtesy of KIMBRIDGE REALTY, LLC. 407-755-7367
1000 S Semoran Boulevard Unit 306, Winter Park
$138,000
1 Beds ⋅ 1 Baths ⋅ R4911525 MLS ⋅ 3 BLDG.
Virtually Staged. Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool and other amenities. Water and sewer is though HOA fees , nice bonus for tenants. This condo home is investment property with a long term tenant but can be ready for an owner occupant Current tenant is under market rent… opportunity to make some changes here. Schedule a showing today!

1000 S Semoran Boulevard Unit 306, Winter Park

Listing courtesy of KIMBRIDGE REALTY, LLC. 407-755-7367
3381 Cedar Springs Place Unit 151, Winter Park
$179,900
2 Beds ⋅ 3 Baths ⋅ O6419959 MLS ⋅ 000 BLDG.
Under contract-accepting backup offers. Move right in and enjoy low-maintenance living in the desirable Hidden Oaks community of Winter Park. This meticulous maintained and nicely updated 2-bedroom, 2.5-bath townhome-style condo features two spacious primary suites, each with its own private en-suite bathroom, offering a flexible floor plan and exceptional functionality. The open and inviting layout includes an oversized great room, 12-inch ceramic tile flooring, and a well-appointed kitchen with maple cabinetry, Corian countertops, flat-top range, stainless steel refrigerator, and new microwave, new blinds throughout. The washer and dryer are included, making this home truly move-in ready. Both bathrooms have been tastefully updated, maple cabinetry, one with granite & one with Corian countertops for a cohesive, modern look. Enjoy outdoor living on the private rear patio, complete with space for grilling and an additional storage closet. Hidden Oaks is a beautifully maintained community featuring mature landscaping, a community pool, and a convenient Winter Park location near shopping, dining, entertainment, major employers, and highly rated Winter Park schools. The monthly condo fee includes water, sewer, trash, exterior maintenance, grounds maintenance, and community amenities, creating an easy lock-and-leave lifestyle. Conveniently located near Full Sail University, the University of Central Florida, Downtown Winter Park, and major roadways, this home offers an excellent opportunity for owner-occupants, those seeking a second home, or buyers looking for a long-term investment property. Don't miss the chance to own a well-maintained and move-in-ready home in one of Winter Park's most convenient locations.

3381 Cedar Springs Place Unit 151, Winter Park

Listing courtesy of MAINFRAME REAL ESTATE. 407-513-4257
7488 Whisperwood Drive Unit 28, Winter Park
$199,000
2 Beds ⋅ 3 Baths ⋅ O6419151 MLS ⋅ Na BLDG.
Rare Two-Story 2BR/2.5BA Condo with Two Private Suites in Winter Park. Highlights: Two-story floor plan condominium with a townhome-style layout, 2 spacious bedrooms, each with its own private ensuite bathroom, 2.5 bathrooms, Functional kitchen with stainless steel appliances, Open-concept living and dining area, Private fenced patio – perfect for relaxing, grilling, or entertaining, Covered parking plus additional guest parking, Community pool. The HOA covers exterior maintenance, roof, trash, landscaping and community pool, allowing owners to enjoy a low maintenance lifestyle. Why You'll Love It !! This well maintained townhome offers the perfect combination of comfort, convenience, and value. The bright, open floor plan is ideal for everyday living, while the two upstairs ensuite bedrooms provide privacy for homeowners, guests, or roommates. Enjoy your morning coffee or unwind in the evening on the private fenced patio—your own outdoor retreat. Prime Winter Park Location: Conveniently located just minutes from: Full Sail University, University of Central Florida (UCF), Downtown Winter Park, Major highways (417 & 408), Shopping, dining, parks, and entertainment Great Opportunity, Whether you're a first-time homebuyer, downsizing, or looking for an investment property, this home offers exceptional value in one of Central Florida's most convenient locations. Schedule your private showing today and discover everything this Winter Park townhome has to offer.

7488 Whisperwood Drive Unit 28, Winter Park

Listing courtesy of PARKVIEW REAL ESTATE. 407-312-6472
1500 Gay Road Unit 3C, Winter Park
$235,000
2 Beds ⋅ 2 Baths ⋅ O6417533 MLS ⋅ 3c BLDG.
NEW PRICE/Seller Motivated! WINTER PARK LOCATION ALERT with AMAZING WALKABILITY to SO MANY shopping and dining options! Across from the newly renovated WP Shopping Village that includes top-rated restaurants, a movie theater, boutiques, grocery store and more! This 2bedroom/2 bathroom attractive second-story unit offers an updated kitchen and bathrooms with solid countertops. All solid flooring throughout - tile and laminate for easy care...no carpet. Enjoy the dining space that opens to the large great room and balcony where you'll love sitting in the evenings to relax. SPACIOUS BEDROOMS - Primary bedroom has an attached full bathroom and bedroom 2 has a LARGE walk-in closet. The 2nd Full Bathroom is accessed via a common hallway. The Chateaux Du Luc LAKEFRONT COMMUNITY offers FABULOUS AMENITIES that include an oversized heated pool, clubhouse, community deck, BBQ grill, 2 on-site saunas, updated on-site laundry facilities, and a resident-only boat ramp on skiable Lake Killarney. There's even storage for your Kayak or paddleboard! Roof 2025. Reach out today for your personal showing!!

1500 Gay Road Unit 3C, Winter Park

Listing courtesy of FANNIE HILLMAN & ASSOCIATES. 407-644-1234
101 S New York Avenue Unit 311, Winter Park
$1,775,000
3 Beds ⋅ 4 Baths ⋅ O6416927 MLS ⋅ Douglas Grand BLDG.
Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of Winter Park. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends sophisticated design with everyday comfort. Immediately captivating, the light-filled open floor plan showcases stunning new wide-plank white oak flooring, high ceilings, detailed crown molding, and all-new designer lighting throughout. The chef’s kitchen is a showpiece, featuring crisp white cabinetry, luxurious white quartz countertops, a spacious breakfast bar island, elegant gold hardware, and a built-in desk. A charming breakfast nook offers the perfect setting for morning coffee or casual dining. French doors open to a private enclosed atrium, creating a versatile outdoor retreat ideal for alfresco dining, relaxing, or entertaining guests in style. The expansive living and dining spaces flow effortlessly, while a private first-floor bedroom with en suite bath and walkout balcony provides an ideal space for guests, multigenerational living, or a home office. Upstairs, the primary suite serves as a peaceful sanctuary, complete with an indulgent soaking tub, dual vanities, an oversized walk-in closet, and French doors leading to a large private balcony with sweeping views of Winter Park's iconic Park Avenue—perfect for enjoying sunrise coffee or evening sunsets. A second upstairs en suite bedroom offers its own private bath and generous walk-in closet. Thoughtful features include an upstairs laundry room, a spacious storage closet with potential elevator conversion for future accessibility, and a secure gated garage with two reserved parking spaces. Perfectly positioned in the heart of Winter Park, Douglas Grand places you just steps from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, Winter Park Golf Course, the Winter Park Tennis Center, Winter Park Village, and an array of renowned dining, shopping, and cultural attractions. Enjoy an unparalleled walkable lifestyle in one of Central Florida's most desirable communities. Notable improvements include an interior renovation (2026), front elevation windows and French doors (2024), interior paint (2024), and HVAC system (2022).

101 S New York Avenue Unit 311, Winter Park

Listing courtesy of KELLY PRICE & COMPANY LLC. 407-645-4321
2500 Lee Road Unit 104, Winter Park
$242,400
2 Beds ⋅ 2 Baths ⋅ TB8517242 MLS
Back on market due to buyer circumstances unrelated to property condition. Inspection completed successfully. Price improvement! Move-in ready in Winter Park 32789. This beautifully renovated first-floor 2-bedroom, 2-bath condo features an open layout, custom soft-close cabinetry, high-end quartzite countertops, sleek matching appliances, and stylishly updated bathrooms, including a primary bath with elegant Italian porcelain tile. Major upgrades include a NEW A/C system and air handler and NEW tankless water heater, offering added efficiency and peace of mind. The monthly HOA delivers exceptional value, including water, trash, community insurance, exterior maintenance, lakeside pool access, and an extensive Spectrum package. The package includes high-speed internet, 150+ live TV channels, and streaming services including Disney+, Hulu, ESPN+, HBO Max, Paramount+, Peacock, discovery+, and AMC+ (a $250+ monthly value). Residents enjoy direct Lake Killarney access with a private community dock, clubhouse, pool, abundant guest parking, and a well-maintained community with funded reserves. Recent improvements include community-wide paving, new curbing, and refreshed landscaping, with additional improvements planned. Turnkey, thoughtfully updated, and ready for its next owner. Skip the renovations and start enjoying Winter Park living from day one. Schedule your tour today!

2500 Lee Road Unit 104, Winter Park

Listing courtesy of FLAT FEE MLS REALTY. 813-642-6030
151 North Orlando Avenue Unit 142, Winter Park
$199,900
1 Beds ⋅ 1 Baths ⋅ O6412768 MLS ⋅ 142 BLDG.
**Lakeside Living Meets Urban Convenience in the Heart of Winter Park!** Welcome home to this beautifully updated, turn-key 1-bedroom, 1-bathroom first-floor condominium located in the highly desirable Lake Killarney Condominiums community. Offering the perfect blend of modern interior updates, stress-free maintenance, and an unbeatable location, this unit is an absolute gem for first-time buyers, downsizers, or savvy investors looking to capture the ultimate Winter Park lifestyle. Step inside to an open, inviting living space featuring brand-new, modern Luxury Vinyl Plank (LVP) flooring running seamlessly throughout for a sophisticated look and maximum durability. The kitchen is freshly upgraded with brand-new, gleaming appliances and plenty of counter space. As a coveted first-floor unit, you will enjoy the ultimate convenience of easy, stair-free access, dual private entry points, and a private, screened-in patio perfect for sipping your morning coffee or winding down. One of the standout features of this property is its accessibility. **Great news for buyers shopping with FHA financing: the community is under the limit for single-unit approvals, making this an incredible opportunity to purchase with an FHA loan.** Additionally, the fairly low monthly HOA fee covers water, sewer, trash, pest control, and exterior/grounds maintenance. As a resident of Lake Killarney Condominiums, you will enjoy premium lakeside community amenities: **Sparkling Lakeside Pool** with stunning views over the water. **Private Community Boat Dock & Boat Ramp Access**, ideal for paddleboarding or sunset strolls. **On-site Fitness Room & Laundry Facilities** located steps from your door. **Clubhouse, Shuffleboard Courts, and Picnic Areas** with grills for effortless entertaining. Location is everything, and this address boasts an incredible walkability factor. You are quite literally around the corner from some of Central Florida’s finest dining, shopping, and entertainment: **Walk to Grocery & Dining:** Step next door or take a quick stroll to Trader Joe’s, the iconic Hillstone Restaurant overlooking the lake, and the completely revitalized Winter Park Village, which features a luxury movie theater, boutique shopping, and endless cafes. **Park Avenue District:** Just minutes away is Park Avenue, Winter Park’s historic cobblestone main street, renowned for its upscale boutiques, award-winning sidewalk dining, local art galleries, and the Saturday Farmers Market. **Commuter’s Dream:** The property offers lightning-fast access to Interstate 4 (I-4), putting downtown Orlando, Maitland Center, and major employment hubs just minutes away. The Winter Park SunRail Station is also less than a mile down the road for a stress-free commute. Don't miss out on this rare opportunity to own a fully updated, low-maintenance slice of paradise in one of Winter Park's most vibrant, lakeside neighborhoods. Schedule your private showing today!

151 North Orlando Avenue Unit 142, Winter Park

Listing courtesy of CREEGAN GROUP. 407-622-1111
2500 Lee Road Unit 220, Winter Park
$199,900
2 Beds ⋅ 1 Baths ⋅ O6411927 MLS ⋅ 220 BLDG.
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 2500 Lee Road, Unit 220, in Winter Park, a beautifully maintained condominium offering stylish, low-maintenance living in one of Central Florida's most convenient locations. Inside, the condo features 2 bedrooms and 1 bathroom with a functional layout suited for everyday living. Thoughtfully updated throughout, this unit features a modern kitchen with stainless steel appliances, charcoal quartz countertops, and a spacious island with ample storage. The bathroom has also been updated with contemporary finishes, while the unit's clean, modern design creates an inviting atmosphere throughout. A new A/C installed in 2025 provides added comfort and peace of mind. The floorplan includes comfortable living and dining areas, while the secondary bedroom offers flexibility for guests, a home office, or additional storage. The unit overlooks a beautifully landscaped courtyard and is conveniently located near designated parking. Residents enjoy access to a variety of community amenities, including a clubhouse, pool, laundry facilities, park areas, and dock access on Lake Killarney. The lakefront setting provides a peaceful environment and an opportunity to enjoy the surrounding natural beauty. Located in the heart of Winter Park, the condo is close to shopping, dining, parks, and popular destinations such as Winter Park Village, Park Avenue, College Park, Maitland, and Downtown Orlando. With its desirable community amenities and prime Winter Park location, this move-in-ready condo offers exceptional value and convenience.

2500 Lee Road Unit 220, Winter Park

Listing courtesy of KELLER WILLIAMS REALTY AT THE PARKS. 407-629-4420
4798 Tangerine Avenue Unit 4798, Winter Park
$175,000
2 Beds ⋅ 2 Baths ⋅ S5150136 MLS ⋅ 4798 BLDG.
Under contract-accepting backup offers. Welcome to this charming and well-maintained condominium located in the desirable Winter Park area, offering the perfect blend of comfort, convenience, and low-maintenance living. This inviting residence features a spacious and functional layout filled with natural light, creating a warm and welcoming atmosphere ideal for everyday living or entertaining. Enjoy an open living and dining area that flows seamlessly to a private screened porch with additional storage space, perfect for relaxing and enjoying the peaceful surroundings. The home offers generous room sizes, ample storage throughout, and a comfortable living environment within a quiet and established community. Residents enjoy access to community amenities including a sparkling swimming pool, fitness center, clubhouse/conference room, beautifully maintained grounds, and ample parking. HOA benefits may include exterior maintenance, landscaping, water, trash service, and roof maintenance, providing added convenience and value. Ideally situated in East Winter Park, this property offers exceptional access to everything Central Florida has to offer. Conveniently located just minutes from Full Sail University, the University of Central Florida (UCF), Rollins College, Downtown Winter Park, Baldwin Park, and Downtown Orlando. Enjoy nearby shopping, dining, entertainment, golf courses, parks, grocery stores, and everyday conveniences all within close proximity. Commuters will appreciate the easy access to major highways including SR-417 and SR-408, while Orlando International Airport is only a short drive away. Whether you are a first-time homebuyer, downsizing, investing, or searching for a centrally located primary residence, this home presents an outstanding opportunity to enjoy the Winter Park lifestyle in a peaceful and well-connected community.

4798 Tangerine Avenue Unit 4798, Winter Park

Listing courtesy of LPT REALTY, LLC. 877-366-2213
311 E Morse Boulevard Unit 6-12, Winter Park
$275,000
1 Beds ⋅ 1 Baths ⋅ O6413554 MLS ⋅ 6 BLDG.
Under contract-accepting backup offers. Welcome to easy living in the heart of Winter Park. Located just two blocks from Park Avenue, this studio condo puts you right in the center of it all—award-winning restaurants, boutique shopping, coffee shops, museums, and the iconic Winter Park boat tour are all just steps away. Situated on the third floor of Building 6 with convenient elevator access, this light-filled unit offers a surprisingly flexible layout. The current owner has creatively configured the space with separate living and dining areas, while the enclosed porch serves as a bedroom. The updated kitchen features decorative tile flooring, stainless steel appliances, and solid wood cabinetry. Sliding glass doors lead to a bonus room that can easily function as a home office, guest space, workout room, or additional living area. The bathroom includes a single vanity and tub/shower combination, and you'll appreciate the abundance of storage throughout the unit. One of the biggest advantages of this property is the peace of mind that comes with a monthly HOA fee that covers nearly everything—including electric, water, sewer, trash, building insurance, landscaping, pool maintenance, and on-site management. . Whispering Waters recently passed its structural integrity inspection and reserve study with excellent results, reflecting the care and quality of this well-managed community. Residents also enjoy access to beautiful Lake Osceola, where you can launch a kayak, relax by the water, or take in breathtaking sunset views. Whether you're looking for a full-time residence or a seasonal retreat this condo offers an unbeatable Winter Park location and true lock-and-leave convenience.

311 E Morse Boulevard Unit 6-12, Winter Park

Listing courtesy of FANNIE HILLMAN & ASSOCIATES. 407-644-1234
193 Lewfield Circle, Winter Park
$248,900
2 Beds ⋅ 3 Baths ⋅ O6409075 MLS ⋅ N/A BLDG.
Virtually Staged. Welcome to 193 Lewfield Cir, Winter Park, FL 32792, a spacious two-story end-unit townhome offering 2 bedrooms, 2.5 bathrooms, and 1,300 square feet of comfortable living space in the Stratford A Winter Park Condo community. This 2-bed townhouse in Winter Park features an open floorplan with a large living and dining area, updated wood-look flooring throughout the main living spaces and bedrooms, recessed lighting, ceiling fans, and sliding glass doors that bring in natural light. The kitchen offers ample cabinet storage, stainless steel appliances, tile flooring, and a functional pass-through breakfast bar that opens to the main living area, creating a seamless layout for everyday living and entertaining. Upstairs, the oversized primary suite includes a walk-in closet, private en-suite bathroom, and generous floor space, while the secondary bedroom also features wood-look flooring, natural light, and easy access to the second full bathroom. Additional highlights include inside laundry, updated lighting fixtures, open parking, and plenty of storage throughout. Residents enjoy access to community amenities including a pool, fitness center, tennis courts, sidewalks, and maintained grounds, with HOA dues covering water, exterior maintenance, recreational facilities, and grounds maintenance. Conveniently located near Howell Branch Rd and SR 436, this Winter Park townhome provides quick access to shopping, dining, Downtown Winter Park, Maitland, Full Sail University, UCF, and Downtown Orlando. Located near highly rated Seminole County schools, parks, restaurants, and everyday conveniences, this property offers low maintenance living in a well-connected Central Florida location.

193 Lewfield Circle, Winter Park

Listing courtesy of COLDWELL BANKER REALTY. 407-352-1040
700 Melrose Avenue Unit J24, Winter Park
$350,000
1 Beds ⋅ 1 Baths ⋅ R4911307 MLS ⋅ 700 BLDG.
Fully updated ..Amazing modern Winter Park Lake Front location! This is a DELUXE corner unit fully remodeled and totally updated one bedroom unit has just been completed. All new paint, porcelain flooring, all new fixtures, bathroom, appliances, new wood cabinets, new stone counters. All NEW The desirable condo community of Winter Park Gardens is nestled between Mead Gardens, Azalea Tennis Center and upcoming Winter Park's Progress Point. Unit is located on the second floor but there is an elevator and stairs to help to the location. Spacious 1 bedroom , 1 bath unit has large open floor plan. Main living area has an additional glass sunroom which provides additional space and breath-taking views of the beautifully landscaped and private courtyard. With its prime location in Winter Park, you'll have easy access to a many of the dining opportunities, shopping, and entertainment options. This is a 55+ community Whether you're strolling through the charming downtown area of Park Avenue or Hannibal Square or immersing yourself in the thriving arts and culture scene, with the Orlando Museum of Art right around the corner This property is centrally located to Downtown Orlando and Downtown Winter Park… no need to use the expressways! !THIS UNIT DOES NOT REQUIRE OWNER TO BE OVER 55+ furniture can convey with purchase.

700 Melrose Avenue Unit J24, Winter Park

Listing courtesy of KIMBRIDGE REALTY, LLC. 407-755-7367
300 Carolina Avenue Unit 402C, Winter Park
$710,000
3 Beds ⋅ 2 Baths ⋅ O6410016 MLS ⋅ C BLDG.
Virtually Staged. Welcome to Park West Condominiums — one of Winter Park’s most coveted and rarely available condominium communities, ideally located just one block from the boutiques, dining, and charm of Park Avenue. This unique 4th floor residence offers an exceptional combination of space, privacy, and potential. Featuring 3 bedrooms and 2 bathrooms, the expansive floor plan has been enlarged by enclosing two patios, creating generous living spaces rarely found in condominium living. Vaulted ceilings, skylights, and abundant natural light enhance the open, airy feel throughout the home, while the top-floor location provides remarkable tranquility and privacy. The spacious kitchen offers ample counter space, a breakfast bar, and excellent cabinet space, while the living area is anchored by a fireplace — another uncommon feature in condo living. Large bedrooms, a sizable in-unit laundry room with extensive storage, and an oversized attic provide an extraordinary amount of storage seldom seen in comparable properties. The primary suite features vaulted ceilings, a walk-in closet, and a spacious bathroom layout. For maximum flexibility, the second bedroom, featuring a bright Sun Room alcove, connects to the primary bedroom so it could also be utilized as a private den. Recent unit improvements include a NEW HVAC system, a NEW Water Heater, and Plumbing updates. A reserved covered parking space is included, along with plentiful guest parking for visitors. Residents of Park West enjoy a secure gated entrance, community pool, tennis court, on-site community manager, and beautifully maintained grounds with extensive recent community improvements completed. Association fees include water, sewer, and trash service, creating a truly low-maintenance “lock-and-leave” lifestyle ideal for travelers or seasonal residents. While this condo presents an exciting opportunity for personalization, the location, floor plan, and features make this an exceptional offering with tremendous potential. Opportunities in Park West are exceedingly rare — this is your chance to create something truly special in the heart of Winter Park.

300 Carolina Avenue Unit 402C, Winter Park

Listing courtesy of FANNIE HILLMAN & ASSOCIATES. 407-644-1234
269 E Canton Avenue Unit 269, Winter Park
$989,500
1 Beds ⋅ 2 Baths ⋅ O6404706 MLS ⋅ Villages Of Winterset BLDG.
Winterset is celebrated for its boutique scale, mature landscaping, and timeless Winter Park character. Residents enjoy glimpses of Lake Osceola, tranquil surroundings beneath stately oaks, and the privilege of living in a community where privacy and exclusivity are paramount. This fully remodeled Penthouse Suite's location is unmatched—one block to Park Avenue, offering effortless access to fine dining, boutique shopping, the Morse Museum, Rollins College, and the scenic Chain of Lakes. Whether you’re downsizing, escaping winter months or seeking a refined second home, this residence delivers the perfect blend of luxury, simplicity, and prestige. Designed for comfort and ease, the home welcomes you with a bright, open living space enhanced by crown molding, warm natural light, and a seamless flow ideal for both quiet escapes and intimate entertaining. The primary suite features a generous walk-in closet, while the kitchen offers modern functionality with quality appliances and thoughtful storage. This unit offers its own washer/dryer combo unit, large exterior storage closet, assigned parking space under canopy and extra open parking spaces. Please note rentals are not allowed and no pets except for Service Animals.

269 E Canton Avenue Unit 269, Winter Park

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211
2923 Antique Oaks Circle Unit 34, Winter Park
$180,000
2 Beds ⋅ 2 Baths ⋅ S5150301 MLS ⋅ 34 BLDG.
PRICE IMPROVEMENT! TOP FLOOR CORNER UNIT in the heart of Winter Park! This well-maintained 2-bedroom, 2-bath condo offers spacious living, abundant natural light, and a functional open layout perfect for everyday living or investment potential. A NEW A/C SYSTEM INSTALLED IN 2026 adds extra peace of mind for the next owner. Step inside to find a bright and airy living and dining area with sliding glass doors leading to a private screened-in balcony — the perfect spot to relax and enjoy the Florida weather. The kitchen comes complete with stainless steel appliances, ample cabinet and counter space, and a convenient pass-through opening overlooking the main living area for easy entertaining. Both bedrooms are generously sized with similar layouts, while the two full bathrooms provide everyday comfort and convenience. The interior laundry space adds functionality to the home. Located in Parkview Village Condominium, residents can enjoy community amenities including a clubhouse, community pool, gazebo, and more. This well-maintained community is surrounded by mature trees and landscaping and offers a prime location just minutes from Downtown Winter Park, Full Sail University, UCF, shopping, dining, entertainment, and major roadways including 417 and 436. Whether you’re looking for a primary residence, seasonal getaway, or investment opportunity, this centrally located condo offers comfort, convenience, and low-maintenance living.

2923 Antique Oaks Circle Unit 34, Winter Park

Listing courtesy of EXP REALTY LLC. 407-846-0940
3243 Forest Oaks Court Unit 117, Winter Park
$172,000
2 Beds ⋅ 2 Baths ⋅ O6406448 MLS ⋅ Hidden Oaks BLDG.
Welcome to this beautifully maintained 2-bedroom, 1.5-bathroom townhouse-style condominium located in the desirable Hidden Oaks Condominium community. This charming unit features a spacious living and dining area with tile flooring throughout the first floor, along with a well-appointed kitchen, breakfast nook, and convenient indoor laundry room. The home has been freshly updated with new interior paint and new blinds throughout, and all appliances are included for added convenience. Step through the sliding glass doors off the kitchen to enjoy a private fenced patio, complete with an additional exterior storage room — perfect for extra storage space or outdoor essentials. Upstairs, you’ll find comfortable carpet flooring throughout, including a generously sized primary bedroom with a large closet, as well as a spacious guest bedroom with ample closet space. Residents of Hidden Oaks Condominium enjoy access to excellent community amenities, including a sparkling community pool and a fenced playground area. The monthly HOA fee includes water and trash services. Ideally located near Full Sail University, University of Central Florida, and Valencia College, with convenient access to shopping, dining, Downtown Orlando, Downtown Winter Park, FL-408, and FL-417. This move-in ready home offers comfort, convenience, and an excellent location. Schedule your private showing today — this opportunity won’t last long!

3243 Forest Oaks Court Unit 117, Winter Park

Listing courtesy of SOGO REAL ESTATE SERVICES LLC. 407-730-3100
7327 Forest Hill Court Unit 223, Winter Park
$175,000
2 Beds ⋅ 3 Baths ⋅ O6403841 MLS ⋅ 7327 BLDG.
Looking for the perfect starter home or great little rental. This townhhouse-style condo with 2 master suites. With granite countertop on kitchen. Open floor plan, inside laundry closet off the dinette. Tile flooring downstairs and carpet up, additional exterior storage room and fenced in patio. garbage. Hidden Oaks community features community pool & fenced playground area. Zoned for Winter Park Schools. Conveniently located just: 10 minutes to Downtown Orlando, 15 minutes to Orlando International Airport, 10 minutes to shopping and dining, 15 minutes to Valencia College, 25 minutes to UCF, 30 minutes to Disney World. Easy access to FL-408 & FL-417.

7327 Forest Hill Court Unit 223, Winter Park

Listing courtesy of M L VAZ REALTY INC. 407-380-9397
1695 Lee Road Unit B210, Winter Park
$89,000
1 Beds ⋅ 1 Baths ⋅ O6375872 MLS ⋅ B BLDG.
Under contract-accepting backup offers. This great second floor one bedroom 1 bath condo is in the quiet community of Waterfall Cove just off LeeRoad and 17-92 intersection. Conveniently located walking distance from shopping, dining, and Winter Park Village. Close to Park Avenue,Maitland 's Lake Lilly Park with the Farmer's Market and to Rollins College. Easy I-4 access. Open floor plan, walk in closet, and stack-able washer and dryer. Assigned parkingspace. Community features swimming pool, tennis court and playground. Rent price includes use of the amenities, free basic cable TV, free internet, and pest control.

1695 Lee Road Unit B210, Winter Park

Listing courtesy of GM SUNSHINE REALTY LLC. 407-376-1261
3371 River View Way Unit 46, Winter Park
$205,000
3 Beds ⋅ 3 Baths ⋅ O6403947 MLS ⋅ 3371 BLDG.
Under contract-accepting backup offers. Welcome to Unit 46 at Hidden Oaks, a townhome-style condo nestled in one of Winter Park's most convenient and well-established communities. Ideal for first-time buyers, down-sizers, or investors looking for location and lifestyle in one. The floor plan offers three bedrooms upstairs with two full bathrooms, plus a half bath on the main level — perfect for guests and everyday living. Two reserved parking spots included. The HOA covers the community pool, water, trash, grounds maintenance, and structural upkeep, making this a truly low-maintenance lifestyle. Pets welcome. Hidden Oaks lives up to its name with lush, mature landscaping throughout. Unbeatable location — minutes from Full Sail University, UCF, and Valencia College, with easy access to major Central Florida employers. Downtown Winter Park's dining, shopping, and Park Avenue charm are all within reach. Properties in this community move quickly — schedule your showing today.

3371 River View Way Unit 46, Winter Park

Listing courtesy of REALTY ONE GROUP EVOLVE. 386-368-7222
106 S Interlachen Avenue Unit 518, Winter Park
$1,795,000
3 Beds ⋅ 2 Baths ⋅ O6400228 MLS ⋅ 106 BLDG.
Under contract-accepting backup offers. Designer-Curated Coastal Renovation with Exceptional Lakefront Vistas! This sophisticated reimagining was taken down to original framework and meticulously rebuilt with elevated design and superior finishes throughout. The result is an expansive openness illuminated with natural light and accented by European oak wide-plank flooring, Level 5 smooth-finish walls and ceilings, architectural recessed lighting, and custom-tailored interior doors with modern glass knob hardware. With two walls of glass, the main living space extends to a generous wraparound balcony set among lush treetops and endless lake views—the perfect backdrop for morning coffee, sunset cocktails, and open-air entertaining. A restored floor-to-ceiling brick fireplace is a dramatic centerpiece, pairing modern simplicity with timeless appeal, that adds warmth and ambiance. The striking kitchen blends clean lines with elevated finishes. Crafted maple cabinetry rises to the ceiling, complemented by sleek hardware and under-cabinet lighting that softly highlights a dimensional subway tile backsplash for added depth and texture. Crisp quartz countertops provide a seamless surface, while a suite of premium Jenn Air appliances delivers both statement-making design and top-tier performance. A large peninsula offers generous seating and gathering space—ideal for casual dining or entertaining—and incorporates a discreetly integrated pet station, a thoughtful detail that enhances daily living. Open to the surrounding spaces, the entire space feels cohesive, inviting, and effortlessly functional. The primary suite is thoughtfully planned to provide a calm and comfortable retreat, featuring truly custom closet cabinetry for streamlined storage. Expansive windows frame serene lake views and a lush green backdrop, creating a tranquil, ever-changing setting—wake to soft morning light shimmering across the water and unwind in the evening with a sense of quiet ease. Also designed with intention and precision, the primary bath maximizes space with more custom cabinetry for additional clothing storage, a streamlined vanity with quartz counter, integrated laundry cabinet, and glass-enclosed shower—all executed in a refined palette that feels both elevated and livable. The inviting second bedroom is enhanced by a built-in closet offering a polished and highly functional storage solution. Equally well considered, the second bath features quartz counters and lots of custom cabinetry for a clean, detailed look. A seamless glass shower is complimented by a strategically placed frosted entry panel offering privacy without sacrificing natural light, while a full-width mirror amplifies the sense of space. The third bedroom offers a thoughtfully designed double desk, a customized closet for added style and function and sliding glass doors to the balcony for natural light and an outdoor connection. New laundry room is both functional and refined, featuring folding counter, abundant cabinetry, and a dedicated hanging area with a built-in bench & storage drawer. Custom integrated doors discreetly conceal mechanicals. The residence also includes assigned covered parking. Residents of The Cloisters enjoy a lakefront lifestyle with dock access, boat slips, along with/ other amenities including a fitness center, and renovated clubhouse w/ kitchen, putting green and pool—all supported by a professional on-site management and beautifully maintained grounds.

106 S Interlachen Avenue Unit 518, Winter Park

Listing courtesy of FANNIE HILLMAN & ASSOCIATES. 407-644-1234
7454 Wynnewood Square Unit 188, Winter Park
$229,000
3 Beds ⋅ 3 Baths ⋅ O6386578 MLS ⋅ 7454 BLDG.
Updated Winter Park Townhome!! If you are looking for LOCATION this is the property for you. This well maintained unit is move in ready: two-story 3 Bedrooms 2.5 Bath townhome style condo with two designated parking spaces. Upon entering you are greeted with a large living and dining room space. Tiled floors, tons of light, neutral colors, wet bar area are a few of the amazing qualities of this space. Just off the dining room you will find the kitchen and eat in kitchen area.few stainless steel appliances and tons of storage. The eat in kitchen space is highlighted with a decorative wall and sliders leading to your fully fenced private backyard space. Upstairs you will find hardwood flooring, three bedrooms and master bathroom with a single vanity . Hidden Oaks community features on-site security, community pool & fenced playground area. Near Full Sail, UCF, Valencia & Rollins College, with easy access to shopping, Winter Park schools, Medical Facilities, Downtown Orlando, Downtown Winter Park, FL-408, FL-417 and the airport. This wonderful unit has it all...the only thing missing is YOU!

7454 Wynnewood Square Unit 188, Winter Park

Listing courtesy of APPLE REALTY. 407-647-6766
5143 Lazy Oaks Drive Unit 5143, Winter Park
$275,000
2 Beds ⋅ 2 Baths ⋅ O6398856 MLS ⋅ 5143 BLDG.
Virtually Staged. Quiet Living in the Desirable Lazy Oaks Community of Winter Park. Welcome to the peaceful, well-established community of Lazy Oaks in highly sought-after Winter Park. This hidden gem offers beautifully landscaped grounds, meticulous maintenance, and the added benefit of a low HOA. This lovingly maintained 2-bedroom, 2-bath home features a spacious, thoughtfully designed floor plan with an attached garage. The home is ideally located near top-rated schools, shopping, dining, and provides convenient access to major highways. Inside, you’ll find a neutral color palette complemented by ceramic tile and wood laminate flooring throughout. The efficient kitchen boasts gleaming white countertops, rich wood cabinetry, and a large pantry for ample storage. The expansive great room offers flexible space for both dining and living areas, complete with a cozy wood-burning fireplace—perfect for relaxing or entertaining. Sliding glass doors open to a large, screened private lanai, ideal for morning coffee or evening unwinding. The spacious primary suite features an en suite bath with dual sinks, a large vanity, walk-in shower, and a generous closet. A split-bedroom layout provides added privacy, with a secondary bedroom and additional full bath. Additional highlight: HVAC replaced in 2021. Don’t miss this opportunity to make your home in one of Winter Park’s most charming and convenient communities!

5143 Lazy Oaks Drive Unit 5143, Winter Park

Listing courtesy of KELLER WILLIAMS REALTY AT THE PARKS. 407-629-4420
3021 Aaron Burr Avenue Unit 3, Winter Park
$140,000
2 Beds ⋅ 3 Baths ⋅ S5147382 MLS ⋅ L BLDG.
Townhouse opportunity—ideal for either personal residence or investment—featuring 2 bedrooms and 2.5 bathrooms. Conveniently located near supermarkets, shops, universities, and public transportation. At closing, all outstanding HOA special assessments will be paid off. The Townhome is rent $1,600. The unit is located in Winter Park Area HOME GUARANTY OF AMERICA HWA 13 MONTH INCLUDED.

3021 Aaron Burr Avenue Unit 3, Winter Park

Listing courtesy of NAIM REAL ESTATE LLC. 818-268-9917
1695 Lee Road Unit D211, Winter Park
$102,500
2 Beds ⋅ 1 Baths ⋅ O6396190 MLS ⋅ D BLDG.
Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom. Durable vinyl flooring with cozy carpeted bedrooms with a spacious walk in in closet in the primary bedroom. You will get a private balcony perfect for morning coffee or evening relaxation and the convenience of your our laundry with washer and dryer hookups included. This condo is perfectly located in a desirable area of Winter Park close to tons of and amenities.

1695 Lee Road Unit D211, Winter Park

Listing courtesy of LOKATION. 954-545-5583
7300 Daniel Webster Drive Unit M7, Winter Park
$159,000
2 Beds ⋅ 3 Baths ⋅ O6388668 MLS
Welcome home to this stunningly updated two-story condo that perfectly combines modern elegance with everyday comfort. Featuring 2 spacious bedrooms and 2.5 baths, this home has been thoughtfully updated with high-end designer finishes throughout. The first floor showcases stunning new tile flooring in a striking neutral pattern, creating a modern and inviting living space, while the second floor features durable and stylish vinyl flooring for added comfort. The fully renovated bathrooms boast contemporary designs and quality craftsmanship, and a brand-new AC system ensures year-round efficiency and peace of mind. Natural light pours into every corner of the home, enhancing the open layout and highlighting the elegant upgrades. Ideally located just minutes from shopping, dining, and top-rated schools, this condo offers both luxury living and everyday convenience. Don’t miss the opportunity to own this move-in-ready gem in a prime location!

7300 Daniel Webster Drive Unit M7, Winter Park

Listing courtesy of STIRLING INTERNATIONAL REAL ES. 407-250-1000
3027 Aaron Burr Avenue Unit L1, Winter Park
$159,000
2 Beds ⋅ 3 Baths ⋅ O6390662 MLS ⋅ Na BLDG.
Step into this beautifully renovated two-story condo offering the perfect blend of modern style and everyday comfort. Featuring 2 spacious bedrooms and 2.5 updated bathrooms, this home has been thoughtfully upgraded from top to bottom. The first floor showcases elegant marble-look tile flooring, creating a sleek and durable living space ideal for both relaxing and entertaining. Upstairs, you’ll find stylish and low-maintenance vinyl flooring throughout, adding warmth and continuity to the private living quarters. The fully renovated bathrooms boast contemporary finishes and fixtures, delivering a fresh, spa-like feel. A brand-new AC system ensures year-round comfort and energy efficiency. With its modern upgrades, functional layout, and move-in-ready condition, this condo is a perfect choice for buyers seeking both style and convenience.

3027 Aaron Burr Avenue Unit L1, Winter Park

Listing courtesy of STIRLING INTERNATIONAL REAL ES. 407-250-1000
1807 Hammerlin Avenue Unit G, Winter Park
$499,000
3 Beds ⋅ 3 Baths ⋅ O6391277 MLS ⋅ Terrazo Del Sol BLDG.
Virtually Staged. **Price Improvement** Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Michelin-star dining, local boutiques, and the vibrant East End Market. On weekends, enjoy leisurely strolls to the area’s popular farmers markets and neighborhood events. Situated in the heart of Winter Park, this residence offers the perfect blend of lifestyle, convenience, and charm in one of Orlando’s most sought-after communities. Designed for both everyday comfort and effortless entertaining, the first floor features an open-concept kitchen and living area filled with abundant natural light, along with a convenient half bath—ideal for hosting guests. Upstairs, the spacious primary suite boasts a private ensuite bathroom, walk-in closet, and a newly refinished balcony—perfect for morning coffee or evening cocktails. Two additional bedrooms provide generous space and share access to a second balcony, creating a seamless indoor-outdoor living experience. Recent upgrades include a new dishwasher and smart refrigerator (2022), new water heater (2025), refinished front balcony (2025), new roof, and new carpet upstairs (2026). Updated light fixtures and primary bedroom flooring within the last five years add a modern touch throughout. The $400 monthly HOA fee includes landscaping and insurance, offering low-maintenance living and added peace of mind. Zoned for some of Orlando’s top-rated schools and walking distance from the new Audubon Park K-8 School, this home presents a rare opportunity to enjoy the very best of Winter Park living. Don’t miss your chance to call this exceptional property home.

1807 Hammerlin Avenue Unit G, Winter Park

Listing courtesy of ALL REAL ESTATE & INVESTMENTS. 407-917-8206
1500 Gay Road Unit 20D, Winter Park
$245,000
2 Beds ⋅ 2 Baths ⋅ O6385626 MLS ⋅ Building 20 BLDG.
Under contract-accepting backup offers. DRASTIC PRICE REDUCTION! LAKEFRONT COMMUNITY WITH SPECTACULAR SUNSETS OVER BEAUTIFUL LAKE KILLARNEY. LOCATED IN THE CHARMING AND ELLEGANT NEIGHBORHOOD OF WINTER PARK, IN A FULLY REVITALIZED AREA. CONVENIENT TO I-4, PARK AVENUE, FARMER'S MARKETS, TRADER JOE'S, AS WELL AS A MOVIE THEATER, BOUTIQUE SHOPS, RENOWNED RESTAURANTS AND A NATIONALLY RATED ART FESTIVAL - ALL WITHIN A SHORT WALKING DISTANCE. BRIGHT SUN-FILLED 2 BEDROOM, 2 BATH USTAIRS UNIT WITH AN OPEN FLOOR PLAN AND PRIVATE BALCONY. THE PRIMARY BEDROOM IS A SUITE, AND THE SECOND BEDROOM FEATURES A SPACIOUS WALK-IN CLOSET. SOFT, WARM COLORS, TILE AND LUXURY VINYL FLOORS, RAISED KITCHEN CEILING AND GRANITE COUNTER ENHANCE THE SPACE. BRAND NEW WATER HEATER 6/2026! LARGE ROOMS MAKE IT EASY TO ARRANGE FURNITURE. ENJOY BOATING, SKIING AND WILDLIFE OF LAKE LIVING. COMMUNITY DECK, BOAT RAMP, HEATED POOL AND SAUNAS. MAKE AN APPOINTMENT TODAY TO SEE WINTER PARK'S BEST KEP SECRET!

1500 Gay Road Unit 20D, Winter Park

Listing courtesy of REALCOM REAL ESTATE SERVICES INC. 407-740-5300
630 Killarney Bay Court Unit 3, Winter Park
$475,000
2 Beds ⋅ 3 Baths ⋅ O6375307 MLS ⋅ 1 BLDG.
Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedrooms, 2.5 baths, and a one-car carport. This spacious residence features an open living and dining area that flows to a screened porch, perfect for relaxing and enjoying tranquil lake views in a well-maintained complex. Both bedrooms are upstairs for privacy, each with its own bath. A convenient half bath is on the main level for guests. Enjoy community amenities including a swimming pool and a waterfront deck just 30 feet away, ideal for soaking in sunsets and lakeside breezes. All of this in an unbeatable location, just minutes from Winter Park Village, Trader Joe’s, Whole Foods, Park Avenue, dining, and shopping, with easy access to major roads for commuting.

630 Killarney Bay Court Unit 3, Winter Park

Listing courtesy of FLORIDA ONE REAL ESTATE LLC. 407-599-7070
205 Lewfield Circle Unit 205, Winter Park
$182,900
2 Beds ⋅ 2 Baths ⋅ S5141588 MLS ⋅ 8 BLDG.
Virtually Staged. NEW PRICE! Motivated seller! Move-in ready! Exceptional value in the heart of Winter Park! Welcome to this beautifully maintained 2-bedroom, 2-bath ground-floor condominium, where comfort, convenience, and an unbeatable location come together. The thoughtfully designed floor plan features an open-concept living and dining area, a screened patio overlooking peaceful landscaped gardens, and recent upgrades and maintenance, including a new electrical panel (2024), washer & dryer (2024), dishwasher (2023), refrigerator (2020), and a complete A/C system service (2025). Enjoy resort-style amenities at Stratford at Winter Park, including two swimming pools, two lighted tennis courts, a fitness center, clubhouse, and car care facilities, all within a beautifully maintained community. Perfectly located just minutes from Park Avenue, Baldwin Park, Full Sail University, Rollins College, AdventHealth Winter Park, shopping, dining, cafés, golf courses, and major highways, this home offers the ideal balance of everyday convenience and the sought-after Winter Park lifestyle. Competitively priced and offering exceptional value in today's market, this move-in-ready home presents the perfect, investor-friendly environment with high rental potential, while also serving as an ideal primary residence or seasonal getaway. Schedule your showing today! Note: Some photos have been virtually staged for illustrative purposes.

205 Lewfield Circle Unit 205, Winter Park

Listing courtesy of LPT REALTY, LLC. 877-366-2213
2500 Lee Rd. Unit 222, Winter Park
$184,400
1 Beds ⋅ 1 Baths ⋅ O6368580 MLS ⋅ 1 BLDG.
Rent-to-own or lease option available with negotiable terms—Lakefront Lifestyle in Winter Park—Under $200K! Live the resort life for less! This stunning, move-in ready retreat in the heart of Winter Park offers rare, direct access to the 239-acre, spring-fed Lake Killarney. Enjoy exclusive resident-only amenities, including a private boat launch, boat slips, an updated dock, and a tranquil lakefront gazebo. Perfectly located just minutes from the world-class shopping and dining of Winter Park Village, this home provides the ultimate balance of peaceful lakeside serenity and city convenience. The interior is just as impressive as the location. This charming, sun-drenched unit features an open-concept layout with gorgeous engineered wood flooring and a sleek kitchen upgraded with granite countertops. It’s a smart, stylish, and incredibly rare find that’s perfectly priced to sell. Whether you are looking for a low-maintenance home or a serene weekend getaway, this property delivers. Don't let this opportunity slip away—schedule your private showing today!

2500 Lee Rd. Unit 222, Winter Park

Listing courtesy of HOMESMART. 407-476-0461
151 N Orlando Avenue Unit #115, Winter Park
$285,000
2 Beds ⋅ 1 Baths ⋅ O6362403 MLS ⋅ # 151 BLDG.
Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake Killarney. Inside, you’ll find a bright, natural light–filled living space with an intimate, inviting feel. The efficient galley kitchen flows seamlessly into the living and dining area, making the home feel larger than its square footage. A rare bonus for condo living, the home includes a separate laundry room, offering added convenience and additional storage. Step outside to your private patio space, perfect for morning coffee, quiet evenings, or creating your own cozy outdoor retreat. There’s even room for a foosball table, making it a great spot to unwind, entertain, or simply grab a Coke and smile as you enjoy the Florida breeze. Residents enjoy an impressive list of community amenities, including a sparkling private pool, lush green spaces, and access to Lake Killarney’s private community dock, ideal for launching kayaks and paddleboards, fishing, or taking in serene lakefront views. Enjoy evening sunset strolls, weekend boating, or a relaxing afternoon by the pool. The community also offers convenient on-site laundry facilities, beautifully maintained grounds, and a welcoming neighborhood atmosphere. With strong rental appeal, an unbeatable location, and timeless Winter Park charm, 151 N Orlando Ave #115 is an ideal choice for first-time buyers, downsizers, or investors seeking long-term value in one of Central Florida’s most desirable lakefront communities. Schedule your private showing today and experience the lifestyle waiting for you at Lake Killarney.

151 N Orlando Avenue Unit #115, Winter Park

Listing courtesy of CREEGAN GROUP. 407-622-1111
311 Scottsdale Square Unit 311, Winter Park
$109,400
1 Beds ⋅ 1 Baths ⋅ O6355536 MLS ⋅ 311 BLDG.
This 1 bedroom, 1 bath condo at 311 Scottsdale Sq, Winter Park, FL 32792 is leased to a reliable long-term tenant paying $1,450 / month. Located on the first floor in the established Winter Park Woods community, this unit features an open-concept layout as soon as you walk in. The HOA includes water, access to two community pools, a playground, and tennis courts. Winter Park Woods is also zoned for highly rated schools in Florida, which helps with both property value and long-term rental demand. The location is a major plus. This condo sits in the heart of Winter Park / Winter Park Pines / Goldenrod area, close to Full Sail University, UCF, AdventHealth, Orlando International Airport, and main highways for easy commuting. You’re just minutes from shopping, grocery stores, restaurants, gyms, parks, and Winter Park’s retail corridors. You also have quick access to downtown Winter Park, Orlando, and major job centers, which keeps rental demand very strong in this area.

311 Scottsdale Square Unit 311, Winter Park

Listing courtesy of EMPIRE NETWORK REALTY. 407-440-3798
7471 Canford Court Unit 19, Winter Park
$199,000
2 Beds ⋅ 2 Baths ⋅ G5103114 MLS ⋅ 3 BLDG.
One of the lowest-priced homes in Winter Park with nearly 1,400 square feet, a private carport, screened balcony, community pool, and easy access to UCF, Full Sail, Rollins, Valencia East, Orlando International Airport, and downtown Orlando! The monthly HOA covers many exterior maintenance items so you can enjoy low-maintenance living.This 2 bedroom, 1.5 bathroom condo features a townhome style layout with spacious living areas. Recent enhancements include the removal of dated laminate to reveal ceramic tile flooring throughout the main level, installation of stylish luxury vinyl plank on the upper level, new carpeting on the staircase and landing, and a full interior repaint. In addition, the sliding glass doors were professionally serviced, including roller replacement, track repairs, and installation of new locks to ensure smooth, secure operation. Deluxe vinyl fencing was installed throughout the community by the HOA replacing the older wooden fencing. The fencing was replaced with the vinyl after the listing photos were taken, please view the video to see the replacement vinyl fencing. Enjoy convenient features including an in-unit washer and dryer combo, storage under the stairs, and a large carport with an attached storage shed. The spacious primary bedroom opens to a large screened-in balcony. Whether you’re a first-time home buyer, student, investor, or looking to make your move into Winter Park, this home offers affordability, convenience, and plenty of potential!

7471 Canford Court Unit 19, Winter Park

Listing courtesy of IAD FLORIDA LLC. 407-720-0020
2336 Sun Valley Circle Unit BLDG 20, Winter Park
$285,000
2 Beds ⋅ 2 Baths ⋅ O6342993 MLS ⋅ 20 BLDG.
Welcome to this spacious 2-bedroom, 2-bathroom condo with a versatile loft, ideally located in desirable Winter Park. Featuring one of the largest floor plans in the community, this home offers an abundance of living space and a flexible layout perfect for relaxing, entertaining, working from home, or creating a guest space. Recently painted and filled with natural light, the home features charming skylights and a welcoming atmosphere throughout. Located on a quiet, tree-lined street, this peaceful community offers a wonderful combination of privacy, convenience, and amenities. Residents enjoy access to a community pool, tennis court, pickleball court, and clubhouse/club room — providing plenty of opportunities for recreation and gathering with friends and neighbors. The location is hard to beat, with easy access to shopping, dining, parks, major roads, and all the amenities of Winter Park. Located within Seminole County schools, this condo is an excellent opportunity for those looking for a spacious home in a quiet community with an ideal Winter Park location. Come see why this one stands out!

2336 Sun Valley Circle Unit BLDG 20, Winter Park

Listing courtesy of PR REAL ESTATE SERVICES. 407-447-9500
2948 Antique Oaks Circle Unit 94, Winter Park
$150,000
1 Beds ⋅ 1 Baths ⋅ O6342254 MLS ⋅ 2948 BLDG.
Welcome to this bright and cozy 1-bedroom, 1-bathroom corner unit located in the highly desirable Winter Park area of Orlando. This well-maintained condo features ceramic tile flooring throughout, a spacious walk-in closet in the master bedroom, a laundry closet with washer and dryer included, and modern light fixtures. Enjoy the outdoors on your very nice private balcony, and take advantage of private stairs from the outside entrance—a rare and convenient feature. Located in a beautifully kept community with easy access to shops, restaurants, and all of Winter Park's charm. Ideal as a first home, seasonal getaway, or investment opportunity!

2948 Antique Oaks Circle Unit 94, Winter Park

Listing courtesy of THE PAMPAS REAL ESTATE GROUP, LLC.. 561-234-7771
311 E Morse Boulevard Unit 7-11, Winter Park
$279,000
1 Beds ⋅ 1 Baths ⋅ O6337061 MLS ⋅ Whisering Waters BLDG.
Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue! Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to offer. Located on the second floor, this spacious studio boasts an updated kitchenette, generous storage, and abundant natural light. Enjoy secure garage access, mail and package delivery to your door, and a relaxing retreat with sunrise views, osprey sightings, and even rocket launches visible from the community patios. Community Amenities: Sparkling pool, Club room for social gatherings, Peaceful outdoor patios overlooking Lake Osceola and Professional on-site management. Location Highlights include being one block to Park Avenue’s boutiques, cafes, and fine dining. Close to The Alfond Inn, museums, and galleries. Walkable to SunRail & Amtrak station. Moments from the Winter Park Farmers’ Market. This is a rare opportunity to own a stylish, low-maintenance home in the heart of downtown Winter Park where ELECTRIC, GAS, WATER, SEWER and TRASH are included in condo fee. Whether you're looking for a weekend retreat or full-time residence, this pied-à-terre is truly one-of-a-kind. Call today for your private viewing of this condo.

311 E Morse Boulevard Unit 7-11, Winter Park

Listing courtesy of FANNIE HILLMAN & ASSOCIATES. 407-644-1234
3370 Cedar Springs Place Unit 156, Winter Park
$179,990
2 Beds ⋅ 3 Baths ⋅ O6326460 MLS ⋅ Hidden Oaks BLDG.
Ideally situated just minutes from Full Sail University, UCF, and major retailers, this well-appointed 2-bedroom, 2.5-bath townhome-style condo offers both comfort and convenience. No rear neighbors. The main floor features a spacious living and dining area with a breakfast nook, a guest half bath, and updated appliances. Upstairs, you’ll find two generously sized master suites, each with its own private bathroom. Step outside to a fenced-in patio that overlooks a serene water canal and conservation area—perfect for relaxing or entertaining. Additional features include an outdoor storage room and extra storage space under the stairs. The Hidden Oaks community offers residents access to a beautiful pool and playground. Whether you're a first-time homebuyer, an investor, or simply looking for a cozy place to call home, this property presents a standout opportunity close to major highways, universities, and popular dining spots in Central Florida.

3370 Cedar Springs Place Unit 156, Winter Park

Listing courtesy of SPRINGHILL PROPERTIES LLC. 646-236-0299
151 N Orlando Avenue Unit 118, Winter Park
$299,999
2 Beds ⋅ 1 Baths ⋅ O6311340 MLS ⋅ 118 BLDG.
Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix, Trader Joe's, Regal Movie Theater, and a variety of restaurants and bars. Join this vibrant community and make this beautiful condo your new investment property or dream home!

151 N Orlando Avenue Unit 118, Winter Park

Listing courtesy of FLORIDA DREAMS REALTY GRP INC. 407-654-9992
3071 George Mason Avenue Unit 5, Winter Park
$89,900
1 Baths ⋅ O6289736 MLS ⋅ 3071 BLDG.
Charming Studio Condo Near UCF & Full Sail – Ideal Investment or Cozy Retreat! Welcome to this well-maintained ground-floor studio condo, offering 549 square feet of comfortable living space in a prime location near UCF and Full Sail University. Perfect for a student, professional, or investor, this move-in-ready unit features tile flooring throughout, making it clean and easy to maintain. Enjoy a bright and open layout, a well-equipped kitchen, and a full bathroom, all designed for convenience and efficiency. Step outside to your private covered patio, where you can relax while overlooking the serene courtyard setting. Whether you’re looking for a low-maintenance home or a smart investment opportunity, this condo checks all the boxes. Schedule your showing today!

3071 George Mason Avenue Unit 5, Winter Park

Listing courtesy of CASTLE & COTTAGE REALTY LLC. 407-620-9405
1695 Lee Road Unit C202, Winter Park
$205,000
3 Beds ⋅ 2 Baths ⋅ O6285607 MLS ⋅ Waterfall Cove C-202 BLDG.
This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This property can be leased. You must see for any possibilities come and check for yourself. Registered owner is brother of the realtor. SELLER MIGHT HOLD FIRST MORTGAGE WITH A GOOD DOWN PAYMENT.

1695 Lee Road Unit C202, Winter Park

Listing courtesy of PRIMESTATE REALTY, INC.. 407-850-9494
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Winter Park Florida Condominiums

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