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$695,500
O6341378 MLS
Under contract-accepting backup offers. Fantastic location in the heart of the City of Winter Park. This free standing Professional Office building, zoned O-2, sits on a spacious corner lot with ample parking both on-site and along the street. The building's current layout features five office areas, plus a large front entry that can be divided, two private entrances, two baths, a small kitchen, original hardwood floors, and fenced in backyard. Nestled within a charming two-block district of small business offices - including medical, financial, and fitness that are surrounded by highly desirable residential neighborhoods. Walking distance to Advent Health, restaurants, shops,and Ward Park-a 66.4 acre sports complex with the Loch Lomond Trail. Rollins College and popular Park Avenue are also just minutes away.

1977 Dundee Drive, Winter Park

Listing courtesy of HOMEVEST REALTY. 407-897-5400

$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

$139,500
1 Beds 1 Baths O6337083 MLS Parkview Village BLDG.
Under contract-accepting backup offers. PRICE IMPROVEMENT!! What better value! Accepting offers. Clean, Crisp and Fresh! Welcome home! NEWLY RENOVATED BATHROOM on deck. Is Winter Park your destination or desire? Investment Potential, Student Sanctuary or just a long-awaited life. Centrally located at your fingertips. Location, Lifestyle, Luxurious Zip Code, Friends, Culture and Community. Discover an unparalleled opportunity to own a piece of prime real estate in the heart of Winter Park, Florida. This beautifully appointed condo apartment is located within a vibrant, amenity-rich HOA community offering a perfect blend of convenience and value. Whether you're a first-time buyer, a savvy investor seeking strong rental return, a student prioritizing location and community or a loving and supportive parent wanting to be closer to your excelling child, this unit checks every box, all at an exceptional, reasonable price point. The very best luxury boutiques, fine dining, sidewalk cafes, and vibrant art festivals. Instant access to top tier schools and hospitals. Directly across from Full Sail University, minutes to Rollins College, UCF, Valencia College and major medical centers like AdventHealth and Orlando Health facilities, making it ideal for any resident, and or faculty. Transportation is easily accessible to Downtown Orlando where the famous Lake Eola Park is, Winter Springs, Oviedo, The Orlando International Airport, Cady Way Trail, biking, hiking, swimming, volleyball, pickleball, tennis and painting at The Crealde School of Art. There's just so much within reach. Explore local gatherings, social events and community connections. For all investors, strong rental income potential and appreciation value. There's low maintenance and worry-free ownership opportunities. Let's build a portfolio together or get you owning immediately. Let's get your private tour scheduled.

3019 Antique Oaks Circle Unit 124, Winter Park

Listing courtesy of COLDWELL BANKER REALTY. 407-696-8000

$399,900
4 Beds 2 Baths O6333863 MLS
This beautifully renovated Winter Park home feels warm, inviting, and easy to love. Bright natural light highlights a brand-new kitchen with modern appliances, a waterfall countertop, and soft wood finishes. Both bathrooms have been transformed with elegant marble look tile and spa style showers. You’ll fall in love with the large private backyard, perfect for summer barbecues, outdoor entertaining, play space, or even adding your own backyard oasis. All of this with no HOA and close to top rated Winter Park schools, popular dining, shopping, and parks. This move-in ready home offers lifestyle, comfort, and value you have to see in person, so schedule your showing today before it’s gone! ***Seller offering a $10,000 credit toward the buyer’s allowable closing costs and prepaid expenses. ***

1849 Viburnum Lane, Winter Park

Listing courtesy of REAL BROKER, LLC. 407.279.0038

$4,500,000
O6331207 MLS
RARE 0.48 ACRE VACANT LOT IN DOWNTOWN WINTER PARK - OFFERED AT $4,500,000! Zoned R-3, this multi-family, prime piece of land is ready for development. Luxury townhomes or condos, nothing but pure potential. Located near the intersection of N. Interlachen Avenue and Canton Avenue, this parcel is just 1-block to Park Avenue's boutique shops, award-winning restaurants, and esteemed businesses. Future residents will enjoy picturesque walks along Winter Park's famous brick streets just off the shores of the chain of lakes. Nearby attractions like the Winter Park Farmer's Market, the Winter Park Golf Course, a highly rated 9-hole gem in the center of town, Casa Feliz, Central Park, and more are all within just a few minutes stroll.

503 N Interlachen Avenue, Winter Park

Listing courtesy of KELLY PRICE & COMPANY LLC. 407-645-4321

$630,000
4 Beds 2 Baths O6332168 MLS
Under contract-accepting backup offers. Welcome to your dream home! This exceptional 4-bedroom residence features a desirable split floor plan, offering both privacy and functionality. Nestled on a quiet corner lot in the serene Winter Park Pines community, this property is just a few steps away from the scenic Cady Way Trail, perfect for outdoor enthusiasts.This home is surrounded by recreational opportunities, including a refreshing pool, pickleball courts, and miles of trails for jogging, biking, or leisurely strolls. Enjoy the outdoors while being in close proximity to shopping, dining, and the celebrated Winter Park schools.Recent updates make this home truly special. The new A/C system and upgraded electrical panel—complete with room for additional breakers—ensure your comfort and convenience. The manifold system has also been updated, and the roof was newly installed in 2018 for peace of mind.Additionally, half of the windows have been replaced with high-quality Anderson windows, enhancing both energy efficiency and natural light.Don’t miss the opportunity to own this well-maintained home in a vibrant neighborhood that perfectly balances recreation and relaxation. Schedule your showing today! Also listed for rent

744 Cornwall Road, Winter Park

Listing courtesy of VERSALIS REALTY POWERED BY SELLSTATE. 407-608-9593

$639,500
3 Beds 3 Baths O6329628 MLS
FULLY PAID SOLAR PANELS INCLUDED — NO SOLAR LOAN TO ASSUME! A rare added value for the next owner: enjoy the benefits of solar energy with the system included in the sale and no remaining solar panel balance. Welcome to 2758 Banchory Rd, a beautifully maintained 3-bedroom, 2-bath pool home in desirable Winter Park Pines. This charming ranch-style home offers a bright open layout, mature landscaping, a fully fenced backyard, private swimming pool, covered outdoor living space, storage shed, and no HOA. Located just steps from the Cady Way Trail and minutes from Cady Way Park, Winter Pines Golf Club, Baldwin Park, AdventHealth Winter Park, Full Sail University, Downtown Winter Park and Park Avenue. Enjoy the privacy of a quiet street with convenient access to shopping, dining, recreation and major roadways. PRIVATE POOL + PAID-OFF SOLAR + NO HOA + PRIME WINTER PARK LOCATION. An exceptional combination of lifestyle, location and long-term value. Schedule your private showing today.

2758 Banchory Road, Winter Park

Listing courtesy of MR VARGAS PROPERTY MANAGEMENT LLC. 407-338-3382

$182,500
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

$3,750,000
4 Beds 6 Baths O6321143 MLS
Under contract-accepting backup offers. In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement with organic warmth. Now offered at a compelling new price, the home presents a rare opportunity to experience architecturally distinctive new construction in the Vias neighborhood. Conceived, developed & designed by Steve & Jodie Konold of Scout & Co., the 3,826-sf residence offers 4 beds & 5.5 baths, w/ a layout thoughtfully arranged to provide the intentional privacy of a luxury retreat. Beyond its terraced walkway—envisioned in collaboration w/ architect Cynde Norris—French antique gates open to a native-planted entry garden, creating a soft transition to the interior. A glass foyer featuring a woven rattan chandelier, sourced & designed in London, leads to a sculptural stairwell positioned just off the main living spaces. The great room includes soaring ceilings, a sleek, custom plaster fireplace & walls of glass doors & windows. Ten-inch baseboards meet level 5 drywall in a clean reveal, paired w/ micro-crete flooring on the main level & wide-plank European oak upstairs. The kitchen is appointed w/ a Thermador dual-fuel range, matching plaster hood, full refrigerator & freezer columns & a large island with seating topped in honed black quartzite. The surrounding cabinetry features hand-carved V-groove panels w/ soft-close hardware & integrated pullout storage. Caesarstone surfaces line the perimeter while steel-and-glass open shelving w/ a sculptural black sconce balances the composition. A vintage chandelier from Prize Home & Garden sourced in Round Top completes the room. The main floor primary suite is accessed through antique doors that open to a light-filled gallery overlooking the rear courtyard & pool. The primary bath features an extended vanity w/ dual sinks, matte black fixtures, a freestanding tub, walk-in shower w/ built-in bench & separate water closet. On the mezzanine level, the powder bath makes a dramatic statement w/ a floating black quartzite trough sink paired w/ a handwoven mirror. Across the hall, the laundry room blends beauty w/ utility w/ custom cabinetry, matching quartzite surfaces, matte black fixtures & a side-by-side front-load washer & dryer. A nearby bedroom suite is marked by an antique door entry. Each guest bedroom features an en-suite bath introduced by a hand-painted tile threshold, complemented by designer lighting, distinctive mirrors & continuous European oak flooring. The rooftop terrace is accessed from the second-floor hallway. The detached casita opens to the pool courtyard through accordion glass doors on two walls & includes a woven rattan chandelier & a full bath—ideal as a studio, gym or office. Other outdoor spaces include 2 garden courtyards, a heated saltwater pool & a newly constructed outdoor kitchen designed to accommodate a built-in grill & Big Green Egg. A spacious gravel courtyard is ideal for dining or relaxing and is enveloped by mature bamboo that creates exceptional privacy. Additional features include a lower-level two-car garage, storage closet, 3 HVAC systems, Rinnai tankless water heater, Sierra Pacific windows, customized closets, solid core doors, 6” round gutters & a Barcelona barrel tile roof. Thoughtfully designed & beautifully executed, 1150 Via Salerno offers a refined lifestyle within one of Winter Park’s most exclusive enclaves.

1150 Via Salerno, Winter Park

Listing courtesy of KELLY PRICE & COMPANY LLC. 407-645-4321

$175,000
2 Beds 2 Baths O6297570 MLS Lakeside Manor BLDG.
Under contract-accepting backup offers. This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfort and convenience. Featuring tile and luxury vinyl plank flooring throughout, this home provides durability and style for modern living. The HVAC was replaced in 2020 and water, cable and internet are included in the monthly COA fee. Located in a picturesque community ON THE SHORES OF A SKI LAKE, residents will enjoy access to boat slips (based on availability, charge is $30/month), a boat ramp, a sparkling pool, a welcoming clubhouse, and mature landscaping that enhances the serene environment. Outdoor enthusiasts will appreciate the multiple barbeque grills and tables, ideal for courtyard or lakeside dining. Additional amenities include two on-site laundry rooms, on-site storage, and convenient proximity to key destinations. COA approval is required. The application fee is $85.00. Situated in Winter Park, the community is less than 10 minutes from Winter Park Village, Maitland, and Downtown Winter Park, about 10 minutes from College Park, and approximately 15 minutes from Downtown Orlando and Lake Mary. This prime location ensures easy access to shopping, dining, entertainment, and the vibrant city lifestyle.

2500 Lee Road Unit 208, Winter Park

Listing courtesy of KELLER WILLIAMS REALTY AT THE PARKS. 407-629-4420

$89,900
1 Baths O6289736 MLS 3071 BLDG.
NEW PRICE!!! 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

$1,050,000
3 Beds 2 Baths O6250417 MLS
Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards allow (but is grandfathered in), this backyard provides an ideal place to launch your water adventures, soak up scenic sunsets, and travel by lake to Hillstone for a meal. The CUSTOM POOL is waiting to be enjoyed! It features a custom waterfall, grotto, built-in seating/table and adjacent koi pond, all with a lake view. Recent updates to the home include: shingled roof (2018), DOUBLE PANE WINDOWS (2015), and HVAC (2016). Travertine and tile floors cover the entire home, there is no carpet. The back family room has multiple French doors and offers an expansive view of the lake. Fireplaces are featured in both the office and living room. The convenience of 632 Country Club is unmatched. It is approximately .6 miles from grocery shopping like Whole Foods and Publix or the Winter Park Village - a vast outdoor mall featuring a 20-screen Regal Cinema, Ruth's Chris Steakhouse and Bar Italia, to name a few. For everyday errands like HomeGoods, or workouts at LA Fitness, there is an even closer shopping plaza. An Interstate 4 (I-4) onramp is approximately 2 miles away. Winter Park is bursting with Old Florida charm and was named #38 historic world destinations in 2008 by National Geographic Magazine. At its heart is Park Avenue, famed for its cobblestoned and tree-lined streets with over 140 boutiques, museums, a train station, and world-class dining. 632 Country Club is approximately 1.5 miles from luxurious Park Avenue and 5 miles from downtown Orlando.

632 Country Club Drive, Winter Park

Listing courtesy of KELLER WILLIAMS ADVANTAGE REALTY. 407-977-7600

$562,000
4 Beds 3 Baths O6137445 MLS
Under contract-accepting backup offers. NO HOA. Dual Master Suites. One main, and one mother-in-law or guest suite. All single story, no stairs. NEW POOL DECK. NEW POOL PUMP. POOL RESURFACED.NEW ROOF (installation in progress). Totally renovated. NEW HOT WATER HEATER. NEW FLOORS. POOL RESURFACED. NEW POOL DECK. NEW POOL PUMP. NEW ALL TURF BACK LAWN (NO Mowing). NEW PUTTING GREEN (for your backyard golfer). Full Security system. Get ready to relax & have fun enjoying your new home!! Accessible and convenient, with a fabulous all-turf backyard to unwind, entertain, or make fantastic memories with those you love. Your deepwater private pool (that used to have a diving board) is the highlight of this sunny Florida oasis, including a Mini-golf putting green, outdoor dining, and plenty of space to lounge and relax when you're not on the go. Just 14 miles (30 mins) from Orlando International Airport. 20 mins to the Amway Center, Exploria Stadium, and the Dr. Philips Performing Arts Center for MLS soccer games, concerts, conferences, ballet, theater, NBA basketball games, and more. With both the University of Central Florida (UCF) and Valencia Campuses at similar proximity, this property is close to everywhere you want to be. Take the dogs for a walk around Lake Baldwin, just south, or enjoy the beachside dog park there. Ideal for a brisk run, a rejuvenating bike ride, or an invigorating rollerblade the Cady Way Train connects to the Lake Baldwin path, so you can expand your adventurous outings an additional 13 miles, beyond the 2.5 miles that wrap around the quaint peaceful lake. Baldwin Park is the best place to gather or getaway on your day-to-day. Visit the Winter Park Farmers Markets every Saturday, and take a stroll up Park Ave or take a world-class boat tour of the Winter Park Chain of Lakes after a fantastic Sunday Brunch at any of the local restaurants you know and love. Whether you're gathered around the dining room table laughing and playing board games after dinner, or cuddled up on the sofa in your open great room, watching the flickering fire on a brisk winter day, or streaming your favorite binge-worthy show, there is plenty of room for you to live your life in the best possible way. The split-floor plan gifts privacy from the master wing located off the kitchen and convenient to the backyard oasis/pool. The ensuite guest bath is a rare treat for company and residents alike. Kissed with glowing natural light in every room, this well-laid-out functional flow makes it easy to enjoy every tranquil moment your new home offers you. Turn these moments into memories and live your best life daily! POOL RESURFACED. TURN-KEY OPTIONAL (furniture optional in separate private purchase). Ring Camera. Security System. Updated/Renovated Bathrooms. Bright. Open. Airy. Comfortable. Welcoming. Fun. Cozy. Entertaining. Easy. Relaxing. Refreshing. Peaceful. Happy. Inviting. Private. Convenient.

5233 Lake Howell Road, Winter Park

Listing courtesy of CADENCE LIFESTYLE REAL ESTATE.

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