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$249,000
2 Beds ⋅ 2 Baths ⋅ 226024603 MLS
Welcome to Winter Park! Ready for its next owner, this charming 2-bedroom, 2-bathroom centrally located condo is a fantastic find. It features hurricane-resistant windows and a delightful patio perfect for your morning coffee. Well-priced and full of potential, this home is waiting for your personal touches! The location is truly unbeatable—just 3 miles from the famous beaches of Naples and the vibrant shops and restaurants on Olde Naples' 5th Avenue. Plus, you can easily walk to Kings Lake Square, which offers a Publix, various shops, and multiple dining options.

3816 Snowflake Lane Unit 1303, Naples

Courtesy of Broker Brothers LLC
$200,000
2 Beds ⋅ 2 Baths ⋅ 226023287 MLS
Best Value in Winterpark, LOWEST PRICED UNIT! This beautifully maintained END UNIT second-floor residence with soaring vaulted ceilings is offered turnkey furnished and is ready for immediate enjoyment or seasonal rental income. The association carries flood insurance on the building, an important benefit for buyers seeking conventional financing, and the community has recently completed the installation of new underground utilities, enhancing both aesthetics and infrastructure reliability. The thoughtfully maintained interior features a fully renovated primary bath and a partially renovated guest bath, providing a fresh and comfortable living experience. Ideally located just minutes from Downtown Naples, residents enjoy convenient access to upscale shopping, fine dining, entertainment, and Naples' world-famous white sand beaches. Winterpark offers an exceptional lifestyle with resort-style amenities including a community pool, tennis and pickleball courts, bocce, and an active clubhouse with regularly scheduled social events—all just steps from your door. Whether you're seeking a seasonal retreat, investment opportunity, or year-round residence, this home presents an outstanding opportunity in one of Naples' most desirable locations. *The Buildings are in the process of being painted afresh neutral light gray with a blue trim/shutters

3420 Frosty Way Unit 12, Naples

Courtesy of Downing Frye Realty Inc.
$248,000
2 Beds ⋅ 2 Baths ⋅ 226020005 MLS
Discover a pristine Naples paradise with this meticulously maintained 2 bedroom, 2 bathroom condominium at Winter Park that shines with amazing amenities and a luxurious location. Enjoy a condo that benefits from splendid design choices, including vaulted ceilings, plentiful natural light, and split bedrooms. The primary suite is a relaxing retreat, featuring a walk-in closet and a stylish barn door that leads to the en-suite master bath with a sparkling shower. The unit comes turnkey; all you have to bring is your suitcase! This condo is fully equipped with much-desired impact windows and sliders to protect your paradise. Additional in-unit perks include a spacious laundry and utility room with a dedicated washer and dryer and room to spare, as well as a clever small storage area tucked under the stairs, perfect for storing bikes and beach chairs. Tile and carpet flooring throughout. Winter Park boasts an absolutely stacked lineup of amenities that includes one of the LARGEST resort-style community pools in Naples, a beautiful clubhouse with an expansive library, separate pickleball and tennis courts, bocce and shuffleboard courts, and bike and jog path; a sensational lineup of community activities for a fabulous community. What’s more - this particular condo is situated well in this robust community, enjoying close proximity to all of these amenities. Just minutes from world-renowned 5th Avenue, scintillating shopping, and beautiful beaches, this location is absolutely rich with convenience. No matter what your real estate goal is, this Winter Park wonderland offers the quintessential Southwest Florida lifestyle!

3532 Antarctic Circle Unit 2216, Naples

Courtesy of Re/Max Alliance Group
$329,900
2 Beds ⋅ 2 Baths ⋅ 226019156 MLS
4140 Looking Glass Ln #3815 is a move-in-ready 2-bedroom, 2-bath condo for sale in Winterpark, one of Naples’ established communities with resort-style amenities and a convenient location. Offered at $329,900, this updated Naples condo features a fully redesigned kitchen with white cabinetry, stainless steel appliances, a stylish backsplash, large breakfast bar, and an open layout connecting the kitchen, dining, and living areas. The interior has a clean coastal feel with updated flooring, recessed lighting, modern finishes, and a spacious living room overlooking a peaceful outdoor setting. The owner’s suite includes custom closet space and an updated bathroom with a walk-in shower. The second bedroom and bathroom provide flexibility for guests, seasonal use, or a home office. A standout feature is the custom laundry and wine cellar area, adding valuable function and a unique touch. Winterpark amenities include a resort-style community pool, clubhouse, community room, pickleball, tennis, bocce court, bike and jog path, bike storage, extra storage, and internet access. The HOA includes cable, insurance, internet/WiFi access, irrigation water, lawn and land maintenance, reserves, sewer, street lights, street maintenance, trash removal, and water. For buyers searching for Naples condos for sale, a move-in-ready condo in Winterpark, or a well-updated property near shopping, dining, beaches, and downtown Naples, this is a strong opportunity.

4140 Looking Glass Lane Unit 7, Naples

Courtesy of Keller Williams Realty Naples
$249,000
2 Beds ⋅ 2 Baths ⋅ 226017233 MLS
Welcome to an exceptional opportunity to own an upstairs residence in the highly sought-after Winterpark community—where value meets vision and the potential to create your dream Naples retreat awaits. Positioned in a prime Naples location, this 2-bedroom, 2-bath condominium offers a light-filled layout with an expansive living and dining area, ready to be reimagined with your personal style and design vision. The screened balcony provides a peaceful outdoor space overlooking lush tropical landscaping—perfect for morning coffee or unwinding after a day at the beach. Inside, you’ll find a spacious primary suite, in-unit laundry, and a functional floor plan that serves as the perfect canvas for updates, renovations, or a full custom transformation. What truly sets this property apart is its placement within Winterpark—one of Naples’ most desirable, amenity-rich communities known for its vibrant lifestyle and classic Florida charm. Residents enjoy access to one of the largest resort-style pools in Naples, beautifully maintained grounds, newly updated pickleball and tennis courts, and an active social atmosphere that makes it easy to feel at home. Located just minutes from 5th Avenue South and Olde Naples, as well as world-renowned Gulf beaches, this property offers unmatched convenience to fine dining, boutique shopping, art galleries, and coastal living at its finest. Whether you’re seeking a seasonal escape, investment opportunity, or a full-time residence to customize and make your own, this is your chance to unlock the full potential of Naples living in a community that truly embodies the Florida lifestyle.

3420 Frosty Way Unit 4910, Naples

Courtesy of William Raveis Real Estate
$239,000
2 Beds ⋅ 2 Baths ⋅ 226016168 MLS
One or more photo(s) has been virtually staged, AI generated or rendered. One or more photo(s) has been virtually staged, AI generated or rendered. Beautiful lake-view condo just minutes from everything Naples has to offer! Located only 8 minutes from the beach and close to 5th Ave South and downtown, this desirable second-floor unit offers privacy, natural light, and beautiful Lake views. Featuring 2 bedrooms and 2 bathrooms, this home boasts vaulted ceilings, an updated Tile and carpet flooring throughout, and a spacious primary suite with a walk-in closet. The living area is enhanced with impact windows, providing both peace of mind and energy efficiency. Whether you're looking for a full-time residence, seasonal getaway, or income-producing rental investment, this unit checks all the boxes. Allows up to 12 rentals per year with a 30-day minimum, offering excellent flexibility and strong income potential making it a fantastic opportunity for investors seeking Airbnb-style or seasonal rental income.

4050 Ice Castle Way Unit 2812, Naples

Courtesy of Waterfront Realty Group Inc
$209,100
2 Beds ⋅ 2 Baths ⋅ 226014616 MLS
This unit is THE LOWEST PRICED unit in Winterpark and move in ready sold Turnkey Furnished. Great Location near the Wonderful Amenities Winterpark has to offer. A quick walk to the resort size Pool, Bocce Court, Tennis Courts and Community Center. If interested in renting for season, it is perfect for that also! Very well maintained, clean and no carpet. Close to Grocery Shopping, Starbucks, 5th Ave Restaurants and Naples finest beaches. The building has Flood insurance which means that lender approval will not be an issue. Polybutylene plumbing has been replaced.

3511 Antarctic Circle Unit 2406, Naples

Courtesy of Downing Frye Realty Inc.

Selling Office: .

$309,900
2 Beds ⋅ 2 Baths ⋅ 226015387 MLS
Charming 2 Bed, 2 Bath in Desirable Winterpark – Prime Naples Location Nestled in the heart of sunny Naples, this beautifully updated 2-bedroom, 2-bathroom condo in Winter park offers the perfect blend of comfort, style, and convenience. The open-concept layout is ideal for entertaining, while the spacious screened-in lanai provides a peaceful space to relax and unwind. Located just a short drive to 5th Avenue, Naples Beach, Publix, and a variety of restaurants and shops, this highly sought-after community.

4030 Northlight Drive, Naples

Courtesy of Premier Property Management
$280,000
2 Beds ⋅ 2 Baths ⋅ 226014881 MLS
THIS WINTERPARK VIII ASSOCIATION CONDO HAS LOWEST HOA FEES IN WINTERPARK + INCLUDES FLOOD INSURANCE. Experience effortless Naples living in this beautifully renovated two-bedroom, two-bath second floor condo, ideally located with convenient access to the vibrant energy of downtown Naples. Thoughtfully updated throughout, this light-filled condominium blends modern sophistication with a relaxed coastal aesthetic. Cathedral ceilings elevate the main living space, enhancing the open, airy feel, while luxury vinyl plank flooring flows seamlessly throughout. The stunning kitchen is a true focal point, featuring distinctive ceiling details, quartzite countertops, and stainless-steel appliances—perfectly designed for both everyday living and entertaining. Enjoy tranquil landscaped views from the screened lanai, creating a private retreat for morning coffee or evening relaxation. Impact-resistant doors and windows provide both peace of mind and energy efficiency. Offered beautifully furnished, this condo provides the perfect opportunity for instant enjoyment. This pet-friendly community includes an impressive array of amenities, including a resort-style pool, clubhouse, scenic walking paths, bocce courts, pickleball, and tennis. A rare opportunity to own a move-in-ready coastal escape in one of Naples’ most convenient locations.

4240 Jack Frost Court Unit 6, Naples

Courtesy of John R Wood Properties
$252,900
2 Beds ⋅ 2 Baths ⋅ 226012540 MLS
Experience effortless Florida living in this charming 2-bedroom, 2-bath first-floor condo located in the desirable Winterpark community. Offered beautifully furnished and turnkey, this home presents a rare opportunity for immediate enjoyment with a seamless move-in experience or investment. The entire condo features new plank-style tile floors, creating a cohesive and modern look with the latest style. The kitchen has been tastefully refreshed with professionally painted cabinetry, a new faucet, and a new vent hood, creating a clean and modern aesthetic. Both bathrooms now feature new Quartz Custom Countertops and cabinets and and modern lighting. adding a touch of elegance and style. Additional updates include updated lighting, and plantation shutters that add both style and functionality. The spacious primary suite offers a serene retreat, complete with a walk-in closet for ample storage and organization. Additional highlights include a spacious in-residence laundry room with ample storage, as well as a large, convenient outdoor storage area—perfect for bicycles, beach gear, or seasonal items. The unit also benefits from a full replacement of polybutylene plumbing for added peace of mind. Enjoy the screened-in front porch, an ideal space to relax with your morning coffee or unwind in the evening. Residents of Winterpark enjoy an exceptional array of amenities, including a resort-style pool, clubhouse, tennis and pickleball courts, bocce, and scenic walking paths, all within a beautifully maintained, amenity-rich environment. The property’s convenient location, is just a short drive away from Fifth Avenue and Third Street, where you can indulge in a variety of restaurants, parades, upscale shopping and holiday events. Close to the beautiful Napes Gulf beaches, offering a perfect spot for relaxation and breathtaking sunsets. This move-in-ready condo is an excellent opportunity for a variety of lifestyles. schedule your showing today!

4250 Jack Frost Court Unit 4505, Naples

Courtesy of London Foster Realty

Selling Office: .

$284,900
2 Beds ⋅ 2 Baths ⋅ 226012607 MLS
Welcome to Winterpark, one of Naples most sought-after communities just minutes from downtown and the pristine Gulf beaches. This beautifully updated 2-bedroom, 2-bath 1st floor condo offers a perfect blend of modern style and effortless Florida living. Step inside to an open, light-filled layout designed for both comfort and entertaining. Darkwood accents & cabinetry in the kitchen and breakfast bar, custom tile work and exquisite finishes throughout. Enjoy your morning coffee or unwind in the evening on the spacious lanai, a perfect private retreat with a relaxing, tropical feel. Winterpark is known for its resort-style amenities, including one of the largest pools in Naples, newly updated pickleball and tennis courts, and a vibrant, active social atmosphere. Surrounded by lush green spaces and charming scenery, the community captures the essence of classic Florida living. Ideally located just minutes from 5th Avenue South, Olde Naples, shopping, dining, and the beach, this property is perfect as a full-time residence, seasonal getaway, or investment opportunity. Come experience it for yourself—this one won’t last.

4150 Looking Glass Lane Unit 3903, Naples

Courtesy of LPT Realty, LLC
$267,000
2 Beds ⋅ 2 Baths ⋅ 226012425 MLS
Move-in ready and beautifully furnished, this 2BR/2BA second-floor condo features an open-concept layout with vaulted ceilings, bamboo flooring in the main living areas, and recessed lighting in the kitchen. Both bathrooms are updated with natural limestone showers and glass enclosures. Enjoy tranquil pond views from the living room and primary bedroom, along with a screened lanai overlooking landscaped grounds. Offered turnkey furnished, this residence is well-suited for seasonal living, investment, or full-time use. Highlights: Hurricane impact windows throughout; vaulted ceilings (2nd-floor units only); pond views from living area and primary bedroom; newer washer/dryer; exterior storage for bikes and beach gear; community roof replaced in 2018. Amenities: Resort-style heated pool, tennis, pickleball, bocce, clubhouse. Location: Minutes to 5th Ave South, Bayfront, and beaches; walk to Publix and dining at Kings Lake Square. Community: Leasing permitted 3 times per year (30-day minimum / 180-day maximum). Pets: one dog (up to 50 lbs) or cat for owners (no pets for tenants).

4070 Northlight Drive Unit 1612, Naples

Courtesy of Beycome of Florida LLC

Selling Office: .

$250,000
2 Beds ⋅ 2 Baths ⋅ 226011974 MLS
Nicely appointed 2ND FLOOR UNIT with screened-in deck. Ready to move in. Newer refrigerator and Range in kitchen. A/C is 3 years old. Extensive amenities in the complex including, Tennis Courts, Pickleball, Bocce Ball, Shuffleboard, and a Resort style pool. Walking distance to shopping(Home Depot ,Publix, Walgreen's) and restaurants. Pets are Allowed.

4031 Ice Castle Way Unit 3306, Naples

Courtesy of Realty World Top Producers Rlt
$310,000
2 Beds ⋅ 2 Baths ⋅ 226011021 MLS
This Beautifully updated condo is on first floor in the Winterpark 1 community. Unit was completely remodeled in 2021, with tile flooring throughout unit, stainless KitchenAid appliances, new cabinets, new countertops, light fixtures, coffered ceiling in living room, hurricane rated windows and sliders throughout, custom closets 2022, updated master bath and guest bathroom too! Screened in lanai in front of unit as well as NEW screened in lanai in back of unit added in 2024. Beautiful, landscaped views with lots of room in a tranquil setting. There is a dedicated parking spot with unit as well. This wonderful diamond in the ruff community has an amazing resort style pool with a clubhouse, and 8 pickleball courts along with bocce and tennis. Minutes to the beaches, restaurants and downtown Naples. You don't want to miss this amazing unit!

3569 Antarctic Circle Unit 2105, Naples

Courtesy of John R Wood Properties

Selling Office: .

$209,500
2 Beds ⋅ 2 Baths ⋅ 2026009632 MLS
Best Value in Winterpark – First Floor • Turnkey • Impact Windows • New A/C • Conventional Financing On of the Lowest-priced first-floor condo in Winterpark. This turnkey-furnished home offers an incredible opportunity to own in one of Naples’ most desirable communities while leaving room in your budget to update and personalize it over time. The home offers a comfortable, functional layout with one nicely updated bathroom while providing an opportunity to personalize the remaining spaces to your own taste and style. Major improvements have already been completed, including updated plumbing, impact windows and an impact sliding glass door, a new A/C (2024), and a new water heater (2023), allowing you to focus on making it your own. For added peace of mind, the condominium association carries a master flood insurance policy. The property also qualifies for conventional financing, offering greater flexibility for buyers. Winterpark is known for its lush, walkable setting, spectacular resort-style pool, tennis courts, and welcoming atmosphere. Ideally located just minutes from downtown Naples, 5th Avenue South, shopping, dining, and the beautiful Gulf beaches, you’ll enjoy everything Southwest Florida has to offer. Quarterly HOA dues are $1,920 and include outstanding community amenities and exterior maintenance. Pets and rentals are permitted, adding to the property’s versatility. Motivated sellers have priced this home to sell. If you’ve been searching for an affordable opportunity to own in one of Naples’ most popular communities, this is one you won’t want to miss.

4070 Looking Glass Lane Unit 3101, Naples

Courtesy of Century 21 AllPoints Realty
$240,000
2 Beds ⋅ 2 Baths ⋅ 226009042 MLS
Seller Says Sell! Price reduction for this amazing condo in highly sought after Winterpark. Discover the perfect blend of comfort, style, and location in this spacious second-floor corner condo in beautiful Naples. Featuring vaulted ceilings and serene garden views, this light-filled residence offers privacy and tranquility within the lush, peaceful community of Winterpark. This updated 2-bedroom, 2-bath home showcases an open, airy layout with neutral tones that complement any décor. The remodeled kitchen features modern cabinetry, quartz countertops, stainless steel appliances, and a convenient breakfast bar that flows seamlessly into the expansive living and dining areas—ideal for entertaining or relaxing at home. Both bathrooms have also been tastefully renovated. Other updates include a newer A/C, a brand new water heater, and a roof that's only a year old for added peace of mind. Flood insurance is covered by the association. Another advantage is the in-unit laundry room with washer, dryer, and abundant storage. Enjoy Florida living year-round from the screened porch overlooking the garden, the large heated community pool, tennis courts and other playing courts, as well as walking and jogging paths. Other features include private assigned parking and plenty of additional guest parking for even more convenience. Extra private storage accompanies this property to store your bike or anything else you may need. The location is perfect, only a few minutes to Downtown Naples and its world renowned beaches, plus easy access to exceptional dining, shopping and entertainment options. Pet-friendly, rental-friendly and without age restrictions, this condo presents an excellent investment opportunity or seasonal retreat. While other units may be available in the community, this beautifully updated corner residence truly stands out—one you must see in person to fully appreciate.

4100 Looking Glass Lane Unit 3002, Naples

Courtesy of Saggio Realty, Inc
$225,000
2 Beds ⋅ 2 Baths ⋅ 2026010114 MLS
Welcome home to this beautifully maintained Winter Park condo offering over 1,200 square feet of comfortable living space with peaceful green space views. This spacious residence features 2 bedrooms and 2 bathrooms, providing an ideal layout for both everyday living and entertaining. Enjoy a vibrant, resort-style community with exceptional amenities, including a sparkling resort swimming pool, pickleball and tennis courts, bocce ball, scenic walking trails, and a variety of organized social activities. Recent major improvements include a newer A/C system and roof, offering added value and peace of mind. The monthly condo fee covers water, sewer, exterior insurance, exterior maintenance, cable service, landscaping, and full access to all community amenities, helping simplify ownership. Whether you're searching for a primary residence, seasonal retreat, or investment opportunity, this property offers flexibility with both short-term and annual rentals permitted, subject to community restrictions.

4200 Looking Glass Lane Unit 4204, Naples

Courtesy of Portside Property Group
$239,000
2 Beds ⋅ 2 Baths ⋅ 226005021 MLS
PRICE IMPROVED!! BRING AN OFFER!! Enjoy the best of Naples living without the premium price tag! Located just 9 minutes from Downtown Naples and beaches, this second-floor 2 bed/2 bath condo offers an incredibly convenient lifestyle in a prime in-town location, all for under $240K. Whether it’s dinner on 5th Avenue, a beach day, or everyday shopping and errands, everything is close by and easy to reach. Inside, vaulted ceilings and impact-resistant windows and doors create a bright, comfortable space that feels open and secure. The condo has been exceptionally well cared for and is truly easy to move right into. Major building improvements have already been completed, including the full replacement of polybutylene plumbing and aluminum wiring, a newer roof, and a recent professional vent cleaning for improved air quality and peace of mind. Outside, you can enjoy a screened in front porch and a second access point into the kitchen through the impact sliders. The HOA maintains flood insurance that supports Fannie Mae and Freddie Mac financing, and the community and its board are a reflection of strong, proactive management. Amenities are just steps away, including one of the largest community pools in Naples, multiple tennis and pickleball courts, bocce, and an active clubhouse. It’s a setting that makes everyday living feel like a getaway, yet keeps you close to everything that makes Naples so desirable!

3450 Frosty Way Unit 5210, Naples

Courtesy of Coldwell Banker Realty
$339,000
2 Beds ⋅ 2 Baths ⋅ 226005552 MLS
Discover comfortable and easy Florida living in this inviting 2-bedroom, 2-bath condo located in the highly desirable Winterpark community. This first-floor residence offers a well-designed floor plan with a welcoming living and dining area, a thoughtfully arranged kitchen, and two comfortably sized bedrooms with excellent closet storage. The primary suite includes an en-suite bath and relaxing views of the community’s green space. Step outside to enjoy Winterpark’s resort-style amenities, including one of the largest community pools in Naples, a clubhouse, pickleball and tennis courts, bocce, and beautifully maintained walking paths. Residents appreciate the convenient East Naples location—just minutes from downtown 5th Avenue, shopping, dining, and Naples’ world-famous beaches. Whether you're seeking a seasonal retreat, full-time residence, or investment property, this Winterpark condo offers wonderful value and a uniquely comfortable Naples lifestyle.

4180 Looking Glass Lane Unit 4102, Naples

Courtesy of Premiere Plus Realty Company
$210,000
2 Beds ⋅ 2 Baths ⋅ 226005257 MLS
WINTERPARK IS A HIDDEN GEM WITH A VERY DESIRABLE LOCATION... ONLY 2-3 MILES TO BAYFRONT, 5TH AVE, DOWNTOWN RESTAURANTS AND SHOPS, AND THE BEACHES... 2 BDRM 2 BATH FIRST FLOOR UNIT WITH LARGE SCREENED IN PATIO LOOKING OUT TO LUSH LANDSCAPING... SNOWFLAKE LANE IS RIGHT NEXT TO THE RESORT STYLE POOL (ONE OF THE LARGEST IN NAPLES) / FIVE TENNIS COURTS, FOUR PICKLEBALL COURTS, BOCCE... FULLY FURNISHED TURNKEY... NEW HW TANK, CEILING POLY PIPES RECENTLY CHANGED IN LAUNDRY ROOM, AND NEWER MSTR BATH... THIS IS A VERY FRIENDLY ACTIVE COMMUNITY WITH GREAT RENTAL POTENTIAL... ENJOY YOUR WINTERS IN THE SUNSHINE!

3832 Snowflake Lane Unit 1207, Naples

Courtesy of ERA Naples Realty Services

Selling Office: .

$260,000
2 Beds ⋅ 2 Baths ⋅ 226004763 MLS
Nestled at the end of a cul-de-sac, this first-floor end-unit condo offers a level of privacy and accessibility that’s hard to find in Naples at this price. With no road noise from Davis Boulevard and no building directly in front or to the side, this residence feels peaceful and secluded yet remains close to everything. The lush grassy side and back yards feel like your own private oasis, and with the walking path just steps from your back door, a nice stroll takes you right to the resort-style amenities. This two-bedroom, two-bath unit has been thoughtfully updated, allowing you to skip the renovations and start enjoying the Naples lifestyle immediately. Its freshly painted interior features impact windows and doors, tile flooring throughout, stainless appliances, white cabinetry and stone counter tops, and modern tile-surround step-in showers. AC system and roof were replaced in 2022. Owners are permitted to have one household pet. Winterpark offers its residents one of Naples’ largest community pools, tennis and pickleball courts, and a community room. Centrally located, the beaches and downtown shops and restaurants are just minutes away and conveniences like Publix, Starbucks and Home Depot are right around the corner.

4000 Ice Castle Way Unit 2601, Naples

Courtesy of John R Wood Properties

Selling Office: .

$222,500
2 Beds ⋅ 2 Baths ⋅ 226002662 MLS
Tucked away End Unit, no road noise from Davis Blvd. Private feel entrance with lanai that over looks a lovely grass area with beautiful floral blooming trees which is rare and hard to find in this community. No building directly in front or to the side of this unit. Well maintained interior ready for your own touch or for an investor to Seasonally rent. Great rental income in this community due to proximity to downtown and Naples Beaches. Building has Flood Insurance and Poly pipes have been replaced so no issues with getting a loan on the property. All assessments have been paid in full. Original owners, never used as a rental unit. Renovated throughout the years. Winterpark is a large, well-established condominium complex known for its resort-style amenities like a large pool, clubhouse, tennis, and pickleball courts, and its convenient location near beaches, shopping, and dining

4140 Looking Glass Lane Unit 3816, Naples

Courtesy of Downing Frye Realty Inc.

Selling Office: .

$232,500
2 Beds ⋅ 2 Baths ⋅ 225084742 MLS
Well-maintained second-floor apartment located in the desirable Winterpark community in Naples. This 2 bedroom, 2 bathroom unit offers a bright and functional layout with an open living and dining area, perfect for everyday living or seasonal use. The unit features spacious bedrooms & ample closet space.Winterpark is a well-established community with mature landscaping and convenient amenities. Excellent location close to shopping, dining, beaches, downtown Naples, and major roads. Ideal as a primary residence, second home, or investment property.

4220 Looking Glass Lane Unit 4302, Naples

Courtesy of Key & Legacy Realty LLC

Selling Office: .

$172,500
2 Beds ⋅ 2 Baths ⋅ 225083101 MLS
LOWEST PRICE IN WINTERPARK! 2 bedrooms 2 baths TURNKEY FURNISHED ground floor condo in Winterpark! With 1,246 square feet of air conditioned living area, the living areas are tiled with 18" neutral tone tile. Extra storage closet outside your front door. Winterpark amenities include a spectacular heated, resort-style community pool which is one of the largest swimming pools in Naples. There are bike and jogging trails, beautiful landscaping, 5 tennis courts and 4 pickle ball courts, 2 bocce courts and a clubhouse with a library and lots of social activities if you so desire. You can walk to Kings Lake Square for grocery shopping at Publix and some of the area's tasty and affordable restaurants! This is AN IDEAL year-round or seasonal residence! Please note that the owners never experienced any flood or water intrusion from storms or any thing else, in their nearly 16 years of ownership. Winterpark is just a short drive to renowned Fifth Ave. South with an eye-popping variety of shopping and dining options and Naples beautiful sandy beaches. This condo is an ideal opportunity to own your perfect winter retreat, affordably priced for you to add your personal touches and improvements

4150 Looking Glass Lane Unit 5, Naples

Courtesy of Downing Frye Realty Inc.

Selling Office: .

$267,000
2 Beds ⋅ 2 Baths ⋅ 225077102 MLS
Tropical Paradise - Winterpark IX! This 2-bedroom, 2-bathroom condo is ideal as a Florida tropical vacation home, a full-time residence or investment property. Offered Furnished. Ground-floor unit- no stairs and no hassle. Only a few buildings in Winterpark community feature a screened lanai; perfect for enjoying your Florida morning coffee or a glass of wine at sunset. New roof-2024, A/C-2020, Water Heater-2016, new piping, Impact Resistant windows and doors. Check out this property on our 360° Virtual Tour! Located just a short walk to the community amenities - no need to cross a busy street, unlike owners in some other buildings. A rare opportunity to purchase in one of the most desirable buildings. Up to 12 leases are allowed per year, making it an excellent investment property, or a vacation home. Prime location with quick access to Naples Downtown, white-sand Naples beaches, shopping, dining, and local attractions. Simple and cozy - this is how we live on the Gulf in Naples. Take a short trip to swim and sunbathe on one of the Naples beaches, play tennis or pickleball, dine and watch the sunset at one of the finest restaurants, or enjoy a fun day of shopping and then relax in the large resort-style pool right in the community. The amenities include a spacious resort-style pool, tennis and pickleball courts, a clubhouse, and bocce. Naples also welcomes everyone to enjoy its cultural and entertainment venues, including the Gulfshore Opera, Artis, The Baker Museum, Gulfshore Playhouse, The Naples Players Theater, Naples Botanical Garden, Naples Zoo, and numerous public parks with miles of walking paths, and even the Sun-N-Fun Lagoon water park. Don’t miss Fifth Avenue South and Third Street South in Olde Naples, as well as The Village Shops on Venetian Bay in Park Shore, Waterside Shops in the Pelican Bay area, Mercato, and much more. Make this home yours today, spend this winter season in sunny Florida!

4085 Northlight Drive Unit 5607, Naples

Courtesy of Premiere Plus Realty Company

Selling Office: .

$180,000
2 Beds ⋅ 2 Baths ⋅ 2025017302 MLS
MOTIVATIVE SELLER, MAKE AN OFFER ...Roof was replaced in 2022. Charming 2-Bedroom, 2-Bathroom First-Floor Condo in Naples, FL A nicely maintained 2-bedroom, 2-bathroom first-floor condo, in the heart of Naples, FL. Features all-tile flooring throughout, impact-resistant windows fand sliding door for added peace of mind, and updated kitchen and bathrooms. Enjoy granite countertops and sleek stainless steel appliances. Offers spacious living, open floor plan. Amenities: resort-style pool. Recreation: pickleball, shuffleboard, tennis, and bocce courts. Location: Located in a desirable Naples neighborhood, this condo is just minutes away from beautiful beaches, shopping and dining ion 5th Ave, and all the attractions that make Naples a premier destination. Whether you’re here for the season or looking for a primary year round residence, this location provides the best of Florida living. Affordable HOA: The HOA fee is $1,560 paid per quarter, breaks down to about $520.00 on a monthly basis; offering great value for the exceptional amenities and well-maintained grounds. A lockable storage area, guest parking spots available. Don’t miss out on the opportunity to make this charming condo your new home!

4001 Ice Castle Way Unit 3607, Naples

Courtesy of Century 21 Allpoints Realty

Selling Office: .

$182,500
2 Beds ⋅ 2 Baths ⋅ 225076778 MLS
FIXER UPPER - INVESTOR SPECIAL (TLC) ! Discover an exceptional opportunity to own one of only 8 unique corner units in this celebrated Naples community. The moment you step inside, your eyes are drawn upward to the breathtaking cathedral ceilings, creating an immediate sense of grandeur and space. Updated Flooring, elegant floors flow throughout, providing a perfect , polished canvas for your final touches. This 2 Bedroom / 2 Bath condo offers the perfect blend of resort-style living and prime location. You have the freedom to add your personal flair and complete the minor updates needed to create your spectacular dream home. Live the vibrant Naples Lifestyle, with Downtown Naples, Beautiful Beaches, Tin City and Celebration park all just minutes away. The community itself is a destination, boasting a resort-style pool, clubhouse, pickleball and tennis courts. This is more than a home; it's an investment in a highly sought-after , luxurious Florida Lifestyle at a low cost. THIS FIXER UPPER is perfect for investors or DIY buyers seeking to build equity in Prime Location. Solid structure awaiting cosmetic upgrades - Bring your Designer / Contractor - Exceptional Value / Priced to Sell!

3560 Antarctic Circle Unit 2202, Naples

Courtesy of REMAX Affinity Mercato

Selling Office: .

$259,000
2 Beds ⋅ 2 Baths ⋅ 2025014071 MLS
Excellent unit, less than 5 minutes from Naples' pristine beaches, pier, restaurants, and more. This bright and spacious second-floor condo unit is perfect for a small family or as a vacation rental. Very well-maintained, you will not be disappointed. Reasonable HOA fees and amazing amenities, including a pool, multiple tennis courts, and many more, in this great community. Furniture is negotiable

4079 Northlight Drive Unit 1802, Naples

Courtesy of Atlas Realty Company, Inc.
$270,000
2 Beds ⋅ 2 Baths ⋅ 225073392 MLS
Newly renovated 2 bedroom, 2 bathroom Condo Available! Just 4 miles to beautiful downtown Naples, 5th Avenue! Complete renovation includes a beautiful new kitchen with updated cabinetry, countertops and appliances. New flooring, lighting, plumbing fixtures, and new hot water heater and furnace. Enjoy pickleball, tennis, Boccee Ball, Walking, Bike Paths, and a resort style community pool, great for socializing!

4200 Looking Glass Lane Unit 4202, Naples

Courtesy of Waterfront Realty Group Inc

Selling Office: .

$185,000
2 Beds ⋅ 2 Baths ⋅ 225071808 MLS
Welcome to your slice of paradise in the sought-after Winterpark community! This beautifully maintained 2nd-floor condominium offers serene views of the resort-style pool and is ideally situated in a premier location within the community—tucked away from busy streets for added peace and privacy. Boasting over 1,200 square feet of living space, this spacious unit features a thoughtfully designed open floor plan with two bedrooms, two bathrooms, and a dedicated laundry room. The entire unit has been replumbed and is free of polybutylene piping, offering peace of mind and long-term reliability. Inside, you'll find elegant tile flooring throughout—NO carpet—creating a clean, modern aesthetic that's easy to maintain. Impact-resistant windows provide enhanced safety, energy efficiency, and quiet comfort. The layout is perfect for both seasonal getaways and year-round living, with generous natural light and a welcoming ambiance. Offered turnkey, this residence is move-in ready and fully furnished for effortless living. Located just minutes from downtown Naples and the pristine Gulf beaches, you'll enjoy convenient access to world-class dining, shopping, and entertainment. Whether you're seeking a vacation retreat or a full-time residence, this condo delivers the perfect blend of comfort, style, and Florida charm.

3750 NORTHWINDS Drive Unit 1010, Naples

Courtesy of John R Wood Properties

Selling Office: .

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