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$248,000
2 Beds 2 Baths 226020005 MLS Winterpark BLDG.
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 CIR Unit 2216, Naples

Courtesy of Re/Max Alliance Group.

$249,000
2 Beds 2 Baths 226017233 MLS Winterpark BLDG.
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.

$252,900
2 Beds 2 Baths 226012540 MLS Winterpark BLDG.
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 CT Unit 4505, Naples

Courtesy of London Foster Realty.

Selling Office: .

$209,500
2 Beds 2 Baths 2026009632 MLS Winterpark BLDG.
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 LN Unit 3101, Naples

Courtesy of Century 21 AllPoints Realty.

$240,000
2 Beds 2 Baths 226009042 MLS Winterpark BLDG.
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 LN Unit 3002, Naples

Courtesy of Saggio Realty, Inc.

$239,000
2 Beds 2 Baths 226005021 MLS Winterpark BLDG.
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.

$267,000
2 Beds 2 Baths 225077102 MLS Winterpark BLDG.
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 DR Unit 5607, Naples

Courtesy of Premiere Plus Realty Company.

Selling Office: Premiere Plus Realty Company.

$185,000
2 Beds 2 Baths 225071808 MLS Winterpark BLDG.
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 DR Unit 1010, Naples

Courtesy of John R Wood Properties.

Selling Office: John R Wood Properties.

$275,000
2 Beds 2 Baths 225053787 MLS Winterpark BLDG.
THIS WINTERPARK VIII ASSOC CONDO HAS LOWEST HOA FEES IN WINTERPARK + INCLUDES FLOOD INSURANCE!!! Perfectly positioned with easy access to downtown Naples and area beaches, this 2B/2BA unit is ideal for buyers looking to downsize or escape the harsh winters up north. The completely remodeled open floor plan features a custom-built wall unit in living room with lots of storage, (2023) HVAC unit, vaulted ceiling, smart thermostat and modern updates with an inspiring crisp/clean grey & white interior color palette throughout to compliment the wood-like plank tile flooring. Kitchen boasts sleek white + charcoal Euro-style cabinets, glass tile backsplash, dramatic quartz waterfall counter w/ bar seating and stainless-steel appliances. Both baths have been modernized as well. The primary ensuite also features Euro-style sleek cabinetry, 3" thick counters, dual sinks & showerheads. Guest bath has stunning white vanity with glass countertop, decorative tile, jetted tub w/ rain showerhead and bluetooth fan. In addition, this bright and sunny second floor unit offers a screened outdoor patio to relax and unwind with a book or favorite beverage. Pet friendly and great resort-style amenities including large community pool, bocce, shuffleboard, pickleball and tennis courts. Truly a coastal get-a-way you'll love coming home to.

4220 Looking Glass LN Unit 4304, Naples

Courtesy of John R. Wood Properties.

Selling Office: Downing Frye Realty Inc..

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.

Winterpark Condos