The community of Winterpark is located in Naples. Ideally situated for access to all of the Naples area amenities and advantages available.

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20 listings match your search criteria.
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Active
3532 Antarctic Cir  2216 Naples
$248,000
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1986Year Built
$248,000

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…

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4140 Looking Glass Ln  7 Naples
$329,900
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$329,900

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…

Active
3420 Frosty Way  4910 Naples
$249,000
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1987Year Built
$249,000

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…

Active
4080 Looking Glass Ln  2905 Naples
$282,000
  • 2Bedrooms
  • 2Bathrooms
  • 1212Sq Ft
  • 1988Year Built
$282,000

READY TO SELL...... Discover easy Florida living in this inviting 2-bedroom, 2-bath condo located in the highly desirable Winterpark community. This first-floor corner unit features a bright open floor plan with great views overlooking the peaceful walking path. FURNITURE OPTIONAL. LOCATION LOCATION Enjoy a split-bedroom layout for added privacy, along with a welcoming living and…

Active
4230 Jack Frost Ct  4402 Naples
$275,000
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$275,000

One or more photo(s) has been virtually staged, AI generated or rendered. Charming second-floor 2-bedroom, 2-bath condominium located in the highly desirable Winterpark community, specifically within Winterpark VIII, which offers the lowest HOA fees in the neighborhood. Ideally positioned for convenient access to the vibrant downtown Naples area, this residence is set within a…

Active
4050 Ice Castle Way  2812 Naples
$245,000
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1988Year Built
$245,000

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…

Active
4030 Northlight Dr   Naples
$309,900
  • 2Bedrooms
  • 2Bathrooms
  • 1200Sq Ft
  • 1986Year Built
$309,900

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…

Active
4240 Jack Frost Ct  6 Naples
$299,000
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$299,000

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…

Active
4150 Looking Glass Ln  3903 Naples
$284,900
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1988Year Built
$284,900

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…

Active
4031 Ice Castle Way  3306 Naples
$250,000
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1986Year Built
$250,000

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.

Active
4070 Looking Glass Ln  3101 Naples
$215,000
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1988Year Built
$215,000

Welcome to this beautifully maintained first-floor condo in the highly desirable Winterpark community of Naples. This immaculate 2-bedroom, 2-bath residence is being offered turnkey furnished—simply bring your suitcase and start enjoying the Florida lifestyle. Thoughtfully updated, the unit has been repiped and features impact windows for added peace of mind. The building carries an association flood…

Active
4100 Looking Glass Ln  3002 Naples
$259,900
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1988Year Built
$259,900

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…

Active
4001 Ice Castle Way  3605 Naples
$298,000
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1987Year Built
$298,000

Fully renovated in March 2022 with brand new kitchen, floors and bathrooms. Quartz countertops, glass tile backsplashes, stainless steel appliances, new AC and water heater, luxury vinyl flooring, new hurricane windows and doors. Beautifully furnished/decorated with new furniture and art, this well-appointed home is being sold turnkey. The condo also features a…

Active
4200 Looking Glass Ln  4204 Naples
$230,000
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$230,000

Welcome home to this spacious Winter Park condo featuring 2 bedrooms, 2 bathrooms, and over 1,200 square feet of comfortable living space with serene green space views. Residents enjoy resort-style amenities including a sparkling pool, bocce ball, pickleball, tennis courts, walking trails, and organized social activities. Major updates include a newer A/C and roof. The…

Active
3420 Frosty Way  4902 Naples
$265,000
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1987Year Built
$265,000

A 1-year home warranty is included with the purchase of this property! Welcome to Winterpark, the tropical paradise! This spacious upper-floor 2-bedroom, 2-bath END-UNIT condo features a front screened balcony, perfect for enjoying your Florida morning coffee or a glass of wine at sunset. Partially furnished (inventory list available). Cathedral ceilings are available only in…

Active
3450 Frosty Way  5210 Naples
$239,000
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1988Year Built
$239,000

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…

Active
3430 Frosty Way   12 Naples
$284,900
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1987Year Built
$284,900

Welcome to Winterpark, one of Naples’ most popular communities just minutes from downtown. This beautifully updated 2-bedroom, 2-bath corner condo has been fully remodeled from top to bottom. The brand-new kitchen features all new appliances, cabinets and counter tops, both bathrooms have been updated, the plumbing, HVAC and water heater has been redone, and there’s fresh…

Active
4180 Looking Glass Ln  4102 Naples
$339,000
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$339,000

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…

Active
4079 Northlight Dr  1802 Naples
$269,000
  • 2Bedrooms
  • 2Bathrooms
  • 1234Sq Ft
  • 1987Year Built
$269,000

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…

Active
3574 Antarctic Cir  2107 Naples
$270,000
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1986Year Built
$270,000

Welcome to this beautifully updated condo in the desirable Winterpark community. Inside, you’ll find a completely renovated kitchen with brand new stainless steel appliances, an electric cooktop, countertops, new cabinetry, and a modern backsplash. The guest bathroom has been fully updated. Additional upgrades include new light fixtures, ceiling fans, fresh interior paint throughout, and even…

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