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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23 listings match your search criteria.
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Active
4080 Looking Glass Ln  2905 Naples
$298,999
  • 2Bedrooms
  • 2Bathrooms
  • 1212Sq Ft
  • 1988Year Built
$298,999

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 dining area, a…

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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…

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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…

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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
4250 Jack Frost Ct  4505 Naples
$252,900
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1990Year Built
$252,900

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…

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
4070 Northlight Dr  1612 Naples
$290,000
  • 2Bedrooms
  • 2Bathrooms
  • 1234Sq Ft
  • 1987Year Built
$290,000

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…

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
3410 Frosty Way  4802 Naples
$260,000
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1987Year Built
$260,000

Welcome to this beautifully maintained 2-bedroom, 2-bath second-floor end unit in the highly sought-after western section of the Winterpark community of Naples, FL. This light-filled home enjoys a desirable southern exposure, allowing sunshine to pour through the spacious rear windows and brighten the open living area all day long. Inside, you’ll appreciate the tasteful tile…

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
4200 Looking Glass Ln  4207 Naples
$229,000
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$229,000

Most of the updating has already been taken cared of! Select a vinyl flooring of your choice to lay over existing tile for a totally remodeled look! Close to Beautiful Downtown Naples and the Naples Beach! This 2 bedroom, 2 bath condominium has an Open Floor Plan with Split Bedrooms and offers a totally remodeled/upgraded…

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
3832 Snowflake Ln  1207 Naples
$254,900
  • 2Bedrooms
  • 2Bathrooms
  • 1300Sq Ft
  • 1985Year Built
$254,900

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…

Active
4001 Ice Castle Way  3607 Naples
$220,000
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1986Year Built
$220,000

MOTIVATIVE SELLER, MAKE AN OFFER ...Charming 2-Bedroom, 2-Bathroom First-Floor Condo in Naples, FL A beautifully maintained 2-bedroom, 2-bathroom first-floor condo, in the heart of Naples, FL. Features all-tile flooring throughout, impact-resistant windows for added peace of mind, and updated kitchen and bathrooms. Enjoy granite countertops and sleek stainless steel appliances. Offers spacious living, open…

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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