The community of Winterpark is located in Naples. Ideally situated for access to all of the Naples area facilities and conveniences has to offer.

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29 listings match your search criteria.
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Active
3430 Frosty Way Way  12 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1987Year Built
$299,000

Welcome to the amazing Winterpark community just minutes from downtown Naples! This 2 bed 2 bath condo has been remodeled from top to bottom! Starting with the brand new kitchen and all new appliances. Updated bathrooms, plumbing and all new flooring! This condo will be a great winter getaway or investment property. Winterpark has…

Active
4200 Looking Glass Ln  4206 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$297,000

Looking for a Winter Park unit with everything done under $300k? This sparkling and well-maintained home will delight you - updated kitchen and baths with Uba Tuba granite, large owners suite with walk in closet, engineered wood floors, high ceilings, impact windows and slider, plumbing and AC updated. Extra storage under breakfast bar. Reserved parking…

Active
4092 Northlight Dr  1707 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1264Sq Ft
  • 1987Year Built
$288,000

Light and Bright First Floor Condo. This large 2 bedroom/ 2 bath Split Bedroom home has Sunny Southern Exposure and Private backyard landscape views. Winterpark is located just 3 miles from 5th Avenue and The Pristine Gulf Beaches. It is an amenity rich community with a Newly Refurbished, large Resort Style Pool, Brand New Pickleball Courts,…

Active
4200 Looking Glass Ln  4202 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$279,900

Newly renovated 2 bedroom, 2 bath Condo Available! Just 4 miles to beautiful downtown Naples! 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, Bocce, Walking and Bike Paths, and a resort style community pool. Great for…

Active
4080 Looking Glass Ln  2908 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1300Sq Ft
  • 1990Year Built
$279,500

Bright and spacious 2 bdrm/2 bth 2nd floor condo with all new storm impact windows, newly renovated bathrooms, tile throughout, laundry rm in residence... spectacular location only 2 miles to Bayfront, 5th Ave shops, dining, and beaches... the Winterpark community amenities include tennis courts, pickleball, shuffleboard, bocce, large resort style community pool surrounded by palm…

Active
3519 Antarctic Cir  2410 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1986Year Built
$279,000

Winterpark Condo- close to downtown Naples, Low HOA fees and great amenities! Relax in this 2 bedroom/ 2 bath condo conveniently located close to downtown Naples and all the wonderful beaches, restaurants and shopping Naples has to offer! This second floor condo has been updated with new laminate flooring throughout! No Carpet! The master bathroom…

Active
3750 Northwinds Dr  1010 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1985Year Built
$274,900

This is an amazing listing! Winterpark in Naples truly seems like a dream for someone looking to enjoy an active and vibrant lifestyle. The proximity to the pool (right in the back yard) plus all the fantastic amenities like pickleball, tennis, bocce, and that huge resort pool, make it very attractive. The updates (new air conditioner,…

Active
3832 Snowflake Ln  1207 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1300Sq Ft
  • 1985Year Built
$269,000

WINTERPARK IS A HIDDEN GEM WITH A VERY DESIRABLE LOCATION... 2 BDRM 2 BATH FIRST FLOOR UNIT WITH LARGE SCREENED IN PATIO LOOKING OUT TO LUSH LANDSCAPING... 2-3 MILES TO BAYFRONT, 5TH AVE, DOWNTOWN RESTAURANTS AND SHOPS, AND THE BEACHES... ... WALK TO RESORT STYLE POOL (ONE OF THE LARGEST IN NAPLES) / FIVE TENNIS…

Active
4130 Looking Glass Ln  3802 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$259,990

Discover this investor's dream in the heart of Winterpark! This 2 bedroom 2 bathroom end unit, top floor condo is READY TO SELL! CASH BUYERS ONLY... No financing contingency. With high ceilings and an abundance of natural sunlight streaming through every room, you'll immediately feel the warmth and openness of this inviting space. NEWLY added…

Active
3480 Frosty Way  4 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1987Year Built
$259,900

Welcome to WinterPark! This spacious and bright turnkey 2-bedroom condo features soaring volume ceilings, an open and efficient floor plan, hurricane impact windows, a screened-in front porch and additional storage under stairs. The bedrooms are generously sized with large closets, and the laundry room offers additional storage. Upgrades include new CPVC plumbing (2020), a…

Active
4210 Looking Glass Ln  4210 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$254,900

you will be impressed with the light and bright and spacious feel in this 2 bedroom, 2 bath condo. It has vaulted ceilings and is tastefully turnkey furnished. The furniture is negotiable. There is extra storage too. Shopping and restaurants are within walking distance of the condo. there is a resort…

Active
4040 Ice Castle Way  2807 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1990Year Built
$245,000

***WINTERPARK***QUAINT CONDO***2BEDS/2BATHS***FULLY FURNISHED***DOGS ALLOWED*** Welcome to this charming 2-bedroom, 2-bathroom condo located in the beautiful city of Naples, FL. This cozy home is perfect for those seeking a comfortable and convenient living space. The unit comes fully furnished, allowing you to move in hassle-free and start enjoying your new home right away. The community offers a…

Active
4001 Ice Castle Way  3602 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1987Year Built
$234,000

This is the best value in Winterpark! This spacious well cared for 2 bedroom condo offers soaring ceilings, an open, efficient floor plan, updated kitchen, hurricane impact windows and more! The bedrooms are spacious with large closets and the laundry room offers additional storage, as well as outdoor storage under the stairs. This condo…

Active
4150 Looking Glass Ln  5 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$219,000

BEST DEAL 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. Seller never had any flood damage or water intrusion at all, in the 15…

Active
3608 Arctic Cir  514 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1250Sq Ft
  • 1985Year Built
$4,200

Check out this charming second-floor condo in Winterpark Community. It's super spacious, filled with light, and features a split-level layout. Just a short walk to the pool and tennis courts, Winterpark boasts a resort-style pool and lovely open spaces. Plus, it's conveniently located just minutes from 5th Avenue, where you can enjoy dining, shopping,…

Active
4180 Looking Glass Ln  4104 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$4,000

SEASONAL RENTAL AVAILABLE (APRIL 2025) LOCATED IN CLOSE PROXIMITY TO NAPLES BEACHES, 5TH AVE IN DOWNTOWN NAPLES, & THE BEST SHOPPING & DINING NAPLES HAS TO OFFER! This condo has been completely remodeled and is fully furnished with designer quality finished and equipped for your winter getaway. The community features a newly renovated resort style…

Active
3400 Frosty Way  5 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1284Sq Ft
  • 1987Year Built
$3,500

Gorgeous 1st floor 2 bedroom / 2 bath turnkey furnished condo in Winterpark. Property features granite countertops, stainless steel appliances, wood plank tile, and a split floorplan that is perfect for entertaining guests. The primary suite has a spacious walk-in closet and a tranquil landscaped view. Property features two screened in outdoor areas that…

Active
4084 Northlight Dr  1703 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1284Sq Ft
  • 1987Year Built
$3,500

Must see 1st floor 2 bedroom / 2 bath turnkey furnished condo in Winterpark available for the 2026 Winter. Property features granite countertops, wood plank tile, and a split floor plan that is perfect for entertaining guests. The primary suite has a spacious walk-in closet and a tranquil landscaped view. Guests enjoy the community's resort-style…

Active
3511 Antarctic Cir  2406 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1986Year Built
$3,500

AVAILABLE FOR JANUARY, FEBRUARY, AND MARCH 2026 AND NOW TAKING RESERVATIONS FOR THOSE DATES. THIS IS A NICE TWO BEDROOM UNIT IN WINTERPARK DEVELOPMENT WITH A CLOSE PROXIMITY TO DOWNTOWN, BAYFRONT, TIN CITY, FIFTH AVE, AND THE BEAUTIFUL WHITE SAND BEACHES OF NAPLES. THIS CONDO IS FULLY FURNISHED AND READY FOR YOUR COMFORTABLE STAY.

Active
4210 Looking Glass Ln  4210 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1300Sq Ft
  • 1989Year Built
$3,300

Very nice 2 bedroom, 2 bath 2nd floor condo with resort style community pool and tennis courts. Close to shopping and restaurants and only a short drive to Naples famous pristine beaches and fabulous world renowned restaurants and boutiques. Turnkey furnished.

Active
4010 Ice Castle Way  7 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1314Sq Ft
  • 1988Year Built
$3,200

Available short term or long term. Lovely 2 bedroom 2 bath close to Downtown, Beaches and shopping. 1st floor, newer kitchen, all tile. Fabulous resort style amenities. Walk to shopping and dining.

Active
3676 Arctic Cir  112 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1985Year Built
$2,700

AVAILABLE FOR 6 MONTHS AT A TIME. AVAILABLE APRIL-DEC 2025. Recently updated with tile flooring, granite counter tops and painted in neutral gray tones. Winter Park has one of the largest pools in Southwest Florida, with tennis, pickleball, bocce Courts and a clubhouse. It is only 5 miles from 5th Avenue and Downtown Naples! Book…

Active
4240 Jack Frost Ct W 4410 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1990Year Built
$2,300

AVAILABLE IN MARCH 2025. Beautiful condo, spacious and bright. Fully furnished available for a yearly lease. Close to downtown Naples, Beaches, Restaurants and shopping. Great floor plan, good size bedrooms and spacious laundry room and storage. Water included in monthly rent. Rented turnkey. Computer and printer do not convey.

Active
4100 Looking Glass Ln  3008 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1250Sq Ft
  • 1988Year Built
$2,250

Completely remodeled condo. Close to downtown and beaches. Water and trash included.

Active
4060 Ice Castle Way  10 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1988Year Built
$2,200

Short Term or Long Term Rental Available. Perfectly appointed 2 bedroom, 2 bath condo. This entire home has been renovated and tastefully decorated. Primary bedroom offers King size bed, bathroom with walk in shower. The 2nd bedroom has a Queen size bed. The guest bathroom will surprise you with a wonderful Jacuzzi tub for…

Active
4270 Jack Frost Ct  5 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1250Sq Ft
  • 1990Year Built
$2,000

AVAILABLE MAY 15TH-DECEMBER 31ST, 2025! Lovely updated ground-floor condo in the popular Winterpark community! This unit is beautifully furnished, tastefully decorated & well maintained, with new paint, tile floors, updated baths with tub and shower. Kitchen features new cabinets, granite countertops & stainless steel appliances. Enjoy all the wonderful amenities that this community has to…

Active
4230 Jack Frost Ct  4402 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1990Year Built
$1,900

Situated in one of Naples' most coveted areas, this rental property boasts an unbeatable location. Nestled within less than 2 miles of Naples' pristine beaches, downtown attractions, upscale shopping districts, renowned dining establishments, and the charming waterfront destination of Tin City, residents will experience the epitome of convenience and coastal living. This second-floor end unit…

Active
4261 Jack Frost Ct  4707 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1990Year Built
$1,870

Annual rental , first floor end unit condo in Winterpark close to the Kings Lake Plaza. 2 bedrooms, 2 bathrooms. New luxury tile vinyl flooring, just painted, patio in front, large laundry room, exterior storage closet by the front door. Spacious condo, great location, available March 1, once approved by the HOA.…

Active
3511 Antarctic Cir  2406 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1986Year Built
$1,650

GREAT PRICE ON THIS LONG TERM TWO BEDROOM, TWO BATH CONDO AVAILABLE APRIL 2 TO DECEMBER 27, 2025! FULLY FURNISHED FOR YOUR COMFORT AND CONVENIENCE. WINTERPARK HAS MANY AMENITIES INCLUDING CLUBHOUSE, COMMUNITY POOL, COMMUNITY SPA, EXERCISE ROOM, TENNIS AND MORE.... JUST A SHORT DRIVE TO FIFTH AVE, TIN CITY, BAYFRONT, DOWNTOWN, AND THE BEAUTIFUL WHITE…

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