Winterpark Real Estate in Naples, Florida

The Winterpark neighborhood is another outstanding Naples community represented by Calusa Bay Properties. For more information on real estate listings in Winterpark or any other specific Naples property, contact our expert team of Naples realtors at Calusa Bay Properties.

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49 listings match your search criteria.
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Active
4053 Northlight Dr Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1314Sq Ft
  • 1987Year Built
$309,000

Fantastic location, only five minutes from Downtown and the pristine beaches of Gulf of Mexico. Indulge in the thoughtfully crafted split floor plan that seamlessly accommodates both entertainment and ample bedroom space. Beautifully updated 1st floor unit with 2 bedrooms, 2 baths impact resistant windows. Resort style pool, tennis, pickleball, bocce court…

Active
4130 Looking Glass Ln Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$284,900

Rare opportunity alert! Quiet second floor END UNIT with rare exterior side windows in the living room and dining room that bring an abundance of natural light throughout the day and views of the beautiful landscaped grounds surrounding the coveted Winterpark community. Boasting 2 bedrooms, 2 baths, and brand new stainless steel appliances, this gem…

Closed
3470 Frosty Way Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1987Year Built
$277,500

Welcome to this spacious first-floor end unit condo located just 3 miles from the heart of downtown Fifth Avenue and the stunning Naples beaches. Conveniently situated on Frosty Way just steps away from a plethora of amenities which include, pickleball, tennis, bocce, and a large beautiful resort style pool, ensuring endless entertainment options at…

Active
4018 Northlight Dr Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1986Year Built
$280,000

OPEN TO THE PUBLIC SATURDAY APR 27TH FROM NOON - 2:00PM! Discover the allure of this 2-bed, 2-bath Winterpark residence featuring a private southern rear exposure and recent enhancements. The kitchen boasts tons of cabinets, new stainless steel appliances, and a convenient breakfast bar. Indulge in the thoughtfully crafted split floor plan that seamlessly accommodates…

Active
3832 Snowflake Ln Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1200Sq Ft
  • 1985Year Built
$310,000

WINTERPARK IS A HIDDEN GEM WITH A VERY DESIRABLE LOCATION... 2-3 MILES TO BAYFRONT, 5TH AVE, DOWNTOWN RESTAURANTS AND SHOPS, AND THE BEACHES... 2/2 FIRST FLOOR UNIT WITH LARGE SCREENED IN PATIO... WALK TO RESORT STYLE POOL (ONE OF THE LARGEST IN NAPLES) / EIGHT TENNIS COURTS... FULLY FURNISHED TURNKEY... NEW HW TANK, POLY PIPES…

Active
4070 Looking Glass Ln Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1988Year Built
$340,000

This spacious 2 bedroom, 2 bathroom condo is located in the condo community of Winterpark located off Davis Blvd in East Naples. The condo is being sold turnkey with contemporary/modern furniture and includes many upgrades, faux wood tile flooring, newer built in kitchen cabinets, granite countertops, modern contemporary decor, stainless steel appliances. Amenities include, large…

Closed
4130 Looking Glass Ln Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$275,000

This 2 bedroom 2 bath condo features tile throughout. The unit is in the community of Winterpark. Winterpark is close to King's Lake Square with a Publix, dining and shopping.

Active
3558 Antarctic Cir Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1986Year Built
$340,000

Impeccable designer-renovated ground floor turnkey 2 bedroom/2 bath end unit condo in the desirable Winterpark community! This condo features a stunning brand new kitchen with quartz countertops, high-quality white cabinets, herringbone backsplash and stainless steel appliances. Modern seamless tiling throughout the unit with a beautiful master suite featuring a spacious walk-in closet and brand new…

Active
3480 Frosty Way Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1987Year Built
$295,000

Come see this 2BR/2BA condo in Winterpark located 3 miles to downtown 5th Ave area. Condo features new floors and high impact glass - no road noise! This condo is sold 'Turnkey' and is ready for immediate occupancy. These condos make great renatls becuase of the location and 10,000 sq ft pool! Additional community features…

Active
4030 Ice Castle Way Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1988Year Built
$319,000

Winterpark Condominiums are conveniently located close to Downtown Naples shopping, fine dining, entertainment and world-renowned white sand beaches. Recently renovated Kicthen with White Shaker soft close cabinets, white subway tile backsplash and gorgeous quartz counter tops with silver flecks, bathrooms have been remodeled with new vanities and custom mirrors and updated lighting, fresh coat of…

Active
4200 Looking Glass Ln Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$280,000

Buyer was denied financing. Inspection was spotless and report available. 2 bed/2 bath, 2nd floor condo in the popular Winterpark community With a MASSIVE RESORT-STYLE POOL, pickleball, tennis, bocce, paved walking/bike paths and organized activities. Only 3 miles to beautiful downtown Naples. Enjoy the Gorgeous white sand gulf beaches and the Naples…

Active
3678 Arctic Cir Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1985Year Built
$319,900

This unit is what living in Florida is all about. FIRST FLOOR 2 bedroom/2 bath condo in the wonderful WINTERPARK Community. The location of this unit is steps to the incredible RESORT-STYLE pool, clubhouse, bocci & newly renovated tennis & pickleball courts. The kitchen is a dream, newly updated. The living-dining area is extremely spacious…

Closed
3805 Snowflake Ln Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1256Sq Ft
  • 1985Year Built
$290,000

Welcome to 3805 Snowflake Ln, located in the beautiful Winterpark Community. This 2 bedroom, 2 bath condo is situated on the first floor and within walking distance of the big resort style pool, club house, and newly renovated tennis courts. Enjoy the views of the pool from your patio, and the convenience of having…

Closed
4021 Ice Castle Way Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1248Sq Ft
  • 1988Year Built
$320,000

Stunning Designer Renovated And FURNISHED!!!! Large 2/2 1246 sq ft,MOST DESIRED 1st floor Chic Beach Coastal Condo TURNKEY in the very Desirable Winterpark community. Proudly having one of the Larges Resort Style Swimming Pools in Naples,with tennis courts,bocce, and walk to Publix,Starbucks,restaurants,and downtown 5th ave is all close by.Airport 25 min away. Kitchen has…

Closed
3574 Antarctic Cir Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1986Year Built
$260,000

With full price offer, there will be a $10,000 Seller Concession at closing. Exceptional affordable condo in Naples, Florida. This stunning residence offers the perfect combination of convenient location, luxurious amenities, and an enviable coastal lifestyle. Close proximity to the beach and downtown Naples with world-class shopping, dining, and recreational opportunities, this condo presents an…

Active
4210 Looking Glass Ln Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$300,000

Very nice 2 bedroom, 2 bath condo. Within walking distance of shopping and other amenities and only 4+ miles to Naples famous beaches and all the ambience of Olde Naples historic district, such as excellent restaurants, boutiques and other specialty shops. Community resort style pool and tennis courts. Turnkey furnished…

Active
4210 Looking Glass Ln Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1985Year Built
$260,000

**EXCELLENT INVESTMENT OPPORTUNITY WITH A HUGE REDUCTION IN PRICE!** This 2 Bedroom/2 Bath downstairs unit is located in the desirable community of Winterpark which features a resort style pool, a Clubhouse & tons of additional amenities. This downstairs' units are desirable because they provide an additional entertaining area in the lovely landscaped backyard where you…

Active
4150 Looking Glass Ln Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$288,000

Winterpark Condominiums are conveniently located close to Downtown Naples shopping, fine dining, entertainment and world-renowned white sand beaches. The amenities include resort-style community pool, tennis & pickle ball courts, bocce and the community clubhouse with regular activities just steps away. This Turn key well kept unit is 2 bed 2 bath 1246 sq ft with:…

Active
3730 Northwinds Dr Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1985Year Built
$289,000

This Turn-Key Condo is the one you've been looking for! It overlooks the resort style pool and is ready to move in to. Winterpark features bike and jogging trails, tennis and pickle ball courts, bocce ball and a wonderful clubhouse that has a library and lots of activities! The Winterpark community is ideally located only…

Active
4080 Looking Glass Ln Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$309,500

This immaculate 2-bedroom, 2-bath home boasts a pristine interior with a laundry in residence for your convenience. Enjoy the luxury of completely renovated bathrooms, complemented by elegant plantation shutters in the bedrooms for added charm. The updated kitchen features stylish countertops and a contemporary backsplash. The owner has thoughtfully enclosed the front lanai, providing a…

Closed
3645 Arctic Cir Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1985Year Built
$315,000

This is the Best Location in Naples. It's just a 5 minute drive to the beachs, downtown Naples, shopping and more! This Very well maintained Updated 1st floor unit has New Hurricane windows, New plumbing, New Bathrooms with a walk in shower in the Master. The kitchen offers quartz countertops with New kitchen Cabinets. …

Closed
3400 Frosty Way Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1296Sq Ft
  • 1987Year Built
$310,000

Superbly located close to Downtown Naples shopping, fine dining, entertainment and world-renowned beaches. The Winterpark community amenities include resort-style community pool, tennis & pickle ball courts, bocce and the community clubhouse with regular activities just steps away. Completely renovated 2 bedroom, 2 bathroom, first floor condo has Tile and laminate flooring throughout the spacious open…

Closed
3676 Arctic Cir Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1985Year Built
$310,000

Beautifully renovated condo in much sort after Winterpark community. This unit is turnkey, with everything you need to enjoy your time in Naples. Spacious 2 bed/2 bath condo with open floor plan, and split bedroom design. Upgrades include: new kitchen cabinets, granite countertops, tile flooring, new plumbing, bathroom vanities, hurricane impact window and a new…

Closed
3666 Arctic Cir Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1985Year Built
$187,000

First-floor end unit with 2 bedrooms and 2 full baths in the community of Winterpark. Beautifully maintained and updated and uniquely redesigned to create formal dining. Updates include wood flooring in the kitchen and dining room with crown molding. New hot water heater, new water pipes, newer vinyl clad windows, A/C in 2015 and very…

Closed
4070 Looking Glass Ln Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1988Year Built
$192,500

Lovely unit features nice updates in kitchen & bathrooms. New A/C system 12/2020, shaker cabinets in kitchen with granite counter-tops, subway tile backsplash, stainless appliances and plank flooring throughout. Wintepark offers resort style swimming pool, newly renovated clubhouse tennis and pickle ball courts. Enjoy the convenience of local shopping and just minutes to downtown.…

Closed
4060 Ice Castle Way Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1988Year Built
$154,000

PRICED TO SELL! This is the lowest priced unit in Winterpark! Being sold turnkey, master walk-in closet, vaulted ceilings, open floor plan. This unit has lots of potential ! Great location !

Closed
3624 Arctic Cir Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1985Year Built
$178,000

This well maintained , Spacious 2BR/2Bath Unit is being sold Turnkey. It is well appointed and well stocked. Newly updated kitchen with granite countertops and new stainless steel appliances. Newer A/C unit & hot water heater. New Roof. Beautiful tile floor. Spacious laundry room with full size washer & dryer in unit with…

Closed
3569 Antarctic Cir Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1986Year Built
$210,000

This 2019 completely remodeled to the studs, ground floor condo, only 10 minutes from the beach and downtown Naples, is waiting for you to call home or make it your vacation home! The gourmet kitchen is complete with new custom built cabinets, quartz countertops, and new stainless steel appliances. Step out to your lanai off…

Closed
4031 Ice Castle Way Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1988Year Built
$305,000

This is a lovely and spacious 2 bedroom first floor condominium in Winterpark V with nice tile flooring, beautiful kitchen with breakfast bar and stainless appliances. There is a large laundry room and the air conditioning equipment was new in 2020. Nice tile flooring throughout. There is a front screened porch and the designated…

Closed
4030 Ice Castle Way Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1988Year Built
$250,000

This is a handyman's dream! What a great opportunity to own just minutes to Naples' award winning white sand beaches! This condo needs some TLC but is very spacious and has many possibilities! The bedrooms are large with great closet space and the great room area is huge. The …

Closed
4001 Ice Castle Way Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1987Year Built
$177,000

This the best value in Naples - just minutes to the beach and conveniently located to great restaurants, shopping, banks and more! This lovely 2 bedroom condo has been meticulously cared for and is ready to move into! Some of the many great features and updates include hurricane impact windows and doors, plantation…

Closed
3654 Arctic Cir Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1985Year Built
$365,500

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Active
4220 Looking Glass Ln Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$309,000

Discover refined living in this exquisite 2-bed, 2-bath sanctuary on the second floor. As you enter, the soaring ceilings create an immediate sense of openness, complemented by exquisite tile flooring throughout.The kitchen is a masterpiece, featuring granite countertops, new cabinets, new AC 2024 and state-of-the-art appliances that redefine modern living. Entertaining is a joy in…

Active
4084 Northlight Dr Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1284Sq Ft
  • 1987Year Built
$299,900

This Winterpark 2 bed, 2 bath unit is a must-see with its private southern rear exposure and recent renovations. The kitchen boasts hard wood cabinets, granite countertops, and a breakfast bar, the split floor plan is perfect for entertaining guests or for working from home in your home office. Newer carpet and wood plank tile…

Closed
4250 Jack Frost Ct Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1990Year Built
$275,000

LOWEST PRICED UNIT ON THE MARKET AND AND END UNIT!!! Ohhhh the view...wide open green space....check this out! You rarely get this view and private feel in Winterpark and this unit is an End unit so it has only one shared wall and extra outdoor storage. This condo unit is move in ready sold…

Closed
3552 Antarctic Cir Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1986Year Built
$300,000

Move-in ready and completely renovated, this two-bedroom, two-bath condominium is just five miles from downtown Naples and beaches. The sparkling white kitchen has custom cabinets, quartz countertops and stainless steel appliances. Both bathrooms have been completely remodeled including raised ceilings. Updated flooring and beautiful plantation shutters throughout complete this sanctuary. Save on electric bills with…

Closed
3712 Northwinds Dr Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1985Year Built
$300,000

LOCATION, LOCATION, LOCATION!! Only 3 miles from Naples Down Town, fine dining, shopping and the sandy Naples Beaches . This two bedroom, two bath updated and very well maintained condo located only steps from the resort style Winterpark pool is move in ready. This very active community offers you one of…

Closed
3504 Antarctic Cir Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1986Year Built
$230,000

END UNIT - 2 bedroom/2 bath condo in the highly desired WINTERPARK Community....The unique feature of this condo is it's location...directly across and steps away from the incredible RESORT-STYLE pool, CLUBHOUSE, and TENNIS/PICKLEBALL COURTS. This condo lives very large with 1246 Sq Ft plus a front screened lanai. The living-dining area is extremely…

Closed
3838 Snowflake Ln Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1987Year Built
$275,000

FOR SALE!! Nice two bed room two bath second floor condo in WINTERPARK sells turn key furnished. Stunning view and walking distance to pool and tennis courts. Conveniently located only minutes to Naples Down Town, shopping, fine dining and the beautifully Naples beaches.

Closed
3460 Frosty Way Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1987Year Built
$273,000

Lowest Priced unit in Winterpark! 2nd Floor Vaulted Ceiling End Unit! It is all about location in this superbly located community close to Downtown Naples shopping, fine dining, entertainment and world-renowned white sand beaches. The amenities include resort-style community pool, tennis & pickle ball courts, bocce and the community clubhouse with regular activities just steps…

Closed
4001 Ice Castle Way Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1987Year Built
$315,000

Prepare to be amazed by what this must-see condo has to offer less than 3 miles from 5th Avenue. Move-in ready with recent renovations. Beautifully remodeled kitchen including white shaker cabinets and quartz counters for a stylish and modern culinary space. Home features all-tile, hardwood and laminate flooring, making it easy to clean and maintain.…

Closed
3627 Arctic Cir Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1985Year Built
$265,000

Location, Location, location!! This condo is less than 3 miles from the beach, and the Olde Naples exquisite shopping & dining district. Also only a 20 minute walk (1 mile) to the King's Lake plaza that offers just about everything...Publix, Starbuck's, banks, several restaurants, pet supermarket, dry cleaning and so much more! This condo…

Closed
4020 Ice Castle Way Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1988Year Built
$299,999

This completely renovated unit is just 8 minutes away from the beach, 5th Ave South, and downtown Naples. This 1st floor condo features 2 bedrooms, 2 bathrooms, a walk in master closet, updated title flooring, renovated kitchen, new stainless steel appliances with an extra 10 year transferable manufacture warranty. Perfect to live in or use…

Closed
4050 Ice Castle Way Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1990Year Built
$299,000

2 bedroom, 2 bathroom first floor END UNIT condo with A LOT OF PRIVACY!!! Being offered TURNKEY FURNISHED. A front screened in lanai, extra storage closet and a patio setting in the backyard. Great AMENITIES: LARGE clover leaf shaped community pool (IT IS HUGE), tennis courts, bocce and shuffle board. Winterpark is close to…

Active
4180 Looking Glass Ln Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$299,900

Seller would love an offer! This gorgeous well maintained first floor (no stairs!) 2 bedroom 2 bath condo is only 3 miles from downtown Naples - shopping, restaurants, entertainment, and the sandy beaches. The master suite has a full bath plus a large walk-in closet. Impact/hurricane windows throughout. Enjoy your morning coffee or happy hour…

Active
3834 Snowflake Ln Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1985Year Built
$315,000

LOCTION, LOCATION, LOCATION, this nicely furnished and very well maintained 2. floor condo sells turnkey furnished. Stunning view from living room and master bed room. Screened in front lanai. Hurricane resistant windows, new water pipes. Very close to the big resort style pool. Winterpark is conveniently located only minutes to Naples down town, shopping ,…

Active
4140 Looking Glass Ln Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$399,900

LOCATION! LOCATION!! LOCATION !!! New water heater / New HVAC System / New hurricane impact windows and doors throughout. Experience luxurious living in this fully updated and upgraded 1st floor end-unit, ideally situated in the sought-after Winterpark Community, moments away from restaurants, shops, and grocery stores. Featuring 2 bedrooms and 2 bathrooms in 1246 square feet…

Active
4200 Looking Glass Ln Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$310,000

Looking for a Winter Park unit with everything done? 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 right outside…

Active
3512 Antarctic Cir Winterpark Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1986Year Built
$289,000

Don't miss out on this incredible opportunity to purchase a turnkey 2 bedroom, 2 bath condo in the resort community of Winterpark! This second floor condo features soaring ceilings, updated kitchen with white cabinets, granite counters and stainless appliances, tile floor throughout on the diagonal, plantation shutters, tons of storage in the expansive laundry room…

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