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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Active
4140 Looking Glass Ln  7 Naples
  • 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
4030 Northlight Dr   Naples
  • 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
3400 Frosty Way  5 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1284Sq Ft
  • 1987Year Built
$299,000

Welcome to Winterpark—one of Naples’ most convenient, low-maintenance communities—just minutes from 5th Avenue, Bayfront, Tin City, and the Gulf. This first-floor 2 bedroom, 2 bath residence has undergone an extensive and impeccable REMODEL, delivering a bright, open split-bedroom plan designed for easy living and privacy. Every finish feels intentional and move-in ready. Tile flooring flows…

Active
4073 Northlight Dr  1803 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1234Sq Ft
  • 1987Year Built
$265,000

First-floor 2BR/2BA condo in the highly desirable Winter Park community and located in Winter Park IV. This light and spacious home features an inviting screened front porch, a bright open living and dining area with modern flooring, and a stylish kitchen with white cabinetry, granite counters, stainless steel appliances, and a mosaic tile backsplash. The…

Active
4001 Ice Castle Way  3605 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1987Year Built
$265,000

Fully renovated in March 2022 with brand new kitchen, floors, hurricane windows & doors, and new 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…

Active
3420 Frosty Way  4902 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1987Year Built
$262,000

One or more photo(s) has been virtually staged, AI generated or rendered. Move-in ready, exceptionally well-maintained condo. Welcome to Winterpark, a tropical retreat in the heart of Naples. This cozy high-ceilings 2nd-floor END-UNIT condo offers 2 bedrooms, 2 bathrooms, and a desirable concept floor plan with a spacious living area, designed for comfortable Florida…

Active
4230 Jack Frost Ct  7 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1988Year Built
$259,900

Offered turnkey furnished with desirable western exposure, this spacious, light-filled first-floor condominium presents an exceptional opportunity to enjoy the Naples lifestyle with low fees, resort-style amenities and outstanding convenience. Featuring two bedrooms, two full baths and 1,246 square feet of thoughtfully designed living space, this inviting residence offers a comfortable blend of updated interiors, ample…

Active
3574 Antarctic Cir  2107 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1986Year Built
$255,000

Looking for that perfect seasonal sanctuary or cozy abode in the heart of Naples? Look no further! This first floor two bedroom, two bathroom is ready for move in. With amazing updates all throughout, this condo shows like new. A beautifully updated and spacious kitchen has brand new stainless steel appliance that have never been…

Active
4100 Looking Glass Ln  3008 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1250Sq Ft
  • 1988Year Built
$255,000

Welcome to **4100 Looking Glass Ln #8**, a great opportunity to own in Naples! This inviting residence offers a comfortable and functional layout with plenty of natural light and a relaxed Florida feel. Conveniently located near shopping, dining, entertainment, golf, downtown Naples, and the beautiful Gulf beaches. Whether you're looking for a future residence or…

Active
4031 Ice Castle Way  3306 Naples
  • 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
4065 Northlight Dr  1807 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1234Sq Ft
  • 1987Year Built
$250,000

!!!You cannot get a better location and square footage for the money this close to town in any other community!!! PET-FRIENDLY -- spacious FIRST floor 2BR/2BA garden apartment is only a few minutes to downtown Naples and all the wonderful activities, shopping, restaurants, entertainment and of course, the world-renowned beaches! The updated residence is LIGHT…

Active
4038 Northlight Dr  1506 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1234Sq Ft
  • 1986Year Built
$249,900

Lake views and a prime in-town Naples location define this move-in-ready 2-bedroom, 2-bath second-floor condo in Naples Winterpark IV. Enjoy water views over the community lake from a screened porch made for Southwest Florida mornings and evenings. The bright split-bedroom plan offers comfortable living and dining space, a full appliance package, and ceiling fans throughout. Ownership includes…

Active
3532 Antarctic Cir  2216 Naples
  • 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…

Active
4096 Northlight Dr  1709 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1986Year Built
$239,000

For sale is this 2 bedroom 2 bath 1st floor end unit beautiful Winterpark Naples condo. A short drive or walk to Naples world famous white sandy sunny beaches. Northlight dr is a great location and you just can not beat this wonderful community.

Active
4050 Ice Castle Way  2812 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1988Year Built
$239,000

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
4230 Jack Frost Ct  4402 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$230,000

One or more photo(s) has been virtually staged, AI generated or rendered. Soaring vaulted ceilings. Exceptional amenities. Prime Naples location. Great value! Located in the quiet and well-established Winterpark community, this spacious 2 BR / 2 BA condo offers 1,246 s/f and a blank canvas ready for its next owner’s vision. Step inside to…

Active
3816 Snowflake Ln  1303 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1985Year Built
$224,000

Welcome to Winter Park! Ready for its next owner, this charming 2-bedroom, 2-bathroom centrally located condo is a fantastic find. It features hurricane-resistant windows and a delightful patio perfect for your morning coffee. Well-priced and full of potential, this home is waiting for your personal touches! Roof 2 years old - AC 2018 - Water…

Active
4079 Northlight Dr  2 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1234Sq Ft
  • 1987Year Built
$220,000

Welcome to this spacious and beautifully updated second-floor end-unit condo in the desirable Winterpark community. Freshly painted throughout, this home features an upgraded kitchen and bathrooms, high ceilings, and exceptional storage, including an attic, a spacious laundry room, and an outdoor storage closet. Smart-home features add modern convenience, including Lutron Caséta lighting controls, a smart thermostat,…

Active
4001 Ice Castle Way  1 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1987Year Built
$215,000

FIRST FLOOR, END UNIT, PAVERED PATIO! Sun-drenched END UNIT with natural light from sunrise to sunset. Escape to this meticulously maintained 2-bedroom condo featuring a NEW air conditioning system, hurricane windows and doors, plus PLANTATION SLIDERS and SHUTTERS. The open, spacious floor plan offers large bedrooms and abundant storage, with California Closets beautifully…

Active
4200 Looking Glass Ln  4204 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$209,000

Welcome home to this beautifully maintained Winter Park condo offering over 1,200 square feet of comfortable living space with peaceful green space views. This spacious residence features 2 bedrooms and 2 bathrooms, providing an ideal layout for both everyday living and entertaining. Enjoy the resort-style community with exceptional amenities, including a sparkling resort swimming pool,…

Active
3608 Arctic Cir  514 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1250Sq Ft
  • 1980Year Built
$4,200

Welcome to 3608 Arctic, a beautifully furnished rental offering flexible short-term accommodations in a highly desirable location. This well-maintained home features a bright, open living space, a fully equipped kitchen, and comfortable sleeping arrangements—perfect for vacationers, relocating professionals, or seasonal residents. Enjoy a move-in-ready experience with stylish furnishings, modern conveniences, and inviting indoor-outdoor living areas designed…

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

OFF SEASON RENTAL AVAILABLE STARTING APRIL 2027. 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…

Active
3563 Antarctic Cir  2102 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1200Sq Ft
  • 1986Year Built
$3,800

What a great rental opportunity in the highly sought after community of Winterpark! This 2 bedroom, 2 bathroom condo is a second floor end unit and is immaculate! Wood floors with custom wood working all throughout the condo. The kitchen is beautifully updated with stainless steel appliances and a massive granite countertop. Entertain your guests…

Active
4060 Ice Castle Way  10 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1988Year Built
$3,600

Your Perfect Naples Home Away from Home! and you can bring your pet too! Short-Term Rental Available! Welcome to your beautifully renovated and tastefully decorated 2-bedroom, 2-bath condo, offering the perfect blend of comfort, style, and convenience for your Naples getaway. The spacious primary bedroom features a luxurious king-size bed and a private bathroom with a walk-in shower.…

Active
3602 Arctic Cir  515 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1985Year Built
$3,200

Ideally located in the sought-after Winterpark community, this first-floor unit is just minutes from Downtown Naples and the beautiful beaches! This bright and spacious home features modern finishes throughout, an updated kitchen with stainless steel appliances, stylish bathrooms, and an open-concept living area. Winterpark offers fantastic resort-style amenities, including a large community pool, tennis and pickleball…

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

Enjoy easy Florida living in this 2-bedroom, 2-bath first-floor condo, conveniently located just minutes from Downtown Naples, Gulf beaches, shopping, and dining. The condo features an updated kitchen, newer finishes, and tile flooring throughout. The primary bedroom offers a comfortable king bed, while the guest bedroom includes twin and full-size beds, making it ideal for family…

Active
4069 Northlight Dr  1805 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1234Sq Ft
  • 1987Year Built
$3,000

Available Seasonally! This quaint 2-bedroom, 2-bath first-floor condo in the highly desirable Winterpark community is waiting for you. The home features a well-designed layout with a comfortable living and dining area, a practical and nicely appointed kitchen, and two inviting bedrooms with generous closet space. Residents enjoy access to Winterpark’s impressive amenities, including one of…

Active
3420 Frosty Way  4910 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1987Year Built
$3,000

Welcome to your opportunity to lease an upstairs residence in the highly sought-after Winterpark community—where resort-style living meets everyday convenience in the heart of Naples. This 2-bedroom, 2-bath condo offers a bright, open layout with an expansive living and dining area, ideal for comfortable living and easy entertaining. The screened balcony provides a tranquil outdoor…

Active
4030 Northlight Dr   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1200Sq Ft
  • 1986Year Built
$2,680

Centrally located in sunny Naples lies a 2 Bed 2 Bath property in Winterpark that is welcoming to your seasonal desires! Screened in Lani is set for your enjoyment and remodeled open concept is open to entertaining guests. Neighborhood amenities such as a heated pool and fitness center. This is a highly sought after community…

Active
4001 Ice Castle Way  5 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1987Year Built
$2,150

Welcome to your dream condo in Naples/Winter Park! This stunning unit boasts 2 bedrooms, 2 bathrooms, granite counters, stainless steel appliances, and tile flooring throughout. The screened-in front lanai is the perfect spot to enjoy your morning coffee or evening cocktail. Located on the first floor, this condo offers easy access to the lanai from…

Active
4130 Looking Glass Ln  3807 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1986Year Built
$2,150

Well appointed first floor unit, thats been updated with todays design elements. Soft close kitchen cabinets, drop in sink, update appliances and a screened patio that sits off the kitchen for some outdoor enjoyment. Sorry no pets are allowed... Oversized laundry room that grants storage space, an outdoor storage closet. Winter Park has an amazing…

Active
4200 Looking Glass Ln  4207 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1985Year Built
$1,950

ANNUAL RENTAL AVAILABLE NOW! Enjoy easy first-floor living in this spacious 2-bedroom, 2-bath condo in Winterpark. Highlights include a renovated kitchen, tile flooring throughout—no carpet—and a large in-unit laundry room with additional storage. An open front porch offers a welcoming spot to relax. Community amenities include a resort-style pool, tennis and bocce courts. Conveniently located…

Active
4230 Jack Frost Ct  5 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1989Year Built
$1,900

Move right into this beautifully updated Winter Park home featuring new cabinets, new flooring in the kitchen, and refreshed bathrooms amenities. Fresh, modern finishes enhance every space, creating a light and inviting atmosphere. Ideally located close to shopping, restaurants, downtown Naples, and Gulf beaches, this property is perfect for year-round living.

Active
4000 Ice Castle Way  5 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1988Year Built
$1,895

Welcome to 4000 Ice Castle Way #5 in Naples, Florida, a spacious 2-bedroom, 2-bath annual rental located in the desirable Winterpark community. This first-floor condo offers a comfortable open-concept living and dining area, a well-equipped kitchen with granite countertops, stainless-steel appliances, breakfast bar seating, and an in-unit washer and dryer. The residence features generous living space,…

Active
3574 Antarctic Cir  2107 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1986Year Built
$1,850

Looking for that perfect annual rental? Look no further! This first floor two bedroom, two bathroom is ready for rent. With amazing updates all throughout, this condo shows like new. A beautifully updated and spacious kitchen has brand new stainless steel appliance that have never been used! Large beautiful tile all throughout with clean carpeting…

Active
4021 Ice Castle Way  4 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1246Sq Ft
  • 1988Year Built
$1,850

*Available now through December 2026 and April 2027 and on!* Beautifully updated condo in the popular Winterpark community! This second floor condo has vaulted ceilings, tile throughout, granite countertops, stainless steel appliances, updated kitchen and bathrooms, and is tastefully furnished and decorated. Large spacious living room with open floor plan to the dining & kitchen,…

Active
4210 Looking Glass Ln  4210 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1300Sq Ft
  • 1989Year Built
$1,850

This turnkey furnished 2 bedroom, 2 bath condo is in a great location! Within walking distance of shopping, restaurants and other amenities. It is in a very friendly community and is well maintained. And within 6 miles to Naples world famous beaches, restaurants, boutiques and the ambience of historic Olde…

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