Winterpark Naples Real Estate - 1 Home, 20 Condos For Sale

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 relaxing views of the community’s green space. Step outside to enjoy Winterpark’s resort-style amenities, including one of the largest community pools in Naples, a clubhouse, pickleball and tennis courts, bocce, and beautifully maintained walking paths. Residents appreciate the convenient East Naples location—just minutes from downtown 5th Avenue, shopping, dining, and Naples’ world-famous beaches. Whether you're seeking a seasonal retreat, full-time residence, or investment property, this Winterpark condo offers wonderful value and a uniquely comfortable Naples lifestyle.

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 connecting the kitchen, dining, and living areas. The interior has a clean coastal feel with updated flooring, recessed lighting, modern finishes, and a spacious living room overlooking a peaceful outdoor setting. The owner’s suite includes custom closet space and an updated bathroom with a walk-in shower. The second bedroom and bathroom provide flexibility for guests, seasonal use, or a home office. A standout feature is the custom laundry and wine cellar area, adding valuable function and a unique touch. Winterpark amenities include a resort-style community pool, clubhouse, community room, pickleball, tennis, bocce court, bike and jog path, bike storage, extra storage, and internet access. The HOA includes cable, insurance, internet/WiFi access, irrigation water, lawn and land maintenance, reserves, sewer, street lights, street maintenance, trash removal, and water. For buyers searching for Naples condos for sale, a move-in-ready condo in Winterpark, or a well-updated property near shopping, dining, beaches, and downtown Naples, this is a strong opportunity.

This Beautifully updated condo is on first floor in the Winterpark 1 community. Unit was completely remodeled in 2021, with tile flooring throughout unit, stainless KitchenAid appliances, new cabinets, new countertops, light fixtures, coffered ceiling in living room, hurricane rated windows and sliders throughout, custom closets 2022, updated master bath and guest bathroom too! Screened in lanai in front of unit as well as NEW screened in lanai in back of unit added in 2024. Beautiful, landscaped views with lots of room in a tranquil setting. There is a dedicated parking spot with unit as well. This wonderful diamond in the ruff community has an amazing resort style pool with a clubhouse, and 8 pickleball courts along with bocce and tennis. Minutes to the beaches, restaurants and downtown Naples. You don't want to miss this amazing unit!

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 and unwind. Located just a short drive to 5th Avenue, Naples Beach, Publix, and a variety of restaurants and shops, this highly sought-after community.

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 through the living spaces, anchored by a granite kitchen that opens to the dining and living areas. The primary suite is generously sized with a walk-in closet; the second bedroom and full bath are ideal for guests or seasonal use. A newly screened lanai extends the living space outdoors for morning coffee or sunset dinners. Thoughtful updates include impact-rated windows and doors, a newer roof, and a newer water heater. In-unit laundry and assigned parking add everyday ease. Residents enjoy one of the larger community pools in Naples, plus tennis, bocce, a clubhouse, and extra storage, all set among mature landscaping. Whether you are looking for a full-time home, a seasonal retreat, or a well-located rental, this fully remodeled, TURNKEY-furnished, move-in-ready condo delivers the Naples lifestyle without the upkeep.

Welcome to Winter Park, one of Naples’ most desirable communities just minutes from Downtown Naples, Olde Naples, and the beach. This beautifully updated 2-bedroom, 2-bath corner condo is offered fully furnished and completely move-in ready. Fully remodeled from top to bottom, it features a brand-new kitchen with new appliances, cabinets, and countertops, updated bathrooms, new flooring throughout, plus updated plumbing, HVAC, and water heater. Winter Park offers resort-style amenities including one of the largest pools in Naples, brand-new pickleball and tennis courts, lush green spaces, and an active social atmosphere.

Tropical Paradise - Winterpark IX! This 2-bedroom, 2-bathroom condo is ideal as a Florida tropical vacation home, a full-time residence or investment property. Offered Furnished. Ground-floor unit- no stairs and no hassle. Only a few buildings in Winterpark community feature a screened lanai; perfect for enjoying your Florida morning coffee or a glass of wine at sunset. New roof-2024, A/C-2020, Water Heater-2016, new piping, Impact Resistant windows and doors. Check out this property on our 360° Virtual Tour! Located just a short walk to the community amenities - no need to cross a busy street, unlike owners in some other buildings. A rare opportunity to purchase in one of the most desirable buildings. Up to 12 leases are allowed per year, making it an excellent investment property, or a vacation home. Prime location with quick access to Naples Downtown, white-sand Naples beaches, shopping, dining, and local attractions. Simple and cozy - this is how we live on the Gulf in Naples. Take a short trip to swim and sunbathe on one of the Naples beaches, play tennis or pickleball, dine and watch the sunset at one of the finest restaurants, or enjoy a fun day of shopping and then relax in the large resort-style pool right in the community. The amenities include a spacious resort-style pool, tennis and pickleball courts, a clubhouse, and bocce. Naples also welcomes everyone to enjoy its cultural and entertainment venues, including the Gulfshore Opera, Artis, The Baker Museum, Gulfshore Playhouse, The Naples Players Theater, Naples Botanical Garden, Naples Zoo, and numerous public parks with miles of walking paths, and even the Sun-N-Fun Lagoon water park. Don’t miss Fifth Avenue South and Third Street South in Olde Naples, as well as The Village Shops on Venetian Bay in Park Shore, Waterside Shops in the Pelican Bay area, Mercato, and much more. Make this home yours today, spend this winter season in sunny Florida!

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 overlooking landscaped grounds. Offered turnkey furnished, this residence is well-suited for seasonal living, investment, or full-time use. Highlights: Hurricane impact windows throughout; vaulted ceilings (2nd-floor units only); pond views from living area and primary bedroom; newer washer/dryer; exterior storage for bikes and beach gear; community roof replaced in 2018. Amenities: Resort-style heated pool, tennis, pickleball, bocce, clubhouse. Location: Minutes to 5th Ave South, Bayfront, and beaches; walk to Publix and dining at Kings Lake Square. Community: Leasing permitted 3 times per year (30-day minimum / 180-day maximum). Pets: one dog (up to 50 lbs) or cat for owners (no pets for tenants).

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 features a large convenient outdoor storage for bicycles or beach toys which is perfect for enjoying Florida's sunny lifestyle. The community is complete with a Clubhouse, Resort-Style Pool, tennis, pickle ball and bocce courts and a lovely walking trail. Conveniently located in the heart of Naples with a short distance to the beach, downtown, 5th Avenue South, Publix and Interstate 75. First floor unit with assigned parking and low association fees.

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 large laundry room offers exceptional storage, complemented by an additional exterior storage closet. Winter Park residents enjoy one of Naples’ largest resort-style pools, tennis, pickleball, bocce, a clubhouse, and beautifully landscaped walking areas. HOA fees include water, sewer, basic cable, and WiFi—leaving only electric as your utility bill. All just minutes from 5th Avenue South, Downtown Naples, and Naples’ world-famous beaches. A prime location with outstanding amenities and move-in-ready appeal.

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 living. The screened front balcony provides the perfect setting for morning coffee or an evening glass of wine while enjoying the peaceful Florida sunsets. Second-floor residences are the only homes in Winterpark with soaring cathedral ceilings, creating a bright and open atmosphere throughout. Kitchen side wall removed to enhance the kitchen and living area. The owner's suite features an added barn door for more privacy. With no carpet throughout, partially furnished interiors (inventory list available), a large laundry room with an oversized private storage closet, additional attic storage, and an exterior storage unit, this home offers exceptional convenience. Major updates provide peace of mind, including approximately 2-year-old appliances, a 2022 roof, CPVC plumbing, and a water heater replaced at the end of 2025. And a one-year home warranty is included with the purchase! Ideally located just a short walk from the community amenities. Winterpark residents enjoy an active resort-style lifestyle featuring a large swimming pool, tennis and pickleball courts, bocce courts, and a welcoming clubhouse. This residence also offers quick access to Downtown Naples, world-famous white-sand Gulf beaches, premier shopping, dining, and entertainment. Beyond the community, Naples offers an exceptional blend of recreation and culture, including Gulfshore Opera, Artis—Naples, The Baker Museum, Gulfshore Playhouse, The Naples Players, Naples Botanical Garden, Naples Zoo, and countless parks and nature preserves. Popular destinations such as Fifth Avenue South, Third Street South, Venetian Village, Waterside Shops, and Mercato offer outstanding shopping, dining, and entertainment. Whether as a full-time residence, seasonal retreat, or investment opportunity, this property represents outstanding value in one of Naples' most desirable locations.

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 used! Large beautiful tile all throughout with clean carpeting in the bedrooms. Bath bathrooms have been updated as well and are clean and bright. The front lanai is screened in and is a perfect place to BBQ or enjoy your morning coffee. Feel free to build your own outdoor screened lanai with the communities new approval! Winterpark has great amenities and is close to downtown Naples and the surrounding area.