Winterpark Homes with Pickleball Amenities

Welcome to Winterpark, a vibrant and inviting subdivision nestled in the heart of Naples, Florida, within the picturesque Collier County. Known for its lush landscapes and serene environment, Winterpark offers residents a unique blend of tranquility and community spirit, making it an ideal place to call home.

This charming neighborhood features a diverse selection of homes, each designed with comfort and style in mind. From cozy single-family residences to spacious villas, there’s something for everyone in Winterpark. The community is particularly appealing to those who appreciate an active lifestyle, as it boasts exceptional pickleball amenities. Whether you’re a seasoned player or a curious beginner, you’ll find well-maintained courts that foster both competition and camaraderie among neighbors.

Living in Winterpark means enjoying the best of Naples, with its stunning beaches, upscale shopping, and delectable dining options just a short drive away. The community is also conveniently located near top-rated schools and lush parks, making it perfect for families of all sizes.

Residents can take advantage of various social events and activities, creating a warm and welcoming atmosphere that truly feels like home. With the added bonus of pickleball courts, Winterpark is not just a neighborhood; it's a lifestyle. Embrace the joy of living in a community that encourages wellness, social interaction, and the pursuit of leisure. Come discover your dream home in Winterpark, where every day feels like a vacation!

Newest Winterpark Homes with Pickleball Amenities

$262,000

2 Beds ⋅ 2 Baths ⋅ 226027202 MLS ⋅ Winterpark BLDG.

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. One or more photo(s) has been virtually staged, AI generated or rendered.

3420 Frosty WAY Unit 4902, Naples

$249,000

2 Beds ⋅ 2 Baths ⋅ 226024603 MLS ⋅ Winterpark BLDG.

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! The location is truly unbeatable—just 3 miles from the famous beaches of Naples and the vibrant shops and restaurants on Olde Naples' 5th Avenue. Plus, you can easily walk to Kings Lake Square, which offers a Publix, various shops, and multiple dining options.

3816 Snowflake LN Unit 1303, Naples

$248,000

2 Beds ⋅ 2 Baths ⋅ 226020005 MLS ⋅ Winterpark BLDG.

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 and a stylish barn door that leads to the en-suite master bath with a sparkling shower. The unit comes turnkey; all you have to bring is your suitcase! This condo is fully equipped with much-desired impact windows and sliders to protect your paradise. Additional in-unit perks include a spacious laundry and utility room with a dedicated washer and dryer and room to spare, as well as a clever small storage area tucked under the stairs, perfect for storing bikes and beach chairs. Tile and carpet flooring throughout. Winter Park boasts an absolutely stacked lineup of amenities that includes one of the LARGEST resort-style community pools in Naples, a beautiful clubhouse with an expansive library, separate pickleball and tennis courts, bocce and shuffleboard courts, and bike and jog path; a sensational lineup of community activities for a fabulous community. What’s more - this particular condo is situated well in this robust community, enjoying close proximity to all of these amenities. Just minutes from world-renowned 5th Avenue, scintillating shopping, and beautiful beaches, this location is absolutely rich with convenience. No matter what your real estate goal is, this Winter Park wonderland offers the quintessential Southwest Florida lifestyle!

3532 Antarctic CIR Unit 2216, Naples

$329,900

2 Beds ⋅ 2 Baths ⋅ 226019156 MLS

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.

4140 Looking Glass LN Unit 7, Naples

$249,000

2 Beds ⋅ 2 Baths ⋅ 226017233 MLS ⋅ Winterpark BLDG.

Welcome to an exceptional opportunity to own an upstairs residence in the highly sought-after Winterpark community—where value meets vision and the potential to create your dream Naples retreat awaits. Positioned in a prime Naples location, this 2-bedroom, 2-bath condominium offers a light-filled layout with an expansive living and dining area, ready to be reimagined with your personal style and design vision. The screened balcony provides a peaceful outdoor space overlooking lush tropical landscaping—perfect for morning coffee or unwinding after a day at the beach. Inside, you’ll find a spacious primary suite, in-unit laundry, and a functional floor plan that serves as the perfect canvas for updates, renovations, or a full custom transformation. What truly sets this property apart is its placement within Winterpark—one of Naples’ most desirable, amenity-rich communities known for its vibrant lifestyle and classic Florida charm. Residents enjoy access to one of the largest resort-style pools in Naples, beautifully maintained grounds, newly updated pickleball and tennis courts, and an active social atmosphere that makes it easy to feel at home. Located just minutes from 5th Avenue South and Olde Naples, as well as world-renowned Gulf beaches, this property offers unmatched convenience to fine dining, boutique shopping, art galleries, and coastal living at its finest. Whether you’re seeking a seasonal escape, investment opportunity, or a full-time residence to customize and make your own, this is your chance to unlock the full potential of Naples living in a community that truly embodies the Florida lifestyle.

3420 Frosty WAY Unit 4910, Naples

$309,900

2 Beds ⋅ 2 Baths ⋅ 226015387 MLS ⋅ Winterpark BLDG.

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.

4030 Northlight DR, Naples

$250,000

2 Beds ⋅ 2 Baths ⋅ 226011974 MLS ⋅ Winterpark BLDG.

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.

4031 Ice Castle WAY Unit 3306, Naples

$240,000

2 Beds ⋅ 2 Baths ⋅ 226009042 MLS ⋅ Winterpark BLDG.

Seller Says Sell! Price reduction for this amazing condo in highly sought after Winterpark. 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 décor. The remodeled kitchen features modern cabinetry, quartz countertops, stainless steel appliances, and a convenient breakfast bar that flows seamlessly into the expansive living and dining areas—ideal for entertaining or relaxing at home. Both bathrooms have also been tastefully renovated. Other updates include a newer A/C, a brand new water heater, and a roof that's only a year old for added peace of mind. Flood insurance is covered by the association. Another advantage is the in-unit laundry room with washer, dryer, and abundant storage. Enjoy Florida living year-round from the screened porch overlooking the garden, the large heated community pool, tennis courts and other playing courts, as well as walking and jogging paths. Other features include private assigned parking and plenty of additional guest parking for even more convenience. Extra private storage accompanies this property to store your bike or anything else you may need. The location is perfect, only a few minutes to Downtown Naples and its world renowned beaches, plus easy access to exceptional dining, shopping and entertainment options. Pet-friendly, rental-friendly and without age restrictions, this condo presents an excellent investment opportunity or seasonal retreat. While other units may be available in the community, this beautifully updated corner residence truly stands out—one you must see in person to fully appreciate.

4100 Looking Glass LN Unit 3002, Naples

$225,000

2 Beds ⋅ 2 Baths ⋅ 2026010114 MLS ⋅ Winterpark BLDG.

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 a vibrant, resort-style community with exceptional amenities, including a sparkling resort swimming pool, pickleball and tennis courts, bocce ball, scenic walking trails, and a variety of organized social activities. Recent major improvements include a newer A/C system and roof, offering added value and peace of mind. The monthly condo fee covers water, sewer, exterior insurance, exterior maintenance, cable service, landscaping, and full access to all community amenities, helping simplify ownership. Whether you're searching for a primary residence, seasonal retreat, or investment opportunity, this property offers flexibility with both short-term and annual rentals permitted, subject to community restrictions.

4200 Looking Glass LN Unit 4204, Naples

$339,000

2 Beds ⋅ 2 Baths ⋅ 226005552 MLS ⋅ Winterpark BLDG.

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.

4180 Looking Glass LN Unit 4102, Naples

$259,000

2 Beds ⋅ 2 Baths ⋅ 2025014071 MLS ⋅ Winterpark BLDG.

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 this great community. Furniture is negotiable

4079 Northlight DR Unit 1802, Naples

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.