Winterpark Homes with Non-Gated Community Type

Welcome to Winterpark, a delightful non-gated community nestled in the heart of Naples, Florida, within the picturesque Collier County. This charming subdivision is known for its inviting atmosphere and friendly neighbors, making it an ideal place for families, retirees, and anyone seeking a vibrant community lifestyle.

Winterpark boasts a diverse selection of homes, each exuding unique charm and character. From cozy single-family residences to spacious villas, there’s something to suit every taste and budget. The well-maintained streets and lush landscaping create a serene environment, perfect for evening strolls or morning jogs. With no gated restrictions, residents enjoy the freedom to come and go as they please, fostering a sense of openness and connection among neighbors.

One of the standout features of Winterpark is its prime location. Just a short drive away, you’ll find the stunning beaches of Naples, renowned for their soft sands and crystal-clear waters. Additionally, the area is rich in dining, shopping, and recreational opportunities. Whether you’re exploring the eclectic boutiques of downtown Naples or savoring fresh seafood at a waterfront restaurant, there’s always something to enjoy.

For families, Winterpark is conveniently located near top-rated schools and parks, providing ample opportunities for outdoor activities and community events. The sense of camaraderie among residents adds to the charm of this exceptional neighborhood.

If you’re looking for a welcoming community in Naples, Winterpark is the perfect place to call home. Experience the allure of Florida living in a neighborhood that truly feels like family.

Newest Winterpark Homes with Non-Gated Community Type

$250,000

2 Beds ⋅ 2 Baths ⋅ 226028571 MLS ⋅ Winterpark BLDG.

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 an open living area enhanced by dramatic vaulted ceilings that make the home feel even larger, while the screened front porch offers a comfortable place to enjoy the Florida air. With a spacious layout and a true blank-canvas feel, the condo offers the freedom to personalize, reimagine, and create a space that reflects your own style. Winterpark is known for its outstanding amenities, highlighted by an expansive community pool surrounded by a tropical setting, along with pickleball, tennis, bocce, and clubhouse facilities. Whether you are looking for a full-time residence, seasonal retreat, or investment property, the community offers a peaceful neighborhood atmosphere while keeping you close to everything that makes Naples so desirable. Downtown Naples, 5th Avenue South, Tin City, Gulf beaches, shopping, dining, and everyday conveniences are all just a short drive away. Rental flexibility allowing up to 3 leases per year with a 30-day minimum adds even more appeal for buyers looking for income potential or seasonal use. With generous living space, exceptional community amenities, and a location that keeps the best of Naples within easy reach, this condo offers an inviting opportunity to create a home that truly feels like your own. Come see firsthand why this could be the Naples opportunity you’ve been waiting for.

4230 Jack Frost CT Unit 4402, Naples

$255,000

2 Beds ⋅ 2 Baths ⋅ 226028684 MLS ⋅ Winterpark BLDG.

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.

3574 Antarctic CIR Unit 2107, Naples

$245,000

2 Beds ⋅ 2 Baths ⋅ 226026798 MLS ⋅ Winterpark BLDG.

Escape to this meticulously maintained two-bedroom condo featuring a brand-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 finishing out the master en suite. Outdoor living is enhanced by a screened front patio and a rear patio, perfect for year-round enjoyment. As an end unit, it’s flooded with natural light, from sunrise to sunset. Enjoy resort-style amenities including a pool, clubhouse, tennis, and pickleball courts—all with low association fees and a never-flooded property. You’re steps from the pool, with convenient parking right outside your door, and just minutes to the beach, downtown Naples, and local shopping.

4001 Ice Castle WAY Unit 1, Naples

$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.

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

$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

$239,000

2 Beds ⋅ 2 Baths ⋅ 226016168 MLS ⋅ Winterpark BLDG.

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 offers privacy, natural light, and beautiful Lake views. Featuring 2 bedrooms and 2 bathrooms, this home boasts vaulted ceilings, an updated Tile and carpet flooring throughout, and a spacious primary suite with a walk-in closet. The living area is enhanced with impact windows, providing both peace of mind and energy efficiency. Whether you're looking for a full-time residence, seasonal getaway, or income-producing rental investment, this unit checks all the boxes. Allows up to 12 rentals per year with a 30-day minimum, offering excellent flexibility and strong income potential making it a fantastic opportunity for investors seeking Airbnb-style or seasonal rental income.

4050 Ice Castle WAY Unit 2812, 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

$284,900

2 Beds ⋅ 2 Baths ⋅ 226012607 MLS ⋅ Winterpark BLDG.

Welcome to Winterpark, one of Naples most sought-after communities just minutes from downtown and the pristine Gulf beaches. This beautifully updated 2-bedroom, 2-bath 1st floor condo offers a perfect blend of modern style and effortless Florida living. Step inside to an open, light-filled layout designed for both comfort and entertaining. Darkwood accents & cabinetry in the kitchen and breakfast bar, custom tile work and exquisite finishes throughout. Enjoy your morning coffee or unwind in the evening on the spacious lanai, a perfect private retreat with a relaxing, tropical feel. Winterpark is known for its resort-style amenities, including one of the largest pools in Naples, newly updated pickleball and tennis courts, and a vibrant, active social atmosphere. Surrounded by lush green spaces and charming scenery, the community captures the essence of classic Florida living. Ideally located just minutes from 5th Avenue South, Olde Naples, shopping, dining, and the beach, this property is perfect as a full-time residence, seasonal getaway, or investment opportunity. Come experience it for yourself—this one won’t last.

4150 Looking Glass LN Unit 3903, 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

$209,500

2 Beds ⋅ 2 Baths ⋅ 2026009632 MLS ⋅ Winterpark BLDG.

Best Value in Winterpark – First Floor • Turnkey • Impact Windows • New A/C • Conventional Financing On of the Lowest-priced first-floor condo in Winterpark. This turnkey-furnished home offers an incredible opportunity to own in one of Naples’ most desirable communities while leaving room in your budget to update and personalize it over time. The home offers a comfortable, functional layout with one nicely updated bathroom while providing an opportunity to personalize the remaining spaces to your own taste and style. Major improvements have already been completed, including updated plumbing, impact windows and an impact sliding glass door, a new A/C (2024), and a new water heater (2023), allowing you to focus on making it your own. For added peace of mind, the condominium association carries a master flood insurance policy. The property also qualifies for conventional financing, offering greater flexibility for buyers. Winterpark is known for its lush, walkable setting, spectacular resort-style pool, tennis courts, and welcoming atmosphere. Ideally located just minutes from downtown Naples, 5th Avenue South, shopping, dining, and the beautiful Gulf beaches, you’ll enjoy everything Southwest Florida has to offer. Quarterly HOA dues are $1,920 and include outstanding community amenities and exterior maintenance. Pets and rentals are permitted, adding to the property’s versatility. Motivated sellers have priced this home to sell. If you’ve been searching for an affordable opportunity to own in one of Naples’ most popular communities, this is one you won’t want to miss.

4070 Looking Glass LN Unit 3101, Naples

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