Winterpark Real Estate

Welcome to Winterpark, a hidden gem nestled in the heart of Naples, Florida, within the vibrant Collier County. This charming neighborhood offers a perfect blend of tranquil suburban living and convenient access to the bustling activities that Naples is renowned for.

Winterpark is characterized by its lush landscapes, tree-lined streets, and beautifully maintained homes, creating an inviting atmosphere for families and individuals alike. The community is known for its friendly neighbors and a strong sense of belonging, making it an ideal place for those seeking a close-knit environment.

Residents of Winterpark enjoy a wealth of amenities right at their fingertips. The neighborhood features scenic parks, walking trails, and recreational facilities that cater to outdoor enthusiasts. Whether you’re jogging through the park or enjoying a picnic with friends, the natural beauty of Winterpark is sure to inspire.

For those who love shopping and dining, the nearby Naples area boasts an array of upscale boutiques, charming cafes, and exquisite restaurants. Take a leisurely stroll down Fifth Avenue South or visit the renowned Waterside Shops to indulge in a day of retail therapy.

Additionally, Winterpark’s prime location provides easy access to some of Florida's most stunning beaches, where you can soak up the sun or partake in water sports. With excellent schools and a variety of community events, Winterpark is not just a neighborhood; it’s a lifestyle.

Whether you’re looking to settle down or invest in a vacation home, Winterpark offers the perfect balance of relaxation and recreation. Come discover the allure of Winterpark and experience a community that truly feels like home.

Newest Listings in Winterpark

3816 Snowflake LN Unit 1303, Naples image

3816 Snowflake LN Unit 1303, Naples — Winterpark $249,000

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...

2 Beds
2 Baths
226024603 MLS
Winterpark Bldg.

3532 Antarctic CIR Unit 2216, Naples image

3532 Antarctic CIR Unit 2216, Naples — Winterpark $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 ...

2 Beds
2 Baths
226020005 MLS
Winterpark Bldg.

4140 Looking Glass LN Unit 7, Naples image

4140 Looking Glass LN Unit 7, Naples $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 co...

2 Beds
2 Baths
226019156 MLS

3420 Frosty WAY Unit 4910, Naples — Winterpark $249,000

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 yo...

2 Beds
2 Baths
226017233 MLS
Winterpark Bldg.

4050 Ice Castle WAY Unit 2812, Naples image

4050 Ice Castle WAY Unit 2812, Naples — Winterpark $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 c...

2 Beds
2 Baths
226016168 MLS
Winterpark Bldg.

4030 Northlight DR, Naples — Winterpark $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 Winte...

2 Beds
2 Baths
226015387 MLS
Winterpark Bldg.

4150 Looking Glass LN Unit 3903, Naples image

4150 Looking Glass LN Unit 3903, Naples — Winterpark $284,900

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 1s...

2 Beds
2 Baths
226012607 MLS
Winterpark Bldg.

4031 Ice Castle WAY Unit 3306, Naples image

4031 Ice Castle WAY Unit 3306, Naples — Winterpark $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 i...

2 Beds
2 Baths
226011974 MLS
Winterpark Bldg.

4070 Looking Glass LN Unit 3101, Naples image

4070 Looking Glass LN Unit 3101, Naples — Winterpark $209,500 ▼

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 turn...

2 Beds
2 Baths
2026009632 MLS
Winterpark Bldg.

4100 Looking Glass LN Unit 3002, Naples image

4100 Looking Glass LN Unit 3002, Naples — Winterpark $240,000 ▼

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 s...

2 Beds
2 Baths
226009042 MLS
Winterpark Bldg.

4200 Looking Glass LN Unit 4204, Naples image

4200 Looking Glass LN Unit 4204, Naples — Winterpark $225,000 ▼

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 r...

2 Beds
2 Baths
2026010114 MLS
Winterpark Bldg.

4180 Looking Glass LN Unit 4102, Naples image

4180 Looking Glass LN Unit 4102, Naples — Winterpark $339,000 ▼

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 off...