Winterpark Homes with Pool Amenities

Welcome to Winterpark, a hidden gem nestled in the heart of Naples, Florida, within the beautiful Collier County. This charming subdivision offers a serene and picturesque environment, perfect for those looking to escape the hustle and bustle of city life while still enjoying the vibrant culture and amenities that Naples has to offer.

Winterpark is known for its beautifully landscaped streets and friendly community atmosphere, making it an ideal place for families, retirees, and everyone in between. Residents enjoy a close-knit community feel, with plenty of opportunities to socialize and make lasting connections. The area is also conveniently located near shopping, dining, and recreational activities, ensuring that everything you need is just a short drive away.

One of the standout features of homes in Winterpark is the abundance of properties with pool amenities. Imagine stepping out into your own backyard oasis, where you can relax by the pool, host summer barbecues, or simply enjoy the warm Florida sun. These homes are designed for both comfort and luxury, offering spacious layouts and modern finishes that cater to your lifestyle needs.

With a variety of floor plans and styles available, you’re sure to find the perfect home in Winterpark that suits your taste and budget. Whether you’re seeking a cozy retreat or a spacious family home, this subdivision has something for everyone. Experience the best of Naples living in Winterpark, where community charm meets the beauty of Florida’s natural landscape. Come and discover your dream home today!

Newest Winterpark Homes with Pool Amenities

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...