Winterpark Real Estate

Welcome to Winterpark, a picturesque subdivision nestled in the heart of Naples, Florida, within the scenic Collier County. This charming community offers a serene and inviting atmosphere, perfect for families, retirees, and anyone seeking a slice of paradise in the Sunshine State.

Winterpark is renowned for its lush landscapes, beautifully manicured lawns, and an array of stunning homes that cater to diverse tastes and lifestyles. Whether you’re looking for a cozy single-family home or a spacious villa, this subdivision has something to suit every preference. The architectural styles reflect the warm, coastal vibe of Naples, ensuring that your home is not only a sanctuary but also a reflection of the vibrant community around you.

One of the standout features of Winterpark is its prime location. Just a short drive away, you’ll find Naples’ pristine beaches, upscale shopping districts, and delectable dining options. Enjoy the sun-kissed shores of the Gulf of Mexico, or explore the charming boutiques and art galleries that line the streets of downtown Naples. For outdoor enthusiasts, the nearby parks and nature preserves offer a plethora of recreational opportunities, from hiking and biking to birdwatching and kayaking.

Community spirit thrives in Winterpark, with friendly neighbors and regular social events that foster connections among residents. The well-maintained amenities, including walking trails, a community pool, and recreational facilities, further enhance the quality of life here.

Discover the beauty and charm of Winterpark, where your dream home awaits amidst the stunning backdrop of Naples, Florida. Embrace the lifestyle you’ve always wanted in this idyllic community!

Newest Listings in Winterpark

4001 Ice Castle Way Unit 1, Naples image

4001 Ice Castle Way Unit 1, Naples $245,000

Escape to this meticulously maintained two-bedroom condo featuring a brand-new air conditioning system, hurricane windows and doors, plus plantation sliders and shutters....

2 Beds
2 Baths
Winterpark SubDv.

3420 Frosty Way Unit 4902, Naples $262,000

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 i...

2 Beds
2 Baths
Winterpark SubDv.

3816 Snowflake Lane Unit 1303, Naples image

3816 Snowflake Lane Unit 1303, Naples $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
Winterpark SubDv.

3532 Antarctic Circle Unit 2216, Naples image

3532 Antarctic Circle Unit 2216, Naples $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
Winterpark SubDv.

4140 Looking Glass Lane Unit 7, Naples image

4140 Looking Glass Lane 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
Winterpark SubDv.

3420 Frosty Way Unit 4910, Naples $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
Winterpark SubDv.

4050 Ice Castle Way Unit 2812, Naples image

4050 Ice Castle Way Unit 2812, Naples $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
Winterpark SubDv.

4030 Northlight Drive, Naples $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
Winterpark SubDv.

4150 Looking Glass Lane Unit 3903, Naples image

4150 Looking Glass Lane Unit 3903, Naples $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
Winterpark SubDv.

4031 Ice Castle Way Unit 3306, Naples image

4031 Ice Castle Way Unit 3306, Naples $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
Winterpark SubDv.

4070 Looking Glass Lane Unit 3101, Naples image

4070 Looking Glass Lane Unit 3101, Naples $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
Winterpark SubDv.

4100 Looking Glass Lane Unit 3002, Naples image

4100 Looking Glass Lane Unit 3002, Naples $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...