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

4038 Northlight Drive Unit 1506, Naples image

4038 Northlight Drive Unit 1506, Naples $259,900

Lake views and a prime in-town Naples location define this move-in-ready 2-bedroom, 2-bath second-floor condo in Naples Winterpark IV. Enjoy open water views over the co...

2 Beds
2 Baths
Winterpark SubDv.

4100 Looking Glass Lane Unit 3008, Naples image

4100 Looking Glass Lane Unit 3008, Naples $255,000

Welcome to **4100 Looking Glass Ln #8**, a great opportunity to own in Naples! This inviting residence offers a comfortable and functional layout with plenty of natural l...

2 Beds
2 Baths
Winterpark SubDv.

4027 Northlight Drive Unit 4, Other image

4027 Northlight Drive Unit 4, Other $259,900

Welcome to 4027 Northlight Drive #4 in the desirable Winterpark community, offered at $259,900! This light and breezy second-floor, 2-bedroom, 2-bath condo features an up...

2 Beds
2 Baths
Winterpark SubDv.

4230 Jack Frost Court Unit 4402, Naples image

4230 Jack Frost Court Unit 4402, Naples $250,000

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...

2 Beds
2 Baths
Winterpark SubDv.

3574 Antarctic Circle Unit 2107, Naples image

3574 Antarctic Circle Unit 2107, Naples $255,000

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 a...

2 Beds
2 Baths
Winterpark SubDv.

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 $224,000 ▼

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...