Winterpark Homes with Shingle Roof

Welcome to Winterpark, a charming community nestled in the heart of Naples, Florida, within the picturesque Collier County. This delightful development offers a perfect blend of luxury and comfort, making it an ideal destination for families, retirees, and anyone seeking a serene lifestyle in the Sunshine State.

Winterpark features an array of beautifully designed homes, each adorned with classic shingle roofs that not only enhance their aesthetic appeal but also ensure durability and protection against the elements. These homes are thoughtfully crafted to provide spacious living areas, modern amenities, and lush outdoor spaces, making them perfect for both relaxation and entertaining.

Residents of Winterpark enjoy a vibrant community atmosphere, complete with beautifully landscaped common areas, walking trails, and recreational facilities. The neighborhood fosters a sense of belonging, where neighbors become friends and families can thrive together. With a strong emphasis on community engagement, Winterpark hosts various events throughout the year, allowing residents to connect and create lasting memories.

Located just minutes away from Naples' stunning beaches, world-class dining, and upscale shopping, Winterpark offers the convenience of urban living while maintaining the charm of a close-knit community. The area is also known for its top-rated schools, making it an excellent choice for families looking to settle down.

Whether you're searching for your dream home or a peaceful retreat, Winterpark in Naples, Florida, promises a lifestyle filled with warmth, beauty, and endless opportunities for adventure. Come discover the magic of Winterpark, where your ideal home awaits!

Newest Winterpark Homes with Shingle Roof

3400 Frosty Way Unit 5, Naples $310,000

Welcome to Winterpark—one of Naples’ most convenient, low-maintenance communities—just minutes from 5th Avenue, Bayfront, Tin City, and the Gulf. This first-floor 2 bedro...

2 Beds
2 Baths
Winterpark SubDv.

4073 Northlight Drive Unit 1803, Naples image

4073 Northlight Drive Unit 1803, Naples $265,000

First-floor 2BR/2BA condo in the highly desirable Winter Park community and located in Winter Park IV. This light and spacious home features an inviting screened front po...

2 Beds
2 Baths
Winterpark SubDv.

4038 Northlight Drive Unit 1506, Naples image

4038 Northlight Drive Unit 1506, Naples $249,900 ▼

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 water views over the communi...

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 $230,000 ▼

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.

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...