Winterpark Homes with Shingle Roof

Welcome to Winterpark, a charming and vibrant subdivision nestled in the heart of Naples, Florida, within the scenic Collier County. This delightful community is known for its picturesque landscapes and a warm, welcoming atmosphere that makes it an ideal place to call home.

Winterpark boasts a variety of beautifully designed homes, many featuring classic shingle roofs that not only enhance their aesthetic appeal but also provide durability and protection against Florida's diverse weather. The architecture here marries traditional charm with modern conveniences, offering residents a comfortable and stylish living experience.

As you stroll through the tree-lined streets of Winterpark, you’ll discover a community that values both tranquility and connection. With well-maintained parks, serene walking paths, and friendly neighbors, it’s easy to see why families and retirees alike are drawn to this enchanting enclave. The proximity to Naples' stunning beaches, upscale shopping, and world-class dining options adds to the allure of Winterpark, making it a prime location for those seeking the best of Florida living.

Whether you're looking for a cozy retreat or a spacious family home, Winterpark has something to suit every lifestyle. The community's focus on outdoor living and active engagement ensures that residents can enjoy everything this beautiful area has to offer. Come explore Winterpark, where your dream home awaits amidst the sun-drenched splendor of Naples, Florida!

Newest Winterpark Homes with Shingle Roof

4079 Northlight Drive Unit 2, Naples image

4079 Northlight Drive Unit 2, Naples $247,000

Welcome to this spacious and beautifully updated second-floor end-unit condo in the desirable Winterpark community. Freshly painted throughout, this home features an upgr...

2 Beds
2 Baths
Winterpark SubDv.

4096 Northlight Drive Unit 1709, Naples image

4096 Northlight Drive Unit 1709, Naples $239,000

For sale is this 2 bedroom 2 bath 1st floor end unit beautiful Winterpark Naples condo. A short drive or walk to Naples world famous white sandy sunny beaches. Northl...

2 Beds
2 Baths
Winterpark SubDv.

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 ...