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

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...

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.

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...

2 Beds
2 Baths
Winterpark SubDv.

4200 Looking Glass Lane Unit 4204, Naples image

4200 Looking Glass Lane Unit 4204, Naples $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
Winterpark SubDv.

4180 Looking Glass Lane Unit 4102, Naples image

4180 Looking Glass Lane Unit 4102, Naples $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...