Winfield Homes with Shingle Roof

Welcome to Winfield, a charming subdivision nestled in the heart of Maitland, Florida, within the vibrant Orange County. This idyllic community offers a perfect blend of suburban tranquility and urban convenience, making it an ideal choice for families, professionals, and retirees alike.

Winfield is characterized by its beautiful homes, many of which feature classic shingle roofs that not only enhance the aesthetic appeal but also provide durability and protection against the Florida elements. The architectural charm of these residences is complemented by lush landscaping and well-maintained yards, creating a picturesque neighborhood that you’ll be proud to call home.

Residents of Winfield enjoy a strong sense of community, with friendly neighbors and a welcoming atmosphere. The subdivision is conveniently located near a variety of amenities, including shopping centers, dining options, and recreational facilities. Outdoor enthusiasts will appreciate the nearby parks and lakes, perfect for leisurely strolls, picnics, or weekend adventures.

Families will benefit from the highly-rated schools in the area, ensuring that children receive a quality education close to home. With easy access to major highways, commuting to nearby cities and attractions is a breeze, allowing residents to fully enjoy the best that Central Florida has to offer.

Whether you're looking for your first home, a place to raise a family, or a peaceful retreat, Winfield in Maitland is a delightful community that promises a fulfilling lifestyle. Discover your dream home in Winfield today and experience the charm of this wonderful neighborhood!

Newest Winfield Homes with Shingle Roof

$349,999

3 Beds ⋅ 2 Baths ⋅ O6432604 MLS

Beautiful Winfield Community home in Maitland Florida will not last long. This 3 bedroom/2 bath home has so much to offer. The property recently has had a new roof put on this year in 2026, new AC unit this year in 2026, and freshly painted in 2026. The kitchen features an eat in bar top as well as a large island for plenty of use-able countertop space. The back yard is fully fenced in for privacy. The home comes with a stove, refrigerator, microwave, washer, and dryer. The garage is oversized for 2 cars with extra space for storage. The flooring is ceramic in the main living areas for easy cleaning when needed. Low HOA dues for an upscale community. Dont miss out on this home.

1866 Bobtail Drive, Maitland

$519,999

4 Beds ⋅ 3 Baths ⋅ G5110747 MLS

Welcome to 1776 Bobtail Drive, a home that offers an easy, natural flow and a layout designed for everyday living. This property is now being reintroduced with a refreshed presentation and a full 3D walkthrough experience, giving buyers the ability to explore every space at their own pace before stepping inside in person. Inside, the home features an open-concept layout where the kitchen, dining, and living areas connect seamlessly, creating a comfortable and functional main living space. Upstairs, generously sized bedrooms offer flexibility for families, guests, or home office needs, while the overall layout supports a wide range of lifestyles. Located in highly desirable Maitland, the home offers convenient access to shopping, dining, major roadways, and all Central Florida amenities. Private showings available upon request.they’ve been waiting for.

1776 Bobtail Drive, Maitland

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