Winfield Real Estate

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

Winfield is known for its beautifully landscaped streets and well-maintained homes, providing a warm and inviting atmosphere. The subdivision features a variety of architectural styles, ensuring that there’s a perfect fit for every taste. Residents enjoy spacious lots, creating a sense of privacy and community spirit that is truly unique.

One of the standout features of Winfield is its proximity to an array of amenities. Just a short drive away, you’ll find a selection of shopping centers, dining options, and recreational parks. The vibrant downtown area of Maitland is also within reach, offering cultural attractions, art galleries, and local events that showcase the town’s rich history and community spirit.

For families with children, Winfield is served by highly-rated schools, making it an excellent choice for those seeking quality education. The area’s parks and recreational facilities provide ample opportunities for outdoor activities, whether it’s a leisurely stroll, a day of picnicking, or enjoying a weekend sports game.

With its friendly atmosphere, convenient location, and beautiful surroundings, Winfield is more than just a subdivision; it’s a place to call home. Discover the charm and warmth of Winfield, where community and comfort come together in perfect harmony.

Newest Listings in Winfield

$435,000

3 Beds ⋅ 2 Baths ⋅ Winfield SubDv. ⋅ 32751 Zip Code

Welcome to this beautiful 3-bedroom, 2-bathroom home featuring a sparkling pool and exceptional curb appeal! Nestled among lush landscaping, the backyard is a true private oasis—perfect for relaxing or entertaining. Inside, you'll be greeted by vaulted ceilings, abundant natural light, upgraded flooring, high-end countertops, and a beautifully designed kitchen that's both stylish and functional. The thoughtfully designed split floor plan offers privacy, with the spacious primary suite situated in its own wing and two additional bedrooms on the opposite side of the home. Additional highlights include a charming breakfast nook, a large living room, a dedicated office area, and a convenient indoor laundry room with the washer and dryer included. The attached garage provides ample storage and parking. Ideally located near the thriving Maitland business district, this home is just minutes from shopping, dining, Altamonte Mall, Winter Park, and offers easy access to I-4 and SR 414, making commuting throughout Central Florida a breeze. Don't miss the opportunity to make this exceptional home your own—schedule your private showing today!

2180 Tortoise Shell Drive, Maitland

$519,999

4 Beds ⋅ 3 Baths ⋅ Winfield SubDv. ⋅ 32751 Zip Code

Welcome to 1776 Bobtail Drive — the kind of home that doesn’t just check boxes… it creates emotion, urgency, and that unmistakable “we need this one” reaction the moment your buyers walk through the door. From the very first glance, the curb appeal sets the stage with a warm, polished presence that immediately stands out from the competition. Inside, you’re welcomed by a light-filled, open-concept layout that feels expansive yet comfortable — the perfect balance of elegance and livability. Every space has been thoughtfully designed to flow effortlessly, creating an atmosphere that feels both elevated and inviting. The heart of the home is a beautifully positioned kitchen that seamlessly connects to the main living areas, making it ideal for entertaining, gathering, and everyday life. Whether hosting friends or enjoying a quiet night in, this home delivers the versatility today’s buyers demand. Generously sized living spaces and bedrooms provide comfort, privacy, and flexibility, while the overall layout offers a sense of ease and functionality that appeals to a broad range of buyers — from families to professionals to those simply looking to upgrade their lifestyle. Step outside and experience your own private Florida escape — a backyard setting that invites relaxation, weekend gatherings, and year-round enjoyment. It’s the kind of outdoor space that sells the lifestyle just as much as the home itself. Perfectly positioned in a highly desirable Maitland location, this property offers unbeatable convenience to top-rated dining, shopping, entertainment, and major highways — putting everything Central Florida has to offer right at your fingertips. This is not just another listing — it’s a high-impact, high-demand opportunity that shows beautifully, lives effortlessly, and is primed to sell quickly. Homes with this combination of appeal, location, and lifestyle don’t sit… they move. Bring your buyers with confidence — this is the one they’ve been waiting for.

1776 Bobtail Drive, Maitland

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