Longleaf/Oakland Rep Real Estate

Welcome to Longleaf/Oakland Rep, a charming subdivision nestled in the heart of Winter Garden, Florida, within the vibrant Orange County. This community is a hidden gem that perfectly blends the tranquility of suburban living with the convenience of urban amenities.

Longleaf offers a picturesque setting with beautifully manicured landscapes, tree-lined streets, and an inviting atmosphere that makes it ideal for families and individuals alike. The homes in this subdivision showcase a variety of architectural styles, providing a unique character to the neighborhood. Whether you’re seeking a cozy single-family home or a spacious property for entertaining, Longleaf has something to suit every taste.

Residents of Longleaf enjoy easy access to a plethora of outdoor activities. With nearby parks, walking trails, and recreational facilities, there’s no shortage of ways to soak up the Florida sunshine. The community is also just a short drive from the enchanting downtown Winter Garden, where you can explore delightful shops, dine at local eateries, and partake in seasonal events that bring the neighborhood together.

Education is a top priority in Longleaf, with highly-rated schools and family-friendly programs available for all ages. The community’s close-knit feel fosters lasting friendships and connections among neighbors, making it a wonderful place to call home.

Experience the warmth and charm of Longleaf/Oakland Rep, where community spirit thrives and every day feels like a vacation. Discover your dream home in this idyllic subdivision and enjoy all that Winter Garden has to offer!

Newest Listings in Longleaf/Oakland Rep

$515,000

3 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code

Welcome home to this beautifully maintained 3-bedroom, 2.5-bath home in the highly sought-after Longleaf at Oakland community! From the moment you arrive, you will appreciate the inviting feel, thoughtful layout, and pride of ownership throughout. Inside, enjoy spacious bedrooms, a versatile upstairs loft perfect for a home office, media room, or additional living space, and a comfortable family room designed for everyday living and entertaining. Step outside to a wonderful backyard and porch area, with both the family room and porch pre-wired for speakers—perfect for creating an effortless indoor-outdoor entertaining experience. The two-car garage even features an electric vehicle charging outlet. The location is hard to beat— take a quick 5-minute walk to the West Orange Trail, enjoy the shops, dining, and charm of Downtown Winter Garden just 10 minutes away, and reach the Florida Turnpike in minutes. Beautifully cared for, ideally located, and truly move-in ready—this is the Oakland home you’ve been waiting for!

2696 Bobcat Chase Boulevard, Oakland

$355,000

3 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code

JUST REDUCED!!!!!!!!!!!!!!!!!!!!!! A well-maintained, stunning, and ready-to-move-in townhouse located in the highly desirable Longleaf at Oakland community. Built in 2019, this beautifully maintained home offers 3 spacious bedrooms, 2.5 bathrooms, and 1,620 square feet of bright, open-concept living space designed for both relaxation and entertaining. The inviting front porch is the perfect place to enjoy your morning coffee. Inside, abundant natural light flows through the numerous windows, enhancing the spacious open-concept layout. The large and contemporary kitchen features an island, stainless steel appliances, granite countertops, and an oversized pantry, with premium finishes that seamlessly flow into the main living and dining areas, making it ideal for both everyday living and entertaining. Upstairs, the primary suite serves as your private retreat, featuring an En-suite bath and ample closet space, alongside two additional bedrooms perfect for family, guests, or a dedicated home office. Step outside to the private courtyard, perfect for grilling and enjoying Florida’s beautiful weather with plenty of space for outdoor seating or even a hot tub. The two-car garage offers private rear entry into the home with a spacious driveway that provides additional parking along with guest parking nearby. There is additional parking in the front of this home also. Enjoy being just steps away from the beautiful community pool overlooking the pond and the neighborhood playground. This home and community provides everything the Florida Lifestyle has to offer ! Living here means embracing an incredible Central Florida lifestyle. The Longleaf community features a sparkling resort-style pool with a cabana, a playground, and scenic walking paths. Best of all, you are just steps away from the historic West Orange Trail and the Oakland Nature Preserve, making outdoor adventures effortless. When you want to head out for dinner or shopping, the vibrant culture of downtown Winter Garden and the famous Plant Street Market are only minutes away. Plus, with quick access to major highways like the Florida Turnpike and SR-429, you are seamlessly connected to all of Orlando's world-class theme parks, dining, and entertainment. Don't miss the opportunity to make this beautiful turnkey property your own!

1511 Sweet Apple Street, Oakland

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