Longleaf/Oakland Rep Homes with Pool Community Features

Longleaf/Oakland Rep Homes with Pool Community Features

Welcome to Longleaf/Oakland Rep., a picturesque subdivision nestled in the heart of Winter Garden, Florida, within the vibrant Orange County. This charming community is the perfect blend of modern living and natural beauty, offering residents an idyllic setting to call home.

Longleaf/Oakland Rep. boasts a variety of stunning homes, many of which feature inviting pools that provide a refreshing oasis during the warm Florida summers. Imagine lounging by your private pool, soaking up the sun, or hosting delightful barbecues with friends and family in your backyard paradise. The allure of a poolside lifestyle is just one of the many reasons this community is highly sought after.

Beyond the beautiful homes and sparkling pools, Longleaf/Oakland Rep. is designed with community in mind. Residents enjoy access to well-maintained parks and green spaces, perfect for leisurely strolls, picnics, or playdates with the kids. The neighborhood fosters a strong sense of community, where neighbors become friends and create lasting memories together.

Conveniently located, Longleaf/Oakland Rep. offers easy access to Winter Garden's charming downtown area, filled with boutique shops, delightful dining options, and vibrant community events. With top-rated schools nearby and a wealth of recreational activities, this neighborhood is ideal for families, young professionals, and retirees alike.

Experience the best of Florida living in Longleaf/Oakland Rep. — where your dream home awaits, complete with a beautiful pool and a welcoming community atmosphere. Don’t miss your chance to become a part of this enchanting neighborhood!

Newest Longleaf/Oakland Rep Homes with Pool Community Features

2107 Gopher Tortoise Terrace, Oakland
$364,900
2 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
Beautifully maintained fully furnished six-year-old townhome in the charming town of Oakland! This 2-bedroom, 2.5-bath home features a covered front porch, abundant natural light, and thoughtful upgrades throughout. The open great room welcomes you with Shaw luxury vinyl tile flooring, neutral colors, recessed LED lighting, and dual-pane Low-E windows with cordless faux wood blinds. The kitchen features 42-inch cabinetry, granite countertops, a gray subway tile backsplash, and a spacious island with upgraded pendant lighting and a large undermount sink. Appliances include a Whirlpool Gold microwave, range, and dishwasher, plus an LG French-door refrigerator. A generous pantry with a California Closets shelving system provides exceptional organization. The adjoining dining area features upgraded lighting and access to a private 19-by-15-foot paver courtyard through a full-glass door with built-in blinds. A convenient desk nook with granite countertops, drawers, and cabinetry offers space to work from home. The first-floor laundry room includes a California Closets laundry station and access to ample storage beneath the stairs. A half bath is conveniently located off the stair landing. Upstairs, both spacious bedrooms feature walk-in closets and private bathrooms. The primary suite offers a beautifully organized California Closets system with a built-in vanity. Its ensuite bath includes dual sinks, granite countertops, Moen faucets, a private water closet, and a tiled shower with decorative accents, frameless glass, and an upgraded showerhead. The second bedroom’s bathroom features granite countertops and a tiled tub/shower combination with an accent inlay. The private courtyard connects to a two-car garage with epoxy flooring and a Bluetooth-enabled opener. Additional features include gutters, a Taexx built-in pest control system, Nest thermostat, Ring security system and doorbell, Alexa-compatible front porch lighting, and prewiring for ceiling fans in the great room and bedrooms. Enjoy community walking paths, a playground, and a pool, with lawn care included in the HOA. Conveniently located near the West Orange Trail, downtown Winter Garden, downtown Clermont, Florida’s Turnpike, and Winter Garden Village. Bring your pups—this community has no dog breed restrictions!

2107 Gopher Tortoise Terrace, Oakland
2696 Bobcat Chase Boulevard, Oakland
$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
1511 Sweet Apple Street, Oakland
$334,950
3 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
Virtually Staged. 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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