Longleaf/Oakland Rep Homes with Pool Community Features

Longleaf/Oakland Rep Homes with Pool Community Features

Welcome to Longleaf/Oakland Rep, a charming subdivision nestled in the heart of Winter Garden, Florida, within the vibrant Orange County. This picturesque community is renowned for its serene atmosphere and family-friendly environment, making it the perfect place to call home.

Longleaf/Oakland Rep boasts a variety of beautifully designed homes, many of which feature private pools, offering residents a refreshing retreat right in their own backyards. Imagine basking in the Florida sun, hosting summer barbecues, or enjoying tranquil evenings under the stars—all made possible by the comfort of your own pool. Whether you’re looking for a cozy single-family home or a spacious residence perfect for entertaining, Longleaf has something for everyone.

The community is thoughtfully designed with an abundance of amenities that cater to an active lifestyle. Residents can take advantage of scenic walking trails, lush green spaces, and well-maintained parks, ideal for family outings or leisurely strolls with pets. The neighborhood fosters a strong sense of community, where neighbors become friends, and social gatherings are common.

Longleaf/Oakland Rep is conveniently located near Winter Garden's charming downtown area, offering a delightful mix of boutique shops, delightful eateries, and vibrant entertainment options. With easy access to major highways, residents can enjoy the best of both worlds—peaceful suburban living and the excitement of nearby Orlando attractions.

If you’re searching for a welcoming community with beautiful homes and a poolside lifestyle, look no further than Longleaf/Oakland Rep. Come discover your dream home in this enchanting neighborhood today!

Newest Longleaf/Oakland Rep Homes with Pool Community Features

1218 Painted Bunting Avenue, Oakland
$517,500
3 Beds ⋅ 2 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
Virtually Staged. **WELCOME HOME** Pond views, beautiful upgrades, and an unbeatable location just minutes from Downtown Winter Garden! BUILT IN 2020 with FRESH EXTERIOR PAINT (2026), this SINGLE-STORY home in the charming Longleaf at Oakland community offers a sought-after floor plan, stylish finishes, and a fantastic location with no direct front or rear neighbors. A welcoming COVERED FRONT PORCH overlooks a peaceful community pond, creating a tranquil setting to relax and enjoy the view. Inside, LUXURY VINYL PLANK FLOORING flows throughout the home, complementing the light, bright, and OPEN LIVING SPACES. The home chef will appreciate the well-appointed kitchen featuring QUARTZ COUNTERTOPS, timeless cabinetry topped with crown molding, a gray ARABESQUE MOSAIC TILE BACKSPLASH, stainless steel appliances, a BUILT-IN OVEN and microwave, cooktop with vent hood, and a spacious ISLAND with PENDANT LIGHTING. A convenient BUILT-IN WORK SPACE just off the kitchen is ideal for a home office or homework station. The thoughtfully designed floor plan offers comfortable bedrooms and beautifully finished bathrooms with granite countertops and gray cabinetry, plus CUSTOM CLOSET built-ins in one of the secondary bedrooms. POCKET SLIDING GLASS DOORS open to the SCREENED LANAI, complete with roller shades for added comfort and privacy. Beyond the porch, a FENCED BACKYARD provides a rare bonus for this style of home, offering outdoor space while still enjoying the convenience of a 2-CAR REAR FACING GARAGE with epoxy flooring. Additional street parking is available out front. Even better, the HOA takes care of the lawn maintenance! Longleaf at Oakland is a quaint, welcoming community with a pool and playground just steps from your front door. Outdoor enthusiasts will love being just a 5-minute stroll from the West Orange Trail, while the shops, restaurants, farmers market, and charm of Historic Downtown Winter Garden are all less than 10 minutes away! Commuters will appreciate quick access to the Florida Turnpike, SR 50, and SR 429, with Lake Apopka, parks, shopping, and everyday conveniences all nearby. ZONED FOR TOP RATED SCHOOLS - Tildenville Elementary, Lakeview Middle, and West Orange High School. Enjoy the benefits of NEWER CONSTRUCTION, thoughtful UPGRADES, LOW MAINTENANCE LIVING, and a prime Oakland location without sacrificing proximity to everything Winter Garden has to offer. Schedule your tour today!

1218 Painted Bunting Avenue, Oakland
2107 Gopher Tortoise Terrace, Oakland
$354,900
2 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained, fully furnished, six-year-old townhome in the charming town of Oakland! Featuring 2 bedrooms, 2.5 baths, and a two-car garage, this home combines abundant natural light with thoughtful upgrades and inviting outdoor space. A covered front porch welcomes you into an open great room featuring Shaw luxury vinyl tile flooring, neutral tones, recessed LED lighting, and dual-pane Low-E windows with cordless faux wood blinds. The kitchen offers 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, along with an LG French-door refrigerator. A generous pantry with a California Closets shelving system keeps everything organized. The adjoining dining area features upgraded lighting and a full-glass door with built-in blinds leading to a private 19-by-15-foot paver courtyard—an inviting setting for outdoor dining or relaxing. A built-in desk nook with granite countertops, drawers, and cabinetry provides a convenient workspace. The first-floor laundry room includes a California Closets laundry station and access to under-stair storage, while a half bath is located off the stair landing. Upstairs, both spacious bedrooms offer walk-in closets and private bathrooms. The primary suite features a California Closets organization 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 private bath features granite countertops and a tiled tub/shower combination with an accent inlay. The courtyard connects to the two-car garage, complete 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, this home offers easy access to shopping, dining, recreation, and major roadways.

2107 Gopher Tortoise Terrace, Oakland
1511 Sweet Apple Street, Oakland
$320,000
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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