Longleaf/Oakland Rep Homes with Sidewalks Community Features

Welcome to Longleaf/Oakland Rep, a charming subdivision nestled in the heart of Winter Garden, Florida, within the vibrant Orange County. This delightful community is perfect for those seeking a serene suburban lifestyle while still enjoying the conveniences of modern living.

Longleaf/Oakland Rep boasts an array of beautifully designed homes, many of which feature inviting sidewalks that encourage leisurely strolls and foster a sense of community. Imagine stepping out of your front door, greeted by the gentle Florida breeze, and taking a peaceful walk along tree-lined streets, where neighbors become friends and families thrive. The sidewalks not only enhance the aesthetic appeal of the neighborhood but also provide a safe space for children to play and residents to connect.

The homes in Longleaf/Oakland Rep are thoughtfully crafted to suit various lifestyles, whether you’re a growing family or looking to downsize. With spacious layouts, modern amenities, and a variety of architectural styles, there’s something for everyone. Many properties also feature lush yards and outdoor spaces, perfect for entertaining or simply enjoying the beautiful Florida weather.

In addition to the picturesque surroundings, residents of Longleaf/Oakland Rep enjoy proximity to Winter Garden’s charming downtown area, where you’ll find delightful shops, dining options, and community events. With its perfect blend of tranquility and accessibility, Longleaf/Oakland Rep is more than just a place to live; it’s a community where memories are made and cherished. Discover your dream home in this enchanting subdivision today!

Newest Longleaf/Oakland Rep Homes with Sidewalks Community Features

$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

$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

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