Longleaf/Oakland Rep Homes with Sidewalk Exterior Features

Welcome to Longleaf/Oakland Rep, a picturesque subdivision nestled in the heart of Winter Garden, Florida. This charming community offers a perfect blend of suburban tranquility and modern convenience, making it an ideal choice for families, retirees, and everyone in between.

Longleaf/Oakland Rep is renowned for its beautifully designed homes that showcase impressive architectural styles and thoughtful layouts. Each residence is set against a backdrop of lush greenery, offering residents a serene environment to unwind after a busy day. One of the standout features of this subdivision is its inviting sidewalks, which line the streets and create a friendly atmosphere for leisurely strolls, morning jogs, or evening bike rides. The sidewalks not only enhance the community's aesthetic appeal but also foster a sense of connection among neighbors.

Living in Longleaf/Oakland Rep means enjoying the best of Winter Garden. You’ll find yourself just minutes away from vibrant shopping districts, delightful dining options, and recreational parks. The area is also known for its top-rated schools, making it a sought-after location for families.

With its warm community spirit, beautiful homes, and convenient access to local amenities, Longleaf/Oakland Rep is more than just a place to live; it’s a lifestyle. Whether you’re looking to settle down or invest in a new property, this subdivision offers an exceptional quality of life that you’ll be proud to call home. Come explore the charm of Longleaf/Oakland Rep and discover why so many choose to make this delightful community their own!

Newest Longleaf/Oakland Rep Homes with Sidewalk Exterior 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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