Oakland Park Homes with Sidewalks Community Features

Oakland Park Homes with Sidewalks Community Features

Welcome to Oakland Park, a vibrant and inviting subdivision nestled in the heart of Winter Garden, Florida. Located in the picturesque Orange County, this charming community offers a perfect blend of suburban tranquility and modern convenience, making it an ideal place for families, young professionals, and retirees alike.

One of the standout features of Oakland Park is its commitment to creating a walkable neighborhood. With beautifully designed homes that come with sidewalks, residents can enjoy leisurely strolls through the community, fostering a strong sense of connection with neighbors. The tree-lined streets invite evening walks, morning jogs, or simply a chance to enjoy the Florida sunshine while engaging with the vibrant community.

Oakland Park boasts a variety of well-appointed homes that cater to diverse lifestyles and preferences. From cozy single-family residences to spacious family homes, each property is designed with comfort and style in mind. The community’s architecture harmonizes with the natural beauty of the surrounding landscape, creating a picturesque environment that residents are proud to call home.

In addition to its charming homes, Oakland Park is conveniently located near top-rated schools, shopping centers, and recreational areas. Families can take advantage of nearby parks, playgrounds, and sports facilities, ensuring that there’s always something to do. With easy access to major highways, commuting to nearby cities is a breeze, making Oakland Park a perfect blend of convenience and comfort.

Come discover the charm of Oakland Park, where community spirit thrives, and every day feels like a getaway!

Newest Oakland Park Homes with Sidewalks Community Features

939 Kylee Alley, Winter Garden
$670,000
3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this gorgeous, exceptionally well-maintained home in the highly sought-after Oakland Park community of Winter Garden! Practically brand new, this beautiful residence features 9-foot ceilings, a charming front porch, and a bright, open-concept layout designed for both everyday living and entertaining. The first and second floors feature beautiful luxury vinyl plank flooring, with carpet reserved only for the bedrooms. The stunning kitchen is a true centerpiece of the home, offering beautiful finishes, ample cabinetry, and a functional layout perfect for gatherings. A new tankless water heater adds modern efficiency and convenience.Enjoy the best of the Winter Garden lifestyle, located within the Winter Garden Golf Cart District, with convenient access to nearby shopping, dining, parks, and entertainment. Oakland Park features beautiful tree-lined streets, green spaces, playgrounds, community amenities, and a charming neighborhood atmosphere. The home is just minutes from Downtown Winter Garden, Plant Street Market, the West Orange Trail, Winter Garden Village, and an array of restaurants, breweries, boutiques, and local events. With easy access to major roadways and Central Florida attractions, this beautifully cared-for home offers an exceptional combination of style, comfort, and location.

939 Kylee Alley, Winter Garden
150 Hammock Preserve Loop, Oakland
$879,000
4 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Some homes simply sit in a neighborhood. This one feels like it belongs there. Welcome to 150 Hammock Preserve Loop, a 2023 Rockwell Homes residence tucked into the heart of Oakland Park, where the front porch looks out toward mature oak trees and the best parts of the Winter Garden lifestyle are never far from home. Step inside and you’re immediately greeted by a dedicated office to the left of the entry, creating the perfect work-from-home space while keeping it separate from the main living areas. Throughout the home, thoughtful custom updates give each space a personality of its own. The primary suite is conveniently located on the main floor, while the additional bedrooms and spacious loft are upstairs, creating a layout that offers both separation and flexibility. A rare three-car garage provides the extra space that can be difficult to find in Oakland Park, whether you need room for vehicles, golf carts, bikes, storage, or all of the above. Out back, the generous yard offers plenty of room to create your own outdoor retreat, including space for a future pool. But what makes this home especially difficult to replicate is everything beyond the front door. Oakland Park is one of Winter Garden’s most sought-after communities for a reason. Tree-lined streets, front porches, parks, playgrounds, two resort-style community pools, a clubhouse, dog park, waterfront spaces, and miles of trails create a neighborhood designed to actually be enjoyed. Hop on your bike and connect to the West Orange Trail, or grab the golf cart and head toward Downtown Winter Garden for a morning at the Farmers Market, drinks at Crooked Can, dinner along Plant Street, boutique shopping, community events, and everything surrounding Plant Street Market. Here, weekends can start with coffee on the front porch beneath the oaks, turn into an afternoon by the pool or on the trail, and end with a golf cart ride into Downtown Winter Garden. Built in 2023, filled with custom touches, complete with a dedicated office, rare three-car garage, and a backyard ready for what comes next, 150 Hammock Preserve Loop offers more than a beautiful home. It offers the Oakland Park lifestyle that makes this neighborhood so special.

150 Hammock Preserve Loop, Oakland
910 Trowman Aly, Winter Garden
$638,000
3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Welcome to this modern 3-bedroom, 2 and 1/2-bath residence, 1650 square feet located in McKinnon Square at Oakland Park, nestled within Winter Garden's coveted golf cart district. This Home has a nice welcoming front porch and showcases timeless architecture, upscale designer finishes. Step inside to discover soaring ceilings, beautiful luxury vinyl plank flooring throughout the main living areas. At the heart of the home on the 2nd Story, the Executive kitchen features custom cabinetry with updated hardware, quartz countertops, an island, a gas range, vent hood, tile backsplash, and abundant storage. The open-concept design flows effortlessly into the spacious family room with a Balcony to have coffee in the morning or tea in the evening. The upstairs has a lofty feel has a nice living space. Cathedral ceilings, walk-in closet. One of Winter Garden's most desirable lifestyles. This award-winning, master-planned community of Oakland Park features tree-lined streets, scenic parks, resort-style pools, playgrounds, and miles of walking and biking trails, including direct access to the renowned West Orange Trail. Residents enjoy a true neighborhood atmosphere just a golf cart ride from Historic Downtown Winter Garden, where you'll find award-winning restaurants, boutique shopping, breweries, coffee shops, live entertainment, and the nationally recognized Winter Garden Farmers Market close to Winter Garden Village at Fowler Groves the outdoor Mall and the Orlando International Airport. With convenient access to Florida's Turnpike, SR-429, 408, to downtown Orlando, and Central Florida's world-famous attractions and Themed Parks, this exceptional residence offers the perfect blend of luxury, convenience, community, and lifestyle.

910 Trowman Aly, Winter Garden
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