Oakland Park Homes with Sidewalk Exterior Features

Oakland Park Homes with Sidewalk Exterior Features

Welcome to Oakland Park, a picturesque subdivision nestled in the heart of Winter Garden, Florida. This charming community in Orange County is a hidden gem that perfectly blends suburban tranquility with effortless access to urban conveniences. Oakland Park is designed for those who appreciate a sense of community, with beautifully landscaped streets and a welcoming atmosphere that invites you to explore your surroundings.

One of the standout features of Oakland Park is its commitment to creating a pedestrian-friendly environment. The homes here boast lovely sidewalk exterior features, making it easy for residents to enjoy leisurely strolls through the neighborhood. Imagine taking morning walks with your family or evening jogs while enjoying the beautiful Florida weather—all right outside your front door. The sidewalks create a sense of connectivity, encouraging neighbors to engage and fostering a tight-knit community spirit.

The homes in Oakland Park are thoughtfully designed with modern aesthetics and functional layouts, catering to a variety of lifestyles. Whether you’re a growing family, a young professional, or looking to downsize, you’ll find a home that suits your needs perfectly. With spacious yards and charming architectural details, these residences offer both comfort and style.

Beyond the community, Winter Garden itself is a vibrant city filled with delightful shops, restaurants, and recreational opportunities. From the historic downtown area to the nearby West Orange Trail, there’s always something to explore. Experience the best of Florida living in Oakland Park, where community, convenience, and charm come together seamlessly. Welcome home!

Newest Oakland Park Homes with Sidewalk Exterior Features

$1,125,000
4 Beds ⋅ 4 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Welcome to a life beautifully lived. Situated on a premier corner lot in Oakland Park, Winter Garden's golf cart community, this exceptional residence blends thoughtful design, effortless indoor-outdoor living, & a private tropical retreat. Freshly redesigned professional landscaping with premium weed barrier, smart irrigation, app control, & a mature Medjool date palm creates stunning curb appeal. A custom front door opens to a partially screened wraparound front porch, perfect for morning coffee or evening chats. Inside, rich hardwood floors span the main level, complemented by abundant natural light, crown molding, plantation shutters, designer lighting, brass floor outlets in the living room & office, and ceiling fans throughout. The kitchen features granite countertops, a farmhouse sink, stainless steel appliances, tile backsplash, under-cabinet lighting, a beverage refrigerator, & a new Bosch dishwasher and microwave (2023). Open to the living & dining areas, it overlooks the front porch & connects seamlessly to outdoor living through French doors. A flexible front room serves as an office, study, or playroom. A powder room serves guests. The first-floor owner's suite overlooks the pool & offers dual granite vanities, a spa-style walk-in shower, linen storage, custom California Closets, & direct laundry room access. Upstairs, hardwood flooring continues throughout 3 spacious bedrooms, including one en-suite, plus two full baths and a generous loft ideal for theater, fitness, playroom, or guest retreat. A whole-home Generac natural gas generator keeps lights, air conditioning, & appliances running during outages. Step outside to one of Oakland Park's rare full-size Jandy-iAqualink-controlled saltwater pool & spa. The pool measures approximately 12' x 30' with depths from 3' to 5' & features an 8' x 12' sun shelf with bubbling fountain and umbrella sleeve. The approximately 6' x 8' spa includes four therapy jets and heats in 20-30 minutes. Equipment includes a 2.7 HP Jandy Variable-Speed Energy-Efficient Pump & Jandy 400,000 BTU natural gas heater. A travertine pool deck, oversized covered rear porch, vinyl-fenced yard with dual gates, & three-car garage with built-in storage racks complete the outdoor experience. Oakland Park offers a waterfront, golf-cart-approved lifestyle with two resort-style pools, a clubhouse, dog park, playgrounds, parks, & spectacular sunsets. Two blocks from the waterfront trail, minutes from the 22-mile West Orange Trail, & near multiple parks. Historic downtown Winter Garden is a golf cart ride away, offering Crooked Can Brewery, rooftop dining, boutique shopping, splash park, Farmers Market, live theater, golf cart parades, 5Ks, book clubs, poker nights, and more. Convenient access to major interstates, premier golf courses, shopping, & Central Florida theme parks. Additional features: fresh interior/exterior paint (2021), Apple HomeKit-compatible door locks, thermostats & ceiling fans, Apple Secure Video cameras at the doorbell, front entry, pool area & indoor locations, new remote-controlled high-velocity fans on both porches, Apple HomeKit-controlled owner's bath fan, outlets inside primary bath cabinetry, & a state-of-the-art termite detection and control system with full warranty. Lovingly maintained & thoughtfully enhanced throughout, this one-of-a-kind Oakland Park pool & spa home is a special opportunity. Your oasis is waiting. Make it yours.

925 Easley Avenue, Winter Garden
$595,000
3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained, move-in ready 3-bedroom, 3-bathroom home in Oakland Park, one of Winter Garden’s most desirable communities. Offering a blend of classic architecture, modern updates, and an exceptional location, this turnkey Winter Garden home is designed for comfortable Florida living. Step inside to a bright and spacious open-concept floor plan featuring abundant natural light, soaring ceilings, and generously sized living and dining areas. The flexible layout is ideal for entertaining, working from home, or accommodating guests. At the center of the home is the chef-inspired kitchen, featuring natural gas appliances, ample cabinetry, generous counter space, and an open connection to the main living areas. Whether you're preparing a weeknight dinner or entertaining friends and family, this kitchen is both functional and inviting. The spacious primary suite provides a private retreat with a luxurious ensuite bathroom and generous walk-in closet. Two additional bedrooms and bathrooms offer plenty of flexibility for family, guests, a home office, or additional living space. Throughout the home, you'll find plantation shutters, designer finishes, and quality upgrades that create a polished yet comfortable atmosphere. With thoughtful improvements already in place, you can move in and start enjoying the lifestyle this home and community have to offer. And then there's Oakland Park. Residents have access to an impressive collection of resort-style community amenities, including TWO community pools, beautiful green spaces, parks, playgrounds, walking paths, gathering areas, and the neighborhood’s iconic tree-lined streets and welcoming front porches. Oakland Park is designed to create a true neighborhood feel while offering the amenities buyers want from a premier Winter Garden community. Location is hard to beat. You're just minutes from Historic Downtown Winter Garden, the popular Winter Garden Farmers Market, the West Orange Trail, local restaurants, boutique shopping, parks, and year-round community events. Convenient access to SR 429 and the Florida Turnpike makes commuting throughout Central Florida easy, while Disney, downtown Orlando, and Orlando International Airport are all within a manageable drive. If you're searching for a move-in ready home in Winter Garden, a community with resort-style amenities and pools, or a home close to Downtown Winter Garden and the West Orange Trail, this Oakland Park property checks the boxes. Experience the charm, convenience, and lifestyle that make Oakland Park one of Winter Garden's most sought-after communities.

914 Trowman Alley, Winter Garden
$1,649,999
6 Beds ⋅ 5 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Virtually Staged. Modern Luxury in the Heart of Winter Garden’s Golf Cart District! Welcome to 1101 Eagles Pass Way, an exquisite 6-bedroom, 5-bathroom home situated on a desirable corner lot in the sought-after Oakland Park community—one of the few neighborhoods within Winter Garden’s beloved golf cart district. Just one block from Lake Apopka and less than two miles from the historic downtown shops and restaurants, this home beautifully blends modern luxury with small-town charm. Step inside to discover designer finishes and thoughtful craftsmanship throughout. The gourmet kitchen features top-end Monogram appliances, including a 36” dual-fuel range, warming oven, and a 48” side-by-side refrigerator and freezer. Upgraded quartz countertops, a brick backsplash and hearth with built-in electric fireplace, and engineered hardwood floors elevate the open-concept main living areas. Additional luxury touches include Brizo faucets, custom plantation shutters, and floating shelving systems in every bedroom closet. The owner’s suite offers a spa-inspired retreat with a 6-foot soaking tub, while the upgraded pantry with butcher block countertop, dimmer switches, and ceiling fans throughout enhance everyday comfort. An in-law suite featuring a full bath, family room, and a private staircase above the garage provides the perfect space for guests, extended family, or a private home office. Enjoy peaceful mornings and sunset evenings from the screened front and side porches, adding to the home’s charm and livability. Located in Oakland Park, residents enjoy resort-style amenities including two community pools, multiple parks and playgrounds, scenic walking and biking trails, a clubhouse, and direct access to the West Orange Trail. With tree-lined streets, lake views, and friendly front-porch living, this award-winning community captures the very best of Winter Garden living.

1101 Eagles Pass Way, Winter Garden
$2,098,000
4 Beds ⋅ 4 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Pre-Construction. To be built. Pre-Construction. To be built. A Custom home in the Reserve of the sought-after Oakland Park community. This is a RCB Homes custom-built two story, four-bedroom, four-bath floor plan that you will customize with all the luxury finishes you will pick yourself! The floorplan is an open concept design, but you can still make changes to the floorplan if you want! The lot affords beautiful views of Lake Apopka on a secluded cul-de-sac. The community is conveniently located minutes away from downtown Winter Garden, with a plethora of restaurants, shopping, and more. If outdoor recreation is up your alley, enjoy the various walking trails in the community or explore the 22-mile paved West Orange Trail connecting Oakland/Winter Garden to Apopka! Seize your opportunity to become a part of the luxury lifestyle inside Oakland Park with its multiple community living spaces, pools, playgrounds, and more. Don't settle for a community or home that doesn't have your wants and needs; build this home one to your specifications. Call us to find out more!

1258 Ridge Lake Way, Oakland
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