Oakland Park Homes with Sidewalk Exterior Features

Oakland Park Homes with Sidewalk Exterior Features

Welcome to Oakland Park, a vibrant and inviting subdivision nestled in the heart of Winter Garden, Florida. This charming community, located in Orange County, offers a delightful blend of modern living and small-town charm, 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 pedestrian-friendly environment. With beautifully designed homes featuring sidewalk exterior options, residents enjoy the luxury of strolling through tree-lined streets, taking leisurely evening walks, or biking with friends and family. The sidewalks not only enhance the aesthetic appeal of the neighborhood but also foster a sense of community, encouraging neighbors to connect and engage with one another.

The homes in Oakland Park are thoughtfully crafted, showcasing contemporary designs and high-quality finishes. Each property is tailored to meet the diverse needs of homeowners, offering spacious layouts, modern amenities, and beautifully landscaped yards. Whether you’re looking for a cozy single-family home or a more expansive residence, Oakland Park has something to suit every lifestyle.

Moreover, the location is unbeatable. Just minutes away from Winter Garden's historic downtown, residents can enjoy a variety of shopping, dining, and entertainment options. The nearby parks and recreational facilities provide ample opportunities for outdoor activities, ensuring that you and your family can enjoy the beautiful Florida sunshine year-round.

Discover the charm of Oakland Park, where community spirit thrives, and every day feels like a vacation. Your dream home awaits in this picturesque Winter Garden neighborhood!

Newest Oakland Park Homes with Sidewalk Exterior Features

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
925 Easley Avenue, Winter Garden
$1,075,000
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
1101 Eagles Pass Way, Winter Garden
$1,625,000
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
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