Oakland Park Homes with Sidewalk Exterior features

Oakland Park Homes with Sidewalk Exterior features

Welcome to Oakland Park, a delightful subdivision nestled in the heart of Winter Garden, Florida, within the vibrant Orange County. This charming community is designed for those who appreciate a blend of modern living and natural beauty, making it the perfect place to call home.

Oakland Park is characterized by its picturesque streets lined with lush greenery and beautifully crafted homes. One of the standout features of this subdivision is its commitment to pedestrian-friendly living, evident in the well-maintained sidewalks that grace each neighborhood. Whether you're out for a morning jog, an evening stroll, or simply enjoying the fresh Florida air, these sidewalks provide a safe and inviting pathway for residents of all ages.

The homes in Oakland Park are thoughtfully designed with exterior features that enhance their curb appeal and create a warm, welcoming atmosphere. From charming front porches to manicured gardens, each property reflects a unique character while maintaining a cohesive aesthetic that fosters a strong sense of community.

Residents enjoy easy access to a variety of amenities, including nearby parks, shopping centers, and top-rated schools. The vibrant downtown area of Winter Garden, with its quaint shops and delicious dining options, is just a short drive away, offering a lively social scene.

In Oakland Park, you’ll find not just a home, but a lifestyle that embraces community, convenience, and the beauty of Florida living. Come explore the charm of Oakland Park, where your dream home awaits!

Newest Oakland Park Homes with Sidewalk Exterior features

$779,900
4 Beds ⋅ 4 Baths ⋅ O6425976 MLS
Under contract-accepting backup offers. Welcome to this exceptional 4-bedroom, 4-bath residence with a private office, expansive loft, and 2,831 square feet of beautifully designed living space in the highly sought-after McKinnon Square at Oakland Park, nestled within Winter Garden's coveted golf cart district. Perfectly positioned on a private corner end lot, this stunning home is complemented by a welcoming front porch and showcases timeless architecture, upscale designer finishes, and exceptional attention to detail. Step inside to discover soaring ceilings, abundant natural light, and beautiful white oak luxury vinyl plank flooring throughout the main living areas. A private office just off the foyer provides the ideal work-from-home space or flex room, while custom window treatments, plantation shutters, designer wallpaper, elegant accent walls, and custom built-ins create a warm yet sophisticated atmosphere. At the heart of the home, the gourmet chef's kitchen features custom cabinetry with upgraded hardware, quartz countertops, an oversized island with designer pendant lighting, a gas cooktop, custom vent hood, built-in wall oven, decorative tile backsplash, and abundant storage. The open-concept design flows effortlessly into the spacious family room, where custom built-ins create the perfect gathering space for entertaining or relaxing. The thoughtfully designed floor plan includes a private first-floor guest suite with a full bath, ideal for guests or multigenerational living. Upstairs, an expansive loft offers flexible living space perfect for a media room, game room, or second family room. The luxurious primary suite is privately situated away from the secondary bedrooms and offers tray ceilings, designer accent walls, a spacious walk-in closet, and a spa-inspired en-suite bath featuring dual quartz vanities, a soaking garden tub, and a separate walk-in shower. Two additional upstairs bedrooms each feature walk-in closets, with one offering its own private en-suite bath, while another full bath serves the remaining bedroom and loft. Even the laundry room has been elevated with designer wallpaper, quartz folding countertops, and an included washer and dryer. Outside, the private corner homesite enhances both curb appeal and privacy, offering additional green space and a peaceful setting to enjoy the Florida lifestyle. Living in Oakland Park means embracing 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. With convenient access to Florida's Turnpike, SR-429, downtown Orlando, and Central Florida's world-famous attractions, this exceptional residence offers the perfect blend of luxury, convenience, community, and lifestyle.

944 Kylee Aly, Winter Garden
$1,125,000
4 Beds ⋅ 4 Baths ⋅ O6412977 MLS
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 ⋅ O6410871 MLS
Welcome to this beautifully maintained, move-in ready 3-bedroom, 3-bathroom home in the highly sought-after Oakland Park community of Winter Garden. Combining timeless architecture with modern upgrades, this turnkey home offers the perfect blend of comfort, style, and convenience. Inside, you'll find a bright, open-concept floor plan with abundant natural light, soaring ceilings, spacious living and dining areas, and a flexible layout ideal for entertaining, working from home, or accommodating multigenerational living. The chef-inspired kitchen features desirable gas appliances, generous counter space, ample cabinetry, and seamlessly connects to the main living areas, creating the heart of the home. Thoughtful upgrades throughout include plantation shutters, designer finishes, and quality craftsmanship, providing a low-maintenance lifestyle that allows you to simply move in and enjoy. The spacious primary suite offers a private retreat with a luxurious ensuite bathroom and generous walk-in closet, while the additional bedrooms and bathrooms provide flexibility for family, guests, or a dedicated home office. Step outside and enjoy Oakland Park's signature charm, featuring tree-lined streets, inviting front porches, scenic green spaces, and resort-style amenities that foster a true sense of community. Perfectly located just minutes from Historic Downtown Winter Garden, the award-winning Farmers Market, the West Orange Trail, boutique shopping, popular restaurants, community events, and convenient access to SR 429, the Florida Turnpike, Disney, downtown Orlando, and Orlando International Airport. Families will appreciate the proximity to top-rated schools and nearby parks. Whether you're searching for a primary residence, a second home, or simply a home that offers an exceptional lifestyle in one of Central Florida's most desirable communities, this Oakland Park gem delivers the location, upgrades, and quality you've been waiting for.

914 Trowman Alley, Winter Garden
$1,649,999
6 Beds ⋅ 5 Baths ⋅ O6408835 MLS
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 ⋅ O6373776 MLS ⋅ Rcb Homes BLDG.
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, Winter Garden
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