Oakland Hills Homes with Pool

Oakland Hills Homes with Pool

Welcome to Oakland Hills, a picturesque subdivision nestled in the heart of Winter Garden, Florida, within the charming Orange County. Known for its serene atmosphere and family-friendly vibe, Oakland Hills offers a delightful blend of suburban tranquility and modern conveniences, making it an ideal place to call home.

One of the standout features of Oakland Hills is the stunning homes that grace its tree-lined streets. Many of these residences boast private pools, perfect for those warm Florida days when you want to cool off or entertain friends and family. Imagine lounging by your poolside oasis, soaking in the sun, or hosting summer barbecues while the kids splash around. The presence of pools in these homes not only enhances your lifestyle but also adds an element of luxury and relaxation to your everyday routine.

The community itself is designed for comfort and convenience, with access to top-rated schools, shopping centers, and recreational activities just minutes away. Residents can enjoy the nearby West Orange Trail, perfect for biking, walking, or jogging, and the vibrant downtown Winter Garden, known for its quaint shops, delightful dining options, and community events.

In Oakland Hills, you’ll find a welcoming community where neighbors become friends, and every day feels like a vacation. Whether you’re a first-time homebuyer or looking to upgrade your living situation, this subdivision is a hidden gem that offers the perfect blend of comfort, style, and a touch of Florida sunshine. Come discover your dream home in Oakland Hills—your private paradise awaits!

Newest Oakland Hills Homes with Pool

$2,325,000
4 Beds 5 Baths O6422464 MLS
Perfectly positioned on a quiet cul-de-sac in the sought-after Oakland Hills community near historic downtown Winter Garden. This FULLY FURNISHED and thoughtfully designed custom home on a single level, combines timeless modern farmhouse architecture with today's finest technology and craftsmanship. Curb appeal abounds with a classic mix of Hardie board siding and brick, anchored by a large, shaded front porch glowing with authentic gas lanterns from New Orleans — a true farmhouse welcome. When evening arrives, intentional landscape lighting accentuates the lush grounds and craftsmanship evident in every corner. Inside, the statement grand great room makes an unforgettable first impression with soaring 22+ foot ceilings, exposed beams, and dormer windows that fill the room with natural sunlight from morning to evening. Throughout the home, ten-foot ceilings, custom moldings and baseboards, LBU lighting with LED bulbs, and natural hardwood floors (in all but the media room) keep the ambiance light and welcoming. The heart of this custom residence is a true chef's kitchen: Monogram appliances, two oversized islands, a 36" gas range, paired with Moen and Kohler fixtures, all wrapped in custom Wellborn cabinetry with soft-close doors and drawers. A back second kitchen — the ultimate working pantry — adds double ovens, a microwave, a commercial Keurig, and abundant storage for effortless entertaining. Just off the main living space, a warm and welcoming library/office with custom-built bookcases and Zoom room offers a quiet retreat. The generous primary suite is a luxurious escape, complete with a spa-inspired bathroom centered around an oversized Kohler clawfoot tub. Two additional guest suites offer king beds and ensuite baths with double vanities, while a thoughfully designed bunk room with its own private bath means every guest feels right at home. Movie nights reach a new level in the dedicated media room with a 4K projector and Atmos surround sound. Outdoor living takes center stage on the expansive covered lanai, where a fully equipped summer kitchen with 36" Coyote natural gas grill, exhaust vent, steel doors, and retractable screen — makes alfresco entertaining effortless. Beyond, a private backyard with a heated pool and natural gas fire pit invites year-round gatherings that won't be forgotten. Enjoy smart home living at it's best with a Crestron home automation system, WattBox® UPS battery, Uniview Turret security cameras monitored by Future Home Integration, plus whole-home Wi-Fi with service options from Spectrum or Quantum. Custom closets, two laundry rooms, and an oversized three-car garage with an incredible amount of extra storage. Oakland Hills is an exclusive enclave of just 17 custom homes, minutes from the West Orange Trail, downtown Winter Garden, and Winter Garden Village. Perfectly positioned with easy access to the Turnpike, SR 429, and SR 408, it makes commuting, theme park visits, and airport runs a breeze. Schedule your private tour today and experience everything this meticulous one-of-a-kind home has to offer!

15217 Farm Stand Court, Winter Garden

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