Oakland Hills Homes with HOA Yes/No

Oakland Hills Homes with HOA Yes/No

Welcome to Oakland Hills, a picturesque subdivision nestled in the heart of Winter Garden, Florida. This charming community is located in Orange County, where the lush landscapes and serene surroundings create an idyllic setting for families, retirees, and everyone in between. Oakland Hills is renowned for its friendly atmosphere, making it a perfect place to call home.

The homes in Oakland Hills are beautifully designed, showcasing a variety of architectural styles that cater to diverse tastes. Whether you’re looking for a cozy single-family home or a spacious residence with modern amenities, you’ll find it here. Each property is thoughtfully constructed, with many featuring open floor plans, gourmet kitchens, and private backyards perfect for entertaining or enjoying quiet evenings under the stars.

One of the standout features of Oakland Hills is its homeowners association (HOA), which helps maintain the community’s charm and enhances the overall living experience. The HOA ensures that the common areas are well-kept and provides residents with access to amenities such as parks, walking trails, and recreational facilities. This commitment to community upkeep fosters a sense of pride among residents and promotes a safe and welcoming environment.

In addition to its beautiful homes and community spirit, Oakland Hills is conveniently located near shopping, dining, and top-rated schools, making it an ideal choice for families. With easy access to major highways, residents can enjoy the vibrant lifestyle of Winter Garden while still having the tranquility of suburban living. Discover the charm of Oakland Hills today – your dream home awaits!

Newest Oakland Hills Homes with HOA Yes/No

$2,325,000
4 Beds 5 Baths Oakland Hills SubDv. 34787 Zip Code
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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