Oakland Hills Homes for Sale

Oakland Hills Homes for Sale

Welcome to Oakland Hills, a luxurious subdivision nestled in the heart of Winter Garden, FL. This exclusive community is located in Orange County and offers a serene and sophisticated living experience for residents seeking the perfect blend of comfort and convenience.

Oakland Hills is a coveted neighborhood known for its upscale homes and picturesque surroundings. The meticulously designed properties in this area boast modern amenities, spacious layouts, and stunning architectural details that cater to the discerning homeowner.

If you are in the market for a new home, Oakland Hills is the perfect place to start your search. With a variety of homes for sale, ranging from cozy single-family residences to expansive estates, there is something for everyone in this sought-after community. Whether you are a first-time homebuyer or looking to upgrade to your dream home, Oakland Hills has the perfect property to suit your needs and lifestyle.

Living in Oakland Hills means enjoying a tranquil setting while still being close to all the conveniences of city life. From top-rated schools and shopping centers to dining options and recreational facilities, everything you need is just a short drive away.

Don't miss the opportunity to be a part of this vibrant community. Explore the homes for sale in Oakland Hills today and discover the perfect place to call home in Winter Garden, FL.

Newest Oakland Hills Homes for Sale

$295,000
3 Beds ⋅ 2 Baths ⋅ Oakland Hills SubDv. ⋅ 32714 Zip Code
Excellent opportunity in Altamonte Springs! This 3-bedroom, 2-bath home is ideal for investors seeking income potential as well as future homeowners planning ahead for their next move. The home features a comfortable open floor plan, an updated kitchen with modern appliances, a new roof, and plenty of natural light throughout. The primary suite provides privacy with its own en-suite bath, while the additional bedrooms create flexibility for family, guests, or a home office. Step outside and enjoy the spacious fenced backyard surrounded by greenery, creating an inviting space for outdoor living, entertaining, gardening, or future enhancement. Located in a quiet, established neighborhood, this property places residents close to schools, shopping, dining, parks, and everyday conveniences. With easy access to major highways, commuting throughout Altamonte Springs, Orlando, and the surrounding Central Florida area is simple and convenient. 661 Encino Way brings together location, functionality, outdoor space, and long-term value.

661 Encino Way, Altamonte Springs
$409,900
4 Beds ⋅ 2 Baths ⋅ Oakland Hills SubDv. ⋅ 32714 Zip Code
NEW ROOF! Welcome to this beautifully renovated 4-bedroom, 2-bathroom home in the heart of Altamonte Springs, where modern upgrades meet everyday functionality. Located within a highly sought-after, top-rated school district, this move-in-ready home offers exceptional style and comfort from the moment you arrive. Step inside to discover a bright, open layout featuring all-new flooring, fresh interior paint, and a stunning designer kitchen that serves as the heart of the home. Boasting sleek quartz countertops, abundant cabinetry, an oversized farmhouse sink, and a spacious center island, this kitchen is perfectly designed for entertaining guests or enjoying everyday meals. Both bathrooms have been thoughtfully remodeled with luxurious floor-to-ceiling tile, spacious walk-in showers, and heated toilet seats, creating a spa-inspired retreat with a clean, contemporary feel. Continue outside to the private backyard, where you'll find a brand-new fence and low-maintenance gravel landscaping, offering the perfect space to relax, entertain, or personalize to your lifestyle. With a new roof, extensive interior renovations, new exterior paint, modern finishes throughout, and an unbeatable Altamonte Springs location close to shopping, dining, parks, major roadways, and everyday conveniences, this home is truly turnkey and ready for its next owners. Don't miss your opportunity to make it yours!

682 Durango Way, Altamonte Springs
$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
$595,000
4 Beds ⋅ 3 Baths ⋅ Oakland Hills SubDv. ⋅ 33619 Zip Code
PRICE REDUCTION. MAIN HOME + PERMITTED GUEST HOUSE. Two full residences on one lot. NEW PRICE. 4 bedrooms, 3 baths, and approx. 2,271 total sq ft of 2024 construction on 0.30 acres. The main home offers 3 bedrooms, 2 baths, and 1,679 sq ft of concrete block and stucco construction with high ceilings, granite countertops, and tile flooring throughout; the garage is currently finished as a game room. Steps away, the permitted, detached 500 sq ft guest house includes its own full kitchen, bedroom, and bath flexible as guest quarters, home office, studio, or income opportunity (buyer to verify rental terms). No HOA, no CDD, no rental restrictions. Parking for up to 4 vehicles. Furnishings available under separate contract for a true turnkey option. Minutes to Historic Ybor City, Amalie Arena, Seminole Hard Rock, and Busch Gardens, with quick interstate access throughout Tampa Bay.

6510 E 25th Avenue, Tampa
$289,000
3 Beds ⋅ 1 Baths ⋅ Oakland Hills SubDv. ⋅ 32714 Zip Code
Virtually Staged. Seller to offer credit of up to $5000 to buyer at closing. Welcome to this beautifully refreshed 3-bedroom, 1-bathroom home in the Oakland Hills subdivision, offering 988 square feet of thoughtfully updated living space on a spacious corner lot just under a quarter acre. Completely remodeled in 2023, this home combines modern style with major updates for added peace of mind, including a new roof and HVAC system installed in 2024. Inside, you'll find a bright and inviting interior featuring luxury vinyl flooring throughout and a stunning kitchen designed with crisp shaker cabinetry, stainless steel appliances, and contemporary hardware. Every space has been carefully updated to create a move-in-ready experience. Outside, the oversized corner lot provides plenty of room to enjoy, complete with a fenced backyard that offers endless possibilities for entertaining, gardening, pets, or simply relaxing outdoors. A brand-new storage shed adds extra functionality, while the covered carport provides everyday convenience. The home also includes a new washer and dryer, making it easy to settle in from day one. Perfectly positioned near the area's best amenities, this property is just minutes from the shopping and dining options at Altamonte Mall, the scenic walking trails and events at Cranes Roost Park, and major commuter routes for easy access throughout Central Florida. With extensive upgrades, a generous homesite, and an ideal location, this Oakland Hills gem is ready to welcome its next owner. Mortgage savings may be available for buyers of this listing.

668 Barbuda Way, Altamonte Springs
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