Oakland Hills Real Estate

Oakland Hills Real Estate

Welcome to Oakland Hills, a picturesque subdivision nestled in the heart of sunny Florida. This charming community offers a perfect blend of tranquility and convenience, making it an ideal place for families, retirees, and anyone looking to embrace the vibrant Florida lifestyle.

Oakland Hills is renowned for its beautifully landscaped streets, adorned with lush greenery and mature oak trees that provide a serene backdrop for leisurely strolls. The subdivision features a variety of stunning homes, each reflecting unique architectural styles and modern finishes, ensuring there’s something for everyone. Whether you’re seeking a cozy single-family home or a spacious property with plenty of room to grow, Oakland Hills has you covered.

One of the standout features of this community is its commitment to outdoor living. Residents enjoy access to nearby parks, walking trails, and recreational facilities, perfect for family picnics or weekend adventures. The proximity to Florida’s stunning beaches and vibrant attractions means that residents can easily indulge in sun-soaked days by the shore or explore the rich culture and entertainment options that the state has to offer.

In addition to its natural beauty, Oakland Hills boasts a strong sense of community. Neighbors come together for various events and activities throughout the year, fostering lasting friendships and a welcoming atmosphere. With excellent schools, shopping centers, and dining options just a stone's throw away, Oakland Hills truly embodies the best of Florida living.

Discover your dream home in Oakland Hills, where comfort meets convenience in a community that feels like family. Come and experience the charm of this delightful subdivision today!

Newest Listings in Oakland Hills

$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
$299,000
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
$400,000
3 Beds ⋅ 2 Baths ⋅ Oakland Hills SubDv. ⋅ 33619 Zip Code
Experience modern luxury and coastal elegance in this brand-new, steel-frame construction masterpiece. This stunning three-bedroom, two-bathroom home combines structural integrity with high-end designer finishes, offering a low-maintenance lifestyle perfectly situated for a quick commute to MacDill AFB and Downtown Tampa. The interior is defined by a wide-open floor plan with soaring vaulted ceilings accented by a rustic wood beam, creating an airy and sophisticated atmosphere. Durable flooring flows seamlessly throughout the entire home with absolutely no carpet to be found. The kitchen serves as a gourmet centerpiece, featuring a spacious layout with all-new cabinetry, sleek quartz countertops, and a full suite of new stainless steel appliances. While the living area is impressive, the bathrooms are the undisputed star of the show, both featuring exquisite floor-to-ceiling porcelain tile and designer gold-tone fixtures plus back lit, fog-less mirrors. The primary suite is a true retreat, boasting a large walk-in closet and an ensuite bathroom with a massive walk-in shower equipped with a luxury rain shower head. The guest bathroom is equally impressive, featuring a deep-soaking freestanding tub with shower wand, that adds a spa-like feel for family or visitors. Practicality meets comfort with the inclusion of an energy-efficient tankless water heater and a brand-new septic system. The exterior living spaces are just as inviting, highlighted by a large covered front porch and a fully fenced-in backyard. This home is a rare blend of modern industrial strength and sophisticated interior design, offering a turnkey opportunity in a prime location.

6510 E 23rd Avenue, Tampa
$150,000
Oakland Hills SubDv. ⋅ 33619 Zip Code
The opportunity is to purchase a .79 acre parcel that could be subdivided into up to 4 residential lots. The site is wooded and the approximate dimensions are 115 feet by 299 feet subject to a survey.

6416 E 23rd Avenue, Tampa
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