Oakland Hills Homes with Sidewalk Exterior Features

Welcome to Oakland Hills, an enchanting subdivision nestled in the heart of Winter Garden, Florida. This charming community is a hidden gem within Orange County, offering a perfect blend of suburban tranquility and vibrant local amenities. With its lush landscapes and friendly atmosphere, Oakland Hills is an ideal place for families, retirees, and everyone in between to call home.

One of the standout features of Oakland Hills is its thoughtfully designed homes, each boasting inviting sidewalk exterior features. These sidewalks not only enhance the aesthetic appeal of the neighborhood but also encourage a sense of community. Residents can enjoy leisurely strolls, morning jogs, or evening bike rides while connecting with neighbors and embracing the beautiful Florida weather.

The homes in Oakland Hills are crafted with care, featuring modern designs that cater to various lifestyles. From spacious single-family homes to cozy townhouses, there’s a perfect fit for everyone. Many properties come with lush gardens and outdoor spaces, ideal for entertaining or simply enjoying a quiet afternoon outdoors.

Beyond the beautiful homes, Oakland Hills is conveniently located near a variety of shopping, dining, and recreational options. The vibrant downtown Winter Garden, known for its historic charm and lively farmers' market, is just a short drive away. Residents also have easy access to parks, trails, and top-rated schools, making it a wonderful place to raise a family or enjoy retirement.

Discover the allure of Oakland Hills, where community spirit and natural beauty come together to create the perfect setting for your next chapter. Come explore this delightful neighborhood and see why it’s the perfect place to call home!

Newest Oakland Hills Homes with Sidewalk Exterior Features

$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

$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

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