Oakland Town Homes for Sale

Oakland Town Homes for Sale

Welcome to Oakland Town, a charming subdivision nestled in the heart of Oakland, Florida, within the picturesque Orange County. This vibrant community offers a unique blend of small-town charm and modern conveniences, making it an ideal location for families, retirees, and everyone in between. With its lush landscapes, friendly neighbors, and a strong sense of community, Oakland Town is the perfect place to call home.

As you explore Oakland Town, you’ll discover an array of beautiful homes for sale that cater to diverse tastes and lifestyles. From cozy single-family residences to spacious modern designs, there’s something for everyone. Many of these homes feature open floor plans, updated kitchens, and inviting outdoor spaces, perfect for entertaining or simply enjoying the serene Florida weather. The neighborhood is known for its well-maintained properties and tree-lined streets, creating a welcoming atmosphere that encourages outdoor activities and community interaction.

Residents of Oakland Town enjoy easy access to local parks, recreational facilities, and a variety of shopping and dining options in nearby downtown Oakland. The area is also conveniently located near major highways, providing quick access to the bustling cities of Orlando and Winter Garden, as well as the beautiful Florida coastline.

Whether you’re looking to buy your first home, downsize, or find a peaceful retreat, Oakland Town offers a wonderful opportunity to invest in a thriving community. Discover your dream home in Oakland Town today and experience the perfect blend of suburban tranquility and vibrant community living!

Newest Oakland Town Homes for Sale

$455,000
3 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
Virtually Staged. Welcome to this brand-new construction home in the heart of Oakland! This thoughtfully designed 3-bedroom, 2-bathroom residence offers 1,170 square feet of modern living space on a 0.09-acre homesite. The open-concept floor plan features luxury vinyl plank flooring throughout the main living areas and bedrooms, with porcelain tile flooring in both bathrooms for added durability and style. The kitchen is equipped with quartz countertops, modern cabinetry, stainless steel appliances, and a functional layout that flows seamlessly into the living and dining areas, making it ideal for everyday living and entertaining. Contemporary lighting, designer fixtures, and quality finishes can be found throughout the home. The spacious primary suite includes a walk-in closet and an ensuite bathroom with a quartz vanity and a porcelain tile shower. Two additional bedrooms offer flexibility for family, guests, or a home office. Additional features include an indoor laundry area, energy-efficient windows, modern exterior finishes, and a paver driveway. Conveniently located near downtown Winter Garden, the West Orange Trail, shopping, dining, parks, major highways, and local attractions, this move-in-ready home offers the opportunity to enjoy low-maintenance living in the desirable Town of Oakland. Don't miss your chance to own this newly built home in one of Central Florida's most sought-after communities.

521 W Herriott Avenue, Oakland
$1,125,000
4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
SELLER OFFERING BUYER 20K!!!! TOWARDS CLOSING COSTS AND PREPAIDS. Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms and 2.5 bathrooms. Situated on an oversized lot of nearly 1/2 acre, the property includes a resort-style pool, screened patio, shed, and a 3-car garage. Perfectly positioned between Clermont and Winter Garden, this rare property sits on quiet, charming dirt roads, surrounded by mature LIVE oak trees with NO HOA and direct access to the Winter Garden Trail right from your backyard. Bring your boat, bring your toys—this one has room for it all! From the moment you arrive, the mature landscaping and inviting front porch set the tone for the peaceful retreat that awaits. Step inside to a fully renovated 2026 kitchen featuring upgraded quartz countertops, LVP flooring, subway tile backsplash, refaced cabinets with modern hardware, and a brand-new refrigerator—truly a chef’s dream. Just off the kitchen, new french doors lead to your private patio and show-stopping 2019 salt water pool complete with spa and slide, perfect for entertaining or unwinding after a long day. The first floor includes a large guest bedroom and a spacious primary suite with an oversized walk-in closet and a relaxing ensuite offering a soaking tub and separate shower. Upstairs, you’ll find two generously sized guest bedrooms and a beautifully appointed guest bath. This home is loaded with upgrades for peace of mind and comfort, including 2021 AC units, 2021 roof, 2026 LVP flooring, fresh interior paint and baseboards, newer windows, new fixtures, new landscaping, a new water heater, and a newly painted shed/workshop. Located in the heart of Oakland, you can golf cart to Downtown Winter Garden, Plant Street Market, the Lake Apopka boat ramp, shops, dining, and weekly events. Homes with this level of privacy, upgrades, and location rarely become available—and this one checks every box. Bring your golf cart and don’t miss your chance to own a truly unique custom home in the heart of Oakland. This property will not last! Let’s make it yours.

250 N Walker Street, Oakland
$619,999
4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
NEW PRICE IMPROVEMENT! Seller incentive available! Welcome home to this beautiful 2026 newly built residence in the desirable town of Oakland! This 4-bedroom, 2.5-bath home features modern finishes, an open-concept layout, and a spacious design perfect for today’s lifestyle. Enjoy the benefits of owning a newer construction home with peace of mind, energy-efficient features, and low-maintenance living. Don’t miss the opportunity to own a move-in-ready home in Oakland, conveniently located near parks, trails, and local amenities. Schedule your private showing today!

38 S Pollard Street, Oakland
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