Oakland Town Real Estate

Oakland Town Real Estate

Welcome to Oakland Town, a hidden gem nestled in the heart of Orange County, Florida. This charming subdivision offers a perfect blend of suburban tranquility and modern convenience, making it an ideal place for families, professionals, and retirees alike. With its picturesque tree-lined streets and welcoming community atmosphere, Oakland Town is more than just a neighborhood; it’s a lifestyle.

As you explore Oakland Town, you'll find a variety of beautifully designed homes that cater to diverse tastes and preferences. From contemporary single-family residences to cozy townhomes, there’s something here for everyone. The community is known for its well-maintained properties and lush landscaping, creating a serene environment that residents are proud to call home.

One of the standout features of Oakland Town is its proximity to nature. The subdivision is surrounded by stunning parks and scenic trails, perfect for outdoor enthusiasts. Whether you enjoy hiking, biking, or simply taking leisurely strolls, the natural beauty of the area will captivate you. Additionally, the nearby Lake Apopka offers fantastic opportunities for fishing and boating, making it a favorite spot for water lovers.

Families will appreciate the excellent local schools and the strong sense of community that Oakland Town fosters. With a variety of local shops, restaurants, and recreational facilities just a short drive away, residents enjoy the convenience of urban living while still relishing the peacefulness of suburban life.

Discover the charm of Oakland Town, where community spirit meets the beauty of Florida living. Your dream home awaits in this delightful subdivision!

Newest Listings in Oakland Town

3 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv.

PRICE REDUCED - Accepting Offers! The home has recently been entirely staged on the inside of the property - come tour this BEAUTY! NOTE: to add extra storage, a (large shed) can be added onto the property within the purchase of the home. NO HOA! 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 primary suite includes a walk-in closet and an ensuite bathroom with a quartz vanity and a porcelain tile shower. Two additional bedrooms provide 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

4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv.

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

4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv.

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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