Oakland Town Homes for Sale

Welcome to Oakland Town, a hidden gem nestled in the heart of Orange County, Florida. This charming subdivision offers a perfect blend of small-town warmth and modern convenience, making it an ideal place for families, retirees, and everyone in between. With its picturesque streets lined with mature oak trees and friendly neighbors, Oakland Town exudes a welcoming atmosphere that feels like home from the moment you arrive.

The real estate market in Oakland Town features a variety of homes for sale, catering to diverse tastes and lifestyles. From cozy single-family homes to spacious modern designs, there's something to suit every preference. Many properties boast stunning outdoor spaces, perfect for hosting gatherings or simply enjoying the beautiful Florida weather. With easy access to local parks, walking trails, and community amenities, residents can take full advantage of the vibrant lifestyle that Oakland Town offers.

Conveniently located just a short drive from the bustling cities of Orlando and Winter Garden, Oakland Town provides residents with the peace and tranquility of suburban living while keeping them close to shopping, dining, and entertainment options. The community is also served by highly-rated schools, making it an excellent choice for families looking to settle down in a nurturing environment.

If you're in the market for a new home, Oakland Town is truly a place where you can create lasting memories and enjoy the best of Florida living. Explore the homes for sale today, and discover your perfect sanctuary in this delightful community!

Newest Oakland Town Homes for Sale

$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

$629,999

4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Brand new 2026 construction with Certificate of Occupancy in place and ready for immediate move-in. This 4-bedroom, 2.5-bath home offers 1,872 sqft of modern living space with custom finishes and a functional open layout. Thoughtfully designed with a clean, contemporary style, the home provides low-maintenance living and the flexibility of a non-HOA setting. Now positioned to reflect current market conditions, this property presents an excellent opportunity for buyers seeking newer construction without delays or renovation needs. A compelling option for buyers looking for value, condition, and immediate occupancy.

38 S Pollard Street, Oakland

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