Oakland Town Homes for Sale

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 suburban tranquility and vibrant community spirit, making it an ideal place to call home. With its picturesque tree-lined streets and friendly neighbors, Oakland Town captures the essence of small-town living while being just a stone's throw away from the bustling city of Orlando.

The homes for sale in Oakland Town reflect a variety of architectural styles, catering to diverse tastes and lifestyles. From cozy single-family homes to spacious modern designs, there’s something here for everyone. Many of these residences feature inviting front porches, open floor plans, and beautifully landscaped yards, perfect for family gatherings or quiet evenings under the stars. As you explore the available properties, you'll discover well-maintained homes that are ready to welcome new families, each with its own unique charm and character.

Living in Oakland Town means enjoying a wealth of amenities right at your doorstep. Residents can take advantage of nearby parks, walking trails, and recreational facilities, making it easy to embrace an active lifestyle. The community is also conveniently located near top-rated schools, shopping centers, and dining options, ensuring that everything you need is within reach.

Whether you're a first-time homebuyer or looking to upgrade, Oakland Town offers a welcoming community and a range of homes for sale that are sure to meet your needs. Come experience the warmth and charm of Oakland Town—your dream home awaits!

Newest Oakland Town Homes for Sale

$1,125,000
4 Beds ⋅ 3 Baths ⋅ G5110973 MLS
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

Listing courtesy of COAST TO COAST REAL ESTATE PRO. 352-296-8930
$629,999
4 Beds ⋅ 3 Baths ⋅ O6394442 MLS
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

Listing courtesy of MS LAND & BUILDING LLC. 407-466-7000
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