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 vibrant community spirit, making it an ideal place for families, retirees, and anyone seeking a serene lifestyle.

Oakland Town is characterized by its picturesque tree-lined streets and beautifully maintained homes, each exuding a unique charm that reflects the warmth of the community. With a variety of architectural styles, from cozy single-family residences to modern townhomes, there’s a perfect fit for everyone. Many homes boast spacious yards and inviting outdoor spaces, ideal for enjoying Florida’s sunny weather.

One of the standout features of Oakland Town is its proximity to nature. Residents can take advantage of the nearby West Orange Trail, a scenic pathway perfect for walking, biking, and jogging. The area is also home to several parks, where families can gather for picnics, children can play, and neighbors can connect.

In addition to its natural beauty, Oakland Town offers convenient access to local amenities. Just a short drive away, you’ll find charming shops, delightful dining options, and essential services that cater to your everyday needs. The vibrant city of Orlando is also within easy reach, allowing residents to enjoy all the entertainment, cultural experiences, and employment opportunities it has to offer.

With a welcoming community spirit and a serene environment, Oakland Town is more than just a place to live; it’s a place to thrive. Come discover the charm of Oakland Town and find your forever home in this beautiful Florida enclave!

Newest Listings in Oakland Town

$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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