Oakland Town Real Estate

Welcome to Oakland Town, a charming subdivision located in Orange County, Florida. Situated in the city of Oakland, this community offers a peaceful and family-friendly environment for residents to call home.

Oakland Town is known for its beautiful homes and well-maintained streets. The subdivision features a variety of architectural styles, from traditional to contemporary, ensuring that there is something to suit every taste. With meticulously landscaped yards and tree-lined streets, the neighborhood exudes a sense of tranquility and serenity.

One of the highlights of living in Oakland Town is its convenient location. Situated in Orange County, residents have easy access to all the amenities and attractions of the surrounding area. Whether you're looking for shopping, dining, or entertainment options, you'll find them just a short drive away.

In addition to its proximity to urban conveniences, Oakland Town also offers a close-knit community atmosphere. Neighbors often come together for social events and activities, creating a strong sense of camaraderie and belonging.

Families with children will appreciate the excellent schools in the area, ensuring that their little ones receive a quality education. Additionally, the subdivision is located near parks and recreational facilities, providing ample opportunities for outdoor activities and leisure.

If you're looking for a peaceful and welcoming community to call home, Oakland Town in Orange County, Florida, is the perfect place to settle down. With its beautiful homes, convenient location, and strong sense of community, this subdivision offers an exceptional living experience for residents of all ages.

Newest Listings in Oakland Town

$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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