Oakland Town Homes with Two Story Property Description

Welcome to Oakland Town, a hidden gem nestled in the heart of Orange County, Florida. This charming community offers a perfect blend of suburban tranquility and vibrant local culture, making it an ideal place for families and individuals alike. With its picturesque tree-lined streets and friendly neighbors, Oakland Town is a neighborhood where you can truly feel at home.

One of the standout features of Oakland Town is its stunning two-story homes. These spacious properties are designed with modern living in mind, offering ample room for families to grow and thrive. Each home boasts an array of thoughtful layouts, featuring open-concept living areas that seamlessly connect the kitchen, dining, and living spaces. The two-story design not only enhances the aesthetic appeal but also provides a sense of privacy, with bedrooms often located on the upper level, creating a peaceful retreat away from the hustle and bustle of everyday life.

Residents of Oakland Town enjoy easy access to a variety of local amenities, including parks, shops, and dining options, all just a short drive away. The community is also conveniently located near major highways, making commutes to nearby cities a breeze. With its welcoming atmosphere and beautiful homes, Oakland Town is more than just a place to live; it’s a community where memories are made and cherished.

Whether you’re a first-time homebuyer or looking to upgrade, the two-story homes in Oakland Town offer the perfect combination of style, comfort, and convenience. Come and discover the charm of Oakland Town—your dream home awaits!

Newest Oakland Town Homes with Two Story Property Description

$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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