Oakland Town Homes with Two Story Property Description

Welcome to Oakland Town, a charming subdivision nestled in the picturesque city of Oakland, Florida, within the heart of Orange County. This delightful community offers a perfect blend of suburban tranquility and vibrant local culture, making it an ideal place for families, professionals, and retirees alike.

As you explore Oakland Town, you’ll find a variety of beautiful homes, with a particular emphasis on stunning two-story properties that exude elegance and functionality. These spacious homes are designed to cater to modern living, featuring open floor plans that seamlessly connect living, dining, and kitchen areas. With ample room for entertaining, family gatherings, or simply enjoying quiet evenings at home, the two-story layout provides both comfort and versatility.

Each home in Oakland Town is thoughtfully crafted, often boasting high ceilings, large windows that flood the space with natural light, and stylish finishes that elevate the overall aesthetic. Many properties also include landscaped yards, perfect for outdoor activities or simply enjoying the warm Florida sunshine. Residents can take advantage of the community’s amenities, including parks, walking trails, and nearby recreational facilities, fostering a sense of connection and camaraderie among neighbors.

Located just a short drive from the bustling city of Orlando, Oakland Town offers the perfect escape from the hustle and bustle while keeping you close to shopping, dining, and entertainment options. Whether you’re looking for a family-friendly environment or a peaceful retreat, Oakland Town is a hidden gem waiting to be discovered. Come and experience the charm of this vibrant community, where 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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