Oakland Town Homes with Two Story Property Description

Welcome to Oakland Town, a charming subdivision nestled in the heart of Orange County, Florida. This delightful community in the picturesque city of Oakland offers a perfect blend of suburban tranquility and modern convenience, making it an ideal place for families, young professionals, and retirees alike. With its lush greenery, friendly neighbors, and a strong sense of community, Oakland Town is a hidden gem waiting to be discovered.

One of the standout features of Oakland Town is its stunning two-story homes, which perfectly embody the spirit of contemporary living while maintaining a warm, inviting atmosphere. These spacious residences are designed with families in mind, offering ample room for both relaxation and entertainment. With open floor plans, large windows that flood the interiors with natural light, and stylish finishes, each home provides a comfortable sanctuary for residents.

Imagine hosting gatherings in your expansive living area, cooking up culinary delights in a chef-inspired kitchen, or enjoying quiet evenings on your private patio. The two-story layout allows for distinct living and sleeping spaces, ensuring privacy and comfort for everyone in the household. Many homes also feature beautifully landscaped yards, perfect for outdoor activities or simply soaking up the Florida sunshine.

Located just minutes away from shopping, dining, and recreational opportunities, Oakland Town offers easy access to the vibrant culture of nearby Orlando while maintaining the charm of a close-knit community. Experience the best of both worlds in Oakland Town, 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

Start Your Search