Oakland Town Homes with Two Story Property Description

Welcome to Oakland Town, a charming subdivision nestled in the heart of Oakland, Florida, within the vibrant Orange County. This picturesque community is known for its welcoming atmosphere and lush landscapes, making it an ideal place for families, young professionals, and retirees alike. With its close-knit feel and beautiful surroundings, Oakland Town offers a unique blend of suburban tranquility and urban convenience.

One of the standout features of Oakland Town is its stunning two-story homes, which are designed to cater to a variety of lifestyles. These spacious residences boast modern architecture and thoughtful layouts, providing ample room for both relaxation and entertainment. Imagine hosting family gatherings in your expansive living room or enjoying quiet evenings on your private patio, soaking in the serene views of the neighborhood.

The two-story properties in Oakland Town typically feature multiple bedrooms and bathrooms, offering flexibility for growing families or those looking for a home office space. With large windows that flood the interiors with natural light and high ceilings that create an airy ambiance, these homes are as inviting as they are functional. Many properties also come with beautifully landscaped yards, perfect for outdoor activities or simply enjoying the Florida sunshine.

Living in Oakland Town means enjoying easy access to local parks, recreational facilities, and a variety of shopping and dining options. The community is also conveniently located near major highways, making commutes to nearby cities a breeze. Experience the charm of Oakland Town, where your dream home awaits in a vibrant and friendly community!

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

$629,999

4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

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

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