Oakland Town Homes with Pool

Oakland Town Homes with Pool

Welcome to Oakland Town, a charming subdivision nestled in the heart of Orange County, Florida! This picturesque community in the vibrant city of Oakland is a hidden gem that perfectly balances serene living with modern conveniences. Known for its friendly atmosphere and lush landscapes, Oakland Town offers a delightful escape from the hustle and bustle of city life while remaining conveniently close to all the amenities you need.

One of the standout features of homes in Oakland Town is the abundance of properties boasting private pools. Imagine stepping out into your own backyard oasis, where you can bask in the Florida sun, host summer barbecues, or simply unwind with a refreshing dip after a long day. These homes with pools not only enhance your lifestyle but also provide a perfect setting for family gatherings and entertaining friends, making every day feel like a vacation.

The community is designed with families in mind, featuring well-maintained parks, walking trails, and a strong sense of community spirit. Residents enjoy a peaceful environment while still being just a short drive away from the vibrant attractions of Orlando. With top-rated schools, shopping, and dining options nearby, Oakland Town truly offers the best of both worlds.

Whether you’re looking for a cozy family home or a spacious retreat, Oakland Town has something for everyone. Discover the joys of living in this idyllic community and find your dream home with a pool today! Come experience the charm of Oakland Town, where your perfect Florida lifestyle awaits.

Newest Oakland Town Homes with Pool

$1,125,000
4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv.
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
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