Oakland Town Homes with Private Pool type

Welcome to Oakland Town, a hidden gem nestled in the heart of Orange County, Florida. This charming subdivision offers a perfect blend of tranquility and community spirit, making it an ideal place for families, retirees, and anyone seeking a serene lifestyle. Oakland Town is renowned for its picturesque streets lined with oak trees, creating a warm and inviting atmosphere that welcomes you home.

One of the standout features of Oakland Town is its collection of beautiful homes, many of which come with private pools. Imagine stepping into your backyard oasis, where you can unwind under the Florida sun or host summer barbecues with friends and family. These homes are designed with comfort and luxury in mind, featuring spacious layouts, modern amenities, and lush landscaping that enhances the overall appeal.

Living in Oakland Town means you’re just a short drive away from the vibrant city of Orlando, where you can enjoy world-class dining, shopping, and entertainment options. Yet, when you return home, you’ll appreciate the peaceful ambiance that this subdivision provides. With nearby parks, walking trails, and community events, there’s always something to do and see.

Whether you’re looking for a place to raise a family or a quiet retreat to enjoy your golden years, Oakland Town offers a unique lifestyle that combines the best of suburban living with easy access to urban conveniences. Discover your dream home with a private pool in this enchanting community and experience the true essence of Florida living!

$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

Oakland Town Homes with Private Pool type

Newest Oakland Town Homes with Private Pool type