Oakland Homes with Trees/Woods View

Welcome to the vibrant city of Oakland, Florida, nestled in the heart of Orange County. This charming town is a hidden gem, offering a perfect blend of small-town charm and modern conveniences. Oakland boasts a rich history, with roots dating back to the late 1800s, and today it showcases a delightful mix of picturesque landscapes and a tight-knit community atmosphere.

One of the standout features of Oakland is its stunning natural scenery, particularly the abundance of trees and wooded views that surround many homes in the area. Imagine waking up each morning to the gentle rustle of leaves and the serene sight of towering oaks and pines right outside your window. These homes not only provide a tranquil retreat from the hustle and bustle of city life but also offer an opportunity to connect with nature in your own backyard.

The community is perfect for families, outdoor enthusiasts, and anyone seeking a peaceful lifestyle while still being just a short drive from the vibrant urban offerings of nearby Orlando. Residents enjoy a variety of recreational activities, from hiking and biking along scenic trails to exploring the beautiful lakes that dot the landscape.

In Oakland, you’ll find a welcoming community that values both tradition and progress. With its charming homes surrounded by lush greenery, this is a place where you can truly feel at home. Whether you’re looking for a cozy cottage or a spacious family residence, Oakland’s tree-lined streets and inviting atmosphere make it an ideal choice for your next home. Come discover the beauty and serenity of Oakland, Florida—your future oasis awaits!

$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 Homes with Trees/Woods View

Newest Oakland Homes with Trees/Woods View