Oakland Homes with Trees/Woods View

Welcome to Oakland, Florida, a hidden gem nestled in the heart of Orange County. This charming town is steeped in history and natural beauty, offering a perfect blend of serene living and modern conveniences. With its picturesque landscapes and friendly community, Oakland is an ideal place for families and individuals seeking a tranquil lifestyle without sacrificing access to urban amenities.

One of the standout features of Oakland is its abundance of lush greenery and stunning tree-lined streets. Many homes in the area boast breathtaking views of trees and woods, providing residents with a peaceful retreat right in their backyards. Imagine sipping your morning coffee while basking in the soothing sounds of nature or hosting gatherings under the dappled sunlight filtering through the leaves. These homes not only offer visual appeal but also create a serene atmosphere that promotes relaxation and well-being.

Beyond the charm of its homes, Oakland is conveniently located near major highways, making commutes to nearby cities like Orlando a breeze. The town is also home to a variety of parks, recreational areas, and local shops that foster a strong sense of community. Whether you’re exploring the scenic West Orange Trail or enjoying a weekend at the local farmer's market, there’s always something to do in this vibrant town.

If you’re looking for a place where nature meets community spirit, Oakland, Florida, with its beautiful homes featuring stunning tree and woods views, is the perfect destination to call home. Experience the tranquility and charm of Oakland – your dream home 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