Oakland Homes with Trees/Woods View

Welcome to Oakland, Florida—a charming town nestled in the heart of Orange County. This picturesque community is a hidden gem, offering a delightful blend of small-town charm and modern convenience. With its rich history, vibrant culture, and stunning natural surroundings, Oakland is the perfect place to call home.

One of the standout features of homes in this serene area is their breathtaking views of lush trees and tranquil woods. Imagine waking up each morning to the gentle rustle of leaves and the soft sounds of nature just outside your window. These homes offer a unique opportunity to embrace a lifestyle that harmonizes with the environment, providing a peaceful retreat from the hustle and bustle of city life.

Oakland is known for its friendly community atmosphere, where neighbors become friends and local events bring everyone together. The town is surrounded by beautiful parks and nature trails, perfect for outdoor enthusiasts and families alike. With easy access to nearby attractions such as Lake Apopka and the West Orange Trail, residents can enjoy a variety of recreational activities, from hiking and biking to birdwatching and fishing.

In addition to its natural beauty, Oakland boasts a charming downtown filled with quaint shops, delicious eateries, and a strong sense of community pride. Whether you’re exploring the local farmers market or attending one of the many seasonal festivals, you’ll quickly discover why so many people are drawn to this vibrant town.

If you’re seeking a home that offers stunning views of trees and woods, combined with the warmth of a close-knit community, Oakland, Florida is the perfect place to plant your roots. Come discover the magic of living in this enchanting town!

$1,049,000

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

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