Oakland Homes with Trees/Woods View

Oakland Homes with Trees/Woods View

Welcome to the vibrant city of Oakland, Florida, nestled in the heart of Orange County! Known for its charming small-town atmosphere and rich history, Oakland offers a unique blend of suburban tranquility and easy access to urban amenities. With its picturesque landscapes, friendly community, and a strong sense of pride, this delightful town is perfect for those looking to settle down in a serene environment.

One of the standout features of Oakland is its stunning homes that boast breathtaking views of lush trees and serene woods. Imagine waking up each morning to the gentle rustle of leaves and the soothing sounds of nature right outside your window. These homes provide not just a place to live, but an immersive experience that connects you to the beauty of the outdoors. Whether you’re sipping coffee on your porch or enjoying a peaceful evening stroll, the natural surroundings create a calming backdrop for your daily life.

In addition to its scenic views, Oakland is conveniently located near major highways, making it easy to access the bustling cities of Orlando and Winter Garden, where you can enjoy shopping, dining, and entertainment. The town is also home to several parks and recreational areas, perfect for outdoor enthusiasts and families alike.

With its enchanting homes surrounded by trees and woods, Oakland, FL, offers an idyllic lifestyle that harmonizes nature with community. Discover your dream home in this charming town and experience the perfect blend of tranquility and convenience!

Newest Oakland Homes with Trees/Woods View

250 N Walker Street, Oakland
$999,000
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
Start Your Search

How much is your home worth?

Get instant property value now!