Oakland Homes with Trees/Woods View

Welcome to Oakland, Florida – a hidden gem nestled in the heart of Orange County. With its picturesque landscapes, charming small-town atmosphere, and a community that embraces both nature and neighborliness, Oakland is the perfect place to call home. As you stroll through the tree-lined streets, you’ll quickly discover why this area is cherished by its residents.

One of the standout features of Oakland is the abundance of homes with stunning views of trees and woods. Imagine waking up each morning to the gentle rustle of leaves and the soothing sounds of nature right outside your window. These homes are designed to blend seamlessly with the surrounding environment, creating a serene retreat that invites relaxation and tranquility. Whether you’re sipping your morning coffee on the porch or hosting a family gathering in your backyard, the lush greenery provides a beautiful backdrop for every occasion.

In addition to its natural beauty, Oakland boasts a vibrant community with a rich history and a variety of local events that bring residents together. Enjoy the charm of downtown with its quaint shops, delightful eateries, and community parks, perfect for family outings or leisurely strolls. With easy access to nearby attractions, including lakes and trails, outdoor enthusiasts will find endless opportunities for adventure.

If you’re searching for a home that offers both comfort and a connection to nature, Oakland, Florida, is the ideal destination. Here, you’ll find not just a house, but a place where you can create lasting memories amid the beauty of trees and woods. Welcome home!

$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