Oakland Homes with Trees/Woods View

Welcome to Oakland, Florida – a hidden gem nestled in the heart of Orange County. Known for its picturesque landscapes and charming small-town atmosphere, Oakland offers a unique blend of natural beauty and vibrant community life. With its lush greenery and serene surroundings, it’s no wonder that this area has become a sought-after destination for homebuyers looking for tranquility just a stone's throw from the bustling city of Orlando.

One of the standout features of Oakland is its stunning homes that boast breathtaking 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 properties are designed to harmonize with their natural surroundings, offering a perfect retreat for those who appreciate the great outdoors. Whether it’s sipping coffee on your porch or enjoying a leisurely stroll through the nearby trails, the homes in Oakland provide an idyllic setting for a fulfilling lifestyle.

The community in Oakland is rich with character, featuring quaint shops, local eateries, and a strong sense of camaraderie among residents. The town hosts various events throughout the year, fostering connections and creating lasting memories. Additionally, with easy access to major highways, you can enjoy the convenience of city life while retreating to your peaceful haven in the woods.

If you’re in search of a home that offers both comfort and a connection to nature, Oakland, Florida, with its homes surrounded by trees and woods, is the perfect place to call home. Discover the charm of this delightful community and let your dream home become a reality!

$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