Oakland Homes with Trees/Woods View

Welcome to the charming city of Oakland, Florida, a hidden gem nestled in the heart of Orange County. Known for its lush landscapes and inviting community, Oakland offers a perfect blend of small-town charm and modern amenities. With its rich history and vibrant culture, this picturesque town provides residents with a serene lifestyle while being just a stone's throw away 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 homes are designed to harmonize with the natural surroundings, offering a tranquil retreat that promotes relaxation and peace. With spacious layouts and expansive windows, each residence captures the essence of Florida’s natural beauty, allowing sunlight to flood in and frame the picturesque outdoor scenery.

In addition to the beautiful homes, Oakland is surrounded by an array of outdoor recreational opportunities. Residents can explore the scenic trails, enjoy picnics in the parks, or take leisurely strolls along the charming streets lined with oak trees. The community is also home to various local events and farmers' markets, fostering a strong sense of connection among neighbors.

If you’re looking for a place that combines the allure of nature with a friendly community atmosphere, Oakland, Florida, is the perfect destination. Discover your dream home with a stunning woods view and experience the tranquility that this delightful city has to offer!

$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