Oakland Homes with Trees/Woods View

Welcome to Oakland, Florida – a hidden gem nestled in the heart of Orange County! This charming town is known for its picturesque landscapes, friendly community, and a rich history that dates back to the late 1800s. With its serene atmosphere and proximity to the bustling city of Orlando, Oakland offers the perfect blend of tranquility and convenience, making it an ideal place to call home.

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 are designed to harmoniously blend with their natural surroundings, providing a peaceful retreat from the hustle and bustle of everyday life. The abundance of greenery not only enhances the aesthetics of the neighborhood but also promotes a healthy lifestyle, encouraging outdoor activities and family gatherings in nature's embrace.

Living in Oakland means you’re just a stone's throw away from endless recreational opportunities. From scenic parks and nature trails to charming local shops and restaurants, there’s something for everyone to enjoy. Whether you're an outdoor enthusiast or someone who appreciates the beauty of nature, the homes with tree and woods views in Oakland offer a unique opportunity to experience the best of Florida living.

Come explore the enchanting community of Oakland and discover your dream home surrounded by nature's beauty. With its welcoming spirit and stunning surroundings, you’ll find that Oakland is more than just a place to live – it's a place to thrive.

$1,049,000

4 Beds ⋅ 3 Baths ⋅ G5110973 MLS

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