Oakland Town Homes with Trees/Woods View

Welcome to Oakland Town, a hidden gem nestled in the heart of Orange County, Florida. This charming subdivision offers an idyllic blend of suburban tranquility and natural beauty, making it an ideal choice for families, retirees, and anyone seeking a peaceful retreat from the hustle and bustle of city life.

One of the standout features of Oakland Town is its stunning homes that boast breathtaking views of lush trees and serene woodlands. Imagine waking up each morning to the gentle rustle of leaves and the soft chirping of birds, all from the comfort of your own backyard. The well-designed properties in this community are thoughtfully positioned to maximize these picturesque views, creating a perfect harmony between indoor and outdoor living.

In addition to the scenic surroundings, Oakland Town is conveniently located near the vibrant city of Oakland, providing residents with easy access to a variety of shopping, dining, and recreational options. Explore local parks, enjoy outdoor activities, or take a leisurely stroll through the charming streets lined with historic homes. The friendly community atmosphere invites neighbors to connect, fostering a sense of belonging that is often hard to find in today’s fast-paced world.

Whether you’re looking for a cozy family home or a peaceful retreat, Oakland Town offers a unique opportunity to embrace a lifestyle surrounded by nature. Come discover the beauty, community, and serenity that await you in this enchanting subdivision. Your dream home with a view of the trees is just around the corner!

$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 Town Homes with Trees/Woods View

Newest Oakland Town Homes with Trees/Woods View