Discover Oakland,
Winter Garden’s Most Charming Neighbor

Nestled in the charming town of Oakland, The Grove is located within the Golf Cart District of both Oakland and Winter Garden, offering effortless access to historic Downtown Winter Garden, Plant Street, and the West Orange Trail.

Just minutes from Oakland’s exciting new retail destinations, boutique shops, dining, and community attractions, our new communities offer the perfect balance of small-town charm and modern convenience.

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Oakland Village

Walkable Retail Center Coming Soon

Oakland Place

Walkable Retail Center Coming Soon

Uptown Oakland

Walkable Retail Center Coming Soon

Old Packing House

Food Hall Coming Soon

West Orange Trail

The scenic West Orange Trail stretches 22 miles through Central Florida, running directly through the heart of Oakland and Downtown Winter Garden. Lined with majestic oaks, charming neighborhoods, and local destinations, this beloved trail offers miles of picturesque paths for walking, running, and cycling, seamlessly connecting nature, recreation, and small-town charm.

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Weekly Winter Garden
Farmers Market

Voted among the best farmers markets in Florida and the USA by American Farmland Trust, the Winter Garden Farmers Market brings Downtown Winter Garden to life every Saturday from 8 AM to 1 PM. Enjoy fresh local produce, artisan vendors, live music, and a pet-friendly atmosphere beside the interactive fountain and Butterfly Sculpture Park.

Location: Downtown Pavilion, 104 S. Lakeview Ave, Winter Garden

Oakland Farmers Market

Experience the charm of small-town living at the Oakland Farmers Market, featuring local vendors, fresh produce, handcrafted goods, and artisan favorites along the scenic West Orange Trail. The market celebrates Oakland’s vibrant community spirit and local businesses. Returning January 2027 with a new schedule of select Saturdays, bringing fresh flavors and community gatherings to the heart of Oakland.

Location: Downtown Oakland, 230 N Tubb St, Oakland

Oakland Nature Preserve

Discover 150 acres of protected natural beauty at the Oakland Nature Preserve, open year-round for outdoor exploration. Enjoy scenic walking trails, a picturesque boardwalk overlooking Lake Apopka, and guided kayak tours, offering a peaceful escape into Florida’s native landscapes and wildlife.