Oakland Village Approved: $35M Shopping and Dining Hub on SR-50
Oakland Village, a $35 million shopping and dining hub, is officially coming to the town of Oakland, just west of Winter Garden. The project brings restaurants, shops, and gathering spaces to one of West Orange County’s fastest-growing corridors.
What Is Oakland Village?
Oakland Village is a planned $35 million retail and dining development with about 85,000 square feet of space across nine buildings and two outparcels. Oakland commissioners gave the project final approval on Sept. 9, 2026, without opposition. Town leaders say the goal is a walkable, community-focused feel similar to Winter Park Village. The project is being developed by Oakland Town Center LLC, led by manager Alex Reece.
Where Is Oakland Village Located?
Oakland Village will sit on 14.8 acres at 15949 W. Colonial Drive, at the corner of State Road 50 and Catherine Ross Road. The site is minutes from Downtown Winter Garden, the West Orange Trail, and the Oakland Nature Preserve. The developer says SR-50 was designed to handle this kind of traffic, so the project shouldn’t require major road changes that could affect the town’s small-town character.
What Will Oakland Village Include?
The project is designed around outdoor dining, gathering spaces, and easy access for nearby neighborhoods. Plans include:
- Restaurants with rooftop and covered patio dining
- About 16,000 square feet of courtyards and green space for markets, music, and seasonal events
- A drive-through spot for coffee or quick service
- Golf cart parking and bike-friendly paths connecting to nearby neighborhoods
Image: Oakland Village
When Will Construction Start?
Construction is expected to begin in early 2027. No tenants have been officially announced yet, but early leasing is now open for restaurant, retail, and medical tenants.
Why Is Oakland Growing So Quickly?
Oakland is attracting new residents and businesses as nearby communities fill up. As Oakland’s town manager put it, “people are outgrowing Winter Garden and Clermont, so we’re kind of the next place.” Oakland Village gives that growing population more places to shop and eat without leaving town.
What This Means
Oakland Village marks a turning point for a town long known for its quiet, residential feel. For residents, it means restaurants, shopping, and community gathering spaces close to home. For the broader Orange County market, it’s another sign that growth along the SR-50 corridor is moving west, bringing new amenities to areas buyers are increasingly considering.
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