Oakland Village Is Coming: New Shopping, Dining and Gathering Space Planned for Oakland, Florida

Oakland, Florida, is preparing for a significant new addition to the community. Oakland Village, a new shopping, dining and gathering destination planned along State Road 50, recently received final approval from the Town of Oakland.

Previously known as Oakland Town Center, the project will be developed on approximately 14.8 acres near the northwest corner of State Road 50 and Catherine Ross Road. Plans call for approximately 85,000 square feet of commercial space, bringing new restaurants, shops and services closer to Oakland residents. Orange Observer

More Than a Traditional Shopping Center

One of the most interesting aspects of Oakland Village is its emphasis on creating a place where people can spend time—not simply another commercial plaza along State Road 50.

Current plans include nine buildings and two outparcels, with restaurants, retail, services and health and wellness uses. The design also incorporates outdoor dining opportunities, landscaped courtyards, pedestrian walkways, bicycle facilities and golf-cart parking. Approximately 16,000 square feet of outdoor amenity space is planned for courtyards, patios and community gathering areas. The Orlando Real

Rooftop and covered patio dining are also part of the concept, helping create the type of walkable social environment that many Oakland residents currently travel to neighboring communities to enjoy. The Orlando Real

Designed With Oakland in Mind

The project went through changes during the approval process after town leaders expressed a desire for the development to better reflect Oakland’s own identity and character.

Even the name changed. Originally proposed as Oakland Town Center, it became Oakland Village to distinguish the development from Oakland’s existing historic downtown area. Updated plans and renderings were subsequently presented before commissioners granted final approval. Orange Observer

The goal is to combine new commercial amenities with outdoor spaces and pedestrian-friendly features while maintaining a connection to the character of the surrounding community.

New Restaurants and Shops — But No Confirmed Tenants Yet

For residents wondering which businesses are coming, it’s still too early for a confirmed list.

Developers are seeking a curated combination of restaurants, retail, services, health and wellness businesses, coffee and dessert concepts and other local amenities. Several restaurant concepts have been mentioned as examples of businesses being targeted, but tenant agreements have not yet been confirmed publicly, so those names should not be considered announced tenants. The Orlando Real

That will make the tenant announcements one of the most interesting developments to follow as Oakland Village moves closer to construction.

Why Oakland Village Matters for the Community

Oakland has experienced considerable residential growth while maintaining a much smaller commercial footprint than neighboring Winter Garden and Clermont.

Oakland Village could begin changing that balance by giving residents additional places to dine, shop, gather and access everyday services closer to home.

The location is also significant. Positioned along the State Road 50 corridor between Winter Garden and Clermont, the project will serve not only Oakland residents but potentially people throughout the surrounding West Orange and South Lake communities. Spectrum News 13

For people considering a move to Oakland, projects like this are worth following because they illustrate how the town is evolving as residential growth continues.

What Happens Next?

Major approvals are now in place, although permitting and final site work still need to move forward. Current plans anticipate construction beginning in 2027, with completion currently projected around 2029. As with any development of this scale, construction schedules can change. Spectrum News 13

I’ll continue following Oakland Village as the project progresses, particularly as construction begins and the first restaurants and businesses are officially announced.

Living in Oakland, Florida

Oakland offers a distinctive alternative within the rapidly growing western side of Central Florida. Its small-town character, proximity to Winter Garden and Clermont, access to the West Orange Trail, and continued residential development have made it an increasingly notable part of the region.

As new projects such as Oakland Village take shape, residents will have access to more amenities while Oakland continues to develop its own identity within Central Florida.

Thinking about making Oakland home? Explore my Oakland real estate guide and current homes for sale, or contact me to learn more about buying or selling a home in Oakland, Florida.