New Developments in Oakland & Winter Garden

New Developments in Oakland and Winter Garden Bring Retail and Housing Growth

September 18, 2025

Story Highlights:

Oakland Town Center, a new 84,000 sq ft retail development, is planned off State Road 50 with restaurants, wellness services, and a possible rock climbing gym.
Plant Street Commons has broken ground in downtown Winter Garden, offering retail, apartments, and townhomes in a walkable, mixed-use design.
Both projects reflect growing demand for walkable, lifestyle-focused communities in West Orange County.

Rendering by Silling Architects

Two major new developments are in the works for west Orange County — one in the quiet town of Oakland, and the other in the heart of downtown Winter Garden. Both aim to boost walkability, offer new retail options, and support the area’s rapid population growth.

Oakland Town Center retail development planned on SR 50

Developer Alex Reece has submitted preliminary plans for a new project called Oakland Town Center, to be built on the north side of State Road 50 next to the Tractor Supply Co.

The plans call for roughly 84,000 square feet of retail and commercial space across seven buildings. The developer’s team is making updates that could add:

• More green space
• Wider sidewalks
• Patio seating areas
• A decorative water fountain

Reece envisions a mixed-use, walkable environment with a variety of businesses including:

• Restaurants and coffee shops
• Health and wellness services
• A fitness facility
• A bank
• A potential rock climbing gym

The goal is to create a destination-style center where people can spend several hours shopping, dining, and exploring.

The center will sit on part of a 50-acre parcel in Oakland and could begin construction within 6 to 12 months, pending final approvals. Reece said the project benefits from its location near Horizon West, Windermere, Clermont, and Winter Garden, all areas seeing significant growth.

Plant Street Commons mixed-use project breaks ground in Winter Garden

In downtown Winter Garden, Atrium Development Group has started construction on a new mixed-use development called Plant Street Commons, located at 419 W. Plant Street at the corner of N. Central Avenue.

This project includes:

5,300 square feet of retail space
10 apartments in a three-story building (retail on the ground floor)
8 two-story townhomes on Central Ave. and Bay St.
27 parking spaces split between retail, apartment residents, and townhomes

Designed by Silling Architects and built by RLH Construction, this development will add more living and shopping opportunities in one of Central Florida’s most walkable downtowns.

West Orange County continues to attract walkable development

Both projects reflect a larger trend: walkable, mixed-use communities are in high demand across West Orange County. With strong population growth and interest in local, lifestyle-driven experiences, these developments are designed to serve both current residents and future growth.

Frequently Asked Questions

1. What is being built in Oakland, Florida?

A new mixed-use development called Oakland Town Center is planned with retail, dining, wellness services, and green space along State Road 50.

2. Where is Oakland Town Center located?

Oakland Town Center will be located on the north side of State Road 50, next to Tractor Supply Co., near the border of Winter Garden.

3. What businesses will be at Oakland Town Center?

Potential tenants include restaurants, coffee shops, health and wellness businesses, a fitness center, and possibly a rock climbing gym.

4. When will Oakland Town Center start construction?

Construction is expected to begin within 6 to 12 months, pending city approvals.

5. What is Plant Street Commons in Winter Garden?

Plant Street Commons is a mixed-use development with retail space, apartments, and townhomes, currently under construction in downtown Winter Garden.

6. Where is Plant Street Commons located?

The project is at 419 W. Plant Street, on the corner of N. Central Avenue in downtown Winter Garden.

7. How many units are in Plant Street Commons?

The development includes 10 apartments, 8 two-story townhomes, and 5,300 square feet of retail space.

8. Why are walkable developments growing in West Orange County?

With rapid population growth in areas like Horizon West, Winter Garden, and Oakland, there’s rising demand for walkable communities with dining, shopping, and housing all in one place.

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