The Downtown Winter Garden Area

Historic Plant Street, the original town center, and the walkable heart of West Orange County

Living in the Original & Downtown Winter Garden Area

What we call the Downtown Winter Garden Area is actually the original town of Winter Garden. This was where the main residential areas were and the citrus groves were found to the South in what is now the Winter Garden Village area and the booming Horizon West area.

The area is centered around the historic downtown core along Plant Street and encompasses roughly 28 distinct neighborhoods. This is the hub of social activity in the city — home to Town Hall, the Garden Theatre, the Saturday Farmers Market, and the year-round events calendar that has earned the district its national reputation.

You will find homes ranging from the early 1900s to new construction with all the latest features. Most properties in this area are single-family homes, but you will also find several townhome options, including the walkable Heritage at Plant Street just steps from the Garden Theatre.

Where is the Downtown Area in Winter Garden?

The Downtown or Original Winter Garden area is now located in what would be just the northern section of the growing Winter Garden area. It sits north of the Florida Turnpike, west of the 429 Expressway, east of the Oakland area, and south of Lake Apopka.

The area includes most of what was considered Winter Garden before the community started growing south toward Disney when the 429 expressway opened former orange groves for development.

Hwy 50 runs east-west through its southern section and Plant Street (438) runs diagonally through the area, including through the heart of Downtown Winter Garden. The area is well known for the popular West Orange Trail running through many of its neighborhoods.

How Far from the Downtown Winter Garden Area to…

Destination	Distance
Downtown Orlando	17 miles
Disney & Universal	17 miles
Orlando International Airport	25 miles
Port Canaveral & Cocoa Beach	70 miles

Downtown Winter Garden Area Neighborhoods

Neighborhoods in the Downtown and northern area of Winter Garden include the following. Many fall within the city's golf-cart zone or sit along the West Orange Trail, making car-free trips to the historic core a daily reality for residents.

• Brandy Creek
• Chapin Station
• Courtlea Oaks
• Courtlea Park
• Covington Chase
• Crown Point Springs
• Daniels Crossing
• Downtown Winter Garden
• Fullers Crossing
• Fullers Landing
• Heritage at Plant Street
• Island Pointe
• Kings Bay
• Lake Cove Pointe
• Lakeview Reserve
• Magnolia Wood
• McAllister Landing
• Oakglen Estates
• Oaks at Brandy Lake
• Park Place
• Regal Pointe
• Stanton Estates
• Sterling Pointe
• Timbercreek Pines
• Traditions
• Trails of Winter Garden
• Tuscany
• Walkers Grove
• Winter Oaks

Attractions Within the Downtown Winter Garden Area

There is always something happening in the Downtown Winter Garden area — whether it's a special holiday celebration, a weekend gathering, or a random Tuesday afternoon on Plant Street. The historic core hosts a steady rhythm of events, plus year-round dining and shopping that keeps residents and visitors returning.

There are also an overwhelming number of dining and bar options available across the historic district — from the 1927 Edgewater Hotel to the food hall at Plant Street Market. Find even more things to do in our comprehensive Winter Garden events guide and explore dining options in our complete Winter Garden restaurants and dining guide.

Explore More of Winter Garden

The Downtown Winter Garden Area sits within a larger city that includes lakefront communities along Lake Apopka, golf neighborhoods west of SR 429, and family communities along the Daniels Road corridor. Discover the rest of the city through our category guides:

Winter Garden arts and culture guide · Winter Garden parks and recreation guide · Winter Garden shopping guide · Winter Garden schools and education guide · Winter Garden sports and athletics guide · Winter Garden health and wellness guide

Last updated: May 2026