Downtown Winter Garden Homes for Sale

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Explore Downtown Winter Garden homes for sale. Discover historic charm, modern living, top neighborhoods, attractions, and lifestyle in the heart of Winter Garden.

Find Your Dream Home in Downtown Winter Garden

The Downtown Winter Garden Area, often called the “original” Winter Garden, is where the community began. This section of town was once surrounded by citrus groves to the south—what is now the Winter Garden Village area and the rapidly expanding Horizon West.

Centered around the historic Plant Street corridor, Downtown Winter Garden is the town’s hub of activity. Here you’ll find Town Hall, cultural venues, dining, shopping, and many of the events that make Winter Garden one of Central Florida’s most vibrant communities.

Housing in this area ranges from historic homes built in the early 1900s to newly constructed properties with modern features. While single-family homes are most common, you’ll also find townhomes sprinkled throughout the area.

Where is the Downtown Area in Winter Garden?

The Downtown/Original Winter Garden area is located in the northern section of the city. It’s:

  • • North of the Florida Turnpike

  • • West of the 429 Expressway

  • • East of the Oakland area

  • • South of Lake Apopka

This section includes much of what was historically Winter Garden before new developments expanded southward toward Disney after the 429 opened.

Hwy 50 runs east-west through the southern edge of the area, while Plant Street (State Road 438) cuts diagonally through the heart of downtown. The popular West Orange Trail also winds through many of the neighborhoods here, connecting residents directly to downtown.

Horizon West Area Neighborhoods

Cove At Hamlin

Del Webb Oasis (NEW)

Harvest at Ovation

Mezzano

Osprey Ranch

Westhaven Ovation

Hamlin Pointe

Hamlin Ridge

Horizon Isle

Lake Star at Ovation

Northlake at Ovation

Parkview at Hamlin

Serenade at Ovation

Silverleaf Oaks

Silverleaf Reserve

Tribute at Ovation