Winter Garden, Florida, is a charming city in Orange County, just west of Orlando, known for its historic downtown and vibrant community spirit. Once a hub for citrus groves, it has transformed into a thriving destination with a blend of small-town charm and modern amenities. The downtown area, centered around Plant Street, features the bustling Winter Garden Farmers Market, boutique shops, diverse restaurants, and the iconic West Orange Trail, popular for biking and walking. With a rich history reflected in preserved buildings and cultural events like the Winter Garden Music Festival, the city attracts families and visitors seeking a welcoming, pedestrian-friendly atmosphere amidst Florida’s sunny landscapes.
Winter Garden currently has 780 single family homes for sale, 167 townhouses for sale, 41 condos for sale, and 30 lots for sale. There are 3 foreclosures for sale, and 12 short sales. For anyone looking for a brand new home, there are 473 new construction homes for sale.
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Winter Garden, FL is served by Orange County School District and Lake School District. The area has 13 elementary schools, 6 middle schools, 4 high school schools.
Orange County School District Elementary, Middle, High School
Hamlin is a master-planned community in western Winter Garden, located along the western edge of the Horizon West area and adjacent to the Orange County National Golf Center. Residents have direct access to the 1,100-acre West Orange Trail and are within a short drive of Walt Disney World and the Winter Garden Village shopping center. The neighborhood is served by the Orange County Public Schools system, including the highly rated Hamlin Elementary and Horizon High School.... Read more
Johns Lake Pointe sits just west of downtown Winter Garden, giving residents quick access to the West Orange Trail, the Plant Street Market, and the shops and restaurants along Plant Street. The neighborhood borders Johns Lake, where residents can launch kayaks or paddleboards from a private community dock. Zoned for the highly rated West Orange County schools, the community pairs lakefront recreation with a short drive to major employers along the Florida Turnpike and SR 429.... Read more
Oakland Park is a residential neighborhood in Winter Garden that sits minutes from downtown Winter Garden’s shops and restaurants as well as the West Orange Trail for walking and biking. Families are drawn to the area because it falls within the Orange County Public Schools district, with nearby campuses such as Lake Whitney Elementary and Ocoee Middle. Its grid of established streets also provides quick access to SR 429 and the Florida Turnpike for commuting to Orlando and surrounding employment centers.... Read more
Stoneybrook West sits along the western edge of Winter Garden, placing residents within a short drive of the West Orange Trail, Winter Garden Village shopping center, and the downtown historic district. The neighborhood’s golf course and surrounding conservation areas create a low-density setting with direct access to outdoor recreation. Families are served by nearby schools in the Orange County district, while commuters reach downtown Orlando in roughly 25 minutes via the Florida Turnpike or SR 429.... Read more
Waterleigh is a master-planned neighborhood in Winter Garden, Florida, positioned west of downtown Orlando with direct access to the Florida Turnpike and State Road 429. The community includes a clubhouse, multiple pools, fitness center, playgrounds, and miles of trails that connect to the West Orange Trail. Families are served by nearby schools in the Orange County Public Schools district, while shopping and dining at Winter Garden Village and the historic Winter Garden downtown district are within a short drive.... Read more
Median price: $570,000
Neighborhoods
View neighborhoods in Winter Garden
Subdivisions in Winter Garden
Winter Garden has 171 subdivisions offering single family homes, townhouses, and condos. Prices range from $165,000 to $4,300,000. 81 subdivisions offer new construction homes. Waterleigh currently has the most active listings with 60 homes for sale.
