Winter Oaks

Winter Oaks in Winter Garden, FL is a single-family home community located near Plant Street and Sunset Oaks Road, approximately 0.2 miles from the West Orange Trail and less than half a mile from downtown Winter Garden. Known for its golf cart access and close proximity to local shops, dining, and community events, this neighborhood offers convenient access to both lifestyle and location. Major roadways like State Road 429 and the Florida Turnpike are also nearby, supporting travel throughout Central Florida.

Winter Oaks Homes for Sale

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Real Estate Statistics

Average Price $600K
Lowest Price $600K
Highest Price $600K
Total Listings 1
Avg. Days On Market 26
Avg. Price/SQFT $274
List to Sell Price Percentage 98 %

Property Types (active listings)

Winter Garden Communities

Homes for sale in Winter Oaks typically range from 3 to 5 bedrooms with approximately 1,300 to over 3,200 square feet. The community features one and two-story homes with rear-facing 2-car garages. Interior features may include arched doorways, spacious primary suites, separate dining areas, and breakfast nooks. Some homes have been updated with modernized kitchens or refreshed flooring, while others offer second-floor lofts or private balconies. Outdoor living is a highlight, with many homes featuring extended enclosed lanais designed for relaxing or gathering.

Winter Oaks includes a community pool with a cabana, an outdoor lounge area, and a large play space in a park-like setting. Nearby Veterans Memorial Park and Walker Field offer additional outdoor recreation, including sports courts and open green space. With the West Orange Trail located so close and downtown Winter Garden within close reach, this location continues to stand out for those exploring homes near the heart of the area.

Winter Oaks Community Information

  • Location: W. Plant Street & Sunset Oaks Road or W. Story Road & Indian Oaks Road, North of Highway 50
  • Number of Homesites: 107
  • Year Built: 2003 - 2007
  • Square Footage: 1,297 - 3,216
  • HOAYes
  • Community Amenities: Community Pool, Playground, Golf Cart District, 0.2 mile to West Orange Trail

Orange County Area Schools

  • Tildenville Elementary School (Grades K-5) - Distance: <1 mile
  • Lakeview Middle (Grades 6-8) - Distance: <1 mile
  • West Orange High School (Grades 9-12) - Distance: 3.5 miles

Dining and Shopping

  • Downtown Historic Winter Garden - Distance: <1 mile
  • Winter Garden Village (Retail, Restaurants, Entertainment) - Distance: 4 miles
  • Grocery Store (Publix at West Point Commons) - Distance: 2 miles
  • Plaza Collina with Costco, dining, services - Distance: 5 miles
  • Restaurant Row - Distance: 14 miles
  • The Mall at Millenia, Retail Shopping Centers, & BJ's Wholesale Club - Distance:  15.5 Miles
  • Downtown Orlando - Distance: 17.5 miles

Parks and Recreation

  • Newton Park (Lakefront Playground, fishing, picnics) - Distance: 1.5 miles
  • Walt Disney World Resort - Distance: 13 miles
  • Universal Orlando Resort - Distance: 17 miles
  • West Orange Trail - Distance: 0.2 mile
  • Oakland Nature Preserve - Distance: 3 miles
  • Stoneybrook West Golf Club - Distance: 5 miles
  • Veterans Memorial Park - Distance: 1 mile
  • Roper YMCA Family Center - Distance: 4 miles

Hospitals

  • AdventHealth Winter Garden - Distance: 4 miles
  • HCA Florida West Orange ER - Distance: 2.5 miles
  • Orlando Health-Health Central Hospital - Distance: 5.5 miles

*Distances are approximately measured from Winter Oaks community entrance.

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