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Winter Garden Shores Real Estate

Explore Winter Garden Shores, a community in Winter Garden with single-family homes for sale. Situated close to the many shopping, dining, and entertainment options of Historic Downtown Winter Garden, this community is located off W Crest and W/E Division Street. 

Winter Garden Shores Homes for Sale

Winter Garden Shores Homes for Sale

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This well-established community offers a variety of home styles and floorplans ranging in size between approximately 1,000 square feet to over 3,200 square feet and offering between 2 and 5 bedrooms, 1 to 4 baths, and 2 to 3 car garages. Its mature trees lining the streets and oversized lots also add to its appeal.

Winter Garden Shores is highly desirable because of its convenient location near activities practically on its doorstep. It’s not uncommon for residents to travel via golf cart to nearby hot spots. With its small-town charm but modern-day options, Historic Downtown Winter Garden is filled with opportunities for residents to enjoy. From the variety of restaurants and bars to its live performance theater, art gallery, and local museum, to its popular and nationally-acclaimed weekly Farmers Market and a multitude of hosted events, fun is always at your fingertips.

Everyday conveniences are nearby, as well. There’s a Publix Grocery Store at West Points Common Shopping Center 2.5 miles away, and the many restaurants and shops of Winter Garden Village are within a short drive.

When it comes to enjoying a day at the park, there are multiple options to explore. Experience the lakefront serenity of Newton Park, the miles and miles of walking and biking trails at West Orange Trail, or fun playground time for the kids at Maple Street Park, all 1 mile away. Jessie Brock Community Center is around the corner and offers a park, sports fields, athletic and exercise programs, dance and art classes, community events, summer camps, and more. There are also two nearby golf courses, Forest Lake Golf Course and West Orange Country Club.

Winter Garden Shores Community Information

  • Location: W Crest and W/E Division Street
  • Year Built: 1940s - 2022
  • Number of Homesites: 257 single-family homesites
  • Square Footage: 1,000 - 3,200+
  • HOA: yes

Orange County Area Schools

  • Dillard Street Elementary School: Grades 1st – 5th Distance: 0.5 miles
  • Lakeview Middle School: Grades 6th – 8th Distance: 2 miles
  • West Orange High School: Grades 9th - 12th Distance: 3 miles

Dining and Shopping

  • West Point Commons with Publix Grocery Store – Distance: 2.5 miles
  • Winter Garden Plaza – Distance: 2.5 miles
  • Shoppes of Winter Garden – Distance: 2.5 miles
  • Winter Garden Regional Shopping Center – Distance: 3 miles
  • Fountains West with Publix Grocery Store – Distance: 3.5 miles
  • Winter Garden Village – Distance: 4 miles
  • Walmart Supercenter – Distance: 5 miles
  • The Shoppes at Windward Cay – Distance: 7.5 miles
  • Shoppes at Lake Butler – Distance: 8 miles
  • Lake Nona Creekside – Distance: 4 miles
  • Downtown Orlando – Distance - Distance: 16 miles

Parks and Recreation

  • Dr. Bradford Memorial Park – Distance: 1 mile
  • Newton Park – Distance: 1 mile
  • Chapin Station – Distance: 1 mile
  • Winter Garden Lake Apopka Shore – Distance: 1 mile
  • West Orange Trail Park – Distance: 1.5 miles
  • Maple Street Park – Distance: 1.5 miles
  • Palm Park – Distance: 2 miles
  • West Orange Park – Distance: 3.5 miles
  • VanderLey Park – Distance: 4 miles
  • Tucker Ranch Recreation and Nature Complex – Distance: 4 miles
  • Tildenview Park – Distance: 4.5 miles
  • Speer Park – Distance: 4.5 miles
  • George Bailey Park – Distance: 4.5 miles
  • Johns Lake Preserve – Distance: 5 miles
  • Amway Center – Distance: 15 miles


  • Walt Disney World Resort – Magic Kingdom – Distance: 20 miles
  • Universal Studios – Distance: 15 miles
  • SeaWorld – Distance: 19 miles


  • AdventHealth Winter Garden Hospital – Distance: 4.5 miles

*Distances are approximately measured from the entrance to the Winter Garden Shores subdivision.