Please ensure Javascript is enabled for purposes of website accessibility
Windermere Crossing Winter Garden Real Estate

Explore Winter Garden real estate in Windermere Crossing, located off Windermere Road and Windermere Crossing Circle. This community with single-family homes for sale is tucked away in a quaint alcove surrounded by trees, a small lake, close to top-rated schools, and an abundance of shopping and dining options. Easy access to the 429 and Florida Turnpike make commuting and day trips a breeze.

Windermere Crossing Homes for Sale

Windermere Crossing Homes for Sale

1 Property Found. Page 1 of 1.
Photo of Listing #O6149580
Reduced 11.1%
MLS® # O6149580
5 Beds, 3 Baths, 2,957 Sf

Windermere Crossing features 156 gorgeous homes ranging from over 2,100+ square feet to over 3,700 square feet with 2 to 3-car garages. Most of the homes here also offer private pools and well-manicured lawns. Twelve homes offer lovely pond views, while another 12 offer gorgeous lake views. All the residences here enjoy a quiet, serene setting that provides great convenience.

Windermere Crossing offers residents an abundance of options, from groceries to retail to restaurants, within a very short drive. Plantation Grove Shopping Center is 1.5 miles to the East. 2 miles to the West is the ever-popular Winter Garden Village offering everything from big box stores to clothing and furniture shops and various restaurants. Windermere Crossing also enjoys easy proximity to Downtown Winter Garden, which features many unique shops, restaurants, and bars, and is host to festivals and a weekly Farmer’s Market.

Not only is the community convenient for those who enjoy retail therapy, but also for those who enjoy the outdoors. George Bailey Park, which features baseball fields, picnic and grill areas, pavilions, and a playground, is across the street from the community. Additional parks are within a few miles, including Warrior Park, a great place to let the pooch run and play. Windermere Recreation Park, a lakeside park, features pavilions, tennis courts, a sand volleyball court, and a covered lakeside fishing pier. And for the golfers in the family, there are several nearby courses, including West Orange Country Club, which is only 4 miles away.

Call us today to find out more about Windermere Crossing.

Windermere Crossing Community Information

  • Location: Windermere Road and Windermere Crossing Circle
  • Year Built: 2000-2002
  • Square Footage: 1,200+ to 3,700+
  • Number of Homesites: 156 
  • HOA: yes
  • Amenities: lakefront park, playground

Orange County Public Schools

  • Lake Whitney Elementary School: Grades K - 5th Distance: .5 miles
  • Sunridge Middle School: Grades 6th - 8th Distance: 6.5 miles
  • West Orange High School: Grades 9th - 12th Distance: 2 miles

Dining and Shopping

  • Meadow Ridge Mall – Distance: 1.5 miles
  • Shoppes at Belmere – Distance: 1.5 miles
  • Winter Garden Village – Distance: 2 miles
  • Shoppes of Winter Garden – Distance: 3 miles
  • Walmart Supercenter – Distance: 3 miles
  • The Shoppes at Winward Cay – Distance: 3 miles
  • Shoppes at Lake Butler – Distance: 3 miles
  • Downtown Winter Garden – Distance: 4 miles
  • West Oaks Mall – Distance: 4 miles
  • Shoppes of Windermere with Walmart Neighborhood Market– Distance: 5 miles
  • The Grove with Publix Grocery Store – Distance: 5 miles
  • Downtown Orlando – Distance - Distance: 14 miles

Parks and Recreation

  • George Bailey Park – Distance: .5 mile
  • Warrior Park – Distance: 1 mile
  • West Orange Park – Distance: 1 mile
  • Roper YMCA Family Center – Distance: 1.5 miles
  • West Orange Soccer Complex – Distance: 1.5 miles
  • West Orange Dog Park – Distance: 1.5 miles
  • Freedom Park – Distance: 2 miles
  • Gotha Park – Distance: 2.5 miles
  • Windermere Recreation Area – Distance: 3 miles
  • Lake Street Park – Distance: 3 miles
  • Park Among the Lakes – Distance: 3 miles
  • Fernwood Park – Distance: 3.5 miles
  • Palmer Park – Distance: 3.5 miles
  • Central Park – Distance: 3.5 miles
  • West Orange Country Club – Distance: 4 miles
  • Walt Disney World Resort – Magic Kingdom – Distance: 10.5 miles
  • Universal Studios – Distance: 10 miles
  • SeaWorld – Distance: 13 miles


  • AdventHealth Winter Garden – Distance: 2.5 miles

*Distances are approximately measured from the entrance to the Windermere Crossing subdivision.

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on June 20th, 2024 at 6:49pm EDT.