Windermere Crossing

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

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New
Timberlane Road, LAKE WALES

$215,000

Timberlane Road, LAKE WALES

0 Beds 0 Baths 0 SqFt Land MLS® # O6448344
New
Timberlane Road, LAKE WALES

$269,000

Timberlane Road, LAKE WALES

0 Beds 0 Baths 0 SqFt Land MLS® # O6448343
New Open House
20 Walden, ORMOND BEACH

$349,900

20 Walden, ORMOND BEACH

3 Beds 2 Baths 1,874 SqFt Residential
Sat, Oct 10th, 2026 @ 12pm - 3pm
MLS® # V4951731
New
Green Lake Drive, EUSTIS

$75,000

Green Lake Drive, EUSTIS

0 Beds 0 Baths 0 SqFt Land MLS® # O6447200
New
Green Lake Drive, EUSTIS

$75,000

Green Lake Drive, EUSTIS

0 Beds 0 Baths 0 SqFt Land MLS® # O6447201
New
Green Lake Drive, EUSTIS

$75,000

Green Lake Drive, EUSTIS

0 Beds 0 Baths 0 SqFt Land MLS® # O6447198
Pending
1624 Sterns Drive, LEESBURG

$285,000

1624 Sterns Drive, LEESBURG

4 Beds 2 Baths 2,936 SqFt Residential MLS® # O6425853
New
3110 Emerald Acres Lane, SANFORD

$374,500

3110 Emerald Acres Lane, SANFORD

3 Beds 3 Baths 1,682 SqFt Residential MLS® # S5159186
New
5714 Cattle Ranch Drive, ST CLOUD

$3,095

5714 Cattle Ranch Drive, ST CLOUD

4 Beds 4 Baths 3,058 SqFt Residential MLS® # O6448300
1211 Nixonton Street, DELTONA

$440,000

1211 Nixonton Street, DELTONA

3 Beds 3 Baths 2,208 SqFt Residential MLS® # V4951068
New
140 Bombay Avenue, WINTER SPRINGS

$355,000

140 Bombay Avenue, WINTER SPRINGS

3 Beds 2 Baths 1,373 SqFt Residential MLS® # O6448262
New
31744 Boadwater Ave, LEESBURG

$369,900

31744 Boadwater Ave, LEESBURG

4 Beds 3 Baths 2,626 SqFt Residential MLS® # O6447594
New
5381 Maddie Drive, HAINES CITY

$399,900

5381 Maddie Drive, HAINES CITY

5 Beds 3 Baths 3,011 SqFt Residential MLS® # O6446669
New Open House
1249 Waterwitch Cove Circle, ORLANDO

$874,900

1249 Waterwitch Cove Circle, ORLANDO

3 Beds 3 Baths 2,715 SqFt Residential
Sat, Oct 10th, 2026 @ 1pm - 4pm
MLS® # O6446291
New
1881 Red Canyon Drive, KISSIMMEE

$310,000

1881 Red Canyon Drive, KISSIMMEE

3 Beds 3 Baths 1,624 SqFt Residential MLS® # O6448530

Sold Homes in Windermere Crossing Winter Garden

Windermere Crossing Real Estate Market Statistics

Average Price $717K
Lowest Price $595K
Highest Price $839K
Total Listings 2
Avg. Days On Market 138
Avg. Price/SQFT $235

Property Types (active listings)

Winter Garden Communities



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

Hospitals

  • AdventHealth Winter Garden – Distance: 2.5 miles

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

Orlando - Windermere Home

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