Windward Cay

Windward Cay is a gated Winter Garden community with single-family homes for sale. Located off Tilden Road and Rockrose Drive, Windward Cay is convenient to community parks, area activities, and top-rated Orange County schools. The one- and two-story homes of Windward Cay range from approximately 2,300 square feet to approximately 3,800 square feet and offer 3 to 5 bedrooms, 2 to 4 baths, and 2- to 3-car garages. Some homes enjoy tranquil views with lots that back up to the conservation area. Many homes have added private pools or screened lanais, ideal for enjoying the Florida lifestyle.

Windward Cay Homes For Sale

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New Open House
1580 Deland Avenue, ORANGE CITY

$329,900

1580 Deland Avenue, ORANGE CITY

3 Beds 2 Baths 1,380 SqFt Residential MLS® # V4951641
25551 Hawks Run Lane, SORRENTO

$925,000

25551 Hawks Run Lane, SORRENTO

5 Beds 5 Baths 4,343 SqFt Residential MLS® # O6346583
New
11347 Pine Ridge Road, LEESBURG

$549,000

11347 Pine Ridge Road, LEESBURG

4 Beds 3 Baths 1,727 SqFt Residential MLS® # G5118779
New
39914 Sunbeam Way, LADY LAKE

$319,999

39914 Sunbeam Way, LADY LAKE

3 Beds 2 Baths 2,034 SqFt Residential MLS® # O6447413
New
3342 Veltre Way, THE VILLAGES

$499,900

3342 Veltre Way, THE VILLAGES

4 Beds 2 Baths 2,013 SqFt Residential MLS® # G5118796
New
2014 W Colonial Drive, ORLANDO

$8,500,000

2014 W Colonial Drive, ORLANDO

0 Beds 0 Baths 62,369 SqFt Commercial Sale MLS® # O6448580
New
1028 S Terry Avenue, LAKELAND

$315,000

1028 S Terry Avenue, LAKELAND

4 Beds 2 Baths 1,705 SqFt Residential MLS® # TB8556329
1721 Freeman Drive, KISSIMMEE

$359,900

1721 Freeman Drive, KISSIMMEE

3 Beds 2 Baths 1,842 SqFt Residential MLS® # O6424008
New
8516 Crystal Cove Loop, KISSIMMEE

$235,000

8516 Crystal Cove Loop, KISSIMMEE

3 Beds 3 Baths 1,291 SqFt Residential MLS® # O6447766
New
6025 Westgate Drive 2518, ORLANDO

$195,000

6025 Westgate Drive 2518, ORLANDO

2 Beds 2 Baths 1,077 SqFt Residential MLS® # S5159084
New
6776 Huntleigh Hammock Road, ST CLOUD

$355,000

6776 Huntleigh Hammock Road, ST CLOUD

3 Beds 2 Baths 1,649 SqFt Residential MLS® # O6447567
New
4925 Clayton Road, KATHLEEN

$350,000

4925 Clayton Road, KATHLEEN

3 Beds 2 Baths 1,664 SqFt Residential MLS® # L4965642
Open House
5100 Greenshade Grove Avenue, APOPKA

$351,990

5100 Greenshade Grove Avenue, APOPKA

4 Beds 3 Baths 1,678 SqFt Residential MLS® # O6431753
New
5685 Arlington River Drive, LAKELAND

$399,000

5685 Arlington River Drive, LAKELAND

5 Beds 3 Baths 2,885 SqFt Residential MLS® # L4965648
Open House
179 Blue Cypress Drive, DAVENPORT

$359,900

179 Blue Cypress Drive, DAVENPORT

4 Beds 3 Baths 1,910 SqFt Residential MLS® # O6433532

Sold Homes in Windward Cay Winter Garden

Real Estate Statistics

Average Price $825K
Lowest Price $800K
Highest Price $849K
Total Listings 2
Avg. Days On Market 5
Avg. Price/SQFT $279
List to Sell Price Percentage 97 %

Property Types (active listings)

Winter Garden Communities

Several parks are within a short drive of Windward Cay, including Braddock Park, which offers baseball and soccer fields, and George Bailey Park, which features a fun covered playground for the little ones, along with pavilions for picnics and outdoor gatherings. Two golf courses are within a few miles of the community, including West Orange Country Club and Stoneybrook West Club Golf Club. For the theme park lovers of the family, Walt Disney World is also only a short drive away.

Residents of Windward Cay also enjoy the convenience of having shopping and dining options very close by, with a grocery store and local favorite Winter Garden Village, which features a variety of shops and restaurants, including a Target, both about 2 miles away. There is also a Walmart Supercenter a few miles from the community. With its diverse flair and hometown charm, Historic Downtown Winter Garden, just a short drive away, features everything from sidewalk cafes and award-winning restaurants to art galleries and history museums to a community theater and a lively weekly farmers market.

Major roadways, including FL-429 and the Florida Turnpike, are convenient to Windward Cay, making this a perfect choice for those seeking an ideal location that enjoys commuter convenience.

Call us today to find out more about Windward Cay.

Orange Cove Community Information

Location: Tilden Road and Rockrose Drive
Year Built: 2002 - 2004
Number of Homesites: 66 single-family homes
HOA: Yes

Orange County Public Schools

  • Keene’s Crossing Elementary School: Grades K - 5th Distance: 3.5 miles
  • Bridgewater Middle School: Grades 6th - 8th Distance: 3 miles
  • Windermere High School: Grades 9th - 12th Distance: 2.5 miles

Dining and Shopping

  • The Shoppes at Windward Cay – Distance: 0.5 mile
  • Winter Garden Village – Distance: 2 miles
  • Cornerstone at Summerport with Publix Grocery Store – Distance: 2.5 miles
  • Windermere Village – Distance: 3 miles
  • Cornerstone at Summerport – Distance: 3 miles
  • Stoneybrook West Village – Distance: 3.5 miles
  • West Point Commons Shopping Center with Publix Grocery Store – Distance: 5 miles
  • Winter Garden Regional Shopping Center – Distance: 5 miles
  • Walmart Supercenter – Distance: 5 miles
  • Downtown Orlando – Distance - Distance: 18 miles

Parks and Recreation

  • Braddock Park – Distance: .5 mile
  • West Orange Country Club – Distance: .5 mile
  • George Bailey Park – Distance: 3 miles
  • Stoneybrook West Golf Club – Distance: 3 miles
  • Warrior Park – Distance: 4 miles
  • West Orange Park – Distance: 4 miles
  • Veterans Memorial Park – Distance: 4.5 miles
  • Maple Street Park – Distance: 4.5 miles
  • Tucker Ranch Recreation and Nature Center – Distance: 5.5 miles
  • West Orange Trail – Distance: 6 miles
  • Kia Center – Distance: 17 miles

Theme Parks

  • Walt Disney World Resort – Distance: 11.5 miles
  • Universal Studios – Distance: 11 miles
  • SeaWorld – Distance: 16 miles

Hospitals

  • AdventHealth Winter Garden ER – Distance: 1.5 mile
  • Orlando Health Health Central Hospital – Distance: 6 miles

*Distances are approximately measured from the entrance to the Windward Cay subdivision.

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