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
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 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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