2002 to 2004Years built
2,750 to 3,400 sq ftHome size
GatedEntry
Stoneybrook & East Winter GardenArea
Why people move here

A gated neighborhood of 66 homes off Tilden Road.

Windward Cay is a gated community of 66 one- and two-story homes off Tilden Road and Rockrose Drive, built from 2002 to 2004.
Community parks and Orange County schools are close, and Stoneybrook West’s shopping and the 429 are a short drive. A small gated neighborhood at an established-home price is a good fit for buyers moving up.
Buyers moving up who want a small gated neighborhood.

Windward Cay at a glance

Location: Tilden Road and Rockrose Drive

Builder: Custom and individual builders

Built: 2002 to 2004

Homes: 66 single-family homes

Home types: Single-family homes

Size: About 2,750 to 3,400 sq ft

Bedrooms: Varies by floor plan

Entry: Gated

Area: Stoneybrook & East Winter Garden

Life here

What Windward Cay has

✨Established neighborhood setting
Proximity

What is close to Windward Cay

  • Winter Garden Village ~2 mi
  • Cornerstone at Summerport with Publix Grocery Store ~2.5 mi
  • Stoneybrook West Village ~3.5 mi
  • West Point Commons Shopping Center with Publix Grocery Store ~5 mi

Approximate distances from the community entrance. Walt Disney World is roughly 15 to 20 minutes away off-peak. SR 50, the 429 interchanges and Avalon Road back up at rush hour, so send me your work address and I will map your real commute.

Schools

🏫 Crossing Elementary

🏫 Bridgewater Middle

🏫 Windermere High

Orange County Public Schools. Zoning changes, so verify every address.

The numbers

Windward Cay market snapshot

Windward Cay had 3 closed sales in the last 12 months. That is too few for a median that means anything, so I price homes here one at a time.

Get the real numbers for Windward Cay

Call or text me at 407.502.4719 and I will send every recent closed sale in and around Windward Cay, straight from Stellar MLS, with what each one tells us about value.

Stellar MLS, residential closed sales, 12 months ending September 30, 2026. Pulled Oct 16, 2026 and refreshed every quarter. Deemed reliable but not guaranteed. For a specific home, request a custom report.

Live MLS listings

Windward Cay homes for sale right now

Straight from Stellar MLS. Save the search and get new Windward Cay listings the day they hit.

Start of list of properties

Free guides

Buying or selling in Windward Cay?

Pick your guide, tell me where to send it, and it opens right away.

🏡 Buyer Guide

How buying in Windward Cay works, from new construction versus resale to what to verify on HOA, CDD and school zoning.

🔑 Seller Guide

Pricing, prep and timing for selling your current home, including how to sell and buy at the same time without moving twice.

Questions buyers ask

Windward Cay FAQ

Where is Windward Cay in Winter Garden?

Windward Cay is in east Winter Garden near Stoneybrook West, Daniels Road and Tilden Road, at Tilden Road and Rockrose Drive.

How far is Windward Cay from Walt Disney World?

Roughly 15 to 20 minutes off-peak from this part of Winter Garden. I will map the exact drive from the entrance before you choose.

When were homes in Windward Cay built?

2002 to 2004. Most homes were built by individual or custom builders.

What amenities does Windward Cay have?

Established neighborhood setting.

Is Windward Cay a gated community?

Yes. Windward Cay has a gated entry. I confirm gate type and access rules for any home before you write an offer.

What schools serve Windward Cay?

Schools commonly listed for this community: Crossing Elementary, Bridgewater Middle, Windermere High. Assignments change, so verify zoning for a specific address with the OCPS School Locator.

Is Windward Cay inside Winter Garden city limits?

Many homes with a Winter Garden 34787 address, including much of Horizon West, sit in unincorporated Orange County rather than the City of Winter Garden. Taxes, utilities and services differ, so I confirm the jurisdiction for every address.

What do homes in Windward Cay sell for?

Too few homes sold in Windward Cay in the last 12 months for a reliable median. Call or text me at 407.502.4719 and I will send recent closed sales in and around Windward Cay from Stellar MLS.

Your next step

Thinking about Windward Cay?

Give me 30 minutes and tell me your timeline. I will send back:

  • Recent closed sales in Windward Cay, straight from Stellar MLS
  • City or county, HOA and CDD for the homes that fit
  • Your real commute, mapped from the entrance

No pressure. If you are selling a home somewhere else first, we will plan both sides together.

Semper Fi to your real estate needs. Jorge Martinez, REALTOR®

Information deemed reliable but not guaranteed. Community details come from public sources and change over time; distances are approximate. Market data from Stellar MLS. Buyers should verify city or county jurisdiction, school assignments, HOA, CDD, lake access and all property details independently. The JEM Property Group is an independently owned and operated real estate team affiliated with Keller Williams Realty. Equal Housing Opportunity.