Winding Bay
Single-family homes and Townhomes · Built 2020 to 2025 · about 2,156 to 4,008 sq ft
K. Hovnanian homes and townhomes with a splash pad and two dog parks.
Winding Bay at a glance
Location: Avalon Road at Mayberry Drive North of Western Way
Builder: Custom and individual builders
Built: 2020 to 2025
Homes: 328
Home types: Single-family homes and Townhomes
Size: About 2,156 to 4,008 sq ft
Bedrooms: Varies by floor plan
Area: Ovation & Near the Parks
What Winding Bay has
What is close to Winding Bay
- Winter Garden Village at Fowler Groves Shopping Center with Super Target ~11.5 mi
- Walt Disney World Resort ~3.5 mi
- Flamingo Crossings Town Center ~3 mi
- Rolling Oaks Commons ~5.5 mi
Approximate distances from the community entrance. Walt Disney World is roughly 5 to 10 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
🏫 Water Spring Elementary
🏫 Water Spring Middle
🏫 Horizon High
🏫 Windermere Preparatory Private
Orange County Public Schools. Zoning changes, so verify every address.
Winding Bay market snapshot
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.
Winding Bay homes for sale right now
Straight from Stellar MLS. Save the search and get new Winding Bay listings the day they hit.
Start of list of properties
MLS# O6422754
Wra Business & Real Estate
MLS# O6427810
Top Housing LLC
MLS# O6424514
Florida Connexion Properties
MLS# O6441092
Keller Williams Advantage III
MLS# O6450178
Alves And Howell Realty
MLS# O6446141
Real Broker, LLC
Buying or selling in Winding Bay?
Pick your guide, tell me where to send it, and it opens right away.
🏡 Buyer Guide
How buying in Winding Bay 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.
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Next step: book a 30 minute call and we will walk through it together for Winding Bay.
Winding Bay FAQ
Where is Winding Bay in Winter Garden?
Winding Bay is in southern Horizon West near Ovation, Hartzog Road and Flamingo Crossings, at Avalon Road at Mayberry Drive North of Western Way.
How far is Winding Bay from Walt Disney World?
Roughly 5 to 10 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 Winding Bay built?
2020 to 2025. Most homes were built by individual or custom builders.
What amenities does Winding Bay have?
Community Pool, Splash Pad, Cabana, Play Field & Lawn, Picnic Area, Small & Large Dog Park, Playground, 3 Ponds.
Is Winding Bay a gated community?
Winding Bay is not listed as gated. Ask me about gated options nearby.
What schools serve Winding Bay?
Schools commonly listed for this community: Water Spring Elementary, Water Spring Middle, Horizon High, Windermere Preparatory Private. Assignments change, so verify zoning for a specific address with the OCPS School Locator.
Is Winding Bay 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 Winding Bay sell for?
Per Stellar MLS, the median sale price in Winding Bay was $727,000 across 23 closed sales in the 12 months ending September 30, 2026. Call or text me at 407.502.4719 for recent sales that match your home.
Thinking about Winding Bay?
Give me 30 minutes and tell me your timeline. I will send back:
- Recent closed sales in Winding Bay, 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.