Winding Bay

Winding Bay is off Avalon Road (CR 545) at Mayberry Drive, in Horizon West. It has Winter Garden mailing addresses but is in unincorporated Orange County.

Winding Bay has 299 single-family homes and 116 townhomes, built from 2019 to 2025, according to Orange County Property Appraiser records. K. Hovnanian entities are the developers on most of the plats, and Rockwell Florida LLC is the developer on the Phase 3 plat; realtor sites name Rockwell Homes as the Phase 3 builder. Single-family homes range from about 1,950 to 4,180 square feet and townhomes from about 1,870 to 2,200 square feet.

Over the past two years (MLS data, October 2026), single-family homes in Winding Bay sold 27 times for a median of about $792,000, ranging from about $520,000 to $1.1 million, with most between about $540,000 and $960,000. Townhomes in the Winding Bay Preserve section sold five times for a median of about $390,000, ranging from about $370,000 to $430,000. For today's listings, see the top of this page.

Recent MLS listings show HOA dues of about $101 to $102 per month for single-family homes and about $338 to $339 per month for townhomes as of October 2026. One real estate site mentions a CDD, but Orange County property records and Florida's official list of special districts don't show a community development district covering Winding Bay, so check the property tax bill for any special assessments. The association is Winding Bay Preserve Homeowners Association, Inc.

Orange County Public Schools' 2026-27 school zones place Winding Bay in Water Spring Elementary, Water Spring Middle and Horizon High School.

Zoning can change and varies by street, so confirm a specific address with Orange County Public Schools' Find My School tool, and compare school grades in the Florida School Accountability Reports.

Winding Bay Preserve is the name on the entrance sign and on the homeowners association, Winding Bay Preserve Homeowners Association, Inc. On Orange County plat records, Winding Bay Preserve is also the name of one section: 88 townhomes on a 2019 plat recorded by a K. Hovnanian entity. The other phases, which include all of the single-family homes and 28 more townhomes, are platted as Winding Bay. The association's management company describes Winding Bay Preserve as a collection of single-family homes and townhomes, so confirm which association covers a specific home.

No Winding Bay-specific rental rules turned up in our research. HOA documents often limit leasing, so confirm the current rules with the association before buying if you plan to rent.