Searching for Winding Trails in Wellington, Florida? This page brings together live homes for sale, community details, school zoning, lot sizes, amenities, and an interactive map.
Winding Trails is a boutique equestrian community in Wellington, Florida, located along Greenbriar Boulevard and Aero Club Drive. The community consists of 8 custom estate homesites on lots ranging from approximately 4.88 to 9.99 acres, each designed to accommodate barns, riding arenas, paddocks, and a primary estate residence in true hacking distance to Wellington International.
Winding Trails Homes for Sale in Wellington Florida
Today's Winding Trails homes for sale update throughout the day. Listings in this community include vacant estate lots, custom barn residences, and turnkey equestrian compounds on large acreage parcels with canal and lake frontage.
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About Winding Trails
| Type | Equestrian community with mandatory POA |
|---|---|
| Homesites | 8 custom estate lots |
| Lot Sizes | Approximately 4.88 to 9.99 acres |
| Location | Greenbriar Boulevard near Aero Club Drive, Wellington FL 33414 |
| Schools | Binks Forest Elementary, Wellington Landings Middle, Wellington High School |
Winding Trails is one of Wellington's most exclusive equestrian enclaves, developed as a boutique alternative to larger subdivisions like Palm Beach Point and Grand Prix Village. Consisting of just 8 homesites on large acreage parcels along Greenbriar Boulevard, the community offers canal frontage, bridle path access, and build-ready acreage with an unmatched position relative to the showgrounds.
Lot sizes range from just under 5 acres to just under 10 acres, with lots 5 and 6 combined into a single nearly 10-acre parcel under one owner. Every homesite is sized and zoned for the full range of equestrian infrastructure, including custom barns, dressage or jumping arenas, multiple paddocks, staff quarters, and a primary estate residence, making Winding Trails a community built for the serious equestrian rather than the casual horse owner.
Winding Trails Amenities and Lifestyle
Winding Trails is centered around private equestrian living on large acreage lots rather than shared community amenities. The value here is in the land, the proximity to the showgrounds, and the freedom to build a fully custom equestrian compound with no cookie-cutter floor plans or builder restrictions.
Community Features
- Canal and lake frontage on select lots
- True hacking distance to Wellington International showgrounds
- Private bridle trail connectivity
- Equestrian zoning supporting barns, arenas, paddocks, and staff quarters
- Public water and sewer connections available
Equestrian Infrastructure
Completed properties in Winding Trails have been built out with the full range of high-end equestrian amenities. Existing barn residences in the community have included 10-stall center-aisle barns, dressage arenas, multiple paddocks, groom and staff apartments, tack and feed rooms, wash racks, fly spray systems, and office and lounge areas. Vacant lots are positioned to accommodate similar builds, with most already cleared, filled, and connected to utilities.
Schools and Zoning
Winding Trails is typically zoned for Binks Forest Elementary Homes for Sale, Wellington Landings Middle Homes for Sale, and Wellington High School Homes for Sale. School boundaries can change over time, so buyers should confirm current assignments with the School District of Palm Beach County during the home search process.
Winding Trails Recent Home Sales and Market Snapshot (Updated Daily)
Below are the latest closed sales in Winding Trails, including final sale price, price per square foot, and days on market, pulled directly from BeachesMLS.
For a broader view of local trends, explore my Wellington market reports. Thinking about selling? Request a community-specific analysis on the What Is My Home Worth page.
This Winding Trails community guide was written and is maintained by Michelle Gibson, a Wellington Realtor since 2001.
Frequently Asked Questions About Winding Trails, Wellington
- Is Winding Trails a gated community?
No. Winding Trails is a non-gated equestrian community in Wellington, Florida. - Is there an HOA in Winding Trails?
Winding Trails has a mandatory Property Owners Association (POA). Fees vary by lot and development stage. Known POA services include manure removal and maintenance of private roads. - How many homes are in Winding Trails?
Winding Trails consists of 8 custom estate homesites. Lots 5 and 6 were combined into a single parcel under one owner, making that holding nearly 10 acres. - What are the lot sizes in Winding Trails?
Lots range from approximately 4.88 to 9.99 acres. All lots have been sold, though they occasionally return to market as resales. - Can properties in Winding Trails accommodate horses?
Yes. Every homesite is zoned and sized for full equestrian use including barns, arenas, paddocks, and staff quarters. The community is in true hacking distance to Wellington International. - Which schools serve Winding Trails?
Winding Trails is typically zoned for Binks Forest Elementary, Wellington Landings Middle, and Wellington High School. Buyers should confirm current zoning with the School District of Palm Beach County. - How has the Winding Trails real estate market performed?
Appreciation has been significant. Lots that sold in 2022 for around $650,000 were relisted in 2025 for over $2 million, reflecting the broader surge in Wellington equestrian land values near the showgrounds.
Wellington Communities Similar to Winding Trails
If you are comparing small private equestrian communities in Wellington with large acreage lots and proximity to the showgrounds, these neighborhoods are often considered alongside Winding Trails.
- Paddock Park 2 homes for sale - Non-HOA equestrian community with approximately 172 custom estate homes on lots typically ranging from 2 to 4+ acres along Wellington Trace.
- Paddock Park homes for sale - Non-HOA community with large equestrian lots and a similar estate setting near the showgrounds.
- Saddle Trail Park homes for sale - Equestrian community with acreage properties, barns, and direct or nearby access to Wellington International.
- Aero Club homes for sale - Non-HOA community with unique estate properties on larger lots directly adjacent to Winding Trails.
- Meadow Wood homes for sale - Non-HOA community with spacious homes on larger lots offering privacy and a more rural feel.
Explore Winding Trails and the Surrounding Area
Interactive map centered on Winding Trails in Wellington, FL. Zoom and click around to explore nearby equestrian venues, schools, shopping, and the Wellington International showgrounds.
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