Winding Trails Wellington FL Homes for Sale & Real Estate

Browse Winding Trails homes for sale in Wellington, Florida, with live MLS listings, neighborhood details, school zoning, HOA information, amenities, photos, and an interactive map all on one page.

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.

1 / 8

$1,600,000

PALM BEACH

COUNTY

2970 Greenbriar Boulevard Wellington, FL 33414

Unimproved Land For Sale

- Active

Prime location! 5 acre lot, that is located a short hacking distance to WEF/Wellington International showgrounds. The lot is already cleared, filled and ready to build a custom barn/estate home with the builder of your choice. Completed survey and bu

1 / 7

$2,400,000

4.96

ACRES

PALM BEACH

COUNTY

2500 Aero Club Drive Wellington, FL 33414

Unimproved Land For Sale

- Active

Nearly five acres. Prime Wellington location. Unmatched equestrian zoning. This final homesite in Winding Trails offers an exceptional opportunity to build a high-value estate in a supply-constrained market. With expansive canal frontage, approved eq

1 / 9

$2,500,000

5

ACRES

PALM BEACH

COUNTY

3102 Greenbriar Boulevard Wellington, FL 33414

Agriculture For Sale

- Active

Exceptional value, extraordinary location! This beautifully cleared 5 acre lot is abounding with potential for both avid and novice equestrians alike to build their dream estate. It represents one of the only remaining available properties located in

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About Winding Trails

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 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.

1 / 1

$1,200,000

5

ACRES

PALM BEACH

COUNTY

2970 Greenbriar Boulevard Wellington, FL 33414

Unimproved Land Sold

- Sold

Location, Location!!! 5 acre lot within short hacking distance to the WEF (now Wellington International) Showgrounds. Build your custom barn, an estate home or build both. Use any builder of your choice. Cleared and filled, public water, bridle path

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For a broader view of local trends, explore my Wellington market reports. Thinking about selling? Request a community-specific analysis on the Winding Trails home value 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 School, Wellington Landings Middle School, 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
• Paddock Park homes for sale
• Saddle Trail Park homes for sale
• Aero Club homes for sale
• Meadow Wood homes for sale

Last updated June 14, 2026