Winston Trails Homes for Sale

Winston Trails is a gated, waterfront community in Lake Worth, Palm Beach County, Florida. Active listings are priced from $649,900 to $689,000. Homes were built between 1995 and 2001. Pure Equity lists homes in Winston Trails and represents buyers. Commission is negotiable, and what we are paid is agreed with you in writing before you commit to anything.

Pure Equity Realty covers Winston Trails and the Lake Worth area. We list for 1%, which includes photography, MLS syndication, and negotiation support. Buyers pay nothing for representation. For current market data, see Florida Realtors' market statistics.

Our MLS feed shows 11 Winston Trails Lake Worth homes for sale as of October 2026. The median asking price is $635,000. Asking prices run from $450,000 to $880,000.

That is 51% above the Lake Worth median of $420,000. On a per-foot basis, homes here ask about $306 per square foot, compared with $250 across Lake Worth. So the median price buys roughly 2,050 square feet of living area.

Listings here have averaged 25 days on the market. That is faster than the Lake Worth average of 103 days. As a result, buyers here should be ready to write an offer soon after a showing.

Homes listed in Winston Trails date from 1995 to 2001. That puts them between 25 and 31 years old.

All of these homes predate Florida's 2002 statewide building code. So roof age, window protection and the wind mitigation report matter a great deal for insurance.

In addition, most Florida insurers ask for a four-point inspection on homes 30 years or older. It covers the roof, electrical, plumbing and HVAC. Updated systems usually make coverage easier to place.

Winston Trails is a gated community. Therefore, expect to register visitors and contractors with the gate before each visit.

Winston Trails includes waterfront homes. Waterfront lots in South Florida often sit in FEMA special flood hazard areas, where lenders require flood insurance. Before you commit, look up the address on the FEMA Flood Map Service Center and ask the seller for an elevation certificate.

Rentals in Winston Trails have a median asking rent of $3,500 per month, across 1 active rental listing. For comparison, the Lake Worth median is $2,405, so rents here run 46% higher.

You can browse current Lake Worth rentals or ask us for a rent estimate on a specific Winston Trails home.

Here is what the median Winston Trails price means in Florida closing terms. At $635,000, a 20% down payment comes to about $127,000, leaving a loan near $508,000.

Florida then taxes that loan twice. First, documentary stamp tax on the note runs 35 cents per $100, or about $1,778. Next, the intangible tax of 0.2% adds about $1,016. Buyers normally pay both at closing.

On the seller side, Florida deed stamps cost 70 cents per $100 of price. At the Winston Trails median, that is about $4,444.

Finally, owner-occupants should file for the Florida homestead exemption by March 1. It removes up to $50,000 of assessed value. After that, Save Our Homes caps yearly assessment increases at 3% or inflation, whichever is lower. To see what these numbers mean for your budget, get pre-approved before you tour.

Recent Winston Trails listings show assignments to Manatee (Palm Beach) (elementary), Christa McAuliffe (middle) and Park Vista (high). However, boundaries can change each year, so confirm the assignment for a specific address with the School District of Palm Beach County.