Winston Park Homes for Sale

Winston Park is a residential community in Key Largo, Florida. Active listings are currently priced from $285K–$620K.

Pure Equity Realty covers Winston Park and the Key Largo 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 3 Winston Park Key Largo homes for sale as of October 2026. The median asking price is $640,000. Asking prices run from $285,000 to $680,000.

That is 25% below the Key Largo median of $859,000. On a per-foot basis, homes here ask about $407 per square foot, compared with $672 across Key Largo. So the median price buys roughly 1,550 square feet of living area.

Listings here have averaged 69 days on the market. That is faster than the Key Largo average of 171 days. As a result, buyers here should be ready to write an offer soon after a showing.

Homes listed in Winston Park date from 1963 to 2026. That puts them between 0 and 63 years old.

The range straddles 2002, when Florida adopted its statewide building code. Therefore two similar-looking homes here can carry very different insurance premiums. Ask for the wind mitigation report on any home you consider, since it drives much of that difference.

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.

Here is what the median Winston Park price means in Florida closing terms. At $640,000, a 20% down payment comes to about $128,000, leaving a loan near $512,000.

Florida then taxes that loan twice. First, documentary stamp tax on the note runs 35 cents per $100, or about $1,792. Next, the intangible tax of 0.2% adds about $1,024. Buyers normally pay both at closing.

On the seller side, Florida deed stamps cost 70 cents per $100 of price. At the Winston Park median, that is about $4,480.

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 Park listings show assignments to Key Largo (elementary), Key Largo (middle) and Coral Shores (high). However, boundaries can change each year, so confirm the assignment for a specific address with the county school district.