Winston Waterways Homes for Sale

Winston Waterways is a residential community in Key Largo, Florida.

Pure Equity Realty covers Winston Waterways 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 a single listing for Winston Waterways Key Largo homes for sale as of October 2026. The median asking price is $2.35M.

That is 174% above the Key Largo median of $859,000. On a per-foot basis, homes here ask about $729 per square foot, compared with $672 across Key Largo. So the median price buys roughly 3,200 square feet of living area. With so few listings, though, treat these figures as a snapshot rather than a trend.

Listings here have averaged 28 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 Waterways date from 2016, so they are about 10 years old.

Every one of these homes went up after Florida adopted its statewide building code in 2002. In practice, that usually means impact-rated openings and stronger roof attachment. A wind mitigation inspection documents those features, and Florida insurers must offer premium discounts for them.

Here is what the median Winston Waterways price means in Florida closing terms. At $2.35M, a 20% down payment comes to about $470,000, leaving a loan near $1.88M.

Florida then taxes that loan twice. First, documentary stamp tax on the note runs 35 cents per $100, or about $6,580. Next, the intangible tax of 0.2% adds about $3,760. Buyers normally pay both at closing.

On the seller side, Florida deed stamps cost 70 cents per $100 of price. At the Winston Waterways median, that is about $16,450.

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.