48 homes sold in Winding Cypress in the last year, at a typical $750K
Almost every sale is a house. Below: what each kind of home sells for, what your budget buys, the best months to buy, how hard you’ll have to bid, and a shortcut to every site where Winding Cypress homes are listed.
Every place Winding Cypress homes are listed, in one stop
We don’t copy listings: the agents’ sites have the photos and the latest price changes. Set what you want once and we open each site already filtered to Winding Cypress.
For sale
Rent
New, land & open houses
Links open the listing sites; TownRatings isn’t paid for them and doesn’t rank one above another. Rentals and government-owned homes come from sources outside the MLS.
Houses are 100% of Winding Cypress’ sales, at a typical $750K
48 homes sold in the year to May 2026.
typical sale · 48 sold in 12 months
- Per square foot
- $395FL $245
- Days to sell
- 126
- Sold over asking
- 4%
- Listings with a price cut
- 31%
More homes sell than most years, at 1.8 times the 2016 price
48 sales in the last year, against 59 in 2021 and a low of 21 in 2016. The typical sale went from $422K in 2016 to $750K.
Source: Redfin Data Center, MLS sales. Typical price and $/sq ft are the monthly medians, weighted by sales.
What $750K buys in Winding Cypress
Check a listing against what Winding Cypress homes sold for
Against the town’s median price per square foot over the last 12 months. A rough check: condition, lot and location within town move a price more than this can see.
Bidding wars in Winding Cypress are rarer than before the pandemic, and more homes are for sale
We read every month of Winding Cypress’ home sales since 2016 so you don’t have to. Each figure covers 12 months, because a single month in a town is too few sales to mean much. Latest: the year to May 2026, 48 sales.
If you’re buying in Winding Cypress
- Shop in February. It brings about 5 new listings a month, close to the busiest month, with fewer bidding wars (0% over asking).
- You can negotiate. 31% of listings have cut their price, against 22% before the pandemic.
- Offer under asking. Buyers paid 94.4% of the list price on average; 4% paid over.
- You’ll usually have time. Only 13% of homes go under contract within two weeks; the typical one takes 126 days.
Winter brings the homes; spring brings the bidding wars
January has the most new listings (about 6 a month), but May is the most competitive: 25% of May sales close over asking. February has the least competition (0%).
Averages for each calendar month, 2015 on.
Calmer than the 2021 frenzy, and calmer than Florida
| Winding Cypress now | 2017–19 | 2021 peak | FL now | |
|---|---|---|---|---|
| Sold over askingShare of sales that closed above the list price | 4% | 11% | 24% | 10% |
| Gone within two weeksShare of homes under contract within 14 days | 13% | 10% | 43% | 20% |
| Listings with a price cutShare of homes for sale that cut their price | 31% | 22% | 24% | 28% |
| Price paid vs. askingAverage sale price ÷ list price | 94.4% | 97.9% | 98.8% | 96.3% |
| Days to sellMedian days from listing to contract | 126 | 107 | 33 | 76 |
18 homes for sale on a typical day
That’s 3.8 times the 2022 low (5), 43% more than in 2017–19 and well under 2024’s 23.
1 in 3 listings has cut its price
31% in the last year, against 22% in 2017–19 and 28% across Florida. More sellers are pricing high and coming down.
Source: Redfin Data Center, city market tracker, January 2016 to May 2026 (MLS sales, not seasonally adjusted). Ratios are weighted by homes sold; price cuts by homes for sale.
Owning the typical Winding Cypress home costs about $4,327 a month
Price: Winding Cypress’ typical sale, last 12 months. Property tax at Winding Cypress’ 0.7% (median bill ÷ median value, Census ACS); insurance at 0.35% of price a year. Before PMI, HOA dues, upkeep and the tax deduction. Whether Winding Cypress is affordable on local pay is on Cost of living.
Six things worth knowing
New listings in January
The month with the most choice. August has the fewest, about 3.
Best time to buyProperty tax, a year
Of a home’s value: the median bill over the median home value. On a $750K home, about $4,970 a year.
Taxes vs. neighborsSchools
The schools grade for Winding Cypress, from test results, graduation and how much students grow.
Schools in Winding CypressTypical commute
The average one-way trip to work for people who live in Winding Cypress.
Work & commuteCheck the flood map
Flood insurance isn’t in a standard policy, and lenders require it in FEMA flood zones. Check the address before you make an offer.
Natural hazardsLook up any property
Assessed value, lot size and every past sale of a home you’re eyeing are public, at the town or county assessor and the registry of deeds.
Verona Walk, Lely Resort, Lely, Marco Shores-Hammock Bay, Berkshire Lakes and Golden Gate sell for less a square foot
The busier markets within 25 miles of Winding Cypress, by what sold. Prices, taxes and how far a paycheck goes next door are on Cost of living.
| Sold | Typical sale | $/sq ft | Over asking | Days to sell | |
|---|---|---|---|---|---|
| Lely Resort | 238 | $655K | $328 | 2% | 90 |
| Golden Gate | 152 | $453K | $299 | 11% | 42 |
| Verona Walk | 111 | $527K | $302 | 3% | 90 |
| Lely | 102 | $310K | $228 | 2% | 107 |
| Berkshire Lakes | 81 | $358K | $242 | 7% | 65 |
| Winding Cypress | 48 | $750K | $395 | 4% | 126 |
| Marco Shores-Hammock Bay | 47 | $363K | $263 | 2% | 108 |
Redfin Data Center, June 2025 to May 2026. Towns with fewer than 20 sales are left out, and Redfin doesn’t report every town separately.
Post your home to Winding Cypress, free
Selling it yourself, renting out an apartment or looking for a roommate? Post it to Winding Cypress. People who follow the town see it, and so do people comparing Winding Cypress with their own town. No commission, no listing fee.
Questions about buying a home in Winding Cypress
What do homes sell for in Winding Cypress, FL?
48 homes sold in the year to May 2026 at a typical $750K, $395 a square foot.
Is Winding Cypress a buyer’s or seller’s market?
A seller’s market: 9 homes were for sale in May 2026 and 6 sold, about 1.5 months of supply. Buyers paid 94.4% of asking on average, and 31% of listings cut their price.
When is the best time to buy in Winding Cypress?
January brings the most new listings. The sales history shows which months have fewer bidding wars.
How much are property taxes in Winding Cypress?
About 0.7% of a home’s value a year. On a $750K home that’s near $4,970.
Where can I see homes for sale in Winding Cypress?
Zillow, Redfin, Realtor.com and Homes.com all carry Winding Cypress’ MLS listings; the search links above open each one filtered to Winding Cypress.
Sales, prices, days on market and listings: Redfin Data Center (MLS, monthly, not seasonally adjusted). Property tax rate: Census American Community Survey. Two-bedroom rent: HUD Fair Market Rent. Typical home value: Zillow Home Value Index. Schools grade: TownRatings (how grades work).