Photo: Joshua Reed · Public domain222 homes sold in Winchester in the last year, at a typical $250K
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 Winchester homes are listed.
Every place Winchester 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 Winchester.
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 93% of Winchester’s sales, at a typical $254K
222 homes sold in the year to May 2026.
typical sale · 206 sold in 12 months
- Per square foot
- $162KY $162
- Days to sell
- 54
- Sold over asking
- 16%
- Listings with a price cut
- 26%
Multi-family (2–4 units): 3 sold, typical $298K
Townhouses: 13 sold, typical $189K
Too few sales in 12 months for reliable figures.
Fewer homes sell than before 2022, at 2.2 times the 2016 price
222 sales in the last year, against 341 in 2021 and a low of 168 in 2012. The typical sale went from $115K in 2016 to $250K.
Source: Redfin Data Center, MLS sales. Typical price and $/sq ft are the monthly medians, weighted by sales.
What $250K buys in Winchester
Check a listing against what Winchester 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 Winchester are back to pre-pandemic levels, with about as many homes for sale
We read every month of Winchester’s home sales since 2012 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, 222 sales.
If you’re buying in Winchester
- Shop in October. It brings about 28 new listings a month, close to the busiest month, with fewer bidding wars (13% over asking).
- You can negotiate. 26% of listings have cut their price, against 22% before the pandemic.
- Bid near asking. Buyers paid 98.1% of the list price on average; 15% paid over.
- You’ll usually have time. Only 39% of homes go under contract within two weeks; the typical one takes 51 days.
Summer brings the homes; spring brings the bidding wars
August has the most new listings (about 34 a month), but May is the most competitive: 23% of May sales close over asking. September and October offer nearly as much choice with fewer homes bid up (17%). January has the least competition (12%).
Averages for each calendar month, 2015 on.
Calmer than the 2021 frenzy, and about like Kentucky as a whole
| Winchester now | 2017–19 | 2021 peak | KY now | |
|---|---|---|---|---|
| Sold over askingShare of sales that closed above the list price | 15% | 15% | 26% | 18% |
| Gone within two weeksShare of homes under contract within 14 days | 39% | 36% | 51% | 36% |
| Listings with a price cutShare of homes for sale that cut their price | 26% | 22% | 24% | 27% |
| Price paid vs. askingAverage sale price ÷ list price | 98.1% | 96.1% | 98.1% | 97.4% |
| Days to sellMedian days from listing to contract | 51 | 39 | 22 | 50 |
67 homes for sale on a typical day
That’s 1.6 times the 2022 low (41), about the 2017–19 level and well under 2013’s 179.
1 in 4 listings has cut its price
26% in the last year, against 22% in 2017–19 and 27% across Kentucky.
Winchester ranks 51st of 77 busy Kentucky markets for bidding wars
Share of sales over asking in the last year, among towns with 60 or more sales. Winchester is in the middle of the pack.
Source: Redfin Data Center, city market tracker, January 2012 to May 2026 (MLS sales, not seasonally adjusted). Ratios are weighted by homes sold; price cuts by homes for sale.
Owning the typical Winchester home costs about $1,455 a month
Price: Winchester’s typical sale, last 12 months. Property tax at Winchester’s 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 Winchester is affordable on local pay is on Cost of living.
Six things worth knowing
New listings in August
The month with the most choice. February has the fewest, about 19.
Best time to buyProperty tax, a year
Of a home’s value: the median bill over the median home value. On a $250K home, about $1,810 a year.
Taxes vs. neighborsSchools
The schools grade for Winchester, from test results, graduation and how much students grow.
Schools in WinchesterTypical commute
The average one-way trip to work for people who live in Winchester.
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.
Mount Sterling, Paris and Irvine sell for less a square foot
The busier markets within 25 miles of Winchester, 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 | |
|---|---|---|---|---|---|
| Lexington | 3,806 | $346K | $191 | 18% | 41 |
| Nicholasville | 508 | $329K | $181 | 16% | 63 |
| Richmond | 484 | $304K | $167 | 16% | 59 |
| Winchester | 222 | $250K | $158 | 15% | 51 |
| Paris | 160 | $216K | $140 | 12% | 46 |
| Mount Sterling | 88 | $256K | $137 | 14% | 82 |
| Irvine | 25 | $169K | $106 | 24% | 131 |
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 Winchester, free
Selling it yourself, renting out an apartment or looking for a roommate? Post it to Winchester. People who follow the town see it, and so do people comparing Winchester with their own town. No commission, no listing fee.
Questions about buying a home in Winchester
What do homes sell for in Winchester, KY?
222 homes sold in the year to May 2026 at a typical $250K, $158 a square foot.
Is Winchester a buyer’s or seller’s market?
A seller’s market: 80 homes were for sale in May 2026 and 24 sold, about 3.3 months of supply. Buyers paid 98.1% of asking on average, and 26% of listings cut their price.
When is the best time to buy in Winchester?
August brings the most new listings. The sales history shows which months have fewer bidding wars.
How much are property taxes in Winchester?
About 0.7% of a home’s value a year. On a $250K home that’s near $1,810.
Where can I see homes for sale in Winchester?
Zillow, Redfin, Realtor.com and Homes.com all carry Winchester’s MLS listings; the search links above open each one filtered to Winchester.
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).