Photo: Nyttend · Public domain70 homes sold in Winchester in the last year, at a typical $151K
Almost every sale is a house. Below: what each kind of home sells for, 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 0% of Winchester’s sales, at a typical — (year to May 2026)
70 homes sold in the year to September 2026.
About as many homes sell as usual, at 3.2 times the 2016 price
70 sales in the last year, against 100 in 2020 and a low of 6 in 2013. The typical sale went from $47K in 2016 to $151K.
Source: Redfin Data Center, MLS sales; from June 2026 each month is a 3-month rolling window, its counts divided by 3. Typical price and $/sq ft are the monthly medians, weighted by sales. Redfin stopped publishing towns’ figures by property type after May 2026, so houses and condos are shown for the year to then.
Bidding wars in Winchester are back to pre-pandemic levels, but half fewer homes come up for sale
We read every month of Winchester’s home sales since 2013 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 September 2026, 70 sales.
If you’re buying in Winchester
- Shop in March. It brings about 6 new listings a month, close to the busiest month, with fewer bidding wars (9% over asking).
- Offer under asking. Buyers paid 94.3% of the list price on average; 10% paid over.
- You’ll usually have time. Only 32% of homes go under contract within two weeks; the typical one takes 38 days.
Summer brings both the most homes and the most bidding wars
June has the most new listings (about 8 a month), and the most competition: 19% close over asking. March offers nearly as much choice with fewer homes bid up (9%). February has the least competition (8%).
Averages for each calendar month, 2015 on.
Nearly as heated as 2021, and calmer than Indiana
| Winchester now | 2017–19 | 2021 peak | IN now | |
|---|---|---|---|---|
| Sold over askingShare of sales that closed above the list price | 10% | 10% | 19% | 17% |
| Gone within two weeksShare of homes under contract within 14 days | 32% | 4% | 5% | 35% |
| Price paid vs. askingAverage sale price ÷ list price | 94.3% | 92.1% | 94.6% | 97.5% |
| Days to sellMedian days from listing to contract | 38 | 89 | 63 | 38 |
16 homes for sale on a typical day
That’s twice the 2024 low (8), 50% fewer than in 2017–19 and well under 2015’s 41.
Winchester ranks 136th of 146 busy Indiana markets for bidding wars
Share of sales over asking in the last year, among towns with 60 or more sales. Winchester is one of the state’s calmer markets.
Source: Redfin Data Center, city figures, January 2013 to September 2026 (MLS sales, not seasonally adjusted; from June 2026 each month is a 3-month rolling window, its counts divided by 3). Ratios are weighted by homes sold; price cuts by homes for sale.
Owning the typical Winchester home costs about $902 a month
Price: Winchester’s typical sale, last 12 months. Property tax at Winchester’s 0.9% (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 June
The month with the most choice. January has the fewest, about 4.
Best time to buyProperty tax, a year
Of a home’s value: the median bill over the median home value. On a $151K home, about $1,370 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.
Union City, Union City, Portland and Dunkirk 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 | |
|---|---|---|---|---|---|
| Greenville | 169 | $182K | $118 | 12% | 49 |
| Winchester | 70 | $151K | $101 | 10% | 38 |
| Portland | 51 | $145K | $94 | 18% | 18 |
| Union City | 43 | $137K | $94 | 22% | 22 |
| Dunkirk | 35 | $102K | $73 | 9% | 57 |
| Albany | 31 | $152K | $108 | 34% | 9 |
| Union City | 22 | $96K | $88 | 34% | 36 |
Redfin Data Center, October 2025 to September 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, IN?
70 homes sold in the year to September 2026 at a typical $151K, $101 a square foot.
Is Winchester a buyer’s or seller’s market?
A seller’s market: 18 homes were for sale in September 2026 and 6 sold, about 2.7 months of supply. Buyers paid 94.3% of asking on average.
When is the best time to buy in Winchester?
June brings the most new listings. The sales history shows which months have fewer bidding wars.
How much are property taxes in Winchester?
About 0.9% of a home’s value a year. On a $151K home that’s near $1,370.
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; from June 2026 each month is a 3-month rolling window, its counts divided by 3). 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).