Mary's River Covered Bridge · Photo: Nyttend · Public domain44 homes sold in Chester in the last year, at a typical $139K
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 Chester homes are listed.
Every place Chester 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 Chester.
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 Chester’s sales, at a typical — (year to May 2026)
44 homes sold in the year to September 2026.
More homes sell than most years, at twice the 2016 price
44 sales in the last year, against 50 in 2021 and a low of 9 in 2012. The typical sale went from $68K in 2016 to $139K.
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 Chester are more common than before the pandemic, with about as many homes for sale
We read every month of Chester’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 September 2026, 44 sales.
If you’re buying in Chester
- Shop in October. It brings about 4 new listings a month, close to the busiest month, with fewer bidding wars (5% over asking).
- Offer under asking. Buyers paid 94.7% of the list price on average; 8% paid over.
- You’ll usually have time. Only 40% of homes go under contract within two weeks; the typical one takes 71 days.
Fall brings the homes; summer brings the bidding wars
November has the most new listings (about 4 a month), but July is the most competitive: 11% of July sales close over asking. September and October offer nearly as much choice with fewer homes bid up (9%). October has the least competition (5%).
Averages for each calendar month, 2015 on.
Nearly as heated as 2021, and calmer than Illinois
| Chester now | 2017–19 | 2021 peak | IL now | |
|---|---|---|---|---|
| Sold over askingShare of sales that closed above the list price | 8% | 2% | 7% | 36% |
| Gone within two weeksShare of homes under contract within 14 days | 40% | 17% | 13% | 45% |
| Price paid vs. askingAverage sale price ÷ list price | 94.7% | 90.9% | 92.7% | 99% |
| Days to sellMedian days from listing to contract | 71 | 103 | 173 | 51 |
16 homes for sale on a typical day
That’s 1.5 times the 2022 low (11), about the 2017–19 level and well under 2020’s 26.
Source: Redfin Data Center, city figures, January 2012 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 Chester home costs about $913 a month
Price: Chester’s typical sale, last 12 months. Property tax at Chester’s 1.6% (median bill ÷ median value, Census ACS); insurance at 0.35% of price a year. Before PMI, HOA dues, upkeep and the tax deduction. Whether Chester is affordable on local pay is on Cost of living.
Six things worth knowing
New listings in November
The month with the most choice. February has the fewest, about 2.
Best time to buyProperty tax, a year
Of a home’s value: the median bill over the median home value. On a $139K home, about $2,260 a year.
Taxes vs. neighborsSchools
The schools grade for Chester, from test results, graduation and how much students grow.
Schools in ChesterCheck 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.
Sparta sells for less a square foot; Ste. Genevieve, Perryville and Red Bud for far more
The busier markets within 25 miles of Chester, 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 | |
|---|---|---|---|---|---|
| Perryville | 95 | $200K | $140 | 30% | 34 |
| Ste. Genevieve | 61 | $206K | $129 | 23% | 71 |
| Chester | 44 | $139K | $85 | 8% | 71 |
| Sparta | 43 | $125K | $80 | 8% | 94 |
| Red Bud | 38 | $209K | $134 | 30% | 41 |
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 Chester, free
Selling it yourself, renting out an apartment or looking for a roommate? Post it to Chester. People who follow the town see it, and so do people comparing Chester with their own town. No commission, no listing fee.
Questions about buying a home in Chester
What do homes sell for in Chester, IL?
44 homes sold in the year to September 2026 at a typical $139K, $85 a square foot.
Is Chester a buyer’s or seller’s market?
A buyer’s market: 16 homes were for sale in September 2026 and 2 sold, about 7 months of supply. Buyers paid 94.7% of asking on average.
When is the best time to buy in Chester?
November brings the most new listings. The sales history shows which months have fewer bidding wars.
How much are property taxes in Chester?
About 1.6% of a home’s value a year. On a $139K home that’s near $2,260.
Where can I see homes for sale in Chester?
Zillow, Redfin, Realtor.com and Homes.com all carry Chester’s MLS listings; the search links above open each one filtered to Chester.
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).