Photo: Daniel Case · CC BY-SA 3.039 homes sold in Chester in the last year, at a typical $401K
Houses and condos split the market almost evenly. 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 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.
Half of Chester’s sales are condos, at $212K less than a house
18 houses and 18 condos sold in the year to May 2026. Condos sell faster and draw more bidding wars.
typical sale · 18 sold in the year to May 2026
- Per square foot
- $254NY $316
- Days to sell
- 41
- Sold over asking
- 50%
- Listings with a price cut
- 30%
typical sale · 18 sold in the year to May 2026
- Per square foot
- $278NY $832
- Days to sell
- 38
- Sold over asking
- 67%
- Listings with a price cut
- 23%
Multi-family (2–4 units): 1 sold, typical $515K
Too few sales in 12 months for reliable figures.
Fewer homes sell than a decade ago, at 2.4 times the 2016 price
39 sales in the last year, against 76 in 2019 and a low of 37 in 2012. The typical sale went from $165K in 2016 to $401K.
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.
What $400K buys in Chester
Check a listing against what Chester 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 Chester are more common than before the pandemic, but a third fewer homes come up 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, 39 sales.
If you’re buying in Chester
- Shop in April. It brings about 7 new listings a month, close to the busiest month, with fewer bidding wars (33% over asking).
- Bid near asking. Buyers paid 101% of the list price on average; 47% paid over.
- You’ll usually have time. Only 4% of homes go under contract within two weeks; the typical one takes 39 days.
Summer brings the homes; spring brings the bidding wars
June has the most new listings (about 8 a month), but May is the most competitive: 44% of May sales close over asking. April offers nearly as much choice with fewer homes bid up (33%). January has the least competition (27%).
Averages for each calendar month, 2015 on.
Calmer than the 2021 frenzy, and hotter than New York
| Chester now | 2017–19 | 2021 peak | NY now | |
|---|---|---|---|---|
| Sold over askingShare of sales that closed above the list price | 47% | 16% | 62% | 39% |
| Gone within two weeksShare of homes under contract within 14 days | 4% | 5% | 3% | 25% |
| Price paid vs. askingAverage sale price ÷ list price | 101% | 97% | 101.3% | 100.5% |
| Days to sellMedian days from listing to contract | 39 | 58 | 45 | 43 |
13 homes for sale on a typical day
That’s 1.7 times the 2022 low (8), 32% fewer than in 2017–19 and well under 2012’s 40.
Since 2019, houses are up 97%, condos 81%
A house typically sold for $548K in the year to May 2026 (18 sales), a condo for $335K (18).
Median sale price, weighted by sales each month. Years with fewer than 4 sales of a type are left out.
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.
Five things worth knowing
New listings in June
The month with the most choice. December has the fewest, about 4.
Best time to buySchools
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.
Florida sells for less a square foot
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 | |
|---|---|---|---|---|---|
| Monroe | 117 | $531K | $288 | 31% | 52 |
| Warwick | 77 | $491K | $320 | 37% | 39 |
| Goshen | 62 | $563K | $275 | 39% | 52 |
| Chester | 39 | $401K | $269 | 47% | 39 |
| Walton Park | 39 | $467K | $288 | 33% | 60 |
| Florida | 27 | $278K | $174 | 29% | 46 |
| South Blooming Grove | 21 | $530K | $309 | 5% | 71 |
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, NY?
39 homes sold in the year to September 2026 at a typical $401K, $269 a square foot. Houses sold for about $548K, condos for about $335K in the year to May 2026.
Is Chester a buyer’s or seller’s market?
A balanced market: 18 homes were for sale in September 2026 and 3 sold, about 4.9 months of supply. Buyers paid 101% of asking on average.
When is the best time to buy in Chester?
June brings the most new listings. The sales history shows which months have fewer bidding wars.
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).