Photo: John Phelan · CC BY 3.022 homes sold in Chester in the last year, at a typical $508K
Almost every sale is a house. Below: what each kind of home sells for, what your budget buys, 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 91% of Chester’s sales, at a typical $516K
22 homes sold in the year to May 2026.
typical sale · 20 sold in 12 months
- Per square foot
- $221MA $368
- Days to sell
- 63
- Sold over asking
- 40%
- Listings with a price cut
- 21%
Multi-family (2–4 units): 1 sold, typical $233K
Condos: 1 sold, typical $550K
Too few sales in 12 months for reliable figures.
Fewer homes sell than a decade ago, at 2.2 times the 2016 price
22 sales in the last year, against 34 in 2019 and a low of 18 in 2024. The typical sale went from $231K in 2016 to $508K.
Source: Redfin Data Center, MLS sales. Typical price and $/sq ft are the monthly medians, weighted by sales.
What $500K 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.
Owning the typical Chester home costs about $3,330 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.
Five things worth knowing
Property tax, a year
Of a home’s value: the median bill over the median home value. On a $508K home, about $8,140 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.
Holyoke sells for less a square foot; Becket, Easthampton and Northampton 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 | |
|---|---|---|---|---|---|
| Westfield | 309 | $376K | $226 | 58% | 24 |
| Northampton | 256 | $500K | $330 | 51% | 28 |
| Holyoke | 239 | $325K | $186 | 54% | 29 |
| Easthampton | 138 | $461K | $289 | 56% | 27 |
| Southwick | 28 | $474K | $254 | 50% | 39 |
| Becket | 27 | $429K | $273 | 19% | 102 |
| Chester | 22 | $508K | $216 | 41% | 62 |
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 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, MA?
22 homes sold in the year to May 2026 at a typical $508K, $216 a square foot.
Is Chester a buyer’s or seller’s market?
A balanced market: 5 homes were for sale in May 2026 and 1 sold, about 5 months of supply. Buyers paid 102.6% of asking on average, and 20% of listings cut their price.
How much are property taxes in Chester?
About 1.6% of a home’s value a year. On a $508K home that’s near $8,140.
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). 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).