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Town Hall Chestertown NYPhoto: Novis-M · Public domain
Housing in Chester

43 homes sold in Chester in the last year, at a typical $416K

Redfin reports Chester’s sales by ZIP code, so these figures are for ZIP 12817, which takes in Chester and the area around it. 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 Chester homes are listed.

Homes sold
43
ZIP 12817 · October 2025 to September 2026
Typical sale price
$416K
median, weighted by sales
Price per square foot
$279
New York $398
Paid vs. asking
96.9%
19% sold over asking
For sale now
29
September 2026 · 3 sold that month
What sold · last 12 months · ZIP 12817

Houses are 72% of Chester’s sales, at a typical $402K (year to May 2026)

43 homes sold in the year to September 2026.

Houses$402K

typical sale · 35 sold in the year to May 2026

Per square foot
$302NY $316
Days to sell
51
Sold over asking
21%
Fewer sales

Condos: 7 sold, typical $178K

Too few sales in 12 months for reliable figures.

14 years of sales

About as many homes sell as usual, at 2.2 times the 2016 price

43 sales in the last year, against 62 in 2020 and a low of 24 in 2012. The typical sale went from $187K in 2016 to $416K.

Homes soldTypical sale price
0255075100$200K$300K$400K$500K2012: 24 sold, typical $176K’122013: 28 sold, typical $206K2014: 33 sold, typical $231K’142015: 34 sold, typical $201K2016: 50 sold, typical $187K’162017: 56 sold, typical $177K2018: 45 sold, typical $228K’182019: 33 sold, typical $160K2020: 62 sold, typical $261K’202021: 58 sold, typical $262K2022: 36 sold, typical $301K’222023: 27 sold, typical $345K2024: 35 sold, typical $343K’242025: 42 sold, typical $288KLast 12 months: 43 sold, typical $416KNow

Source: Redfin Data Center, MLS sales; for ZIP 12817, which takes in Chester and the area around it (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 your budget buys

What $400K buys in Chester

Houseat $302 a sq ft, year to May 2026
The same money in New Yorkat $316 a sq ft, year to May 2026

Is this asking price fair?

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.

What the sales history says · 14 years of sales

Bidding wars in Chester are more common than before the pandemic, but two thirds fewer homes come up for sale

We read every month of home sales in ZIP 12817 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, 43 sales.

If you’re buying in Chester

  • Shop in May. It brings about 7 new listings a month, close to the busiest month, with fewer bidding wars (14% over asking).
  • Offer under asking. Buyers paid 96.9% of the list price on average; 19% paid over.
  • You’ll usually have time. Only 41% of homes go under contract within two weeks; the typical one takes 46 days.
Best time to buy

Summer brings both the most homes and the most bidding wars

July has the most new listings (about 9 a month), and the most competition: 22% close over asking. May offers nearly as much choice with fewer homes bid up (14%). April has the least competition (9%) but only about 4 new listings.

New listings a monthShare sold over asking
02.557.51013%27%40%Sweet spotJan: 2 new listings a month, 13% sold over asking, 178 days to sellJFeb: 2 new listings a month, 13% sold over asking, 160 days to sellFMar: 3 new listings a month, 11% sold over asking, 184 days to sellMApr: 4 new listings a month, 9% sold over asking, 182 days to sellAMay: 7 new listings a month, 14% sold over asking, 228 days to sellMJun: 8 new listings a month, 20% sold over asking, 186 days to sellJJul: 9 new listings a month, 22% sold over asking, 166 days to sellJAug: 8 new listings a month, 19% sold over asking, 134 days to sellASep: 7 new listings a month, 19% sold over asking, 142 days to sellSOct: 5 new listings a month, 16% sold over asking, 139 days to sellONov: 4 new listings a month, 16% sold over asking, 141 days to sellNDec: 2 new listings a month, 14% sold over asking, 122 days to sellD

Averages for each calendar month, 2015 on.

How competitive is it now?

Nearly as heated as 2021, and calmer than New York

Chester now2017–192021 peakNY now
Sold over askingShare of sales that closed above the list price19%9%22%39%
Gone within two weeksShare of homes under contract within 14 days41%1%9%25%
Price paid vs. askingAverage sale price ÷ list price96.9%93.4%96.4%100.5%
Days to sellMedian days from listing to contract4619910243
Supply

15 homes for sale on a typical day

That’s 1.6 times the 2022 low (9), 64% fewer than in 2017–19 and well under 2014’s 67.

2012: 55 for sale’122013: 55 for sale2014: 67 for sale2015: 64 for sale’152016: 52 for sale2017: 46 for sale2018: 44 for sale’182019: 37 for sale2020: 32 for sale2021: 14 for sale’212022: 9 for sale2023: 12 for sale2024: 10 for sale’242025: 12 for saleLast 12 months: 15 for saleNow
Prices by type

Houses and condos, year by year

A house typically sold for $402K in the year to May 2026 (35 sales), a condo for $178K (8).

$125K$250K$375K$500K2013201520172019202120232025NowHouses 2013: $209K, 27 salesHouses 2014: $250K, 31 salesHouses 2015: $214K, 31 salesHouses 2016: $224K, 42 salesHouses 2017: $201K, 46 salesHouses 2018: $242K, 38 salesHouses 2019: $192K, 26 salesHouses 2020: $285K, 53 salesHouses 2021: $295K, 51 salesHouses 2022: $322K, 31 salesHouses 2023: $349K, 23 salesHouses 2024: $382K, 26 salesHouses 2025: $346K, 29 salesHouses last 12 months: $402K, 35 salesHouses $402KCondos 2017: $75K, 5 salesCondos 2021: $115K, 5 salesCondos 2024: $235K, 4 salesCondos 2025: $172K, 7 salesCondos last 12 months: $178K, 8 salesCondos $178K

Median sale price, weighted by sales each month. Years with fewer than 4 sales of a type are left out.

Source: Redfin Data Center, ZIP code tracker; for ZIP 12817, which takes in Chester and the area around it (each month is a 3-month rolling window, its counts divided by 3), January 2012 to September 2026 (MLS sales, not seasonally adjusted). Ratios are weighted by homes sold; price cuts by homes for sale.

Rent or buy?

Owning the typical Chester home costs about $2,501 a month

Mortgage
Property tax
Insurance
Rent

Price: Chester’s typical sale, last 12 months. Property tax at Chester’s 1% (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.

Before you buy in Chester

Six things worth knowing

9

New listings in July

The month with the most choice. February has the fewest, about 2.

Best time to buy
1%

Property tax, a year

Of a home’s value: the median bill over the median home value. On a $416K home, about $3,970 a year.

Taxes vs. neighbors
C

Schools

The schools grade for Chester, from test results, graduation and how much students grow.

Schools in Chester
24 min

Typical commute

The average one-way trip to work for people who live in Chester.

Work & commute
Flood

Check 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 hazards
Records

Look 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.

Nearby markets · last 12 months

Warrensburg, Ticonderoga and Whitehall sell 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.

SoldTypical sale$/sq ftOver askingDays to sell
Chester (ZIP 12817)43$416K$27919%46
Schroon39$427K$31331%50
Ticonderoga36$194K$14221%81
Whitehall28$140K$8521%70
Warrensburg24$240K$15047%24

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.

Selling, or renting out?

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?

43 homes sold in the year to September 2026 at a typical $416K, $279 a square foot.

Is Chester a buyer’s or seller’s market?

A buyer’s market: 29 homes were for sale in September 2026 and 3 sold, about 8.8 months of supply. Buyers paid 96.9% of asking on average.

When is the best time to buy in Chester?

July brings the most new listings. The sales history shows which months have fewer bidding wars.

How much are property taxes in Chester?

About 1% of a home’s value a year. On a $416K home that’s near $3,970.

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; for ZIP 12817, which takes in Chester and the area around it (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).