155 homes sold in Chester in the last year, at a typical $535K
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.
A quarter of Chester’s sales are condos, at $125K less than a house
89 houses and 34 condos sold in the year to May 2026. Houses sell faster and draw more bidding wars.
typical sale · 89 sold in 12 months
- Per square foot
- $278MD $239
- Days to sell
- 78
- Sold over asking
- 17%
- Listings with a price cut
- 33%
typical sale · 34 sold in 12 months
- Per square foot
- $289MD $234
- Days to sell
- 92
- Sold over asking
- 3%
- Listings with a price cut
- 23%
Townhouses: 32 sold, typical $391K
Too few sales in 12 months for reliable figures.
About as many homes sell as usual, at twice the 2016 price
155 sales in the last year, against 198 in 2021 and a low of 79 in 2012. The typical sale went from $268K in 2016 to $535K.
Source: Redfin Data Center, MLS sales. Typical price and $/sq ft are the monthly medians, weighted by sales.
What $550K 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 back to pre-pandemic levels, 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 May 2026, 155 sales.
If you’re buying in Chester
- Shop in April. It brings about 21 new listings a month, close to the busiest month, with fewer bidding wars (18% over asking).
- Some room to negotiate. 30% of listings cut their price, about as many as before the pandemic.
- Bid near asking. Buyers paid 98.4% of the list price on average; 16% paid over.
- You’ll usually have time. Only 21% of homes go under contract within two weeks; the typical one takes 76 days.
Spring brings the homes; summer brings the bidding wars
April has the most new listings (about 21 a month), but June is the most competitive: 24% of June sales close over asking. January has the least competition (12%) but only about 12 new listings.
Averages for each calendar month, 2015 on.
Calmer than the 2021 frenzy, and calmer than Maryland
| Chester now | 2017–19 | 2021 peak | MD now | |
|---|---|---|---|---|
| Sold over askingShare of sales that closed above the list price | 16% | 15% | 32% | 34% |
| Gone within two weeksShare of homes under contract within 14 days | 21% | 18% | 42% | 41% |
| Listings with a price cutShare of homes for sale that cut their price | 30% | 27% | 25% | 27% |
| Price paid vs. askingAverage sale price ÷ list price | 98.4% | 97.8% | 100.2% | 99.8% |
| Days to sellMedian days from listing to contract | 76 | 64 | 37 | 43 |
47 homes for sale on a typical day
That’s 1.6 times the 2022 low (29), about the 2017–19 level and well under 2015’s 72.
1 in 3 listings has cut its price
30% in the last year, against 27% in 2017–19 and 27% across Maryland.
Since 2019, houses are up 49%, condos 164%
A house typically sold for $649K in the last year (89 sales), a condo for $524K (34).
Median sale price, weighted by sales each month. Years with fewer than 4 sales of a type are left out.
Chester ranks 180th of 185 busy Maryland markets for bidding wars
Share of sales over asking in the last year, among towns with 60 or more sales. Chester is one of the state’s calmer markets.
Source: Redfin Data Center, city market tracker, January 2012 to May 2026 (MLS sales, not seasonally adjusted). Ratios are weighted by homes sold; price cuts by homes for sale.
Owning the typical Chester home costs about $3,149 a month
Price: Chester’s typical sale, last 12 months. Property tax at Chester’s 0.8% (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 April
The month with the most choice. December has the fewest, about 10.
Best time to buyProperty tax, a year
Of a home’s value: the median bill over the median home value. On a $535K home, about $4,290 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.
Grasonville sells for less a square foot; Kent Narrows and Annapolis Neck 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 | |
|---|---|---|---|---|---|
| Annapolis Neck | 195 | $887K | $382 | 27% | 50 |
| Stevensville | 157 | $538K | $263 | 20% | 57 |
| Chester | 155 | $535K | $270 | 16% | 76 |
| Cape St. Claire | 108 | $573K | $278 | 41% | 31 |
| Grasonville | 93 | $503K | $235 | 38% | 41 |
| Romancoke | 51 | $520K | $277 | 22% | 80 |
| Kent Narrows | 26 | $742K | $369 | 0% | 74 |
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, MD?
155 homes sold in the year to May 2026 at a typical $535K, $270 a square foot. Houses sold for about $649K, condos for about $524K.
Is Chester a buyer’s or seller’s market?
A buyer’s market: 54 homes were for sale in May 2026 and 8 sold, about 6.8 months of supply. Buyers paid 98.4% of asking on average, and 30% of listings cut their price.
When is the best time to buy in Chester?
April brings the most new listings. The sales history shows which months have fewer bidding wars.
How much are property taxes in Chester?
About 0.8% of a home’s value a year. On a $535K home that’s near $4,290.
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).