80 homes sold in Chesterland in the last year, at a typical $383K
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 Chesterland homes are listed.
Every place Chesterland 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 Chesterland.
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 100% of Chesterland’s sales, at a typical $362K (year to May 2026)
80 homes sold in the year to September 2026.
typical sale · 75 sold in the year to May 2026
- Per square foot
- $183OH $165
- Days to sell
- 35
- Sold over asking
- 39%
- Listings with a price cut
- 31%
About as many homes sell as usual, at 1.7 times the 2016 price
80 sales in the last year, against 100 in 2021 and a low of 67 in 2013. The typical sale went from $226K in 2016 to $383K.
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 Chesterland
Check a listing against what Chesterland 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 Chesterland are more common than before the pandemic, but 62% fewer homes come up for sale
We read every month of Chesterland’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, 80 sales.
If you’re buying in Chesterland
- Shop in May. It brings about 12 new listings a month, close to the busiest month, with fewer bidding wars (28% over asking).
- Bid near asking. Buyers paid 98.9% of the list price on average; 35% paid over.
- Move fast on good ones. 62% of homes are under contract within two weeks.
Spring brings both the most homes and the most bidding wars
May has the most new listings (about 12 a month), but April is the most competitive: 39% of April sales close over asking. December has the least competition (17%) but only about 3 new listings.
Averages for each calendar month, 2015 on.
Calmer than the 2021 frenzy, and hotter than Ohio
| Chesterland now | 2017–19 | 2021 peak | OH now | |
|---|---|---|---|---|
| Sold over askingShare of sales that closed above the list price | 35% | 19% | 46% | 28% |
| Gone within two weeksShare of homes under contract within 14 days | 62% | 36% | 66% | 45% |
| Price paid vs. askingAverage sale price ÷ list price | 98.9% | 97.3% | 100.3% | 98.3% |
| Days to sellMedian days from listing to contract | 31 | 62 | 29 | 45 |
11 homes for sale on a typical day
That’s 1.2 times the 2025 low (9), 62% fewer than in 2017–19 and well under 2012’s 52.
Chesterland ranks 88th of 310 busy Ohio markets for bidding wars
Share of sales over asking in the last year, among towns with 60 or more sales. Chesterland is in the middle of the pack.
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 Chesterland home costs about $2,426 a month
Price: Chesterland’s typical sale, last 12 months. Property tax at Chesterland’s 1.3% (median bill ÷ median value, Census ACS); insurance at 0.35% of price a year. Before PMI, HOA dues, upkeep and the tax deduction. Whether Chesterland is affordable on local pay is on Cost of living.
Six things worth knowing
New listings in May
The month with the most choice. December has the fewest, about 3.
Best time to buyProperty tax, a year
Of a home’s value: the median bill over the median home value. On a $383K home, about $5,140 a year.
Taxes vs. neighborsSchools
The schools grade for Chesterland, from test results, graduation and how much students grow.
Schools in ChesterlandTypical commute
The average one-way trip to work for people who live in Chesterland.
Work & commuteCheck 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.
Kirtland and Mayfield Heights sell for less a square foot; Gates Mills for far more
The busier markets within 25 miles of Chesterland, 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 | |
|---|---|---|---|---|---|
| Mayfield Heights | 247 | $250K | $173 | 39% | 27 |
| Highland Heights | 106 | $475K | $188 | 35% | 32 |
| Willoughby Hills | 81 | $401K | $191 | 30% | 41 |
| Chesterland | 80 | $383K | $185 | 35% | 31 |
| Kirtland | 61 | $388K | $178 | 31% | 23 |
| Mayfield | 35 | $420K | $194 | 22% | 42 |
| Gates Mills | 24 | $963K | $244 | 32% | 80 |
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 Chesterland, free
Selling it yourself, renting out an apartment or looking for a roommate? Post it to Chesterland. People who follow the town see it, and so do people comparing Chesterland with their own town. No commission, no listing fee.
Questions about buying a home in Chesterland
What do homes sell for in Chesterland, OH?
80 homes sold in the year to September 2026 at a typical $383K, $185 a square foot.
Is Chesterland a buyer’s or seller’s market?
A seller’s market: 14 homes were for sale in September 2026 and 8 sold, about 1.7 months of supply. Buyers paid 98.9% of asking on average.
When is the best time to buy in Chesterland?
May brings the most new listings. The sales history shows which months have fewer bidding wars.
How much are property taxes in Chesterland?
About 1.3% of a home’s value a year. On a $383K home that’s near $5,140.
Where can I see homes for sale in Chesterland?
Zillow, Redfin, Realtor.com and Homes.com all carry Chesterland’s MLS listings; the search links above open each one filtered to Chesterland.
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).