Photo: Jim.henderson · CC BY-SA 4.075 homes sold in Pleasantville in the last year, at a typical $874K
About one sale in 3 is a condo. 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 Pleasantville homes are listed.
Every place Pleasantville 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 Pleasantville.
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 third of Pleasantville’s sales are condos, at $451K less than a house
50 houses and 24 condos sold in the year to May 2026. Condos sell faster.
typical sale · 50 sold in the year to May 2026
- Per square foot
- $437NY $316
- Days to sell
- 36
- Sold over asking
- 58%
- Listings with a price cut
- 23%
typical sale · 24 sold in the year to May 2026
- Per square foot
- $520NY $832
- Days to sell
- 26
- Sold over asking
- 63%
- Listings with a price cut
- 50%
Multi-family (2–4 units): 1 sold, typical $965K
Townhouses: 1 sold, typical $1.1M
Too few sales in 12 months for reliable figures.
About as many homes sell as usual, at 1.4 times the 2016 price
75 sales in the last year, against 109 in 2021 and a low of 61 in 2024. The typical sale went from $638K in 2016 to $874K.
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 $850K buys in Pleasantville
Check a listing against what Pleasantville 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 Pleasantville are more common than before the pandemic, but three quarters fewer homes come up for sale
We read every month of Pleasantville’s home sales since 2016 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, 75 sales.
If you’re buying in Pleasantville
- Shop in March. It brings about 11 new listings a month, close to the busiest month, with fewer bidding wars (29% over asking).
- Expect to bid over asking. Buyers paid 103.6% of the list price on average; 59% paid over.
- You’ll usually have time. Only 11% of homes go under contract within two weeks; the typical one takes 30 days.
Spring brings the homes; summer brings the bidding wars
May has the most new listings (about 13 a month), but August is the most competitive: 47% of August sales close over asking. March offers nearly as much choice with fewer homes bid up (29%). February has the least competition (21%).
Averages for each calendar month, 2015 on.
Hotter than in 2021, and hotter than New York
| Pleasantville now | 2017–19 | 2021 peak | NY now | |
|---|---|---|---|---|
| Sold over askingShare of sales that closed above the list price | 59% | 29% | 36% | 39% |
| Gone within two weeksShare of homes under contract within 14 days | 11% | 7% | 13% | 25% |
| Price paid vs. askingAverage sale price ÷ list price | 103.6% | 99.3% | 99% | 100.5% |
| Days to sellMedian days from listing to contract | 30 | 74 | 43 | 43 |
8 homes for sale on a typical day
That’s 72% fewer than in 2017–19 and well under 2016’s 43.
Since 2019, houses are up 45%, condos 42%
A house typically sold for $976K in the year to May 2026 (50 sales), a condo for $525K (24).
Median sale price, weighted by sales each month. Years with fewer than 4 sales of a type are left out.
Pleasantville ranks 121st of 363 busy New York markets for bidding wars
Share of sales over asking in the last year, among towns with 60 or more sales. Pleasantville is in the middle of the pack.
Source: Redfin Data Center, city figures, January 2016 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 May
The month with the most choice. December has the fewest, about 2.
Best time to buySchools
The schools grade for Pleasantville, from test results, graduation and how much students grow.
Schools in PleasantvilleTypical commute
The average one-way trip to work for people who live in Pleasantville.
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.
Thornwood and Briarcliff Manor sell for less a square foot
The busier markets within 25 miles of Pleasantville, 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 | |
|---|---|---|---|---|---|
| Mount Pleasant | 295 | $1M | $482 | 62% | 25 |
| New Castle | 175 | $1.5M | $508 | 64% | 28 |
| Briarcliff Manor | 87 | $1.3M | $435 | 70% | 23 |
| Pleasantville | 75 | $874K | $477 | 59% | 30 |
| Armonk | 49 | $1.5M | $517 | 48% | 31 |
| Chappaqua | 26 | $974K | $555 | 59% | 29 |
| Thornwood | 21 | $1.1M | $450 | 73% | 26 |
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 Pleasantville, free
Selling it yourself, renting out an apartment or looking for a roommate? Post it to Pleasantville. People who follow the town see it, and so do people comparing Pleasantville with their own town. No commission, no listing fee.
Questions about buying a home in Pleasantville
What do homes sell for in Pleasantville, NY?
75 homes sold in the year to September 2026 at a typical $874K, $477 a square foot. Houses sold for about $976K, condos for about $525K in the year to May 2026.
Is Pleasantville a buyer’s or seller’s market?
A seller’s market: 11 homes were for sale in September 2026 and 8 sold, about 1.3 months of supply. Buyers paid 103.6% of asking on average.
When is the best time to buy in Pleasantville?
May brings the most new listings. The sales history shows which months have fewer bidding wars.
Where can I see homes for sale in Pleasantville?
Zillow, Redfin, Realtor.com and Homes.com all carry Pleasantville’s MLS listings; the search links above open each one filtered to Pleasantville.
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).