Should You Underprice Your Home in Orange County NY? 2026 MLS Data Says Yes
Yes, and the reason is not the one most people give. Listings priced at or below what comparable homes actually sold for failed to sell 35% of the time. Listings asking more than 60% over failed 68% of the time. The risk of reaching is not that you get less money. It is that you never sell.
By Brian Caplicki, Caplicki Home Team · Originally published April 1, 2026 · Rewritten with new data August 13, 2026 · 9 min read
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New data · Updated August 2026 The short version: In the Washingtonville school district, listings priced near the market sold about six times in ten. Listings asking 20% or more above it sold two times in ten. Based on Hudson Valley MLS single-family listing outcomes, Orange and Sullivan County, January 1 through mid-August 2026. 3,084 listings, of which 1,306 never sold. Compiled by the Caplicki Home Team. |
We first published this post in April, and the answer has not changed. Pricing at or slightly under what the market is actually paying beats starting high and planning to come down.
What has changed is what we can prove. In April we were working from closed sales, which is what everybody works from. Since then we pulled something different: the listings that never sold. There were 1,306 of them in Orange and Sullivan County this year. They change the argument, and honestly they made a couple of the numbers in our April version look flimsier than we would like. So we rebuilt it.
Why have you not seen these numbers anywhere else?
Because every market report you have ever read, including the ones we have sent, is built only on homes that sold. The homes that did not sell are simply absent from the file. So when a site tells you the typical Orange County home sold for 99% of its asking price, that is true, and it is also survivors talking.
The large listing websites also organize everything by zip code and town name. In Orange and Sullivan County the school district is what actually moves the price, and districts cross town lines constantly. A single Middletown mailing address turns up in five different school districts. So we sorted the year by district ourselves, which is why some of what follows will not match the estimate you got online.
How do you measure whether a house was priced too high?
This part matters more than the numbers, so bear with us for one paragraph.
For every house that got listed this year, we worked out what it should sell for based on its size, lot, bedrooms, bathrooms, age and school district, using the homes that actually closed. Then we compared what the seller asked to that figure. Every group below is set the day the house is listed, before anyone knows how it turns out.
The tempting shortcut, and the one our April version used, is to call a house overpriced if it sat for months and then sold under asking. But that sorts sellers by how badly it went and then announces that it went badly. It cannot produce any other answer. We do not use it here.
How far above the market is too far?
Here is the share of listings that never sold, sorted by how far the asking price sat above what comparable homes closed for.
| Asking price against comparable sales | Listings | Never sold |
|---|---|---|
| At or below comparable sales | 1,455 | 35% |
| Up to 20% over | 731 | 42% |
| 20% to 60% over | 633 | 51% |
| More than 60% over | 265 | 68% |
Source: Hudson Valley MLS single-family listing outcomes, Orange and Sullivan County, January 1 through mid-August 2026. 3,084 listings. Comparable value estimated from size, lot, bedrooms, bathrooms, age and school district.
There is a cushion, and then there is a cliff. Being a little ambitious barely moves the odds. Somewhere around 20% over comparable sales the floor gives way, and your chances go from roughly two in three to worse than a coin flip.
We checked this a second way with no model at all, just asking price per square foot against what is typical for the town, and the shape came out the same. It holds in both counties, in every price range, and in every size of house.
Does dropping the price later fix a high start?
This is the question we get most, usually phrased as "let us start high, we can always come down." Here is what happened to the sellers who did that, among homes that eventually sold.
| What the seller did | Got their final ask | Got their original ask | Time to contract |
|---|---|---|---|
| Never changed the price | 61% | 62% | 31 days |
| Lowered the price | 26% | 4% | 125 days |
Source: Hudson Valley MLS closed single-family sales, Orange and Sullivan County, January 1 through mid-August 2026. 1,811 sales. New York is an attorney state, so time to contract measures listing to going under contract after attorney review.
Read the middle column carefully, because it is deliberately generous to the sellers who reduced. Each group is being measured against its own final asking price, and the reducers had already lowered theirs. They are being graded against an easier target and they still finish 35 points behind.
The last column is the one worth sitting with. Measured against the price they originally wanted, only 4% of the sellers who reduced ever got it. 96% ended up below their first number. The typical one cut $30,000 and closed at about 90% of what they first asked. So the high first price was not a negotiating cushion. It was roughly a tenth of the eventual sale price walking out the door, plus three extra months of showings.
Does this hurt more in some school districts than others?
This is the part nobody else is publishing, and it surprised us. Reaching high does not carry the same risk everywhere. Not remotely.
| School district | Priced near the market | Asking 20%+ over |
|---|---|---|
| Washingtonville | 37% never sold | 81% never sold |
| Fallsburg | 38% | 68% |
| Monroe-Woodbury | 44% | 66% |
| Monticello | 47% | 64% |
| Port Jervis | 31% | 56% |
| Pine Bush | 34% | 51% |
| Newburgh | 32% | 47% |
| Middletown | 29% | 38% |
Source: as above. Districts shown have at least 60 listing outcomes. Each district was re-run thousands of times on random slices of its own sales; the districts above showed the same result in 96% to 100% of runs.
Washingtonville is the sharpest in either county. Sixty-seven listings there asked 20% or more over what was actually selling, and 54 of them never sold to anybody. We checked that one by hand because it looked too extreme to be true. It holds, and it is spread across Monroe, Washingtonville, Rock Tavern and Blooming Grove addresses, so it is not one unlucky development skewing the figure.
Then there are three districts where we cannot find a reliable penalty at all: Warwick Valley, Cornwall and Sullivan West. We want to be careful with those words. Cannot find one is not the same as there is not one.
And the honest reading of those three is not encouraging. Look at what happens there when the price is right. In Warwick Valley, 42% of sensibly priced listings still never sold. In Monroe-Woodbury, 44%. In Sullivan West, 50%. Against 29% in Middletown and 31% in Port Jervis. In those districts a lot of listings fail whatever the price, so there is less room left for a high number to make things worse. That is a harder conversation, not an easier one.
Which districts have the most sellers reaching?
Share of all listings asking more than 20% above what comparable homes sold for:
Sullivan County: Fallsburg 56%, Liberty 49%, Monticello 47%, Eldred 45%, Sullivan West 45%.
Orange County: Port Jervis 37%, Washingtonville 31%, Monroe-Woodbury 26%, Pine Bush 25%, Warwick Valley 25%, Cornwall 21%, Newburgh 20%, Goshen 18%, Middletown 17%, Valley Central 16%, Minisink Valley 14%.
Every Sullivan County district sits at the top. In Fallsburg, more than half of everything on the market is priced above what is actually trading. In Minisink Valley it is one listing in seven.
If you are selling: so should you actually underprice?
Our answer in April was yes and it still is, with one clarification. What works is not dramatic underpricing. It is pricing at or slightly below what comparable homes have genuinely been closing for, which to a seller who has been watching asking prices rather than sold prices often feels like underpricing.
Find out which column your district is in before you pick a number. A Washingtonville seller and a Warwick seller are making the same decision with wildly different stakes, and neither can tell that from a county-wide average or an online estimate.
In Sullivan County, being priced right is a bigger advantage than it looks, precisely because so much of your competition is not. When half the listings around you are priced above what trades, the sensibly priced house stops competing with them and starts standing out.
A high first price is not a cushion. Only 4% of sellers who reduced ever got their original number. If you want room to negotiate, the room has to be real, which means it has to sit above what buyers are paying, not above what other sellers are asking.
And here is the thing we will not tell you, because we cannot: what reaching high costs in dollars. It is tempting to point at a seller who asked $572,000 and closed at $477,000 and call the difference a loss. It is not. If the house was never worth $572,000, that money was never there to lose. What a high asking price actually costs you is time, and the odds of selling at all. Anyone who hands you a precise dollar figure for it is guessing.
If you are buying: where is the room to negotiate?
Every number above flips into a map of where your offer has room.
First the warning. In Fallsburg, Liberty, Monticello, Eldred and Sullivan West, close to half the listings you are scrolling through are priced above what is actually trading, and a good share of those will never sell to anyone. Worth knowing before you fall in love with one, and certainly before you write a full-price offer on one.
Then the opportunity. Among homes that did sell, here is how often the buyer paid below the first asking price, and what they typically saved.
| School district | Paid below first ask | Typical saving |
|---|---|---|
| Sullivan West | 79% | $40,000 |
| Monticello | 75% | $24,210 |
| Cornwall | 65% | $50,450 |
| Monroe-Woodbury | 60% | $35,000 |
| Warwick Valley | 55% | $40,000 |
| Newburgh | 48% | $22,750 |
| Middletown | 42% | $19,900 |
| Pine Bush | 40% | $25,000 |
Source: as above. Closed sales only. Typical saving is the median discount among buyers who paid below the original asking price.
Cornwall is the one most buyers miss. Only about two in three buyers there paid under asking, so the district does not look soft on the surface. But when they did negotiate, the typical saving was over fifty thousand dollars, the largest in either county.
Timing matters as much as district. Across Orange County, 16% of buyers paid below asking on homes listed under two weeks. That rises to 45% at one to two months, 70% at two to three months, 86% at three to six months, and 95% past six months. A house listed three weeks ago and a house listed in April are two different negotiations even at the same price.
And notice the pattern underneath all of it. The districts where sellers reach the furthest are the districts where buyers end up with the most room. Sullivan West sits at the top of both lists. That is not a coincidence, it is the same fact seen from opposite sides of the table.
What is your school district actually worth?
Our district scoreboard has the typical price, time to contract, and how often homes beat their asking price, for every district in both counties. See the scoreboard.
The bottom line
Yes, price at or under what comparable homes have actually been closing for. Not because it squeezes out a higher number, but because the alternative carries a risk most sellers never see: 1,306 listings in Orange and Sullivan County did not sell at all this year, and asking price is the strongest thing about them we can measure.
One honest limit before you go. A house priced above its neighbors is not automatically priced wrong. Some of them really are better, in ways nothing in the MLS records: condition, view, layout, which end of the street. Size, lot, bedrooms, bathrooms, age and district together explain about two thirds of what moves a price around here. The last third is why you walk through a house instead of reading about it. So none of this is a verdict on any one home. It is about odds, across thousands of them.
Selling? Find out what your house should list at.
Start with a free estimate of what your Orange County or Sullivan County home would sell for right now. No phone call, no obligation. Tell us your school district and we will send back the two columns above for your district and price band instead of the county average.
Buying? The same numbers work in reverse. We can show you what has been sitting in your price range, what those sellers have already come down, and what a winning offer has actually taken in your district. Call us at 845-656-4498.
Common questions
Should you underprice your home in Orange County NY?
In this market, yes, in the sense that pricing at or slightly under what comparable homes actually sold for is the safest place to be. Listings priced at or below comparable sales failed to sell 35% of the time. Listings asking more than 20% over failed 51% of the time, and more than 60% over failed 68% of the time. The risk of reaching is not that you get less money. It is that you do not sell at all.
Does overpricing hurt more in some Orange County school districts than others?
Enormously. In the Washingtonville school district, listings priced near comparable sales failed 37% of the time and listings asking 20% or more over failed 81% of the time. In Middletown the same gap is 29% against 38%. In Warwick Valley and Cornwall we cannot find a reliable penalty at all, though those districts have high failure rates whatever the price.
Should I price my house high to leave room to negotiate in Orange County NY?
The 2026 numbers say no. Sellers who never changed their asking price got that price or better 61% of the time and went under contract in about 31 days. Sellers who lowered their price got their new, lower price only 26% of the time and took about 125 days. Measured against what they originally asked, only 4% got it.
How much does overpricing a house cost in Orange County NY?
Not in the way most people mean. If a house was never worth the first number, coming down to reality did not lose anyone anything, because that money was never there. What a high asking price costs is time and the odds of selling at all. Sellers who reduced took about four months instead of one, and 96% of them ended below what they first asked.
Why isn't my house selling in Orange County NY?
Between January and mid-August 2026, 1,306 out of 3,084 single-family listings in Orange and Sullivan County never sold at all. Asking price is the strongest single predictor we can measure. Past roughly 20% above what comparable homes sold for, the odds of selling drop from about two in three to worse than a coin flip. Your school district changes how steep that drop is.
Which Orange County NY school district has the most negotiating room for buyers?
Cornwall is the one most buyers overlook. Only about 65% of Cornwall buyers paid below the first asking price, so it does not look soft, but the typical saving when they did negotiate was $50,450, the largest of any district in either county. In Sullivan West, 79% of buyers paid below asking, typically $40,000 off.
Do sellers in Sullivan County NY ask too much?
More often than in Orange County. In the Fallsburg school district, 56% of listings asked more than 20% above what comparable homes sold for. Liberty was 49%, Monticello 47%, Eldred and Sullivan West both 45%. In the tightest Orange districts, such as Minisink Valley, it is closer to 14%.
How long does it take to sell a house in Orange County NY in 2026?
For sellers who picked a price and never changed it, about 31 days to go under contract. For sellers who had to reduce, about 125 days. New York is an attorney state, so days on market measures the time from listing to going under contract after attorney review, not to closing.
The Caplicki Home Team is a Keller Williams HVU real estate team based in Middletown, NY, serving Orange County, Sullivan County, Ulster County, and the broader Hudson Valley. Reach us at 845-656-4498 or brian@caplickihometeam.com.
