By Brian Caplicki  ·  Caplicki Home Team  ·  Updated November 2026  ·  7 min read

Start by asking which homes like yours are sitting unsold right now, and why. In Orange County, 4.2 out of 10 houses listed this year through September had not found a buyer by late October. A good agent can tell you what went wrong with each one, so yours does not join them.

New data · Updated November 2026 The short version: Ask three things. Which homes like mine are sitting right now, and why? What is the median sale price of similar homes in my school district? What will you change if I have no offer in 30 days? Figures based on OneKey MLS data pulled October 27, 2026. All 3,050 single family houses listed in Orange County, NY between January 1 and September 30, 2026. Put together by the Caplicki Home Team.

Most advice on what to ask a realtor is written for the whole country. Selling in Orange County is different. Your school district affects your price more than your town does. And a house that is priced wrong here can sit unsold for months.

So here are the questions that matter locally, what a good answer sounds like, and what our own numbers say.

What should I ask a realtor about my local market right now?

Lots of agents quote countywide numbers. A county number describes almost nobody. Prices here move by school district, and districts cross town lines constantly. A single Middletown mailing address can fall in five different school districts.

You want someone who can read your district and your zip code, this month. These questions show you fast whether they can:

• "Which homes like mine are sitting right now, and why?" The answer is real local market insight. It shows how to position your house against the ones buyers are passing over.
• "Are those county numbers, or my school district's?" If they cannot tell you, the number is not about your house.
• "How many homes like mine are for sale in my district right now?" That is your competition the day you list.
• "Which homes like mine are under contract right now?" That tells you what buyers are choosing, and what they are passing over.
• "What did the last few similar homes sell for, compared with their asking price?" Recent closed sales show you what buyers actually paid, not what sellers hoped for.
• If your town is split between school districts: "How do prices differ between the districts in my town?" Homes a few streets apart can sell very differently.

A good answer comes with specifics. A district name, a count, a recent sale. A vague answer about "the market" is your sign to keep interviewing.

What should I ask a realtor about pricing my house?

Ask: "What is the median sale price of similar homes in my school district?"

This is the question that separates agents. A good answer gives you that number and shows you the sales behind it. A weak answer is a single big number with nothing behind it.

Then ask: "How did you adjust for my house?" Almost nothing around the Hudson Valley is cookie cutter. Bedrooms, size, condition, the lot and recent updates all move the price. A good agent explains why your house should sell above or below that number.

Here is why it matters. We followed every house listed in Orange County from January through September 2026.

Orange County houses listed January to September 2026

Where they stood on October 27, 2026	Share of houses
Found a buyer (closed or under contract)	5.8 out of 10
Still on the market	2.7 out of 10
Came off the market unsold	1.5 out of 10

Source: OneKey MLS, pulled October 27, 2026. All 3,050 single family houses listed in Orange County, NY, January 1 to September 30, 2026. Full method in our 2026 market study.

If you want to check an agent's number yourself, our Orange County home values by school district page shows the typical sale price in each district, year by year.

What will you change if there is no offer in 30 days?

Most of the time, the answer is price. If similar homes are going under contract and yours is not, buyers are telling you something. A good agent will say so plainly.

But price is not the only thing to look at. When one of our listings has no offer by day 30, we also:

• Rewrite the listing description. New words can bring in buyers who scrolled past the first time.
• Update the photos to match the season. A summer lawn in November tells buyers the house has been sitting.
• Advertise the open house hard. Online and in person, not just a sign on Saturday morning.
• Invite the neighbors. They often know someone who wants to move onto their street.

It works. A house in Tuxedo had expired, unsold, with another brokerage. When we relisted it, it was not a price cut that sold it. New photos, new listing copy and real marketing brought competing offers, and it sold. We saw the same thing with an expired listing in Livingston Manor.

Ask any agent you interview what their day-30 plan is. If they do not have one, that is your answer.

What should I ask about how long it will take to sell?

Ask: "How many days are houses like mine taking to go under contract here?"

Listen for which clock they mean. "Days to contract" and "days to closing" are different numbers, and some agents mix them up.

For houses listed in Orange County from January to September 2026, the typical time from listing to a signed contract was 31 days. Closing usually comes 60 to 90 days after the contract, depending on the buyer's loan.

We break this down further, including how long the unsold houses have been waiting, in how long it takes to sell a house in Orange County NY.

What should I ask about attorneys and fees?

Ask: "Which attorneys do you work with, and what does your fee cover?" New York is an attorney state. After an offer, the inspection happens, then the attorneys review the contract, which takes about two weeks. An agent with steady attorney relationships keeps those weeks moving. Commission is negotiable, so ask for the marketing plan in writing. Here is our marketing plan, if you want something to compare against.

If you are selling: which answers should worry you?

Be careful with the agent who quotes the highest price and nothing else. A big number wins the listing. It does not win a buyer.

And ask what happens if you are not happy. Most listing agreements lock you in for months. Ours lets you cancel any time before an offer, with no penalty. That is our risk-free listing guarantee.

Finally, ask for their track record here, not nationally. You can see ours on our by the numbers page, or compare the best realtors and real estate agents in Middletown NY.

If you are buying: what should I ask a realtor before making an offer?

Ask: "How long has it been listed, and has the price changed?" A fresh, well-priced house in Orange County leaves little room. Of the Orange County houses listed January to September 2026 that have closed, 5.8 out of 10 sold at or above their first asking price. A house that has sat since spring is a different conversation.

Ask: "What did similar houses in this school district sell for?" The same district question works for buyers. It tells you whether the asking price is fair before you fall for the kitchen.

Ask: "What are the actual property taxes?" Get the current bill, not an estimate. Rates change by district and town. Our property tax rates by school district help you compare before you tour.

Ask: "What will I sign with you?" Since August 2024, buyers sign a written agreement with their agent before touring. Read it, ask what it covers, and ask how long it lasts. Our buyer's guide walks through the rest.

The bottom line

The right questions are local ones. Ask which homes like yours are sitting and why, what similar homes in your school district sold for, and what happens on day 30. An agent who answers with real numbers from your area is the one worth hiring.

Selling? See what houses like yours sold for.

Get a free, data-driven estimate of your Orange County or Hudson Valley home's value. No phone call required, no obligation.

Get My Free Home Value Estimate

Interviewing agents? Bring these questions to us. Call 845-237-2368 to set up a pricing conversation. Buying? Call the same number and ask us anything on this list.

Hudson Valley Real Estate FAQ

What is the most important question to ask a realtor when selling in Orange County NY?

Ask which homes like yours are sitting unsold right now, and why. Of the 3,050 Orange County houses listed from January to September 2026, 4.2 out of 10 had not found a buyer by October 27. A good agent knows what went wrong with each one, then prices yours from the median sale price of similar homes in your school district.

How long does it take to sell a house in Orange County NY?

For houses listed in Orange County from January to September 2026, the typical time from listing to a signed contract was 31 days, based on OneKey MLS data as of October 27, 2026. Closing usually follows 60 to 90 days after that, depending on the buyer's financing.

Why do I need an attorney to sell a house in New York?

New York is an attorney state. After an offer is accepted, the inspection happens and the attorneys review the contract, which takes about two weeks. A house only shows as under contract after that, so by the time it does, the fragile part of the deal is usually behind it.

Why does my school district matter more than county data when selling in Orange County NY?

Because prices here move by school district, and districts cross town lines. A single Middletown mailing address can fall in five different school districts. Countywide numbers blend them all together, so ask your agent for your own district's recent sales, homes for sale and homes under contract right now.

Is real estate commission negotiable in New York?

Yes. Commission has always been negotiable in New York, and since August 2024 buyers sign their own written agreement with their agent. Ask any agent you interview what their fee covers, in writing, so you can compare the marketing plan and not just the number.

What should I ask a realtor before making an offer in Orange County NY?

Ask how long the house has been listed and what similar houses in the same school district sold for. Of the Orange County houses listed January to September 2026 that have closed, 5.8 out of 10 sold at or above their first asking price, so a fresh, well-priced listing leaves less room. A house that has sat for months usually leaves more.

How do I check property taxes on an Orange County NY house before I buy?

Ask your agent for the current tax bill, not an estimate, because rates change by school district and town. Our Orange County home values page lists the property tax rate by school district so you can compare before you tour.

The Caplicki Home Team is a Keller Williams Hudson Valley United real estate team based in Middletown, NY, serving Orange County, Sullivan County, Ulster County, and the broader Hudson Valley. Helping local families buy and sell since 2000. Reach us at 845-237-2368 or brian@caplickihometeam.com.