“Jill Fitzpatrick went above and beyond in every way. Saying we were lucky to have her as our real estate agent is an understatement. Working with her was 10/10 in every category! Highly, highly recommend.”
Century 21 C21 North East
- Agent Pronto
- New Hampshire
- Winchester
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Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for June 2026. *
* Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.
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Winchester real estate Market Report.
Information and statistics on the latest trends in the Winchester real estate market. *
Latest Rolling 3-Month Snapshot
Feb 1, 2026 - Apr 30, 2026
Median sale price
$277K
-6.2%
from
Q1 '26
Median list price
$352K
+15%
from
Q1 '26
Active listings
9
+13%
from
Q1 '26
Homes sold
5
-29%
from
Q1 '26
New pendings
3
-40%
from
Q1 '26
New listings
6
-14%
from
Q1 '26
Quarterly Pricing Trends for Winchester
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Winchester
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Winchester
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Inventory and Sales Activity for Winchester
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Winchester
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Winchester
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
30
Seller’s Market
Seller’s Market
Buyer’s Market
0
20
40
60
80
100
0
25
50
75
100
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Feb 2026 - Apr 2026).
In Winchester, the rolling three-month view shows relatively lean inventory with just 9 active listings and 1.8 months of supply. Both homes sold and new listings are down sharply year over year, with closed sales dropping more than 40 percent and new listings falling nearly as much. Pending sales have slowed even more, with contracts down over 60 percent from a year ago, signaling a cooler pace of deals coming together.
Pricing is adjusting alongside this slower flow of activity. The typical home value over the period, reflected by the median sale price, is down about 8 percent from a year earlier, yet the median list price is up more than 20 percent year over year, suggesting sellers are testing higher asking prices. With the average sale-to-list ratio just over 97 percent and only 20 percent of recent sales closing above list, buyers are finding some room to negotiate.
Homes are also taking longer to move, with the median days on market around 61 days in this rolling window, much higher than a year ago. At the same time, roughly one-third of homes still go off the market within two weeks, showing that well-priced or standout properties can attract quick offers even in a slower environment. Whether you are a buyer trying to interpret these mixed signals or a seller adjusting expectations, Agent Pronto can connect you with a Winchester real estate agent who understands this local market.
Learn more about what Winchester has to offer.
Winchester offers residents a close-knit community, abundant outdoor recreation, strong local schools, and a welcoming, safe hometown atmosphere.
Winchester feels distinctly its own compared with nearby options like Keene or Brattleboro, offering a quieter, more close‑knit setting while still keeping daily needs within reach. The town center has a traditional New England layout, with historic buildings, modest local businesses, and community spaces that host events throughout the year. Residents value knowing their neighbors and recognizing familiar faces at spots like the Winchester Town Library or local youth games at Conant Park.
Outdoor life is a big part of the area’s identity. The Ashuelot River provides opportunities for paddling and peaceful walks, while nearby trail networks connect you to broader recreation in Cheshire County. Families appreciate access to the Winchester School District and community programs that give kids room to learn and explore close to home.
For those balancing small‑town living with regional access, it is an easy drive to Keene for shopping, dining, and cultural events, or to Brattleboro and Greenfield for additional work and entertainment options.
Whether you already live in Winchester or are considering a move, timing and preparation matter. A local agent who understands neighborhood trends, school preferences, and the pace of the market can help you position your home effectively or move quickly when the right property appears. Agent Pronto connects both buyers and sellers with the right real estate professional to make the most of the Winchester market.
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“Friendly helpful all the way to the end and beyond. Made everything easy to understand answered all my questions within a few minutes of asking if she didn't have the answers, she got them for me”
Foundation Brokerage Group
“Len went above and beyond during the whole process of selling my mother's home. He was kind, considerate, compassionate and extremely helpful, during an especially stressful time. I would definitely recommend him without hesitation.”
Century 21 North East - Integra
“Sarah is a warm, attentive, and caring individual. She is a seasoned professional and was extremely helpful in guiding and advising on best approaches and strategy to sell my property. It was sold within one week and it is fantastic. One of the best experiences in my dealings with the real estate. Thumbs up for Sarah. I'll definitely hire her again.”
Coldwell Banker Realty
“Michelle Soucy did a fantastic job of locating a home based on my criteria, and satisfied or exceeded my request. She was prompt and knowledgeable at each step of the process in keeping me informed and educated on an out-of-state purchase. She also lined up skilled trades help as needed and took care of the associated details. I highly recommend Michelle to handle your next real estate transaction.”
Foundation Brokerage Group
“Great real estate experience with Charlotte. I recently had the pleasure of working with Charlotte as my realtor, and I cannot express how grateful I am for her outstanding service throughout the entire home buying process. From our initial meeting to the closing day, Charlotte demonstrated a level of professionalism, expertise, and dedication that greatly met my expectations. One of Charlotte's standout qualities is her extensive knowledge of the local real estate market. She took the time to understand my preferences and priorities, providing valuable insights into neighborhoods, property values, and future market trends. Her expertise not only streamlined the decision-making process but also ensured that I made informed choices.”
Berkshire Hathaway Verani Realty
“Sherry Bourque got my house up and sold so quick. We had a high volume of people coming through. The closing process was smooth.I would so recommend Sherry and her team anytime.”
Diamond Key Real Estate
“Shawn and Dee were amazing. They made the process very easy and were always available for questions or guidance.”
Ian Handel Real Estate LLC
“Kim and Wayne were a pleasure to work with In every aspect of the sale, would recommend them to anyone!!”
Berkshire Hathaway Verani Realty
“Salish thank you for all your work. Thank you for your professionalism and patience throughout the purchase process. We are very happy we our home. She is the best.”
LAER Realty Partners
“Joanne was exceptional in doing her due dligence to provide me with the smoothest experience in selling my home. Since I was living in another State, Joanne did a commendable job handling all aspects of the process. She would always offer to take care of a matter for me so I wouldnt have to be there physically to deal with it. If I asked her if she could take care of something for me, she did it selflessly and without question. For example, since the home was part of a Condo Association, she met with and picked up in her own car one of the other Trustees to have a document signed and notarized. She also managed arrangements to have all of the smoke detectors replaced so they would pass inspections, just so I did not have to physically be there myself. Without reservation, I recommend to anyone in need of a Realtor, to pick Joanne Tassoni. You wont be disappointed.”
Berkshire Hathaway HomeServices Verani Realty
“Janna was awesome and was continually looking out for us and making certain everything was on track. She is the best of the best!”
eXp Realty Bean Group
“My experience was so enjoyable. I was very lucky to have Maria for my agent because she made everything so easy. One of the best I've ever dealt with!”
Berkshire Hathaway Verani Realty
“Mark and his team were wonderful!”
Keller Williams Coastal and Lakes & Mountains Realty
“Very satisfied with the connection to realtor Eric Hall! ”
Red Post Realty
“Lori is awesome! Great service and great referral! Great service!”
Berkshire Hathaway Beach Realty
“Chris Cassidy comes across as a very honest, and approachable person. Chris was involve in selling a 2 family for me , which was caught up in the Columbia Gas crisis which occurred shortly after he listed it. The Columbia gas problem affect homes in a huge area.The property for a few months was essential not able to be sold because of the Columbia Gas issue. During this time Chris did his best to show, and the sell the property. Eventual after Columbia Gas finally fixed all the gas lines that were affected Chris was then able to find the buyer for this property. Took months, but Chris never gave up, or showed any disinterest. I plan to work with him in the near future.”
eXp Realty
“I was recommended by a friend to call Kerry Lapiana with Prestige Homes. I am so glad I did. Kerry went up and beyond from the beginning until the end. She was always available with any questions I had and she made the offer process so easy. It didn't end there. She even took time after I closed to ask me how it was going if I needed anything additional. She went up and beyond every step of the way. I would highly recommend Kerry Lapiana and Prestige Homes to friends, family and colleagues.”
Diamond Key Real Estate
“SeMone, you worked tirelessly and quickly in finding our home and you really went out of your way to help us look for the best Home that fit our budget and personality. You acted quick on the sale of this house and helped us along the way with any questions or concerns we had considering this was our first property purchase. You knew what to do and how to act quick. I will recommend anyone to you! Thankyou so much for everything you have done.”
Keller Williams Coastal and Lakes & Mountains Realty
“John Plante was always accessible and professional, and always provided an answer to all my questions. He always kept me up to date on everything he was doing to advertise/sell my property. My property was displayed beautifully on the internet. I would recommend John to anyone looking for a Realtor, as he is very knowledgeable in his field and is licensed in both MA and NH. I would not hesitate to have John as my Realtor again in the future.”
Lamacchia Realty
Frequently Asked Questions
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There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise covering the housing market in and around Winchester. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.
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Choosing a real estate agent to help you buy or sell property is one of the most important decisions you’ll make in your lifetime. You want to make sure your agent is an expert in your area, has a proven record helping people buy and sell similar homes to yours, and is well regarded by their previous clients. Let us know a few details about the property you are selling or the kind of home you want to buy, and Agent Pronto will match you with trusted real estate agents that have the experience you need. And before you interview an agent, check out our top five questions to ask a buyer’s agent and listing agent.
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We consider performance metrics, close rates, specialties, and client reviews to qualify the best full-time agents. We then take the information you provide about the home you are selling or the kind of home you want to buy, and analyze the top local agents with the right experience for your specific needs. For more than a decade, we've helped hundreds of thousands of home buyers and sellers find the right agent. Get started now and find the perfect real estate agent.
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