
School District
Winchester School District Homes for Sale & Schools
Serving Winchester, New Hampshire
11 homes for sale · 5 schools · MLS data updated 11/03/26
The District
About the Winchester School District
Going by the homes MLS listings assign to it, the Winchester School District serves Winchester, in Cheshire County, New Hampshire.
Homes for sale here are zoned to 5 schools, including Winchester School, Hinsdale Sr. High School and Keene High School. Each school page shows only the homes assigned to it. Zoning follows the MLS data, so always confirm the schools for a specific address with the district office.
There are 11 homes for sale in the district right now, with a median asking price of $425,000. Every listing below comes straight from the PrimeMLS feed and refreshes as it does.
Comparing districts? Our New Hampshire school district directory groups every district with homes on the market by region.
Towns in the District
- Winchester
- County
- Cheshire County
Zoned Schools
Schools in the Winchester School District
Elementary Schools(1)
Middle Schools(2)
Schools as MLS listings report them for homes in this district. Zoning can differ street by street, so confirm the schools for a specific address with the district office before you rely on it.
Homes for Sale in the Winchester School District
11 homes for sale right now, straight from the MLS.
- Active
$269,900
3 bd | 3 ba | 1,420 ft²
976 Old Westport Road, Winchester, NH, 03470
Single Family Residence
Listed by Arris Realty
MLS® #5115622
- Active
$589,000
6 bd | 4 ba | 2,880 ft²
49 Keene Road, Winchester, NH, 03470
Single Family Residence
Listed by R.H. Thackston & Company
MLS® #5114832
- Active
$589,000
0 bd | 0 ba | 2,880 ft²
49 Keene Road, Winchester, NH, 03470
Listed by R.H. Thackston & Company
MLS® #5114050
- Active
$349,900
4 bd | 2 ba | 2,018 ft²
44 Gunn Mountain Road, Winchester, NH, 03441
Single Family Residence
Listed by BHG Masiello Keene
MLS® #5112930
- Active
$425,000
0 bd | 0 ba | 3,967 ft²
42 Parker Street, Winchester, NH, 03470
Listed by R.H. Thackston & Company
MLS® #5110811
- Active
$140,000
1 bd | 1 ba | 968 ft²
31 Watson Road, Winchester, NH, 03470
Single Family Residence
Listed by Monadnock Realty Group LLC
MLS® #5109514
- ActivePrice Reduced
$299,000
3 bd | 1 ba | 1,548 ft²
73 Ashuelot Main Street, Winchester, NH, 03441
Single Family Residence
Listed by ACORN REAL ESTATE GROUP LLC
MLS® #5107206
- Active
$599,000
3 bd | 2 ba | 2,516 ft²
484 Scofield Mountain Road, Winchester, NH, 03470
Single Family Residence
Listed by R.H. Thackston & Company
MLS® #5101558
- ActivePrice Reduced
$445,000
3 bd | 2 ba | 1,066 ft²
71 Headlands Road, Winchester, NH, 03470
Single Family Residence
Listed by HKS Associates, Inc.
MLS® #5096976
- ActivePrice Reduced
$3,995,000
4 bd | 6 ba | 3,520 ft²
398 Scofield Mountain Road, Winchester, NH, 03470
Single Family Residence
Listed by Coldwell Banker Realty Bedford NH
MLS® #5086956
- ActivePrice Reduced
$290,000
0 bd | 0 ba | 4,739 ft²
292 Richmond Road, Winchester, NH, 03470
Listed by Realty One Group Next Level
MLS® #5077669

NOTE: This representation is based in whole or in part on data generated by PrimeMLS, Inc., which assumes no responsibility for its accuracy. The data relating to real estate displayed on this site comes in part from the IDX Program of PrimeMLS.
This listing data is intended for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 11/03/26.
Live From the MLS
Market Insights
Homes for Sale in the Winchester School District: what is listed right now, from the live PrimeMLS feed — a snapshot of today's inventory, not a valuation.
- 11
- Homes For Sale
- $726,436
- Average Price
- $425,000
- Median Price
- $140,000 – $3,995,000
- Price Range
- 60
- Avg. Days On Marketactive listings, so far
Current inventory: Single Family Homes (8) · Income Properties (3)
Winchester School District FAQs
How many homes are for sale in the Winchester School District?
There are 11 active MLS listings for homes in the Winchester School District right now. Asking prices currently run from $140,000 to $3,995,000. This page reads the live feed, so the count changes as homes come on the market and go under contract.
What is the average price of homes in the Winchester School District?
Active listings for homes in the Winchester School District currently average $726,436 with a median asking price of $425,000. Averages move with the mix of homes on the market at any moment, so treat them as a snapshot rather than a valuation.
What types of properties are available in the Winchester School District?
The homes for sale in the Winchester School District right now break down as: single family homes (8), income properties (3). Use the filters on the listings on this page to narrow to the kind of property you want.
How long have homes in the Winchester School District been on the market?
The active listings in the Winchester School District have been on the market for an average of 60 days so far. Well-priced homes move faster than that average, so if you are watching this market it pays to see new listings the day they appear.
What towns does the Winchester School District serve?
Homes assigned to the Winchester School District are located in Winchester, according to current MLS listings. Follow a town link to browse every home for sale there.
What schools are in the Winchester School District?
Current and recent MLS listings in this district reference Winchester School, Hinsdale Sr. High School, Keene High School, MonadnockR and Keene Middle School. Each school page shows the homes for sale zoned to it. Always confirm zoning for a specific address with the district office.
How do I tour a home for sale in the Winchester School District?
Reach out to our New Hampshire team through the contact page with the address (or just what you're looking for) and we'll set up a private showing — we tour homes across these towns every week.
Keep Exploring
Explore More NH School Districts
Districts that share a town with this one first, then the busiest districts in the state. The directory lists every district with homes on the market.

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Nashua School District
Serves Nashua.
View District Nashua School District
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SAU #9
Serves Conway, Bartlett, Jackson and 5 more towns.
View District SAU #9Buying With Schools in Mind?
Looking for a Home in the Winchester School District?
Tell us the schools that matter, your budget and how you want to live. Our local team will shortlist the homes worth a look and book private tours on any listing, whichever brokerage holds it.
