Winchester, New Hampshire

One of Cheshire County's southern border towns, Winchester, New Hampshire, is a blue-collar community of just under 4500 residents.  Located in the southwestern corner of the Granite State, Winchester has a strong commercial and industrial presence lending to a relatively low unemployment rate in town.  Families that call Winchester “home” enjoy the natural beauty and quiet country air that this part of the state is so well known for, while visitors absorb the sights and sounds within the rolling hills of the breathtaking mountainous Monadnock Region.

The area to become Winchester was first granted to Colonel Josiah Willard, a military leader who desired a large plot of land on the eastern banks of the Connecticut River.  This was granted to him by the Colonial Massachusetts Government who, at the time, had full control of New Hampshire.  Known by locals as The Arlington Plantation, the settlement was incorporated as a nameless town in 1739.  For unknown reasons, some folks started calling it Winchester, so Willard petitioned the recently-formed New Hampshire government to incorporate the town as such in 1750, but failed.  His second attempt, in 1753, was a success and the town has been known as Winchester ever since.  It is possible that the name of Winchester comes from Charles Paulet, Marquis of Winchester, but as yet cannot be verified.

Winchester has enough small stores in town to meet most of the community’s needs, but if there’s something you need and Winchester doesn’t have it, Keene is just a ten-minute drive north, or Brattleboro, Vermont, is the same distance northwest.  However, since New Hampshire is a sales tax-free state, most Winchester residents prefer to shop within the state’s confines.  Finding things to do in Winchester is easy – the Pisgah Wilderness State Park is a stone’s throw from your front door and offers hiking, wilderness tours, mountain biking, fishing and snowmobiling during those cold winter months.  For other winter activities, you don’t need to travel far at all.  There are several ski resorts within twenty-five miles of Winchester as well as sledding hills that stretch for what seems like miles.  Summertime brings with it more fishing, boating, swimming, and pitching tents at the many campgrounds that dot the landscape of southwestern New Hampshire.  It’s all about the outdoors in this great state.

Winchester is a part of SAU #38.  The Winchester School educates resident children from kindergarten through the eighth grade.  High school age children in Winchester attend the Keene High School, in nearby Keene, NH.  There are no current plans to construct a high school in Winchester.

If you’re looking to buy a home in rural New Hampshire, look no further than Winchester.  Great location and great people are but two of the reasons you should consider purchasing your new home in Winchester.  If the southwestern part of the state isn’t what you’re looking for, perhaps you’d be interested in something closer to the seacoast or nearer to the White Mountains?  Wherever you’re considering, the first step in bringing your plans to fruition is to call Jim Miller Bean Group at (603) 801-3987.  Jim is here for you and you alone, from answering your NH questions to finding you the perfect home.  Call right now and find out just how quickly the dream can become reality.

Winchester School (k-8)

Keene High School (9-12)
(603) 352-0640

Current Winchester New Hampshire Real Estate MLS Listings for Single Family Homes

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $500,000 - $600,000

All Property Types in Winchester from $50,000 to $5,000,000

16 Properties Found. Page 1 of 1.
Photo of Listing #4789603

435 Scofield Mountain Rd, Winchester

$535,000 - 3 Beds, 3 Baths, 4,399 Sf

MLS® # 4789603

Photo of Listing #4744408

20 Snow Rd, Winchester


MLS® # 4744408

Photo of Listing #4794923
New Listing

474 Forest Lake Rd, Winchester

$374,000 - 2 Beds, 2 Baths, 1,656 Sf

MLS® # 4794923

Photo of Listing #4773852

23 Headlands Rd, Winchester

$339,000 - 3 Beds, 2 Baths, 2,168 Sf

MLS® # 4773852

Photo of Listing #4790057

530 Richmond Rd, Winchester

$264,900 - 3 Beds, 2 Baths, 1,751 Sf

MLS® # 4790057

Photo of Listing #4692214

995 Keene Rd, Winchester

$224,000 - 230 Acres

MLS® # 4692214

Photo of Listing #4738222

Keene Rd, Winchester

$199,000 - 64 Acres

MLS® # 4738222

Photo of Listing #4788229

42 Parker St, Winchester

$175,000 - 3,967 Sf

MLS® # 4788229

Photo of Listing #4785087

182 Ashuelot Main St, Winchester

$149,000 - 3 Beds, 1 Baths, 1,496 Sf

MLS® # 4785087

Photo of Listing #4793030

21 Mechanic St, Winchester

$139,900 - 3 Beds, 2 Baths, 2,005 Sf

MLS® # 4793030

Photo of Listing #4752444

180 Ashuelot Main St, Winchester

$125,000 - 3 Beds, 1 Baths, 1,999 Sf

MLS® # 4752444

Photo of Listing #4747211

30 Keene Rd, Winchester


MLS® # 4747211

Photo of Listing #4793971

62 Richmond Rd, Winchester

$114,900 - 3 Beds, 1 Baths, 1,565 Sf

MLS® # 4793971

Photo of Listing #4781208

Lot 37 Bolton Rd, Winchester

$89,900 - 14 Acres

MLS® # 4781208

Photo of Listing #4766280

86 Lake Shore Dr, Winchester

$60,000 - 1 Acres

MLS® # 4766280

Photo of Listing #4511067

411 Warwick Rd, Winchester

$55,000 - 5 Acres

MLS® # 4511067

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Listing information last updated on February 23rd, 2020 at 6:22am EST.