Cheshire County NH Homes for Sale

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View up-to-date homes for sale in Cheshire County, NH. Reach out to Century 21 Highview Realty for more details or to schedule a private tour. Be sure to sign up to save your favorite listings and get notified of new arrivals.

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Cheshire County, NH Real Estate & Homes for Sale

Cheshire County occupies the southwestern corner of New Hampshire, anchored by Keene, the county seat and commercial hub of the Monadnock region. Keene State College and Antioch University New England bring a consistent academic presence to the area, and the city's Elm Street corridor is lined with independent restaurants, galleries, and local retail. Mount Monadnock, one of the most climbed mountains in the world, draws outdoor enthusiasts year-round to the southern part of the county. The inventory across Cheshire County spans in-town single-family homes in New Hampshire and rural properties with acreage in the county's quieter back-road communities.

Frequently Asked Questions

What is the largest city in Cheshire County, NH?
Keene is the largest city in Cheshire County and the commercial and cultural hub of the region. It is home to Keene State College, Antioch University New England, the Colonial Theatre, and one of the widest Main Streets in New England. The city's downtown draws visitors and residents alike with its weekly farmers market and local business community.
Is Cheshire County NH close to Massachusetts or Vermont?
Yes, Cheshire County borders both Massachusetts and Vermont. The southern boundary of the county is adjacent to the Greenfield and North Quabbin areas of Massachusetts, and the western boundary runs along the Connecticut River, which separates New Hampshire from Vermont. Communities like Hinsdale and Chesterfield offer easy access to Brattleboro, Vermont, typically a 30-35 minute drive.
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Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is 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 May 27, 2026 7:53 AM EDT