Cheshire County, New Hampshire

Real Estate in Cheshire County

The Monadnock Region. Explore homes, land, and waterfront property across one of New Hampshire's most distinctive regions.

23
Towns
~76,000
Population
Mount Monadnock
Most Climbed
Keene
College Town

Active Listings in Cheshire County

Updated daily from the MLS

About the Area

Living in Cheshire County

Cheshire County occupies the southwestern corner of New Hampshire, centered around the city of Keene and the iconic Mount Monadnock. Keene State College brings academic energy, while the surrounding countryside is classic New England at its most picturesque.

The Monadnock Region is known for its arts community, covered bridges, and small-town charm. Towns like Peterborough (just across the county line), Jaffrey, and Walpole have attracted artists, writers, and people seeking a slower pace without isolation.

Highlights and Key Features

Why Cheshire County

Mount Monadnock

One of the most climbed mountains in the world. Its presence defines the region's identity and draws hikers year-round.

Keene

A vibrant small city with Keene State College, a historic downtown, strong local food scene, and community events throughout the year.

Arts and Culture

The Monadnock Region has a thriving arts community with galleries, theater companies, and the MacDowell Colony nearby.

Affordable Rural Living

Beautiful farmhouses, colonial homes, and wooded parcels at prices significantly below the state median.

Ready to explore Cheshire County?

Matthew Costantino
Matthew Costantino
Realtor® · Costantino Real Estate LLC

“Every client I work with is trusting me with something important. I don’t take that lightly.”

Contact Matthew