Chesterfield, MA Homes for Sale

Chesterfield, MA, is a rural hillside community in Hampshire County known for its natural beauty and seclusion. With abundant trees, farms, and brooks, Chesterfield offers a peaceful lifestyle, especially appreciated by its 1,200 residents, 40% of whom are aged 60 or over. The town is located about 45 minutes north of Springfield and 15 miles from Northampton, home to Smith College and a variety of retailers and restaurants. Outdoor enthusiasts can enjoy scenic hikes and cross-country skiing at Chesterfield Gorge Reservation, which features a dog-friendly trail along the Westfield River and connects to Gilbert A. Bliss State Forest. Russell Memorial Park provides local amenities such as a playground, skate park, baseball field, and tennis court. Winters can be cold and snowy, often extending into April, but winter recreation options like snowshoeing are available. Homes in Chesterfield are typically farmhouses and Cape Cod-style, many with large lots and waterfront views. Community engagement is fostered through events organized by the Council on Aging and the Chesterfield Library, which hosts the Family Harvest Festival and offers passes to local museums. Dining options are limited within Chesterfield, but the Chesterfield General Store and Café and Bread Euphoria Bakery & Café serve local and organic fare. For more extensive shopping, residents travel to Northampton, 15 miles away. Students attend schools in the Hampshire Regional School District, with New Hingham Regional Elementary and Hampshire Regional High School providing education from prekindergarten through twelfth grade.