Chester, MA Houses for Sale

A diamond in the rough! Located on a country road with expansive views. Rustic ranch-style farmhouse with a western flair. Notable improvements in the last 10 years roof/windows/skylight/furnace and updates to the electric. Generous open floor plan for the kitchen and living room with peaceful outside views to expansive skies. Second floor heated studio with approximately 385sf, potential to

Debra Petrovsky Donovan Real Estate

Tucked just minutes off Route 112, this well-maintained 2,644 sq ft cedar-sided Colonial is located in Chester, with full services provided by the town of Huntington. Set on 4.25 private acres abutting state land, the property offers scenic views, a peaceful pond, and charming stone walls—creating a picturesque and tranquil setting. Inside, the spacious kitchen is ideal for entertaining, with

Darcie Gasperini Taylor Agency

Charming riverfront home in historic Chester, close to all main attractions in Berkshire County and the college towns of Amherst and Northampton. The house has been lovingly maintained as a short-term rental since 2018, with excellent occupancy rates for visitors looking for a quiet getaway with a small town atmosphere while also central to all of Western Massachusetts. Single floor living,

Stephen Daoust STONE HOUSE PROPERTIES, LLC

Complete privacy awaits you in this charming Cape-style home! Perfect for easy entertaining, the home features a spacious three-season lanai with a wet bar, a covered patio, a large level yard, vibrant flowering gardens, and raspberry and blueberry bushes — plus a barn for added versatility. Inside, the cozy living room with a wood stove opens seamlessly to the kitchen, which is outfitted with

Denise DeSellier Berkshire Hathaway HomeServices Realty Professionals