Chester, MA homes for sale & real estate

Chester, MA Homes for Sale

Be the first to live in this newly built split-entry home in Becket. Located in the Sherwood Forest community, it is just a few minute walk away from the private beach and lake. A private, fenced-in yard with gated access welcomes you on arrival. Exterior highlights include a deck overlooking serene wooded views and a covered patio below—perfect for outdoor entertaining. The main level offers an open-concept layout with a light-filled living room flowing into the dining area and kitchen. The kitchen features an island, new stainless steel appliances, shaker cabinets, and quartz countertops. This level also includes two bedrooms and a full bath. The partially finished lower level provi

Chester, MA Homes for Sale

Set in a picturesque rural landscape, this charming 1920s Colonial blends timeless character with the warmth of country living. With over 1,500 sq ft of potential living space and an outbuilding ready for customization, it offers both charm and modern convenience. The kitchen includes plenty of storage a large island and modern appliances, and opens to a welcoming dining room perfect for hosting family and friends. Upstairs, three bedrooms provide ample space for the whole family, with room to grow in the walk-up attic. Recent updates include an oil tank (2023) solar panels (2024) and security system, along with blown in insulation from mass save (APO). The fenced backyard features a swim

Chester, MA Homes for Sale

Waterfront home on Robin Hood Lake. Facing west for sunny days and evening sunsets. Two bedrooms, 1 bath, open floor plan and a big sunny deck. Propane heat and mini splits. Rare opportunity to own a true lakefront home in this price range.

Chester, MA Homes for Sale

Riverside retreat or income opportunity — your choice! Perched along the Middle Branch of the Westfield River, this cozy log home is the perfect mix of rustic charm and modern comfort. Soaring wood ceilings, big windows, and a warm pellet stove set the scene for relaxation. The loft bedroom overlooks the water, and the main floor offers a full bath and laundry. Recent updates include a new septic (2020), newer roof, windows, and well pressure tank. Step onto the riverside deck and let the sound of the water melt the day away, or get creative with the large, versatile shed. Whether you’re dreaming of a peaceful getaway, a year-round haven, or a short term rental, this Huntington

Chester, MA Homes for Sale

Home in need of extensive repair or demolition. An exceptional opportunity awaits with this expansive 58-acre parcel nestled in the scenic hills of Huntington, Massachusetts. Offering thousands of feet of buildable road frontage, this rare tract of land is ideal for residential development, a private estate, or a variety of commercial or agricultural uses (buyer to verify zoning). The gently rolling topography, mature woodlands, and multiple access points from the road make this property uniquely suited for subdivision or large-scale construction projects. With ample road frontage, you’ll find multiple potential driveway or building site locations — minimizing infrastructure cos

Chester, MA Homes for Sale

Set on 47 wooded acres at the end of a private quarter-mile drive, this Worthington retreat blends history, privacy, and craftsmanship. The main residence, an 18th-century style Cape built in 1990, features 2 bedrooms, 1.5 baths, 3 Rumford fireplaces, wide pine floors, shiplap paneling, hand-troweled plaster walls, antique hardware, and a custom kitchen with stone counters and handcrafted cabinetry. Sweeping views of the valley and distant hills. A detached guest house—the Sam Hill House, originally built in 1783 and carefully reassembled here in 1990 provides a study, bedroom, foyer, full bath, plus garage and storage. The grounds are framed by 19th-century stone walls, mature garden