Chester, MA homes for sale & real estate

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

Chester, MA Homes for Sale

Fabulous Estate Property with ponds, rushing streams, huge acreage and a gem of a house. The 220 acres abuts state forest and beautiful Walker & Spark Brooks both run through the property. The 2BR/2.5B home has lovely views of the pond and hills beyond, and was totally renovated to the highest standards in 2023 and 2024. Native stone fireplace, heart pine floors, new kitchen, baths, heating, windows & insulation. There is a large post & beam barn plus stone foundations from an earlier barn. The fishing is great and trails have been cleared for hiking and horseback riding. Total privacy with 4,000 feet of road frontage. Conveniently located near Tanglewood, Jacobs Pillow an

Chester, MA Homes for Sale

Charming 3BR Cape style home with a beautiful solarium, plus a screened porch located on 11 acres. Sit on a bench and enjoy the babbling brook or listen to it from the heated solarium, the screened porch or the deck. This lovingly cared for home is immaculate with a recently renovated kitchen. The walk-out lower level could easily be finished for additional living space. Nicely located on a quiet road, but near Jacobs Pillow, Tanglewood and most other popular Berkshire destinations, the town beach at Center Pond and numerous State Forests and wildlife areas, yet under 3 hrs. to NYC and 2.5 hrs. to Boston.

Chester, MA Homes for Sale

An inviting 5 bedroom, 3 bath Contemporary home nestled on almost 6 acres of woodland. Open floorplan, Master suite on 2nd floor, cozy wood burning fireplace and expansive family room on basement level. Plenty of storage throughout, including walk in closets & 2 cedar closets. 2 large decks both with built in seating- one on the south side of the house, accessible by 2 sliding glass doors & one stand alone with a 6 person hot tub, large seating area, a fridge & storage space, accessible via a lighted stone walkway. Solar roof panels & a Tesla battery power the property. Lovingly cared for home with mature landscaping & irrigation system. All the best that Becke