Discover the perfect setting for your dream home on this gently sloping, 1.4-acre lot located in the rural countryside of Cheshire. With breathtaking views and a cleared, ready-to-build landscape, this property offers the ideal blend of privacy and natural beauty. Situated on a town-maintained road and includes drilled well and perc test. Additional 1.4 acre adjacent lot available.

Welcome to the quaint town of Cheshire, this 2-unit rental is situated in center of town convenient to coffee shop, town hall, post office, Ashuwillticook Rail Trail, local activities & more. Lower level unit is vacant - easy to show. Some charming details remain in the 2nd floor unit - tin ceiling in living room, spacious eat in kitchen. New septic system installed 2025, certificate of compliance.

Welcome to this expansive ranch style home set on a peaceful acre with scenic views of a babbling brook and beautiful woodlands. Designed for easy one-level living, this home features two bedrooms and full bath in addition to a spacious primary en-suite with sliders that open to the outdoors-perfect for enjoying morning coffee or wine under the stars. The living and dinning room combination impresses with soaring vaulted ceilings, wood floors throughout, and a cozy wood-burning fireplace that creates a warm and inviting atmosphere. Plenty of room for hosting all of your family and friends both inside & out! The thoughtfully positioned home overlooks the brook and generous yard, offering both beauty and privacy.

Nestled in the heart of downtown Cheshire, this beautifully updated New England farmhouse blends classic charm with modern comforts. Featuring a convenient first-floor bedroom and full bath, plus two additional bedrooms and a second full bath upstairs. The recently renovated kitchen boasts granite countertops, abundant cabinet space, stainless steel appliances, and an abundance of natural light. Enjoy Berkshire summers relaxing on the spacious back decks or lounging on the shaded front porch, all with new composite decking and railings. Located within walking distance to the scenic Ashuwillticook Rail Trail and less than a mile from Cheshire Lake. New septic system installed in 2022. Current owner has done extensive upgrades and improvements. See full list under Documents.

Super spacious Colonial with amazing mountain views! This 4 bedroom / 3 bath home will check all of your boxes. Located towards the top of the Hutchinson Development this home boasts, an enormous primary bedroom, a wood burning fireplace, a completely finished lower level which contains the family room along with a full bath, Granite kitchen countertops, 2892 sq ft of living space, a large 2 bay garage, multi zone heating system and owned solar panels. Outside you'll enjoy the expansive deck with attached gazebo, above ground pool, fully fenced in back yard, firepit and nice size shed. Come see your new home today!

Home on a dream lot--over 7 secluded acres framed by mountains and backing to the Chalet Wildlife Management Area (7,000+ acres of protected state land). Enjoy total privacy, wide-open views, and dark-night skies away from city lights. Step inside to a grand entrance with a glistening chandelier. The main level features a flowing layout: a spacious kitchen with sufficient storage and generous counter space leading to the bright living room. Another feature on the first floor is that there is an option for private living quarters/in-law suite with its own entrance. The large primary suite offers a cozy fireplace, two walk-in closets, and an en suite bath with shower and jetted tub. Additionally, there is a first-floor laundry off the two-car garage, and an extra room great for an office.

Classic country charm awaits you in the foothills of Cheshire Massachusetts and escape home to privacy and serenity in northern Berkshire to live and play in the great outdoors. Enjoy hiking out your door and follow the Appalachian Trail even reach Mount Greylock, bike ride north and south on the Ashuwillticook Trail exercising and exploring the beautiful farmlands and countryside as you immerse yourself in nature for miles and miles. Stay home and escape on your very own 4.5 wood acres for foraging mushrooms and enjoying your fairytale woodland animals with a trail camera in the comfort and warmth of this Berkshire traditional country colonial. Experience quality craftsmanship with wood paneled walls and ceilings blended beautifully with a country pallet of colors on sheet rocked walls

Property on corner of busy 4 way stoplight in the heart of town with 256 ft of frontage. High visibility and high traffic count: 11,777 on average. Multi-zoned for multiple different uses & possibilities. The source of all representations are from the seller or a public source; broker has not verified same. It is recommended that buyer independently verify all information.

Property on corner of busy 4 way stoplight in the heart of town with 256 ft of frontage. High visibility and high traffic count: 11,777 on average. Multi-zoned for multiple different uses & possibilities. The source of all representations are from the seller or a public source; broker has not verified same. It is recommended that buyer independently verify all information.

Exceptional lakeside commercial opportunity with ~820 ft of frontage abutting the Cheshire Reservoir & the Ashuwilticook Rail Trail. Set on 4.71 acres w/ prominent Rte 8 visibility, expansive water views, & immediate trail access along one of the Berkshires' most active recreational trails. AADT 11,200+; w/ addt'l annual foot/bike traffic of 70,000+. Main building ~6,200 sq ft, formerly a popular restaurant, two lakeview cottages (one recently renovated), finished storage garage w/ covered pavilion area, & addt'l outdoor space. Includes a small waterfront piece on the lake side of the rail trail. Located within the marijuana overlay district. Zoning allows a broad mix of commercial, hospitality, recreational, residential, retail & mixed-use options, subject to approvals. Being sold AS-IS.