655 properties for sale in Cheshire town, Berkshire County Massachusetts

Investment opportunity or owner-occupied two-family flat close to town! This property features a 2-car detached garage, large backyard, and a scenic setting along the Southern Branch of the Housatonic River. The first-floor unit offers 2 bedrooms, 1 full bath, and in-unit laundry, while the second-floor unit includes 1 bedroom and 1 bath. Recent updates include a new roof on both the house and garage in 2022, and a new forced hot air heating system installed in 2020. Additional features include some vinyl replacement windows. A convenient location with easy access to town amenities. This is a solid option for investors or buyers looking to live in one unit and rent the other

8 Unit investment opportunity! Located just outside of downtown Pittsfield and within walking distance to shops, restaurants, schools, and parks. Low maintenance exterior with loads of off street parking. All units feature one bedroom/studio setups with separate heat and electricity. Coin-op laundry located on site for additional income

Live, Love, and Play in Blythewood Estates a private enclave near premier Lake Onota to experience idyllic living in the Berkshire hills. This stunning modern 6000+ sf, 5 Bedroom, 5.5 bath colonial is thoughtfully designed and beautifully set on 3.42 manageable acres with sweeping meadow views nestled perfectly to create peace in nature while centrally located minutes to the culture, arts, museums, fine and eclectic dining and central to Tanglewood and The Clark Art. Three levels of living create a blend of fun and entertainment with a degree of separation on levels. First floor offers one level easy living with a dramatic two story primary bedroom suite. Second floor boasts heightened enjoyment with four spacious bedrooms spanning a second story balcony. Lower level offers a theatre, gym gaming space plus a full bath. Looking to store your collection of toys see the 50 x 40 BONUS outbuilding hosting four bays, oversized doors perfect for the RV-boats, your own private collection of an

Location is a must! Spring cleanup is about to happen. Many improvements by current owners. Roof replaced in past 10 years. Orangeburg pipe replaced from house to street. Furnace replaced. Kitchen redone. Chimney pipe replaced. Just a few updates

Motivated Seller! 1121 North St is a well-cared for home offering comfort, convenience with classic style and some modern updates. Fully fenced backyard. Perfect for pets, gardening, entertaining or relaxing in your own private retreat. Unwind in the bright sunroom with its own gas fireplace for chilly evenings and winter days. The oversized garage opens to a mudroom. Updated kitchen and a half bath on the first floor. Wood floors in dining and living area. Easy access to routes in and out of the Berkshires. Just outside of downtown, yet close to medical facilities, shopping, dining, Pontoosuc Lake, outdoor recreation, cultural activities as well as local ski areas. Come experience the warmth, charm and lifestyle that make this a wonderful place to call home

Welcome to 'Rice Cabin', a charming lakeside retreat on beautiful Onota Lake, one of the Berkshire' most sought-after waterfront destinations. Set on over 150 feet of waterfrontage, this darling wood cabin offers a rare opportunity to enjoy lake living at it best. Spend your days swimming, boating, kayaking, fishing or simply relaxing by the water and taking in the peaceful views. Whether you are seeking a weekend getaway, seasonal escape or the perfect place to create lasting memories, Rice Cabin provides an idyllic setting on one of Berkshire' premier lakes. Opportunities like this are few and far between. Don't miss your chance to own a special piece of Onota Lake waterfront

Cable Mills consists of three former industrial mill buildings restored into beautiful homes featuring 12'-16' tall ceilings, massive windows, exposed brick and beam, steel and timber throughout, stainless steel appliances, granite countertops, gas-ranges, generous closets and in home laundry. Cable Mills offers stunning views of the famed 'Purple Mountains' and the rolling Green River. Homes are one, two or three bedrooms in single level flats, lofts and townhome styles totaling 61 residences. Outdoor spaces including Outdoor Living Room with a fire pit, grills and seating along the river walk. The main building offers a community lounge, gym, interior bike storage, package room, dog wash and on-site professional management. Approximately half a mile to shopping, dining, Williams College and one of the top collegiate golf courses- Taconic Golf Club and in close proximity skiing, hiking, rafting, museums and all the Berkshires has to offer.#CableMills #WilliamstownMA #BerkshiresLiving

Set on Aspen Way in Pittsfield, this well-maintained condo offers a practical layout and easy, low-maintenance living in a desirable community. The main level welcomes you with an open living area featuring a gas fireplace, flowing into a spacious dining area. The kitchen is positioned at the back of the home and is finished with stainless steel appliances and granite countertops, with a slider that opens directly to the deck-an easy extension for outdoor dining or relaxing. The primary suite offers a spacious retreat with a large en-suite bathroom and walk-in closet, while two additional bedrooms share a full bath. Designed for one-level living, the first floor also includes laundry for added convenience. Additional features include a two-car attached garage and a full unfinishe basement, offering ample storage and the potential to create additional living space such as a family room, game room, or home gym. A clean, functional condo with a strong balance of space, convenience, and fu

Bring your vision and creativity to this spacious side-by-side duplex that's been stripped down and prepped for its next chapter. Much of the heavy lifting has already been completed, including extensive demolition work and rough electrical installation. The exterior has also received a 1st of coat of paint. Originally intended to be converted into townhouses and sold separately, the owner's plans have changed, creating an exciting opportunity to customize a property to their needs. One unit offers 4 bedrooms and 1.5 baths, while the second features 3 bedrooms and 1.5 baths. Both units include private enclosed front porches, open rear porches, and spacious layouts ready to be transformed. The walkout basement opens to the backyard and offers additional possibilities. Whether you're looking to create income-producing rentals, pursue a townhouse conversion, or design your dream multi-generational property, this diamond in the rough is packed with potential

Exceptional custom-built home on 3.81 private acres in Pittsfield, offering the perfect blend of luxury, comfort, and privacy. Built in 2003, this well maintained 4-bedroom, 4.5-bath residence features a thoughtfully designed floor plan, driveway alarm, gas fireplace, home theatre system, 2-car heated attached garage with central vac. A private in-law suite, ideal for multigenerational living. An IMPRESSIVE 3,500 sq ft outbuilding providing endless possibilities for contractors, hobbyists, car enthusiasts, storage, or home-based business use. Equipped with a backup generator for added peace of mind. Enjoy peaceful outdoor living with a beautiful koi pond, private surroundings and trails for hiking, ATV's and snowmobiles. A rare opportunity to own a truly unique property in the Berkshires

Opportunity meets lifestyle in this affordable ranch-style home perfectly positioned next to The Spruces-Williamstown's beloved off-leash dog park and walking trail. If you're looking for a budget-friendly entry into the highly desirable Williamstown market, a home within the school district, or a smart investment with strong community appeal, this is it. Just 2 minutes to Williams College and The Clark Art Institute, and 5 minutes to MASS MoCA, offering world-class art and culture nearby. Directly adjacent to The Spruces, enjoy immediate access to scenic trails and a vibrant community space loved by walkers, runners, dog owners, and families alike. Being sold as-is, the home features hardwood floors, high ceilings, and a functional layout. The family room is down to the studs and ready for your finishing touches following a resolved plumbing issue. Update - Brand new subfloor and flooring currently being installed in the sunroom! Bring your creativity, and vision to life-this is an ex

Charming two-family flat offering space, flexibility, and great updates throughout. The first-floor unit features a beautifully updated kitchen and bath, a spacious living room perfect for relaxing or entertaining, and an enclosed front porch filled with natural light. A partially finished basement provides additional living, recreation, or storage space. The second-floor unit offers 2 bedrooms, a bright sunny enclosed front porch, and access to attic space for extra storage. Separate utilities and lead paint compliancy make this property ideal for owner-occupants or investors, while ample off-street parking adds everyday convenience. A wonderful opportunity for rental income, multi-generational living, or investment potential

Tucked into a peaceful wooded setting in Lenox, this architecturally distinctive contemporary home offers 2,189 square feet of living space on a private half acre lot. Designed with an asymmetrical exterior and a split level floor plan spanning three levels, this home offers unique character. Large windows fill the interior with natural light, while the open living areas create an inviting space. With its distinctive contemporary design and solid architecture, this property presents an exciting opportunity for thoughtful updates that can enhance both style and value. A rare chance to create something truly special in one of Lenox's most desirable settings. View in person and experience the warmth, character, and connection to nature that make this home so unique

Offering an affordable path to homeownership, this property is ideal for buyers ready to trade renting for a place of their own or investors looking to expand their rental portfolio. The first floor includes an eat-in kitchen, first-floor laundry, and a flexible room for additional living space. Bring your ideas and make it your own over time. A covered back patio extends your living space outdoors, while the fenced backyard offers room for pets. Conveniently located in the heart of Pittsfield with easy access to downtown, shopping, restaurants, schools, public transportation, and major commuter routes

Uniquely and tastefully renovated one-bedroom end unit condo with open living concept, and fully furnished! (some artwork excluded) Great room with fireplace, recessed lighting, ceiling fans, stainless appliances, microwave with expandable exhaust vent, modern bathroom with double shower, swanstone vanity sink, built in cabinet. Simply move in and live! New central air conditioner in 2012 and new hot water heater in 2015. Pretty laminate floating floor throughout, recessed lighting throughout all with dimmer controls, 7-day programmable thermostats in each room, extra quiet Kitchenaid dishwasher, all soft close upper and lower kitchen and bathroom cabinets, kitchen pullouts, detached garage with automatic opener, big entertaining pavilion and heated inground pool, and low, low HOA fees!

Gorgeous,Cute,Adorable, All three describe this 2 bedroom 1 bath southeast cape. Located on a quiet street this home offers a big private yard and a 2 car garage. The sunroom has new windows and the washer dryer are newer and staying with the house. Gleaming hardwood floors, fireplace and too many other amenities to mention. Come see iit!

Adorable Berkshire Bungalow! Perfect for downsizing or just starting out. A one bedroom, one bath home recently updated. Furnace new in 2021, HW 2024. Privacy screens on deck, look out onto private backyard. The enclosed front porch adds wonderful living space during the warmer seasons. Raised bed gardens are a wonderful for vegetables and flowers

Easy living in this move-in ready contemporary in southeast Pittsfield! Stylishly designed with a flexible floor plan. Enter into a light-filled living space with built-in cabinetry in the entry, spacious oversized eat-in kitchen that that opens to a large rear deck. Kitchen with quartz island/ stainless appliances. Oversized first floor bath with laundry. Additionally find a den/sleeping space with French doors for privacy. Primary suite is the entire upper level and features deep soaking tub. Many options for the finished lower-level walk-out recently enhanced with custom built-in storage. Efficient propane heat/hot water, this is a gem not to be overlooked. Convenient to all Berkshire locations, this like-new home is a must-see for full or part-time living!

Welcome to this impeccably maintained 4-BR, 2 bath residence offering comfort, style, and exceptional outdoor living. The updated kitchen features all new appliances, while the spacious layout provides plenty of room for family, guests, or a home office. Potential 1st floor BR! Step outside and discover your own private backyard retreat. Relax under the covered porch, entertain on the dining patio, or gather around the fire pit on cool evenings. Beautiful gardens add color and charm throughout the seasons, and the above-ground pool provides the perfect place to cool off and enjoy summer fun. Additional features include a one-car garage, well-maintained mechanicals, and pride of ownership evident throughout. Close to dining, shops, bus route and hospital! MOVE IN REA

Perfect vacation or full-time Condo in a great spot at The Pines at Bousquet. Tons of year round activities at your finger tips in the Berkshires. This fabulous End unit has 3 stories of finished space including 5 Bedrooms, 4.5 baths, eat-in kitchen, large living room with gas fireplace and large den in lower level. An abundance of natural light throughout with tons of windows, a great feature for this end unit. A First floor Primary bedroom with en-suite full bath is a bonus. Other features include a screened in porch with an awesome view, lower patio perfect for your grill and entertaining and plenty of windows. Enjoy the 2021 renovations at Bousquet Mountain Complex, plenty of shopping close by and many cultural activities. This condo currently has tenants with a lease in place to Feb. 2028. See Realtor remarks for more details. Don't wait to see this Great Condo with monthly income in place

Located in Southeast Pittsfield, this well-maintained Colonial offers timeless charm, thoughtful updates, and a floor plan that feels just as functional today as it did when it was built. Hardwood floors run throughout the home, and the inviting living room is anchored by a wood-burning fireplace with a bright sunroom just beyond-perfect for a home office, reading nook, or additional living space. The kitchen features granite countertops, cherry cabinetry, stainless steel appliances, and plenty of workspace, while the formal dining room provides the ideal setting for everyday meals or entertaining. Just off the kitchen, a mudroom and full bath create a convenient everyday entrance with direct access to the backyard. Upstairs, you'll find three bedrooms, including a spacious primary bedroom, along with a full bathroom. Step outside to enjoy a deck and patio overlooking the fully fenced backyard, offering a private space to relax, garden, or entertain. Two storage sheds provide plenty of

Located in a desirable neighborhood in Southeast Pittsfield, this three-bedroom, 1.5-bath home offers comfort, versatility, and exceptional value. The main residence features spacious living areas, large primary bedroom with walk in closet and laundry room, and a functional layout designed for everyday living. A standout feature of the property is the attached first floor apartment with an additional bedroom, and additional bathroom, perfect for extended family, guests, rental income, or a private home office. The property also includes an insulated workshop/barn, providing ample space for hobbies, storage, equipment, or small business needs. Enjoy outdoor living in the fenced backyard, ideal for pets, gardening, entertaining, or simply relaxing in your own private retreat

Welcome home to this sweet split-level in desirable Southeast Pittsfield neighborhood. Offering 3 bedrooms and 1.5 baths, this well-maintained home features a spacious, well-appointed kitchen with granite countertops, abundant cabinetry, and great functionality for everyday living. Cozy up by the wood-burning fireplace or unwind in the inviting four-season room overlooking the deck and backyard. A walk out lower level is perfect as a home office, mudroom, or home gym, and there is and abundance of storage in the basement. Generously sized yard offers space to garden, play, or entertain. Just a short distance to nature tralis at both Brattlebrook Park, Kirvin Park and Canoe Meadows, this is a wonderful opportunity to enjoy comfortable living in a location you'll love

Welcome to 184 Melbourne Road in Pittsfield. This ranch style home boast two generously sized bedrooms, full bath, an open concept living room, kitchen and dining room. This home has been beautifully renovated and maintained throughout the years and it shows. Some of the recent updates include freshly refinished hardwood floors throughout, fresh interior paint, granite countertops, a large island complete with prep sink amongst many others. As you enter the home you are warmly greeted by an abundance of natural light. An attached one car garage adds to the functionality of this move in ready home. It is perfectly placed on approximately 0.59 acres of flat terrain. Don't miss the opportunity to make this your forever home!

3 bedroom, 1 bath ranch in Pittsfield's desirable Orchards neighborhood! Featuring beautifully refinished hardwood floors, this home offers comfortable one level living with plenty of potential to make it your own. Enjoy morning coffee or unwind in the screened porch overlooking the backyard. Additional features include a one car garage, full basement offering ample storage or workshop space, and a convenient location close to parks, schools, shopping, restaurants, and downtown amenities. A solid home in a great location. Don't miss this wonderful opportunity!