655 properties for sale in Cheshire town, Berkshire County Massachusetts

Own a Living Masterpiece. Meticulously curated by the current stewards since 2006. This Colonial Revival offers rare fusion of 18th-century authenticity and cutting-edge modern comfort. Designed for both grand-scale entertaining and intimate family life, this c1930, 7,894 sq. ft Colonial Revival offers 6-bdrms and 4.5-baths. The interior is a treasure of artisan craftsmanship from the formal dining room with its magnificent shell-carved cove, to original cabinetry with rare wood inlays, hand-carved bookshelves, a classic butler's pantry, multiple stately fireplaces anchor the formal living spaces. Enjoy panoramic views and privacy from the grand porch overlooking 4 pristine acres. a state-of-the-art kitchen featuring Wolf and Sub-Zero, and no expense spared Geo-Thermal heating/cooling

Enjoy this beautiful property on Williams St. Large yard consisting of 2 lots with pastoral views across the street. This 4 large bedroom, 1 full and 2 half bath home is just waiting for your interior decorating ideas Hardwood floors in most rooms, fireplace living room, large dining room. Central air conditioning, Basement partially finished, including 1/2 bath. New roof in 2020 and solar panels replaced. Updated electrical, furnace serviced 2/25. New sewer line this month Solar Panels are owned and for hot water only

Sweet and Petite Cozy Colonial Centrally located and easily accessible, this charming 2-bedroom, 1-bathroom Colonial is ready to welcome its next owner. Enjoy peace of mind for years to come with recent improvements, including a new roof (2023), new boiler (2024), and an updated electrical panel (2024). Inside, you'll find a freshly painted interior and a refreshed bathroom (2024). Looking for a little extra flexibility' The lower-level bonus room offers great additional space for a home office or hobby room. Set on a manageable, low-maintenance lot, this home allows you to spend your weekends relaxing rather than doing yard work. Come see for yourself!

Spacious Southeast Pittsfield Ranch with great bones and endless potential! Generous room sizes and a thoughtful layout provide a wonderful foundation for additional updates that will make this home your own. A brand-new furnace offers added peace of mind, while the unfinished basement is ready for your vision, whether additional living space, a workshop, or recreation area. Outside, you'll find a dreamy backyard with exceptional privacy, perfect for relaxing, entertaining, or gardening. The property's strong fundamentals, desirable location, and setting make it an outstanding opportunity! Dog lovers will delight in nearby Kirvin Park with it's babbling brook and hiking trails just a half mile away

Welcome home to this three-bedroom, one-bath ranch conveniently located in Pittsfield offering the perfect blend of comfort and convenience. Separate dining area, open to living room with a cozy fireplace and a large picture window. This home offers one-level living and a functional layout perfect for everyday easy living. With a little cosmetic updating, this property presents a fantastic opportunity to add your personal touch and build equity. This property is a wonderful opportunity for first-time buyers, downsizers, or anyone seeking a manageable home. One car attached garage and lovely yard in a desirable location!

This custom-built home seamlessly blends country tranquility with modern convenience. Inside, a gracious foyer leads to formal and informal first floor living spaces designed for comfortable living and gracious entertaining. 4 bedrooms, 3 full and 2 half baths, including a large spacious primary suite, guest room with en suite bath, private home office, well appointed eat- in kitchen with sliders to deck and yard, a screened porch and 2 fireplaces that add warmth and character. The partially finished lower level offers a spacious family room and home gym while the unfinished space provides ample storage. 3 -car garage and spacious mudroom and first floor laundry. A rare opportunity to enjoy privacy, space, and the very best of Berkshire living. Moments from Pittsfield State Forest, Onota Lake, vibrant downtown dining, cultural attractions, and a short drive to Tanglewood, the location is truly exceptional

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

Classic two family brick colonial with many possibilities! Including a front/rear porch, two separate yards on each side, and off street parking. Enter each side into a wide, open hallway with the original hardwood floors throughout. The left side has four bedrooms and one bathroom with potential for a second bathroom off the kitchen. The right side has been split into two smaller units with separate kitchens and bathrooms but originally was a three bedroom apartment. Each unit has its own heating, hot water, and electrical systems

Presenting a distinguished multi-family property located at 53 Orchard St, Pittsfield, MA. This expansive 4 unit spans 2688 square feet of living area, offering a rare opportunity for sophisticated urban living or a strategic investment. This property includes six generously proportioned bedrooms, providing ample private accommodations across its two stories. The property's substantial lot size of 4160 square feet provides a significant footprint within the urban landscape. We invite you to discover the potential and unique character of this Pittsfield address. Three Units are vacant and recently remodeled with market rents averaging about 1395.00 in the area. One Unit is rented month to month at 950.00

Renovated 4-family home, located on a corner lot in a great location in Pittsfield. There are two units on the first floor and two units on the second floor. The upstairs units also feature additional bonus space in the finished attics. Major updates were done in 2023-2024, with improvements that include new roof, new windows, new exterior doors, new second egresses for both upstairs unit, and new custom made fence. This is a solid building with 3,280 Sq ft and lots of character, and one of the most beautiful ones in the city! *Since the property sits on a corner, it is also known as 4 Courtland Pl. Pittsfield, MA 01201

Welcome to this spacious 3-bedroom, 2-bath home offering 1,920 square feet of living space in Pittsfield's desirable Morningside neighborhood. This home blends classic character with several major updates already completed, including a newer roof (2025), replacement windows, oil tank (2024), boiler (2019), and sewer line (2019). The flexible floor plan provides plenty of room for everyday living, entertaining, or multi-generational needs. Enjoy an eat-in kitchen, full basement with interior and exterior access, a detached one-car garage, and a generous lot with mature landscaping. Conveniently located near parks, schools, restaurants, shopping, and downtown Pittsfield. Located in an RM-zoned district, this property may offer future multi-family or investment potential, subject to buyer due diligence. Property is being sold AS IS. A great opportunity for investors, cash buyers, or conventional financing buyers looking to add value while building equity through cosmetic improvements

Own Pittsfield History in this distinctive solidly built Georgian-style brick estate set proudly atop a hill in this coveted enclave of stately residences. Live on historic Crofut St. near the esteemed Pittsfield Country Club, Up Street Cultural Art District and ideally minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional detail and character boasting five bedrooms, two and half baths thoughtfully improved by this long term owners' commitment to preservation and restoration. This prominent manor style home MAY BE coupled with the neighboring Little Red Guest House with 3 bedrooms, 2 bath, first floor in-law suite and 2 car garage to host family, friends. Enjoy carefree ownership central to all that is Berkshire!

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!

Own a Living Masterpiece. Meticulously curated by the current stewards since 2006. This Colonial Revival offers rare fusion of 18th-century authenticity and cutting-edge modern comfort. Designed for both grand-scale entertaining and intimate family life, this c1930, 7,894 sq. ft Colonial Revival offers 6-bdrms and 4.5-baths. The interior is a treasure of artisan craftsmanship from the formal dining room with its magnificent shell-carved cove, to original cabinetry with rare wood inlays, hand-carved bookshelves, a classic butler's pantry, multiple stately fireplaces anchor the formal living spaces. Enjoy panoramic views and privacy from the grand porch overlooking 4 pristine acres. a state-of-the-art kitchen featuring Wolf and Sub-Zero, and no expense spared Geo-Thermal heating/cooling

Welcome to this beautifully built new construction home offering the perfect blend of style, efficiency, and comfort. Featuring 2 spacious bedrooms and 1.5 bathrooms, this thoughtfully designed home boasts an open-concept layout with bright natural light, modern finishes, and quality craftsmanship throughout. The main living area flows seamlessly into the kitchen and dining space, creating an inviting atmosphere ideal for everyday living and entertaining. The kitchen offers sleek cabinetry, contemporary fixtures, and ample counter space. Upstairs, you'll find two generously sized bedrooms and a full bathroom designed with clean, modern touches. Enjoy the convenience of a first-floor half bath, energy-efficient systems, low-maintenance construction, and a first-time live-in experience

Rarely does a property offer both 102 private acres and the convenience of one-level living. Set in the low-tax town of Rowe, this well-maintained home offers peace, privacy, and endless possibilities. The open floor plan features a primary bedroom suite with a private bath and walk-in closet on one side, and two additional bedrooms and a full bath on the other side. First-floor laundry and a versatile mudroom with convenient storage connect to the oversized two-car garage, while a separate shed provides additional space for tools and equipment. The finished lower-level family room adds additional living space. Enjoy the sun-filled enclosed front porch and the 14' x 26' rear deck overlooking a peaceful setting surrounded by nature and wildlife. Just 22 years young, this exceptional property is just minutes from Pelham Lake's resident beach, the Deerfield River, Berkshire East Mountain Resort, and many opportunities for hiking, fishing, skiing, kayak and year-round outdoor recreation

Welcome to 22 Wealthy Ave located in the desirable Yankee Orchards neighborhood. Fresh, bright, and move in ready, this thoughtfully renovated home features beautifully refinished hardwood floors, a main level bedroom and full bath, plus two additional bedrooms upstairs with cedar lined closets, built in dresser drawers, and a newly renovated full bath. The updated kitchen includes a farmhouse sink, dishwasher, refrigerator, and oven/range. An attached garage with a new epoxy floor offers direct access to both the home and basement, where laundry hookups are conveniently located. Close to shopping, parks, schools, and downtown Pittsfield

Welcome to this charming four-bedroom, three-bath home nestled in a desirable Southeast Pittsfield neighborhood. Lovingly maintained and well insulated through the years, this home offers a warm and inviting atmosphere with a wonderful blend of original character and everyday comfort. Inside, you'll find hardwood flooring, spacious bedrooms, two first-floor bedrooms and 2 full bathroom, and an expansive addition at the rear of the home that provides flexible living space to suit your needs. The generous mudroom offers excellent functionality and storage, while updated windows help enhance efficiency and natural light throughout. The partially finished basement provides additional living or hobby space, along with ample storage opportunities. Outside, enjoy beautiful flowering gardens and mature landscaping that create a welcoming setting throughout the seasons. Filled with charm and ready for your own personal updates and touches, this well-cared-for home offers a wonderful opportunity

Welcome to 246 Dalton Ave, a charming colonial-style home nestled in the heart of Pittsfield, MA. This delightful residence features four spacious bedrooms and one and a half baths, perfect for families or those seeking extra space. The home does offer potential for a 1st floor bedroom as well. The classic architecture is complemented by modern updates, providing a cozy yet stylish living environment. Conveniently located, this home is just minutes away from local amenities, parks, and schools, making it an ideal choice for busy lifestyles. The detached two-car garage offers ample storage and parking, adding to the home's functionality. Enjoy the inviting backyard, perfect for gatherings or relaxation. Don't miss the opportunity to make this lovely property your own!

This property has an immaculate fenced in back yard for all your summer activities. Inside boasts beautiful hardwood floors, Full bath on the 1st and 2nd Level. Large mudroom from the main entrance for all you winter and mud season needs. A paved driveway with plenty of private parking. A walkout from the lower level to the parking area with a tuck under car port. Recently painted exterior and a screened in porch in the back. 3 large bedrooms and a perfect den for office space or media room. Centrally located in the Berkshires within close proximity to Shopping, Groceries Stores and Tanglewood!

This 3-bedroom, 2-bath ranch sits on a quiet street in one of Pittsfield's most desirable areas. The home has been meticulously maintained with an efficient layout and no wasted space. The kitchen was fully updated with quartz countertops. The basement has also been updated, adding real living space, not just storage. Both bedrooms have California Closet built-ins. Outside, a 32x16 inground pool with a new gas heater anchors the backyard. A newly installed front patio adds another spot to sit outside. There's also a 2-car garage. Meticulously maintained, right down to the details, this is a rare find on Pittsfield's East Side

Presenting a distinguished multi-family property located at 53 Orchard St, Pittsfield, MA. This expansive 4 unit spans 2688 square feet of living area, offering a rare opportunity for sophisticated urban living or a strategic investment. This property includes six generously proportioned bedrooms, providing ample private accommodations across its two stories. The property's substantial lot size of 4160 square feet provides a significant footprint within the urban landscape. We invite you to discover the potential and unique character of this Pittsfield address. Three Units are vacant and recently remodeled with market rents averaging about 1395.00 in the area. One Unit is rented month to month at 950.00

Move right into the vacant unit and start generating income from the other. The property includes a small, easy-to-maintain yard, perfect for enjoying outdoor space without extensive upkeep. While there is no off-street parking, the property's functional layout and income-producing potential make it an excellent value. Whether you're looking to owner-occupy or expand your investment portfolio, this duplex is ready for its next owner

Welcome to this spacious 3-bedroom, 2-bath home offering 1,920 square feet of living space in Pittsfield's desirable Morningside neighborhood. This home blends classic character with several major updates already completed, including a newer roof (2025), replacement windows, oil tank (2024), boiler (2019), and sewer line (2019). The flexible floor plan provides plenty of room for everyday living, entertaining, or multi-generational needs. Enjoy an eat-in kitchen, full basement with interior and exterior access, a detached one-car garage, and a generous lot with mature landscaping. Conveniently located near parks, schools, restaurants, shopping, and downtown Pittsfield. Located in an RM-zoned district, this property may offer future multi-family or investment potential, subject to buyer due diligence. Property is being sold AS IS. A great opportunity for investors, cash buyers, or conventional financing buyers looking to add value while building equity through cosmetic improvements

Own Pittsfield History in this distinctive solidly built Georgian-style brick estate set proudly atop a hill in this coveted enclave of stately residences. Live on historic Crofut St. near the esteemed Pittsfield Country Club, Up Street Cultural Art District and ideally minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional detail and character boasting five bedrooms, two and half baths thoughtfully improved by this long term owners' commitment to preservation and restoration. This prominent manor style home MAY BE coupled with the neighboring Little Red Guest House with 3 bedrooms, 2 bath, first floor in-law suite and 2 car garage to host family, friends. Enjoy carefree ownership central to all that is Berkshire!