715 properties for sale in Cheshire town, Berkshire County Massachusetts

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!

Prime investment opportunity in a highly desirable location just steps from the post office and within walking distance to downtown amenities, shopping, dining, and services. This well-maintained four-family property offers strong income potential with all separate utilities, allowing tenants to pay their own expenses and helping to maximize owner returns. Recent capital improvements include a new roof installed in 2022 and two high-efficiency gas furnaces added in 2023, providing peace of mind for years to come. Each unit features washer and dryer hookups, while newer hot water boilers, vinyl replacement windows, and low-maintenance vinyl siding contribute to reduced operating costs and enhanced efficiency. Tenants will appreciate the private paved parking area and detached two-car garage. a rare amenity in such a convenient in-town location. Whether you're expanding your portfolio or seeking a turnkey multi-family investment, this property offers an excellent combination of location,

If you are looking for easy one-level living - don't miss this opportunity! The Maplewood is an elegant condo conversion consisting of eighteen units centrally located in downtown Pittsfield. You'll enjoy this light-filled corner/end unit on the first floor. High ceilings and an open-living plan give a very spacious feel to this two-bedroom unit. Kitchen with granite and stainless, hardwood flooring, stack laundry in the unit, central a/c and natural gas heat. Off street parking, plenty of green space to enjoy nature in this in-town oasis. Conveniently located close to shopping, medical, public transportation and all cultural attractions. Priced well below assessment for immediate !

Beautiful end-unit property featuring soaring ceilings and serene wooded views. The home offers open common spaces with excellent natural light, a screened porch, and a first-floor primary en suite. The second level includes two guest bedrooms, a full bath, and a loft overlooking the great room. Additionally, the lower-level walkout provides significant potential to be finished for extra living space. Residents can also enjoy the association's pool. This property is perfectly situated near Bousquet Mountain to enjoy the many cultural attractions here in the Berkshires

Welcome to 34 Daniels Avenue, part of the Westside Legends Attainable Housing Program. This updated Pittsfield home offers a comfortable layout with recent improvements throughout, including new flooring, new appliances, and refreshed bathrooms. The interior feels clean, bright, and move-in ready, while still offering a practical and manageable footprint for everyday living. Conveniently located near downtown Pittsfield, local parks, restaurants, shopping, and cultural attractions, this home provides an excellent opportunity for qualified buyers seeking attainable homeownership in a central Berkshire location

One of the most exceptional homes to come to market, this remarkable property blends timeless elegance with resort-style living. Featuring 5 bedrooms, 3.5 baths, including private guest quarters with bath and secondary staircase, this home offers both sophistication and versatility. The luxurious primary bedroom suite is a true retreat, complete with a spacious en-suite bath designed for comfort and relaxation. A stunning new kitchen serves as the heart of the home, thoughtfully designed for both everyday living and refined entertaining. Impeccably curated interiors extend seamlessly to breathtaking outdoor spaces highlighted by a spectacular heated in-ground pool, extraordinary landscaping, and meticulously maintained grounds. A true masterpiece of design and luxury living. Join the Country Club of Pittsfield for golf, tennis and pickelball just 1.5 miles away. Downtown Pittsfield's restaurants, museum and theaters are a short 15 minute walk. Drive 15 minutes to downtown Lenox and Tan

Discover a fantastic investment opportunity at 96-98 Brown Street, Pittsfield. This two-family home features a cozy 2-bedroom, 1-bath unit on the first floor, perfect for easy living, and a spacious 3-bedroom, 1-bath unit on the second floor, ideal for owner occupied or Investors alike. Recent upgrades include a new roof, some fresh paint, updated 100 amp electrical panels, new windows, and a recently installed boiler, ensuring peace of mind for years to come. Each unit has separate utilities, enhancing convenience and efficiency. Enjoy the added benefit of off-street parking. With the property being vacant at closing, this gem is ready for your personal touches or rental potential!

Enjoy easy living at the beautiful Greylock Village. This bright and beautifully maintained 3-bedroom, 2-bath condominium offers a thoughtfully designed floor plan with abundant natural light throughout. The main living area features a wood burning fireplace and cathedral ceilings which create an open and inviting space perfect for everyday living and entertaining. The living room opens through a sliding glass door to a private rear deck, providing a peaceful spot to relax and enjoy the surroundings. A first-floor bedroom and full bath offer flexibility and convenience for guests, one-level living, or a home office.This move-in-ready home has been well cared for and thoughtfully updated, including replacement windows, added roof insulation, new flooring and a 4 year old furnace. Additional features include an attached garage and driveway parking for one vehicle.Ideally located close to the community tennis courts and swimming pool, this home combines comfort, efficiency, and low-mainte

Exceptional Investment Opportunity: Versatility and Prime Location Discover a property that offers unparalleled flexibility in one of Pittsfield's most active commercial corridors. Situated on a sprawling 0.92-acre lot directly across from Berkshire Crossing, this unique property presents a rare 'blank canvas' for homeowners and investors alike. Currently configured for mixed-use with a professional office space on the main level and a spacious 2-bedroom apartment on the second floor. Easily convertible back into a large Single-Family home for those seeking significant acreage and convenience in the heart of town

Great location in Southeast Pittsfield. Short walk to downtown Pittsfield. Lovely unit with hardwood floors in the Living room and Bedroom. Nice sized balcony (facing the morning sun) to relax on. Coin operated laundry just a few steps down into the lower level. Storage locker is available in an upstairs area through the door on the balcony. The unit sq footage is 617 and is recorded in the Marianne Inn Condominium Trust deed. PLEASE NOTE: THE ELECTRIC BILL FOR 2025 TOTALED $905.83.

Investor Special! This gutted duplex offers a blank canvas with 6 bedrooms, 2 bathrooms, and 2,000 sqft of space, plus the possibility of additional living space in the attic. this property features a large backyard with a serene water stream, A standing garage remains on site for additional storage or future use. Situated on a 13,108 sqft lot, can also be bundled with 40 Pecks Rd and 48 Brown st (Pittsfield) for even greater investment potential. Endless possibilities await, renovate, rebuild, or reimagine this space to maximize returns! Schedule a showing today!

Excellent 8-Unit Investment Opportunity-5 minute walk to the Lake! Clean, well-maintained multifamily property featuring 8 total units with separate utilities. Each unit includes central A/C. Property offers private, dedicated parking for tenants. Prime location-just minutes from major hospitals, large employers, shopping, and public transit. High-demand rental area with strong occupancy history. Ideal for investors seeking turnkey income with upside potential. Great long-term hold in a desirable neighborhood

Prime investment opportunity in a highly desirable location just steps from the post office and within walking distance to downtown amenities, shopping, dining, and services. This well-maintained four-family property offers strong income potential with all separate utilities, allowing tenants to pay their own expenses and helping to maximize owner returns. Recent capital improvements include a new roof installed in 2022 and two high-efficiency gas furnaces added in 2023, providing peace of mind for years to come. Each unit features washer and dryer hookups, while newer hot water boilers, vinyl replacement windows, and low-maintenance vinyl siding contribute to reduced operating costs and enhanced efficiency. Tenants will appreciate the private paved parking area and detached two-car garage. a rare amenity in such a convenient in-town location. Whether you're expanding your portfolio or seeking a turnkey multi-family investment, this property offers an excellent combination of location,

If you are looking for easy one-level living - don't miss this opportunity! The Maplewood is an elegant condo conversion consisting of eighteen units centrally located in downtown Pittsfield. You'll enjoy this light-filled corner/end unit on the first floor. High ceilings and an open-living plan give a very spacious feel to this two-bedroom unit. Kitchen with granite and stainless, hardwood flooring, stack laundry in the unit, central a/c and natural gas heat. Off street parking, plenty of green space to enjoy nature in this in-town oasis. Conveniently located close to shopping, medical, public transportation and all cultural attractions. Priced well below assessment for immediate !

Introducing 39-41 Bartlett Avenue, a classic three-family Victorian in the heart of Pittsfield, offering a fantastic investment opportunity. This fully occupied property provides immediate income potential and features separate natural gas utilities for each unit. The home boasts vinyl siding and replacement windows, combining classic charm with practical updates. Ideally situated just moments from downtown. Whether you're looking to expand your portfolio or owner-occupy this well-located multi-family is one you won't want to miss

Welcome home to this beautifully maintained, ADA-compliant 3-bedroom, 1.5-bathroom ranch-style home, offering the perfect blend of comfort, accessibility, and modern efficiency. From the moment you arrive, you'll love the excellent curb appeal, featuring durable vinyl siding, updated vinyl windows, and a solar system to curb electric costs. Inside, the home boasts a wonderful, flowing floor plan bathed in abundant natural light. Designed for effortless single-level living, the thoughtful layout accommodates all needs with ease. Step outside into your own flat yard complete with a handy storage shed

Beautiful end-unit property featuring soaring ceilings and serene wooded views. The home offers open common spaces with excellent natural light, a screened porch, and a first-floor primary en suite. The second level includes two guest bedrooms, a full bath, and a loft overlooking the great room. Additionally, the lower-level walkout provides significant potential to be finished for extra living space. Residents can also enjoy the association's pool. This property is perfectly situated near Bousquet Mountain to enjoy the many cultural attractions here in the Berkshires

Charming Condominium at South Pond Farm. 2 bedrooms 2-1/2 baths, brand new kitchen. Panoramic views of Richmond Pond from the living room/dining room and bedrooms. The community offers tennis, heated gunite swimming pool, private beach, kayak, /canoe racks, water aerobics, organized book groups and active social environment

Conveniently located near shopping, dining, and the the Ashuwillticook Rail Trail for biking, walking, and outdoor recreation, this 3 bedroom, 2 bath modified Cape with first floor home office/den, offers comfort and opportunity. Featuring hardwood floors, a spacious deck, and a large backyard perfect for outdoor enjoyment. This well built home has great bones and is ready for its next chapter. The flexible floor plan provides ample living space, while the central location makes daily errands and recreation a breeze. A significant improvement is already underway, with the seller installing a brand-new sewer line prior to closing, providing added peace of mind for the next owner. Don't miss this chance to make this well-located home your own

Designed in 1929 by noted architect Henry Seaver (Berkshire Museum, Lenox Town Hall), this distinguished Georgian Colonial was once the centerpiece of Pittsfield's social scene. The home preserves exquisite 18th-century details - mantels, wainscoting, and finely crafted woodwork salvaged from two of the city's earliest residences, making it a living piece of Berkshire history. Set back on 2.5 private acres along prestigious Crofut Street, the estate offers 5 bedrooms and 5 baths, including twin primary suites ideal for hosting friends and family year-round. Gracious living and dining rooms, a peaceful sunroom, a cozy study, and a large eat-in kitchen with Viking range and butler's pantry combine period elegance with modern comfort. This turn-key estate is offered fully furnished and enhanced by a new heating system. Spend summer days by the heated in-ground pool or evenings on the patio savoring the serenity of the lush, private grounds. Perfectly situated just minutes to Lenox and Tan

Welcome to easy living at 691 Crane Ave, Pittsfield! This single-level ranch offers the perfect blend of convenience and peace of mind, highlighted by a 2-year-old roof and a two-car garage. Inside, you'll find a highly functional layout featuring fantastic space in the basement-an ideal setup for your favorite crafts, a home workshop, or weekend hobbies. Step out back to find a standout feature: a large, fully fenced-in yard that provides a wonderful private outdoor retreat. Nestled in a highly convenient location close to local shopping, dining, and schools, this move-in-ready home is designed for an effortless lifestyle. Don't miss this Berkshire gem!

Exceptional Investment Opportunity: Versatility and Prime Location Discover a property that offers unparalleled flexibility in one of Pittsfield's most active commercial corridors. Situated on a sprawling 0.92-acre lot directly across from Berkshire Crossing, this unique property presents a rare 'blank canvas' for homeowners and investors alike. Currently configured for mixed-use with a professional office space on the main level and a spacious 2-bedroom apartment on the second floor. Easily convertible back into a large Single-Family home for those seeking significant acreage and convenience in the heart of town

Compare for value in the Lenox market! Sweet, petite, move-in ready ranch. Living room and bedrooms with hardwood floors; two nicely updated bathrooms; eat-in kitchen opens to spacious, private rear deck. Bonus features include the oversized two car garage, Buderus boiler for natural gas heat, and over a 1/2 acre of open sunny lawn. Easy access to shopping, dining and all of the Berkshires' cultural attractions

Investor Special! This gutted duplex offers a blank canvas with 6 bedrooms, 2 bathrooms, and 2,000 sqft of space, plus the possibility of additional living space in the attic. this property features a large backyard with a serene water stream, A standing garage remains on site for additional storage or future use. Situated on a 13,108 sqft lot, can also be bundled with 40 Pecks Rd and 48 Brown st (Pittsfield) for even greater investment potential. Endless possibilities await, renovate, rebuild, or reimagine this space to maximize returns! Schedule a showing today!