Historic character meets modern updates in this beautifully renovated 1880s home! Thoughtfully updated while preserving its original charm and integrity, the home underwent an extensive renovation in 2016, including new electrical, plumbing, insulation, and much more. Beautiful wood floors flow throughout, adding warmth and character. The first floor offers flexible living with a bedroom or home office and a full bathroom. Upstairs, you'll find three additional bedrooms, another full bath, and the convenience of second-floor laundry. There is also potential to expand the primary suite with space for an additional bathroom that has already been roughed in.

Beach days, porch evenings and Tanglewood concerts make this the perfect three-season Berkshire cottage. Vaulted ceilings and a fieldstone fireplace anchor the living room, while two bedrooms and a versatile loft provide comfortable space for family and friends. The screened in-porch extends the living space for long summer afternoons and evenings, while the dining room is filled with windows that bring nature inside. Set in the welcoming community of Mahkeenac Heights, this cottage is just a short walk to the town beach at Stockbridge Bowl and close to the Berkshires' many cultural attractions. A wonderful retreat for enjoying all the Berkshires have to offer!

Discover a unique condo in a converted mill building where historic factory character meets modern style in the heart of Housatonic. Soaring ceilings and beautiful wood floors throughout complement two generously sized bedrooms, one full bathroom, a large living room with views of Flag rock and a spacious dining room. An enclosed porch offers a cozy spot to unwind while a community deck provides space to relax and gather. Enjoy local restaurants and numerous hiking trails just moments away. Come see what makes this distinctive condo such a special place to call home.

Charming ranch set on a level lot along County Route 32 in North Chatham. This 3-bedroom, 1-bath home offers hardwood floors throughout the main living areas, a bright living room that flows into a formal dining room, and a functional eat-in kitchen with ample oak cabinetry. Three comfortable bedrooms and a full bath round out the main level. Enjoy the outdoors from the deck overlooking the backyard, complete with a screened gazebo -- perfect for morning coffee or evening entertaining. An attached two-car garage and full unfinished basement provide plenty of storage and potential for future finished space. Recent updates include a whole-house water softener and filtration system (2025) and brand-new water heater(2026).

This spacious in-town single family home offers a flexible five bedroom, 2.5 bath layout with generous living space throughout. Thoughtfully designed for comfort and versatility, it's well suited for a large household, multi-use living needs, or anyone seeking extra room to spread out. The second floor hosts 2 full bathrooms, ensuring convenience for all, while the first floor boasts a half bathroom and a huge laundry room for added practicality. The home showcases stunning wood floors throughout most of the home, adding warmth and character to the living spaces. Enjoy your morning coffee or evening relaxation on the inviting front porch, or take advantage of the large back deck and gazebo, offering a private and peaceful setting overlooking the lush property.

Get ready to relax in the Berkshires in your own condo with big windows, high ceilings, plus brand new boiler & A/C! Owner retiring and moving down south, giving up his beloved in town Great Barrington location. You'll love being close to stores and provisions for your various adventures, while being close to all the attractions that the Berkshires have to offer. Come experience worry free living while the condo cuts your grass in the summer, or plows your driveway while you ski. 9 Stanley is simply country living at it's best. Come experience it today!

Two nice properties for one price. A newly renovated single home featuring hardwood floors, wrap around porch, two nice size bedrooms, full bath, dining and living room. The two apartment flat next door have five rooms each, two bedrooms, one bath, hardwood floors, porches. Both buildings have new roofs, vinyl siding, and vinyl windows.

Charming three-bedroom, one full bath ranch offering the ease and convenience of one level living in a highly desirable neighborhood. Situated on a spacious lot, just shy of a half-acre, this home features a large, fenced backyard perfect for entertaining, gardening or simply enjoying the outdoors. Wrap around deck overlooking above ground pool, creating the ideal summer setting. Inside you will find a comfortable eat-in kitchen, front living room, updated bathroom and 3 bedrooms. Partially finished basement that provides additional room for a family room, home office, gym and laundry. Conveniently located close to schools and downtown Lee, ''Gateway to the Berkshires''.

Open house cancelled! Charming Cape Living on 1.16 Acres with Beautiful Views Welcome to 27 Madden Road! This inviting 3-bedroom, 2-bath Cape offers comfortable living and a versatile layout. The main level features an open floor plan with a spacious living room and fireplace, eat-in kitchen, full bathroom, and first-floor primary bedroom. Upstairs are two additional bedrooms and a second full bath. The finished lower level adds extra living area with a walkout, perfect for an office, gym, or hobby space. Set on 1.16 acres, there is plenty of room to relax, garden, entertain, and enjoy the surrounding views. Enjoy EZ Solar and property taxes under $800 per year, making this a great Berkshire getaway or year-round home!

Open House: Sunday, November 1st. 11:00am to 12:30pm. Featuring a slate roof, classic architectural details, and modern interior updates, this versatile property is perfect for an owner-occupant looking for rental income or an investor seeking a turnkey Berkshire property. Sprawling Main Unit: Step into an extraordinarily spacious 4-bedroom, 2.5-bathroom primary residence featuring beautiful hardwood floors throughout. Enjoy the character of vintage interior details paired seamlessly with a completely updated kitchen and modernized bathrooms.Upstairs Unit: A bright and efficient 2-bedroom, 1-bathroom apartment complete with its own dedicated laundry--ideal for long-term tenants, a guest suite.

Welcome to this stunning two-family Victorian residence offering an exceptional blend of historical character and contemporary living. Featuring a slate roof, classic architectural details, and modern interior updates, this versatile property is perfect for an owner-occupant looking for rental income or an investor seeking a turnkey Berkshire property. Sprawling Main Unit: Step into an extraordinarily spacious 4-bedroom, 2.5-bathroom primary residence featuring beautiful hardwood floors throughout. Enjoy the character of vintage interior details paired seamlessly with a completely updated kitchen and modernized bathrooms.

An exceptional side-by-side duplex in Pittsfield's desirable Southeast neighborhood, offering two spacious 3-bedroom, 1-bath residences and an ideal combination of comfortable living and income potential. Both units feature bright, inviting interiors, granite countertops, updated finishes, and well-designed living spaces that feel more like individual homes than traditional apartments. The side-by-side configuration provides privacy and separation, making this an outstanding option for an owner-occupant looking to offset housing expenses or an investor seeking a quality addition to their portfolio. A partially fenced backyard offers flexibility for separate outdoor spaces, while one unit includes access to the garage/outbuilding for additional storage and utility.

Move right in and enjoy the ease of one-level living in this beautifully maintained and thoughtfully updated 3-bedroom, 1-bath Ranch, set on just shy of 2 acres in a peaceful neighborhood! The inviting, open-flow floor plan creates a comfortable feel throughout, while the remodeled kitchen features granite countertops and stainless steel appliances. A modern bathroom, three generously sized bedrooms, abundant storage, and a fully renovated basement family room provide plenty of space to live, relax, and entertain. Step outside to your newly resurfaced Trex deck and enjoy the expansive grounds, offering room to garden, play, entertain, or simply unwind in your own outdoor retreat. Conveniently located near downtown, MASS MoCA, local dining and shopping, and scenic hiking and biking trails,

Attention Contractors and Business Owners! An excellent opportunity to own a versatile 50' x 75' (3,750 SF) pre-engineered metal building situated on approximately 0.75 acres with plenty of outdoor space for equipment, vehicles, materials and storage. Ideally suited for electricians, plumbers, HVAC contractors, landscapers and other skilled trades looking for a central location to operate and grow their business. The building features an open warehouse/workshop area, overhead door, office space and loading area, with ample room for parking and outdoor storage. Conveniently located in Pittsfield with Light Industrial (I-L) zoning, offering flexibility for a variety of commercial and light industrial uses. A great opportunity for an owner-operator or investor! Use subject to muni approval.

Beautifully maintained Victorian-style home. This move-in-ready home offers character and charm with modern function. This home hosts a spacious open kitchen, formal dining, den, living room and a half bath, with gleaming oak hardwood floor on the main level. Second level hosts bedrooms and full baths. Enjoy the wrap-around porch and private corner lot, complemented by a 2-car garage, a two-story barn, and extensive landscaping. Built circa 1890, this historic home combines character with modern updates like a new natural gas boiler (2025). Prime location provides easy access to biking trails, golf courses, cultural attractions, and outdoor recreation.

Opportunity awaits in this spacious 4-bedroom, 3-bath Colonial located in the highly sought-after Orchard neighborhood. Offering generous room sizes throughout, this home features a welcoming family room with a fireplace and skylights that fill the space with natural light. The convenient first-floor laundry enhances everyday living. The partially finished basement provides additional flexible space for recreation, a home office, or storage. Recent updates include newer carpeting and a newer roof, offering a solid foundation for future improvements. Outside, enjoy a fenced backyard with a deck. While the home could benefit from some TLC and cosmetic updates, it presents an excellent opportunity to build equity and customize to your taste in a prime location.

This charming Colonial blends classic character with thoughtful improvements, including a GAF roofing system, new Harvey windows, and new gutters adding long term value. Inside, enjoy a kitchen with ample cabinet space, granite countertops, and a new refrigerator, along with refreshed bathrooms, fresh interior paint, refinished original hardwood floors, and the added convenience of a half bath. The large unfinished basement, with a newer heating system and water tank, offers valuable additional space and plenty of potential for future use. Ideally situated along Main Street, the property provides quick access to local shops and outdoor recreation throughout the Berkshires, while being conveniently close to all of Dalton's schools. A great opportunity to make your own.

Enjoy easy one-level living in this set-back-from-the-road home! Featuring 2 bedrooms, 1.5 baths, an eat-in kitchen, comfortable living room, and convenient mudroom. Additional highlights include owned solar panels, updated windows, newer appliances, a basement with hatchway, and a one-car garage. Nice yard offers room to relax and enjoy the outdoors! All room sizes are approximate.

Opportunity Knocks! Expansive Lenox parcel - currently 2 approved building lots (1.0 acre and 14.91 acres) w/ frontage on East Street and New Lenox Road. Seller has a proposed subdivision that would make it 4 lots (1.0 acre, 3.5 acres, 7.59 acres & 2.98 acres). Build your dream home or take advantage of this unbeatable development opportunity in highly sought after location! Water, sewer & gas on property.

Enjoy mountain living at Jiminy Peak Mountain Resort in this spacious 2-bedroom, 2-bath condo offering 1,346 sq. ft. and a short walk to the ski slopes. Both bedrooms and a full bath are located upstairs, providing privacy and comfort. The main level features a full kitchen, second full bath, and inviting living room with a wood-burning fireplace. Step outside to the back deck with a sitting area and BBQ--perfect for relaxing after a day on the mountain. Includes 2 private parking spaces and a strong rental history. An excellent opportunity for a four-season getaway or investment property! You can live here all year round or rent it out for the season or short term for extra income. Pets are welcome. Don't miss this opportunity to own a year round vacation destination condo.