Discover the charm of downtown living in this Colonial home located in the heart of West Stockbridge. This home features four bedrooms, two full baths, kitchen, living room, dining room and a deck overlooking the river. In addition to the main living area the property also includes an in-law or studio apartment with it's own kitchen and bathroom. With a nice flat yard for outdoor activities, outdoor shed for extra storage and backing up to the picturesque Williams River makes this a wonderful opportunity. Open House Sunday, May 3rd from 11 am to 1 pm!

Set along one of Pittsfield's historic corridors, this circa 1815 Federal-style estate offers a compelling study in early American architecture, enduring design, and modern potential. Once a vibrant estate, the property still echoes its past, where landscaping and period lighting brought warmth and presence to the grounds. Inside, a quiet air of English refinement unfolds. Neoclassical detailing defined by raised panel wainscoting with delicate appliques, subtle gilded accents, graceful arched elements, and richly toned hardwood floors, reflecting a tradition of craftsmanship rooted in proportion and symmetry. This remarkable estate presents an opportunity to thoughtfully restore and reimagine a refined country retreat or boutique destination embracing the discovery of the Berkshires.

You'll find classical charm around every corner in this beautiful Victorian farmhouse nestled in the town of Cheshire. The main residence showcases timeless details including hardwood floors, granite countertops, original millwork, and beautifully preserved staircases and trim. The living space features three bedrooms, a full bath, formal dining room, living room and den. An attached two-bedroom guest house or in-law suite provides ideal accommodations for guests or multi-generational living and can also serve as a potential income-producing apartment. Situated on almost a half acre with an oversized barn-style garage. Relax and enjoy Berkshire summer evenings on the spacious front porch, the perfect spot for a hot coffee and a good book.

4 Bedroom 1.5 bath brick cape on over half acre lot, wood floors throughout, fireplace, newly painted, dining room, eat in kitchen, one car attached garage, breezeway, family room in basement.Includes separate 720 square foot ranch with 2 bedrooms, 1 bathroom on property, front porch, vinyl siding, separate utilities

Welcome home to this peaceful & serene 3 bed, 2.5 bath contemporary offering an open floor plan, main-level primary suite, & a private trail leading to the wild streambed of Glendale Brook! The main level features a spacious living rm & dining area w/ propane stove & sliders to a sunny deck, a kitchen w/ pantry closet, half bath w/ laundry, a first-floor office, & a primary bedroom w/ ensuite bath featuring a jetted tub & shower. The lower level provides flexible living w/ a 2nd office, bonus room, 2 beds w/ forest-facing windows, a shared recreation area, kitchenette, full bath & a built-in sauna! An exterior door opens to private trail along Glendale Brook, leading to a natural dipping pool. Additional features include 2 separate meditation rooms w/ own entrances, & a newly replaced furn

The Hatfield House -- a rare 1793 Sheffield antique offering a unique renovated live/work opportunity, move-in ready; the main residence blends historic character with modern systems; including a new sealed basement. A separate one-bedroom apartment with its own entrance provides income or guest flexibility.Set on 1.5 acres with protected wetland views, commercial/residential zoning allows for gallery, studio, office, or home business use inside the adjacent 1,200 sq ft three-bay barn with electricity. Unusual space and privacy adds versatility for a Main Street location. Formerly a famous antiques destination, this property combines history, functionality, and long-term value just a quick drive from downtown Great Barrington.

An 1825 colonial has much of its original charm and features in place - wide plank floors, beamed ceiling, original hardware and fully renovated kitchen. Many new appliances, new windows, and foam insulation in the basement. The well insulated attic and walls along with a high efficiency furnace gives you modern comfort. The house is a legal two family. The Studio apartment is attached and could be a private primary 1st floor suite. The current owner has solid Air BnB income from it as is, or it could be rented year-round. The fully insulated barn/garage has it's own 100-amp service and is currently being used as a woodworking shop. A wood stove and a large loft for storage adds to its utility.

OPEN HOUSE Sat 7/5/25 11a-12:30p Welcome to your private escape in the heart of the Berkshires on a quiet country road. This expansive ranch-style home offers ample space for large family gatherings, house guests or entertaining. Enjoy the ease of one-level living with a bright, open floor plan and a grand brick fireplace anchoring the spacious main living area. The home features four spacious bedrooms and two updated full bathrooms along with a back deck and screened-in back porch overlooking the woodlands. The lower level offers even more flexibility with a private entrance, an additional bedroom, full bath and convenient kitchenette - perfect for guests, in-laws or potential rental income. There is also a large unfinished room with a second fireplace and walk-out access to

Welcome to this beautifully renovated raised ranch located in a highly desirable neighborhood with convenient access to city amenities and cultural attractions. Thoughtfully updated from top to bottom, this home is move in ready offering the perfect blend of style, comfort and flexibility for the Berkshire lifestyle. The open floor plan showcases new engineered wood flooring and a beautiful kitchen designed for gathering, featuring cherry cabinets, stainless appliances and a wonderful large island with butcher block counter and breakfast bar. The main living area is spacious and inviting, centered around the woodburning fireplace. Three bedrooms & two baths on the main floor including a large primary bedroom and primary bathroom. Fully finished in-law space.

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.

Prime location just a short distance to Stockbridge Village, Tangelwood, Berkshire Theatre Group and many more cultural attractions here in the beautiful Berkshires. Sprawling backyard with Housatonic River views. Open common spaces with ample space, exposed beams, character and wood flooring. The second level offers two bedrooms, full bath, large landing flex space and office/sitting area. Additionally there is an attached first floor In-law apartment with living room, kitchen, bedroom and full bath. Included with the house is a multi level barn with electricity. Lovely setting to relax on the back deck and take in the views or stroll into town to enjoy the cultural amenities This gem has great potential and is ready for the new owners vision

This caterpillar has become the most beautiful butterfly....you have to see it to believe! The most tastefully done unit, gutted and re-built to perfection with all high end fixtures, floors, layout, appliances and functionality. New ebony stained hardwood floors, gorgeous kitchen with stainless steel counters, marble island and back splash, Viking appliances, loads of cabinetry and access to the gorgeous deck for 3 season living. Beautiful master suite with an adjoining study, plus a whole bedroom suite with full bath and study on the lower walk out level. The cut stone fireplace in the living room is magnificent and the placement of rooms affords plenty of privacy for guests and owners alike. This unit is truly unique, a labor of love, and awaiting its next discerning owner!

Tucked into a serene neighborhood w/ scenic views & direct abutment to Canoe Meadows Wildlife Sanctuary, this home offers privacy, natural beauty, & mid-century modern feel. Natural light fills the interior, where cathedral ceilings & open living spaces create an airy, inviting atmosphere. The living room, anchored by a working fireplace, flows seamlessly into the dining area and kitchen-ideal for both everyday living & entertaining. A sunporch, accessible from the primary suite & family room, provides a peaceful retreat.The main level features a primary bedroom w/ en suite bath, a second bedroom, full bath, & convenient laundry. The primary suite also includes walk-in closets and direct outdoor access. Upstairs, a private loft, bedroom, & en suite bath offer an ideal

Completed in 2010 and thoughtfully maintained since, this inviting log home offers a blend of warmth, functionality, and connection to its natural surroundings.A wraparound front deck welcomes you in, setting the tone for the home's relaxed feel. Inside, the main living and dining areas flow comfortably together, anchored by a spacious eat-in kitchen with radiant heat flooring, ideal for both everyday living and gathering. The main level features three bedrooms and two full baths, including a primary suite with its own en-suite.Upstairs, a flexible lofted space can serve as an office, entertainment area, or whatever best fits your needs.Out back, a peaceful setting unfolds with a wildlife pond and frequent visits from local birds and animals, best enjoyed from the rear deck.

Ideally located just a short distance from Lenox town center, this thoughtfully updated home blends comfort, style, and convenience. Featuring 4 bedrooms and 2.5 baths, the interior offers warm hardwood floors and a flexible layout. Recent improvements include roof, electrical, appliances, and beautifully enhanced landscaping and hardscaping. The finished walkout lower level, with separate entrance, adds versatile living space ideal for teens, extended stay guests, work, or recreation. Enjoy outdoor living on the large composite deck overlooking a spacious backyard. Complete with a two-car garage and Tesla charging station, this move-in ready property delivers modern amenities in a sought-after Berkshire setting.

Welcome to 11 Sergeant, ideally located on a quiet side street around the corner from Stockbridge's historic Main Street. This property includes a well-maintained main house and a separate barn with ADU potential. The main house features an updated kitchen that opens to a bright den overlooking the backyard. The first floor also includes a powder room, dining room, and formal living room. Upstairs are 2 spacious bedrooms and 2 full bathrooms, with additional finished space on the third floor. The barn offers flexible use with one garage bay, a first floor studio space, and separate guest quarters on the 2nd floor with a large living room/kitchenette and ensuite bedroom.

This beautiful home offers an abundance of natural light through its large, expansive windows, creating a warm and inviting atmosphere throughout. Post and beam construction, well equipped kitchen open to living room (with 30' ceilings) and dining room create ease of entertaining. First floor primary en-suite with a private deck overlooking the back yard and beautiful view. This home also offers a private, spacious first floor in-law suite, plenty of closet space, and sliders leading out to the pool, ideal for extended family or guests. The den is a comfortable meeting space between the in-law suite and the main part of the home where you can sit by then fire on chilly days. Between the hot tub, in-ground pool, and yard it's a complete package! 20 minutes to Williamstown, MA.

Tucked away on a quiet country road just minutes from the heart of historic Stockbridge, this 3.49-acre property pairs timeless New England charm with modern comforts. The star of the show is a beautifully updated red farmhouse with 3 bedrooms and 2.5 bathrooms, set on a sunny, bucolic lot that feels worlds away--yet is moments from downtown.The main house has been thoughtfully renovated, blending original character with contemporary upgrades. Post and beam construction adds warmth and architectural texture, while a sleek gas fireplace anchors the open living and dining areas. The updated kitchen is ideal for gatherings both casual and festive. The first-floor primary suite includes a walk-in closet and private bath. Upstairs, two additional bedrooms and a full bath complete the

This exceptional home is ideally located within walking distance of the town center and Williams College. Set alongside protected conservation land, the property offers a rare blend of convenience, privacy, and natural beauty and is also located in a highly desirable Williamstown neighborhood. The property has direct backyard access to Lower Linear Park walking trails, the Mohican Trail bike path, a public tennis court, a nearby dog park, and river recreation areas, all just a few minutes' walk away.The home features a spacious and private backyard, secluded from the street, which provides a peaceful setting. The yard is beautifully framed by mature landscaping and is complemented by mountain views of the Appalachian Range, which can be enjoyed from a large deck. SEE MORE TAB

Pride of ownership reasonates through this disctinctive Georgian-style brick home proudly set atop a hill in this coveted enclave of stately residences. Live on this historic Crofut St. near the esteemed Pittsfield Country Club, BUpstreet Cultural District and is ideally just 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 over this long term owners' commitment to preservation and restoration. This prominent manor style home MAY BE coupled with the neighboring guest house featuring 3 bedrooms, 1 bath plus a first floor in-law bedroom suite and a 2 car garage, if one so chooses to accommodate extended family, friends or caregiver