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.

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

OPEN HOUSE SAT 4/11 12-2PMStep into history with this iconic property known as ''The Hatfield's,'' a beloved antique landmark in Sheffield. Built in 1793, the original home showcases timeless charm and classic architecture. A late-1990s addition created a flexible two-family layout with a one-bedroom, easily converted back to a spacious 3-bedroom, 3-bath single-family home. Recent updates include a new septic, refinished large plank wood floors, fresh interior paint, bathroom floors & fixtures, kitchen, new appliances and professionally sealed & graveled basement. The property also features a commercially zoned 1,400 sq. ft. converted barn with three bays, two units, and a central workshop--ideal for business, studio, or retail use. Set on 1.5 acres with scenic views. More photos to come

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

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

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

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

Immaculate 4800 square foot, 5BR, 4 full bath jewel located at arguably the finest condominium community in The Berkshires. Enjoy looking at spectacular foliage with private panoramic wooded views and open space from the magnificent all seasons room, great room and primary suite. The garden level features a full kitchen as well as a screened in porch. The Buterus furnace system powers baseboard heating/3 zone HVAC. The home has a water filter and water softening system. The oversized garage has a washable neoprene rubber surface and two full car mats. There is an attached workshop and stairwell to a spacious attic. SMF is surrounded by mature landscaping an offers the following amenities: pickleball, tennis, swimming pool, basketball, fitness center, clubhouse and library.

The Ultimate Berkshire Retreat: Designer Luxury with Versatile Income Potential.Experience the pinnacle of refined living in this ''essentially brand new'' masterpiece by Wingate Ltd. Spanning 2,748 sq. ft. across three levels, this reimagined residence sits on one of the Berkshires' most scenic corridors, surrounded by rolling dairy farms and dramatic mountain vistas.Designed for Luxury & Flexibility:Upon entry, a dramatic curved staircase leads to one of three primary suites. The open-concept main floor flows seamlessly, featuring wide-plank white oak flooring, a sleek gas fireplace, and a chef's kitchen with stone counters and marble herringbone tile. The primary retreat is a sanctuary of wellness, offering radiant heated bathroom floors, a soaking tub, tray ceilings, SEE MORE

Set on just over seven acres between Lee and Stockbridge, this c.1850 Greek Revival delivers classic Berkshire character with real scale. Nearly 4,700 square feet with a gracious flow, tall windows, and preserved period details. Every bedroom offers an en suite, creating an easy setup for hosting family and friends. Common spaces include a welcoming foyer, two living rooms, a formal dining room, a library, and a large cook's kitchen with eat-in area and pantry. Three period fireplaces add warmth and charm. Outside, mature trees frame open meadow, with room for gardens, games, and long summer evenings. The setting is remarkably convenient. Tanglewood, Lenox, Stockbridge, and downtown Lee are a short drive, and access to Route 7 and the Mass Pike keeps weekend trips simple.

Welcome to one of Southeast Pittsfield's most coveted neighborhoods, where this exceptional Colonial seamlessly blends timeless elegance with modern luxury. Offering 4 bedrooms and 3.5 baths, the home showcases a simply stunning interior highlighted by a chef's kitchen with Omega cabinetry and commercial-grade appliances. Expansive windows bathe every room in natural light, creating effortless indoor-outdoor flow. Outside, unwind to unforgettable sunsets from the private backyard abutting Canoe Meadows, complete with a large wraparound deck, in-ground swimming pool, and pool house. The finished walkout lower level features a second kitchen, full bath, home gym, and generous recreation space ideal for teens, guests, or extended stays. A truly rare offering in an irreplaceable setting.

A Stunning Three-Story Residence with Breathtaking Views for an Easy Care Lifestyle in the Berkshires.Majestic and magical perfectly describe this exquisite three-story mountain top home, designed to capture the stunning and distant views of the Berkshire skyline. With over 5,000 square feet of expansive living space, this centrally located residence offers the perfect opportunity to either escape, join a quaint community or work at home with glorious views of the Berkshire Hills.Prime Location for Nature and Culture.Nestled in a charming small-town neighborhood, this home is bordered by beautiful woodlands, providing direct access to hiking trails and the nearby Appalachian Trail. Its central location places you at the heart of the area's vibrant culture and great outdoors.

Introducing Green River Meadows, a new luxury development that prioritizes healthy, sustainable living--ideal for those seeking an eco-friendly lifestyle without sacrificing luxury. Nestled alongside the Green River in Williamstown, just a short distance from the prestigious Williams College and surrounded by the cultural richness of the Berkshires, this community offers an exceptional lifestyle in a prime location.These to-be-built homes reflect a deep commitment to sustainability, seamlessly blending innovative design with environmental stewardship. Built using Passive House principles, the homes are designed to achieve optimal energy efficiency through superior insulation, triple-pane windows, airtight construction, and continuous fresh air ventilation,