OUTSTANDING COUNTY LIVING in idyllic Monterey with its low real estate taxes and easy access to Lake Garfield and Lake Buel. Butternut Ski Area is only 5 minutes away. 8 minutes to downtown Great Barrington. This Timber Fame (open floor plan) contemporary home features beautiful (wide-plank) pinewood floors, a cathedral ceiling Great Room, and a bonus sleeping loft area. A fireplace on the main level, and a wood stove on the lower level, add warmth and charm. Ready to move right in? With relatively low inventory level, particularly in Monterey, this listing is a lucky strike extra. Schedule your showing today.

Offered for the first time in 40 years, this White Pines condo is a rare opportunity to own a residence within one of Stockbridge's most storied properties. Rich with musical history, both White Pines and this particular residence have fascinating ties to local and international music scenes. Filled with natural light, this gracious two-bedroom, two-bath condominium offers generous living spaces and an inviting, easy flow. The beautiful great room is the heart of the home, with two distinct sitting areas and a dedicated dining space--ideal for both relaxed everyday living and entertaining. A large primary suite provides a private retreat, while the second bedroom and full bath offer flexible space for guests or creative pursuits.

Beautifully updated and maintained four bedroom, three and a half bath colonial. Spacious common areas washed with natural light make this home special. The main level boasts a large eat in kitchen, dining room, expansive living room with wood floors, family room with built ins and fireplace, separate laundry room, half bath, two car oversized garage and beautiful screened porch overlooking the landscaped large yard. The second level has three guest bedrooms, full bath and large primary bedroom with en suite and double closets. The finished lower level offers a media/flex room, office, bathroom and storage. This Convenient location is on the Southeast side of Pittsfield near Lenox and under 15 minutes to Tangelwood!

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.

Discover the charm and character of this inviting Cape, tucked away on a private road in one of Williamstown's most coveted locations. Set on .61 acres, this special property offers scenic views, a fenced backyard, and a peaceful setting in the heart of town, with access to the beautiful grounds of the Clark Art Institute at the end of the street. Inside, timeless character shines through, including three fireplaces, one featuring intricate woodwork salvaged from the demolition of the original Cole Porter Estate. The second-floor primary suite offers its own fireplace and private balcony, while a third fireplace in the kitchen adds warmth and charm. Replacement windows throughout and a new natural gas furnace. A rare opportunity to enjoy classic New England character with scenic views.

Loft 309 at Greylock WORKS is a distinctive north-facing 1BR | 1.5BA Berkshires residence with a generously scaled study, offering approximately 1,340 SF of thoughtfully designed living space. Set on the third floor of the region's most celebrated mill conversion, this home is defined by its warm wood ceilings, varied ceiling heights, and refined blend of historic character and modern finishes. The open living, dining, and kitchen area creates an inviting central gathering space, grounded by restored materials and an easy, functional flow for everyday living and entertaining. Energy Star appliances, Kohler and Grohe fixtures, energy-efficient windows, and an in-unit washer and dryer support both comfort and sustainability.

Experience the ease of downtown living in this immaculate Maple Grove condominium. Positioned just a short walk from Main Street, this residence offers immediate access to local shops, restaurants, and town amenities. The main level centers on a modern, open floor plan defined by beautiful wood floors and abundant natural light. An open kitchen anchors the living space, allowing for seamless interaction during meals and gatherings. The living area extends outward to two distinct private spaces: a screened-in porch for three-season relaxation and a separate private deck. Designed for convenience and longevity, the first floor features a primary bedroom suite complete with a spacious en-suite bathroom and laundry.

Experience the ease of downtown living in this immaculate Maple Grove condominium. Positioned just a short walk from Main Street, this residence offers immediate access to local shops, restaurants, and town amenities. The main level centers on a modern, open floor plan defined by beautiful wood floors and abundant natural light. An open kitchen anchors the living space, allowing for seamless interaction during meals and gatherings. The living area extends outward to two distinct private spaces: a screened-in porch for three-season relaxation & separate private deck. Designed for convenience and longevity, the first floor features a primary bedroom suite complete with a spacious en-suite bathroom and laundry.

This move-in-ready 4-bedroom, 2.5-bath Colonial in Southeast Pittsfield sits on over half an acre and blends classic charm with thoughtful updates. The welcoming chefs kitchen opens to a screened porch and flows into a generous dining room with built-in cabinetry, perfect for everyday living and entertaining. A light-filled living room anchored by a wood-burning fireplace creates a warm and inviting gathering space. Upstairs offers four comfortable bedrooms, two full baths, a large cedar closet, and abundant storage. A two-car garage and partially finished basement with a second wood-burning fireplace complete this exceptional home. Outside, the professionally landscaped, fully fenced backyard offers exceptional privacy and outdoor living space.

Privately set down a long drive in the scenic hills of New Marlborough, this charming shingle-style home sits on over 45 acres of beautiful Berkshire countryside. Built circa 1950, the home offers more than 2,100 square feet of living space with four bedrooms and two full bathrooms. The first floor includes a living room, dining room, kitchen, mudroom, and full bath, while the second floor features four bedrooms and an additional full bath. Surrounded by mature trees and open land, the property offers exceptional privacy and endless possibilities for recreation, farming, or a peaceful country retreat within a Berkshires community.

Showings start: Friday, Sept. 18th. Set in the desirable Longview Terrace neighborhood, this well-maintained contemporary offers mountain views, privacy and a natural setting, with its rear western corner adjoining Burbank conservation land and Chenaille Farm visible beyond. The four-bedroom, two-and-a-half-bath home provides approximately 2,688 square feet of living space, including a finished lower level. Highlights include hardwood floors, a wood-burning fireplace, attached two-car garage, mahogany deck and in-ground swimming pool. Thoughtfully cared for by its longtime owners, the property has benefited from significant improvements to major systems, including the roof, boiler, oil tank, electrical service and drainage. PHOTOS ARE COMING SOON!

Embrace the extraordinary at 395 Park St. North, where history meets opportunity. This stunning red brick 6,833 sq.ft. warehouse, once a bustling trolley barn, boasts high ceilings and a rich industrial charm, with river views while exploring the spacious layout, featuring 3 updated bathrooms, a newer roof and building updates. It has versatile separate offices and garage/shop areas. With ample parking and loading docks, envision endless possibilities from manufacturing to art gallery or more. Conveniently located near dining, parks, and cultural attractions, this property invites you to re-imagine living or workspace with style and creativity. Total acreage and assessment include two lots.

Welcome to this large expansive dwelling that features great privacy! Enjoy outdoor cooking and refreshments on the enlarged deck for these hot summer days. Also featuring a separate personal deck off the Primary bedroom. This great home boasts an oversized living room with a Grand fireplace place that will impress any viewer. An interior balcony from the sizable Primary Bedroom overlooks the oversized living room. A large kitchen leading to your dining room that opens up to the back deck. Updated bathrooms with amazing tilework will be found throughout the home. An oversized garage to store your personal vehicle or off-road vehicles of your choice. The lower level including a bonus room that is currently being used a game room completes the interior. It's a Perfect opportunity to finish

Move in ready with frontage on the Williams River. This beautifully updated and and well maintained contemporary home is the perfect landing spot for easy Berkshire living. The airy living room flows seamlessly into the spacious dining room and efficiently renovated kitchen which is also accessible through the 2 car attached garage. The large en suite primary bedroom is also on the first floor as well as a half bath and laundry area. Upstairs are 2 more bedrooms that share a bath; perfect for guests and/or office or den, as well as a huge storage closet. The property is perfectly located with 3.5 acres on the end of a quiet cul de sac, with frontage on the bucolic and clean Williams River for swimming, floating, and nature watching. Just minutes to downtown GB, Guido's, and Taft Farm's.

This meticulously maintained 1900 farmhouse seamlessly blends timeless historic character with refined modern updates, creating a move-in ready retreat just minutes from the vibrant energy of downtown Great Barrington. Every corner of this classic three-bedroom, two-bathroom home reflects thoughtful care and craftsmanship, offering an ideal balance of warmth, functionality, and quintessential Berkshire charm. At the heart of the residence is a stunning cook's kitchen, thoughtfully renovated and fully outfitted with updated appliances, expansive counter space, and storage. Sunlit living spaces flow naturally throughout the main floor, showcased by rich, beautifully preserved wood floors that anchor the

Charming North Egremont Village colonial. This sweet New England village farmhouse sits tucked into the loveliest setting with a rocking chair front porch, lovely gardens, mature shade trees and a white picket fence. The first floor holds a comfortable open living / dining room with a wood burning fireplace, a wainscotted kitchen, sunny family room, and a full bath with laundry. Upstairs are 3 comfortable bedrooms, a full bath with lots of storage, and a sunny deck off the primary bedroom. Close by is French Park for tennis, and the North Egremont store is just a short stroll away. Also nearby is Prospect Lake for swimming, paddle boarding, and kayaking , as well as the Cliff House, for lake side dining. This charming home is neat and tidy, and ready to enjoy in every season.

Fantastic opportunity to own a home in a peaceful cul-de-sac within the desirable Cornwall Estates. This lovely home sits on a level lot w/ almost 2.5 bucolic acres. Spanning just over 2,000 square feet, the home features a convenient first-floor primary bedroom and bathroom, vaulted ceiling in the living room and a screened in porch that leads to a large, partially fenced in backyard. Many recent updates and upgrades including kitchen,bathrooms as well as furnace and central AC system replacement. All of this and a heated community pool nearby and Great Barrington just minutes away, make this home ready for the next owners to create their own Berkshire journey and memories.

This beautifully renovated luxury duplex with lower-level studio apartment is ideally situated in the heart of North Adams, just moments from downtown shops, restaurants, and MASS MoCA. Thoughtfully renovated down to the studs with meticulous craftsmanship, the property features two beautifully appointed side-by-side residences, each with a private entrance. The larger side offers 4 bedrooms and 1.5 baths, while the second features two bedrooms and 1.5 baths. Both include state-of-the-art kitchens and baths, new laundry facilities, and modern heating and air-conditioning systems. The finished lower level features an open-plan studio with a luxurious bath and gourmet kitchen, perfect as a stylish guest suite. Two patios and beautifully landscaped gardens provide inviting outdoor spaces.

Immaculate and well-maintained contemporary home in an exceptionally convenient location set on 5+ wooded acres. Designed for easy living and low maintenance, this home offers an open floor plan with high ceilings, wood floors, and a beautiful fieldstone fireplace anchoring the main living space. The kitchen opens to another living area creating a comfortable flow for everyday living and entertaining. Enjoy the lovely screened porch and outdoor deck overlooking the natural setting. Three bedrooms and 3.5 baths, including guest quarters or apartment space for added flexibility. Large two-car garage. It is in a very private setting, but is also a short distance (walking distance) to the elementary and secondary schools. Easy transition for a first floor primary bedroom.

Private Lake Buel access is just steps from this one-level, 4-bedroom, 3-bath ranch--your perfect year-round getaway or full-time retreat. Inside, you'll find a striking two-sided fieldstone fireplace anchoring the living and dining areas, complemented by warm wood floors that add timeless charm. Step outside to a spacious back deck overlooking your own private bird sanctuary--an ideal setting for relaxing or entertaining. Enjoy the serenity of lakeside living with plenty of space for family and guests. Complete with a deeded boat dock and storage shed, this property offers everything you need to embrace the ultimate lake lifestyle. Sackman Way is a Private dirt road with 4 houses sharing road maintenance and snow plowing.