Special opportunity to take over the 5BR owners' unit as part of this 4-unit compound and let the other 3 pay your mortgage. Relaxing property in the center of Housatonic village with two charming, recently renovated duplex homes - each with historic details left intact. The front house has a flex 4/5BR 2200 sq. foot owners' unit which feels like its own house. Split on 2 floors, it has 2 full baths, privacy, its own screened-in porch and outdoor BBQ area. Currently operating as a high-end furnished rental. Use it as your FT residence, weekend home or mid-term rental (i.e. traveling nurses), turn-key and ready to go. The remaining 3 x 2BR units are filled with wonderful tenants; each home has their own W/D, outdoor space and there is an expansive shared yard-

Set in a lovely neighborhood just outside downtown Great Barrington, this center-hall Colonial with contemporary flair offers a wonderful combination of space, light, and easy Berkshire living. The sunny, south-facing open floor plan brings together the kitchen, breakfast area, and family room, with granite counters, a center island, and a see-through fireplace connecting to the formal living room. Five bedrooms include a spacious primary suite with large bath, plus flexible in-law, nanny, or rental accommodations with a private entrance. Outside, a beautiful level, sun-filled yard surrounds the in-ground swimming pool for summer entertaining. Walk to the sparkling Williams River and enjoy a location close to downtown Great Barrington. Close to all the Berkshies has to offer.

Just two miles from the center of Stockbridge, this beautiful four bedroom, three and a half bathroom home offers privacy, space and exceptional indoor outdoor living. The spacious primary suite features a large ensuite bath and separate his and her closets, and an additional closet with direct access to a full length deck shared access with the living room. The open floor plan connects the living room, dining area and kitchen, highlighted by soaring beamed ceilings abundant natural light, and a gas fireplace. A bright sunroom to choose a book from its floor to ceiling bookcases. The deck overlooks the mature landscaping, pool, and pool house. The walkout lower level includes a second kitchen, providing space for guests. A Berkshire retreat just minutes from the cultural attractions!

FOR SALE: Prime Downtown Great Barrington Gem - Endless Possibilities! Welcome to 406 Main Street, a rare opportunity in the heart of downtown Great Barrington, MA. Just steps from bustling Main Street shops and restaurants, this versatile 5,180 sq ft building offers exceptional potential for residential, commercial, or creative mixed-use transformation. Zoned B2, the property allows for single-family, multi-unit, or live/work conversion—with no sprinkler system required for up to 3 residential units. Already equipped with 1 full bath and 4 powder rooms, and featuring two finished floors, the layout adapts effortlessly to your vision—be it modern apartments, stylish offices, retail space, or a dynamic studio. • Spacious and bright with 5,180 sq ft across two levels • Excellent bones

Rare 44-acre wooded parcel offering exceptional scale and privacy in scenic Egremont. With over 1,000 feet of road frontage anchored by dual access points at both the east and west ends, the property delivers rare site flexibility and seamless ingress/egress--ideal for a private multi-structure family compound, a substantial country estate, or thoughtful division. The acreage features mature hardwood canopy, rolling topography, and established trails throughout, providing complete rural seclusion just minutes from South Egremont village, Catamount Mountain Resort, and downtown Great Barrington. A versatile South County land holding built for scale.

SET ON A GENEROUS IN -TOWN PARCEL THIS 1850 VICTORIAN IS POISED FOR A MODERN TRANSFORMATION. THE RESIDENCE BEAUTIFULLY RETAINS ITS ORIGINAL STAIRCASE AND PERIOD DETAILS THROUGHOUT. HIGH CEILINGS AND EXPANSIVE WINDOWS ILLUMINATE THE MAIN ENTRY, LIVING AND DINING ROOMS, WHILE THREE FIREPLACES AND MULTIPLE PORCHES ADD TO THE TIMELESS CHARM. UPSTAIRS, THE SECOND FLOOR FEATURES FIVE BEDROOMS AND A BATH, LEADING UP TO AN UNFINISHED THIRD FLOOR WHICH HAS GREAT POTENTIAL.

Up here, it is all about light, height and the mountains. Set on the top floor of Greylock WORKS, Loft 403 is a 1,805 SF one-bedroom + study residence with soaring 16-foot ceilings, south-facing Berkshire mountain views and a private balcony above the historic mill campus. Conceived by celebrated architects LATENT Productions, Greylock WORKS reflects an uncommon respect for the historic mill, its architecture and its Berkshire setting. Historic brick, restored wood floors, massive columns and the scale of the original building have been preserved and celebrated, while highly custom modern interventions bring clarity and timelessness to the old industrial structure. Nothing feels generic. Nothing feels dropped into an old building as an afterthought.

Embark on an entrepreneurial journey to be recreate one of the few lakefront dining spots left in the Berkshires! This exquisite property boasts a stunning waterfront restaurant nestled along the serene shores of Pontoosuc Lake, encompassing just over an acre of prime land. It is fully equipped with a liquor license, a lottery license, and a full commercial kitchen. Furthermore, the property offers exceptional potential for development, complete with direct access to the tranquil waters of the lake.

Discover a peaceful retreat in Alford with this charming 4-bedroom, 2.5-bath Contemporary Cape set on more than 8 acres. Relax on the spacious screened-in porch while listening to the birdsong and the gentle flow of Scribner Brook. Offering an upscale cabin feel in every season, this inviting home provides the perfect escape from the pace of everyday life. Enjoy privacy, natural beauty, and the tranquility of your own wooded retreat.

Completely reimagined from top to bottom, 1790's Colonial blends historic New England character with modern luxury in a truly one-of-a-kind Berkshire setting. Located directly across from Pontoosuc Lake, the property offers stunning lake views, exceptional craftmanship and endless possibilities for live/work, business venture or investment in business/residential zone. Stunning kitchen featuring radiant heat, quartz countertops, high end appliances, oversized center island with dramatic full waterfall quartz sides flowing on every exposed edge. First-floor bath/laundry w/radiant heat. All three bathrooms have been fully renovated with spa like appeal and upscale design. Large living room/dining room, 1st floor bedroom with lake views, 2 sunporches all on main leve

Secluded at the end of a long winding drive, this wonderful three-story Greek Revival home was built in 2001 and sits on over 22 private acres. The main level offers a living room, dining room, kitchen, half bath and a screened porch. Upstairs are two bedrooms and a full bath - all with hardwood floors, while the walkout lower level serves as either a third bedroom or a den, along with the laundry and utility rooms. Hike through your own woodland, then enjoy the area's renowned cultural attractions and outstanding dining, including the Old Inn on the Green and the Southfield Store Café. Nearby Umpachene Falls and York Lake offer swimming, while picturesque Rhoades and Bailey Road is one of the Berkshires' most scenic country roads, lined with beautiful homes. Additional land available.

Rare opportunity to own a spacious four-bedroom, four-and-a-half-bath end-unit town home with three finished levels, a two-car garage, and multiple outdoor, screened in living spaces. Tucked into a quiet cul-de-sac and set back from the road, this inviting home enjoys a peaceful, wooded backdrop, abundant natural light, and convenient access to the community pool--an ideal setting for relaxed everyday living and entertaining. The main level centers around a sun-filled living room with vaulted ceilings, transom windows, and a gas fireplace. A french- door opens to an enclosed screened deck overlooking the woods, creating an easy connection between indoor and outdoor living. The kitchen features granite countertops, stainless

Exceptional Investment opportunity in the heart of the Berkshires! Mixed use building featuring six residential apartments and one street level commercial storefront in a high visibility Main Street location. Minutes from the Massachusetts Turnpike, this property offers easy access as a gateway to the Berkshires. Diversified income potential from residential and commercial tenants. This property offers tremendous upside in a highly desirable location.

Exceptional investment opportunity in the heart of the Berkshires! Mixed use building featuring six residential apartments and one street level commercial storefront in a high visibility Main Street location. Minutes from the Massachusetts Turnpike, this property offers easy access as a gateway to the Berkshires. Diversified income potential from residential and commercial tenants. This property is in a highly desirable location.

Perched on a hill overlooking a scenic valley road, this 4-bedroom Dutch Gambrell offers a secluded country setting just a few minutes from town. This vibrantly-designed home opens into a handsome petrol-green kitchen with polished concrete floors and an ample dining area framed by French doors. The kitchen/dining area flows into an inviting living room anchored by a herringbone tile propane fireplace, a warm gathering space for family and friends. Just off the living room the 1st floor primary suite is a cheerful retreat with it's own striking classic black-and-white tiled bath with glass shower surround. Upstairs 3 guest bedrooms, a full bath and an upstairs playroom/lounge offer plenty of room for guests to relax.

Iconic Berkshire County Property for Sale Formerly home to the renowned Highland Restaurant, this landmark property presents a rare opportunity in the heart of downtown Pittsfield. Located at 100 Fenn Street and adjacent to City Hall, the building is situated within the City of Pittsfield's Downtown Creative District and Housing Development Incentive Program (HDIP) Overlay. With a distinguished history as a longtime gathering place for the community, this prominent property offers exceptional potential for restaurant, hospitality, retail, residential, or mixed-use redevelopment. Opportunities of this caliber are rarely available in Berkshire County.

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,

A thoughtfully designed home with south facing views on 3 acres. Constructed by a reputable local builder offering a perfect blend of luxury and privacy. Situated on the Canaan/New Lebanon line, it boasts breathtaking views and an in-ground pool ideal for relaxation and entertainment on the blue stone patio. Large first-floor primary suite provides a peaceful retreat, complete with large windows and freshly updated en-suite bath. Enjoy cooking in the large EIK that's open to the dining area. Relax after a meal by the fireplace in the living room. First floor half bath and laundry along with a gracious, welcoming mud room complete the first floor. Additional bedroom with bath and open landing on 2nd floor, PLUS a guest suite with kitchenette and bath with it's own private entrance!

Berkshire Estate Near Jiminy Peak Experience the beauty, privacy, and charm of Berkshire country living at this remarkable estate, tucked away at the end of a quiet cul-de-sac on more than three beautifully landscaped sunny acres. Surrounded by expansive lawns, mature plantings, and scenic views of Savage Hill, this property offers an idyllic setting for both relaxation and recreation. Designed for enjoying every season, the grounds feature a stunning in-ground pool, a hot tub perfect for crisp Berkshire evenings, and direct access to outdoor pursuits. Bordering the Town Brook River, where excellent trout fishing awaits just beyond' your backyard. The impressive residence encompasses approximately 4,320 square feet of thoughtfully designed living space. Minutes to Jiminy Peak Ski Resort

SPACIOUS, SINGLE-LEVEL CONTEMPORARY WITH PRIVACY AND HEATED IN-GROUND POOL in the coveted community of Harrington Woods. 6 bedrooms. 3.5 baths. Bright, open floor plan with a spacious kitchen open to the dining area. The Great room has a cathedral ceiling, a wood-burning fireplace, and glass doors leading to a large screened porch and deck. Primary bedroom suite with full bath has cathedral ceiling and glass doors leading to the deck. Finished walkout lower level is perfect for a gym, playroom, game room. In-ground heated pool surrounded by perennial gardens. Access to a community pool, and a tennis/pickleball court. Miles of hiking trails in the area and 15 minutes to swimming at Lake Garfield or kayaking at Lake Buel. 20 minutes to Ski Butternut. 10 minutes to Jacob's Pillow.