Bring your BOAT and enjoy all that the Stockbridge Bowl has to offer. This charming home has deeded rights to the lake, as well as its own dock space! The house was recently renovated with all top of the line mechanicals and appliances. Bosch, Miele, & Fisher Paykel. Central AC. One level living with two bedrooms and two full baths. Open concept living with a large front deck and yard for entertaining. Inside is an original log fireplace for those chilly winter nights. All new cedar lined closets and freshly painted throughout. A three-minute walk to your boatslip and private neighborhood dock, you can sit and watch the sunset from the best spot on the bowl. Make an appointment to view this gem now.

Rare, renovated Berkshire investment compound on 0.59 acres in walkable Housatonic. This turnkey property features two separate legal duplexes (4 units total) offering stellar cash flow. The front home (392 Park St) features a 5BR/2BA unit, a sleek 2BR flat, and a prominent street-front walk-out lower level with incredible commercial/addition potential. The rear Swiss-Gothic home (394 Park St) hosts two updated 2BR units. Enjoy a sprawling backyard with mountain views, a community garden, and fruit-bearing trees. Fully insulated and optimized for easy management with 4 separate heating/electric systems, town sewer/water, and off-street parking for 10+ cars. Walk to Berkshire Mountain Bakery; minutes to Great Barrington & Tanglewood. A rare, turnkey find!

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-

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

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, 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.

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

Tucked away in one of Lenox's most desirable neighborhoods, this contemporary ranch has been completely renovated with no expense spared, offering effortless single-level living and a seamless connection to the outdoors. Vaulted ceilings, walls of glass, and an abundance of natural light create an open, inviting atmosphere, while nearly every room overlooks the beautifully landscaped, private backyard. Designed for both everyday living and entertaining, the thoughtfully planned floor plan centers around a stunning eat-in kitchen featuring quartz countertops, premium Thermador appliances and custom floor to ceiling millwork with an easy flow into the spacious living room with a gas fireplace, formal dining area, and an expansive sunroom with electric heat for extended seasonal enjoyment.

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.

Available for the first time, this recently built 4 season home is a unicorn in the sought after Beachwood community on the south side of the Stockbridge Bowl. Bright, crisp and modern this property comprises an entrance foyer, chef's kitchen with stone counter-tops, living/dining area, gas fireplace, 2 bedrooms and 1 bathroom and washer/dryer downstairs. Two bedrooms, 1 bathroom upstairs with additional flexible seating/work areas. A patio leads onto a deep, level garden and to a barn with a finished upstairs studio and great downstairs storage and an EV charging station. Two zone air-conditioning, generous parking courtyard and proximity to the Beachwood community's private beach and kayak launch. A unique opportunity conveniently situated near Tanglewood and both Lenox and Stockbridge.

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!

THIS is the one! Set on 1.53 beautifully landscaped acres, this 4BR, 3.5BA home delivers 4,298 sq ft of incredible living. The renovated chef's kitchen is what dreams are made of--Sub-Zero refrigerator, Wolf appliances, built-in Miele coffee maker, oversized island & custom cabinetry-plus built-in fridge/freezer drawers in the dining room. Cathedral-ceiling living room with fireplace, sunroom, dedicated office, dreamy laundry room & custom mudroom add to the wow factor. Outside, an expansive Trex entertaining deck is separate from the enclosed saltwater pool, with a fire pit, lush grounds & fruit trees beyond. The finished lower level adds flexible living/fitness space. Upstairs offers generous rooms ready for your personal touch. The price reflects the opportunity to make them your own.

Stunning Contemporary Home in Great Barrington - Perfect Blend of Privacy and ConvenienceDiscover this beautifully designed 2,500 sq. ft. contemporary residence nestled in the desirable Great Barrington area. Offering 3 spacious bedroom suites , this home combines elegant style with everyday functionality.Step outside to your private fantasy backyard -- an entertainer's dream featuring a charming gazebo and a generous deck, perfect for hosting gatherings or relaxing in your own outdoor oasis.The oversized garage provides ample storage and includes a versatile space above, ready for your expansion ideas. With rough plumbing and electrical already in place, customizing this area is effortless. Located 2 min from Monument Mountain Reservation and 6 min to Main Street.

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.

Gracious, elegant, and designed for living well, this exceptional center hall Colonial offers timeless character, beautiful mountain views, and an abundance of space. The welcoming entrance is accented by exquisite English stained glass, with wood floors flowing throughout the home. Five bedrooms and 3.5 baths provide room for family and guests, while grand living and dining rooms are perfect for entertaining. A spacious family room offers a more relaxed gathering space. The primary suite features cathedral ceilings and beautiful mountain views. Outside, covered patios and decks overlook a spectacular in-ground pool, gazebo, and bathhouse--creating a private setting for summer entertaining and relaxation. Thoughtful updates include a 2016 roof, 2023 driveway, and appliances updated 2023-26