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, Upstreet 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 caregivers

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.

An exceptional opportunity awaits on 11 private acres in Sheffield. This unique property, currently utilized as a functional therapy facility, offers a massive footprint and a flexible canvas for your next venture. The centerpiece is an 8,000+ sq. ft. building comprised of over 10 offices, multiple conference rooms, common areas, and three residential apartments, creating an ideal setup for a corporate campus, wellness retreat, or educational center. A separate, barn-style building, once used for deliveries, provides ample space for a workshop, studio, or extensive storage. Surrounded by expansive grounds, the property offers significant potential for additional building sites, making it a rare find for developers, organizations, or those dreaming of a grand family compound.

An exceptional opportunity awaits on 11 private acres in Sheffield. This unique property, currently utilized as a functional therapy facility, offers a massive footprint and a flexible canvas for your next venture. The centerpiece is an 8,000+ sq. ft. building comprised of over 10 offices, multiple conference rooms, common areas, and three residential apartments, creating an ideal setup for a corporate campus, wellness retreat, or educational center. A separate, barn-style building, once used for deliveries, provides ample space for a workshop, studio, or extensive storage. Surrounded by expansive grounds, the property offers significant potential for additional building sites, making it a rare find for developers, organizations, or those dreaming of a grand family compound.

Imagine owning your own secluded sanctuary, where total privacy and tranquility are yours for the taking. This extraordinary property offers the rare opportunity to build your dream retreat on a breathtaking piece of land, untouched by the outside world. With 20-foot-tall mountain laurel trails leading to the top of a mountain with stunning views right at your doorstep, you'll have endless access to nature's beauty, all while remaining completely secluded.The land consists of 6 separate parcels, all being sold together, creating the perfect canvas for whatever you envision. Don't miss out on staking your claim to this hidden gem, an unparalleled escape !

Cable Mills consists of three former industrial mill buildings restored into beautiful homes featuring 12ft to 16ft tall ceilings, massive windows, and exposed brick and beam, steel and timber throughout, stainless steel appliances, granite countertops, gas-fired ranges, generous closets and in home laundry. Cable Mills offers stunning views of the famed 'Purple Mountains' and the rolling Green River. Homes are one, two or three bedrooms in single level flats, lofts and townhome styles totaling 61 residences. Outdoor spaces including the Outdoor Living Room with a fire pit, grills and seating along the river walk. The main building offers a community lounge, fitness center, interior bike storage, package delivery room, dog wash and on-site professional management.

Welcome to a rare waterfront oasis offering over 650 feet of private frontage on the deepest part of Hayes Pond. Your private dock and beach area provide direct access to swimming, kayaking, and fishing, while a perfectly positioned gazebo is ideal for entertaining by the water. Inside, breathtaking water views grace every room through expansive windows. The open-concept design flows seamlessly from the great room to wrap-around decks, blurring the line between indoor and outdoor living. Cathedral hardwood ceilings and beautiful wood floors create an atmosphere of inviting warmth, anchored by a custom tile hearth and wood stove that serves as a stunning focal point. Retreat to the spacious primary suite, complete with its own cozy wood stove and a private en-suite bathroom.

A rare opportunity to own a well-established and respected auto parts store and full-service mechanic shop in the heart of Pittsfield. Located in a high-visibility, high-traffic area, this centrally situated property offers convenience, strong customer reach, and excellent brand recognition built over many decades.With over 11,000 square feet of space, the property features ample off-street parking, multiple service bays, dedicated retail areas, and offices for clerical and accounting functions. This well-organized layout supports efficient operations across both parts sales and mechanical services, including inspections, diagnostics, and general repairs.

Discover a stunning oasis in this custom-built contemporary home, ideally situated in a picturesque and private setting. Enjoy tranquil views of a serene pond, beautiful gardens, and flourishing fruit trees, all while basking in an abundance of natural light. This home is a dream for those who love to entertain. The spacious dining room and inviting living room, complete with a cozy fireplace, provide the ideal backdrop for gatherings, complemented by three spacious decks that extend your living space outdoors. Culinary enthusiasts will delight in the oversized cook's kitchen, featuring charming terra cotta floors, premium appliances, a generous center island, and ample dining space. Retreat to the luxurious first-floor primary bedroom suite, which offers a large walk-in closet,

A Nature-Lover's Haven Awaits Set on an expansive 94-acre stretch bordering the tranquil Tolland State Forest, this distinctive property combines unmatched privacy with exceptional natural charm. Envision life along the serene Farmington River, with hundreds of feet of stunning river frontage and your very own storybook-style covered bridge--an extraordinary hallmark of this countryside escape.Highlights Include:Vast Acreage: 94 acres of secluded, wooded beautyRiverfront Magic: Extensive frontage on the Farmington RiverSignature Feature: Historic-style covered bridge adds character and charm

Step back in time and experience the unmatched elegance of this exceptional 1860s Victorian estate, nestled on nearly 60 acres of private, wooded land. Overflowing with original architectural details and modern comforts, this grand 6-bedroom, 4.5-bath home offers a rare opportunity to own a true piece of history. Inside, the home features soaring ceilings, antique chandeliers, intricate woodwork, and beautifully preserved moldings. The elegant double parlor invites gracious entertaining, while the formal dining room and richly paneled library add to the stately charm. The expansive layout provides ample space for family and guests, blending historic character with thoughtful updates. Outside, enjoy peaceful woodland trails, an inground pool for summer relaxation, and carriage house/barn.

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,

This iconic building has been home to one of the Berkshires most beloved businesses for over 50 years. Built in 1731 as the Egremont Tavern stage coach stop, it was expanded in the 1960s. The 2.2 acre lot provides substantial parking. The historic front section offers unique features like stone floors and exposed beams and fireplaces. The rest of the building consists of a series of lovely rambling spaces with rustic elements on the main and lower levels, and two rental apartments upstairs (one 3/1, one 1/1). This property offers a buyer an extraordinary opportunity: own an incredible income producing property in the bustling town of South Egremont.

WHERE EVERY SEASON FEELS LIKE HOME16 acres at the end of a quiet country road where your shoulders drop the moment you arrive. This five bedroom retreat with over 4,600 square feet gets Berkshire living right: soaring great room with fireplace, granite kitchen, four-season sunroom, and that incredible finished lower level with radiant floors, full bar, and walkout to covered patio. Mudroom with dog shower because real life happens. Views toward mountain ridges, minutes to Knox Trail. The kind of Berkshire home that rarely comes available at this price.You're tucked between Otis & Sandisfield, which means total privacy, but not total isolation. 20 minutes to Lee, 25 to Great Barrington, minutes to swimming, hiking, skiing, everything that makes the Berkshires feel like home!

New Build Contemporary. Timbercraft Homes & Rosengren Architects collaborated to create this Contemporary 1584 square foot 2 bedroom home. Clean lines and simple one level living. Energy efficient Home with beautiful oak floors, custom kitchen open to dining and living room. Primary bedroom spacious and bright with well appointed bathroom and walk-in closet. Fireplace, dual fuel heating and AC. 1 car garage, pre-wired for Electric Car plug-in and Generator. Landscape installations by Mike Stevens. Come and see soon.

Welcome to Serenity Hill.This 1994 Cape style home captures the timeless charm of the Berkshires from the moment you arrive. At the entrance, stately stone pillars and a classic stone wall offer a graceful welcome, setting the tone for the calm, natural beauty that defines life in the Berkshires. Located on the border of Great Barrington, this Sheffield home is on a peaceful, quiet country road. Less than a mile from Wyantenuck Country Club and just five minutes from downtown Great Barrington. This home offers a peaceful sense of seclusion without ever feeling far from the heart of the Berkshires.Inside, you'll find an airy, open layout with natural flow from room to room, designed with both comfort and connection in mind.

Experience breathtaking panoramic vistas over protected land from every angle in this renovated Classic American Farmhouse. Nestled on two parcels, this residence boasts a pool, a detached garage, and gracious proportions throughout. Relax in the majestic long-range mountain vistas. The house is perfectly positioned to experience both sunrise and sunset views.Step inside to discover an extra-large chef's kitchen seamlessly connected to a delightful breakfast room, sunroom, and screened porch, each offering tranquil views of the pool and raised garden beds. The inviting living room, complete with a cozy fireplace, flows effortlessly into the dining area, creating an ideal space for entertaining. Adjacent, find a sunlit den and office area, bathed in natural light.

Experience the rare opportunity to own your own island on beautiful Dudley Pond! This stunning post-and-beam bungalow offers 360 water views and an unmatched sense of privacy. Enter via a cobblestone driveway featuring an antique millstone centerpiece. Inside you'll discover wide-plank pine floors and yellow pine beams dating from the 1700s. The chef's kitchen boasts an oversized quartz island, abundant custom cabinetry, induction cooktop, and double wall ovens. At the heart of the home, a magnificent Russian Fireplace serves as a striking architectural centerpiece. Custom built-in bookcases, two bay windows and light-filled living spaces create warmth and character throughout. Upstairs, a cozy seating area with laundry hidden behind double doors. The primary suite offers a cathedral

Nestled in the lovely gated community of Woodmont Estates, this magnificent Georgian Schultz-designed home offers five bedrooms and five baths, with effortless access to all the Berkshires have to offer. Step through the elegant front entrance into a grand foyer featuring an open stairway, flanked by a formal dining room and spacious living room. Continue on to the expansive chef's kitchen, complete with a large center island and sun-filled breakfast area.Upstairs, the second floor showcases generously sized bedrooms, including a luxurious primary suite with its own private office area.Outdoors, enjoy a stunning wraparound deck overlooking the in-ground pool--perfect for entertainment and relaxation. The beautifully landscaped grounds feature an open outdoor fireplace surrounded by