TAKE WHITE'S LANE ACROSS A BRIDGE SPANNING A STREAM. FOLLOW THE RISE OF TWO HILLS WITH VIEWS OF THE GREENWAY. PASS THROUGH A SMALL WOODS AND A STONE FENCE TO THE HOUSE SITE WITH BEAUTIFUL VIEWS OF SIX ACRES OF OPEN FIELDS, THE GREENWAY, AND A PANORAMIC EASTWARD VIEW OF EAST MOUNTAIN AND BEARTOWN STATE FOREST. PLEASE SEE SUPPLEMENT FOR MORE INFORMATION ABOUT THIS VERY SPECIAL ENVIRONMENT.

Historic village living at its finest. This expansive Turn-of-the-Century Sheffield home is rich with original detail, from its warm wood floors to a magnificent fieldstone fireplace. The property boasts a large, private yard, offering ample space for gardening, recreation, or outdoor entertainment. A substantial barn on the property provides excellent potential for a workshop, studio, or extra storage. Inside, enjoy abundant natural light in the glassed-in sunroom or relax on the multiple porches and decks. A key feature is the large, private in-law apartment, perfect for multi-generational living or rental income. Ideally located in the heart of Sheffield village, you'll enjoy the comforts of downtown just steps from your doorstep.

Set on a private, sun-filled parcel in Otis, this well-maintained contemporary offers four-season Berkshire living with easy access to nature and culture. The open main level features vaulted ceilings, abundant light, and a warm living area with a gas fireplace. Two bedrooms and a full bath complete the main floor. The finished lower level adds a spacious media/game room, third bedroom, full bath, and laundry. Built by a premier local builder in Harrington Woods and owned by the original owners, it features Andersen windows/doors, two-zone HVAC, and excellent insulation. Minutes to Jacob's Pillow and near Tanglewood, Shakespeare & Company, The Mount, Norman Rockwell Museum, and Berkshire Theatre Group. Close to Otis Ridge, Butternut, and Jiminy Peak skiing.

Historic village living at its finest. This expansive Turn-of-the-Century Sheffield home is rich with original detail, from its warm wood floors to a magnificent fieldstone fireplace. The property boasts a large, private yard, offering ample space for gardening, recreation, or outdoor entertainment. A substantial barn on the property provides excellent potential for a workshop, studio, or extra storage. Inside, enjoy abundant natural light in the glassed-in sunroom or relax on the multiple porches and decks. A key feature is the large, private in-law apartment, perfect for multi-generational living or rental income. Ideally located in the heart of Sheffield village, you'll enjoy the comforts of downtown just steps from your doorstep.

Immaculate and beautifully updated free-standing home offering effortless one-level living. The open-concept floor plan seamlessly connects the living, dining, kitchen, and den areas, all enhanced by abundant windows that fill the space with natural light. The chef's kitchen features quartz countertops, stainless steel appliances, and a generous center island ideal for entertaining. Three spacious bedrooms and two full baths provide comfort and flexibility. Highlights include gleaming wood floors, a gas fireplace, and an oversized two-car garage. Enjoy exceptional amenities including a clubhouse, swimming pool, tennis courts, and a fully equipped fitness center. Ideally located with convenient access to all that the Berkshires have to offer.

Exceptional Multi-Use Property. Spacious commercial space complemented by a fully renovated two-bedroom apt. Strategically positioned in a high-traffic location - minutes to bustling Great Barrington - this 4,892 SF property has outstanding potential. Versatile main floor ideal for various commercial ventures, while the residential units provide excellent live/work opportunities. In addition, the property features a separate 1 BR apt. & 2 oversized detached garages, all of which have generated steady rental income. Recent upgrades (electrical, plumbing, HVAC, septic system, and most windows) ensuring modern efficiency. With a proven history of strong income across all units this property presents a great opportunity to run a business while leveraging rental revenue to support your vision.

Maximize your ROI with this versatile asset minutes from downtown Great Barrington and Prospect Berkshires. This property combines a large high-visibility commercial main floor with three consistent revenue streams: a fully renovated 2-bedroom residence, a separate 1-bedroom apartment, and two oversized detached garages. For the entrepreneur, this offers a rare live/work scenario where your overhead is significantly offset by existing rental income. Every major system has been recently upgraded--including electrical, plumbing, HVAC, and windows--ensuring low-maintenance ownership. Whether you're looking for a high-exposure storefront or a pure multi-unit investment, the proven rental history and modern infrastructure make this a strategic acquisition.

Renovated, well-maintained, multi-use building perfect for a live-work situation in prime location! All 4 floors offer opportunity for offices, a studio, storage, retail showroom and more! Highlights include: a large parking lot, handicap accessible ramp, 2 half baths & finished 3rd floor attic. Finished basement w/ vault & video security system. The current retail space is bright & sunny with a large quartz sales counter, display shelves, spot lights, fresh paint, with modern pendant lighting. The impressive metal roof & boiler were both installed in 2019, along with the emergency generator & mini splits throughout. The building's total of 3000 sq ft is based upon renovations. (See floor plans in documents.) B2 zoning offers many options for permitted use! (See GB bylaws in documents.)

Fully renovated, well-maintained, multi-use building in prime location with sparkling retail space, offices and more! The current showroom is bright & sunny with a large quartz sales counter, display shelves, spot lights, fresh paint & modern pendant lighting. All four floors are finished, creating an ideal setup for a live-work opportunity. Highlights include: large parking lot, handicap accessible ramp, handicap 1/2 bath on main floor, & finished attic. Finished basement w/ vault & video security system has ample room for storage. The metal roof, boiler, emergency generator & mini splits were all installed in 2019. The building's total of 3000 sq ft is based upon renovations. (See floor plans in documents.) B2 zoning offers many options for permitted use! (See GB bylaws in documents

Immaculate and beautifully updated free-standing home offering effortless one-level living. The open-concept floor plan seamlessly connects the living, dining, kitchen, and den areas, all enhanced by abundant windows that fill the space with natural light. The chef's kitchen features quartz countertops, stainless steel appliances, and a generous center island ideal for entertaining. Three spacious bedrooms and two full baths provide comfort and flexibility. Highlights include gleaming wood floors, a gas fireplace, and an oversized two-car garage. Enjoy exceptional amenities including a clubhouse, swimming pool, tennis courts, and a fully equipped fitness center. Ideally located with convenient access to all that the Berkshires have to offer.

This approximately 155-acre Berkshire nature preserve has enough frontage on Johnnycake Hill Road to accommodate four building lots. Nestled in the beautiful corner of the world where the Pioneer Valley meets the Berkshire Hills, the property is ideal for a myriad of outdoor uses including horseback riding and cross-country skiing. The land contains well over a mile of logging trails and old roads, past old house and school foundations, wells, and stone walls enclosing abandoned sheep pastures. The property is up the hill from the Chester Theatre, and within easy reach of many cultural venues including Jacob's Pillow, the Mahaiwe, Tanglewood, Mass MoCA, and the vibrant four college community. This peaceful hardwood forest offers a natural wildlife habitat,and significant timber value

Grand, timeless, & beautifully situated in one of Pittsfield's most beloved neighborhoods, this classic 5-bedroom, 5-bath home offers the perfect blend of elegance, character, & space. Its stately presence, gracious proportions, & inviting warmth are just exceptional. Inside, spacious living areas, beautiful architectural details, & abundant natural light create an atmosphere that feels both sophisticated & welcoming. With room for everyone & ideal spaces for entertaining, working from home, or simply enjoying everyday life, this home is as functional as it is beautiful. The sweet, tucked-away location offers privacy & tranquility while remaining close to all the Berkshires has to offer. A rare opportunity to own a truly classic home filled with charm, character & endless possibilities!

Beautiful two bedroom, two bath condo perfectly situated in the center of Lenox, Massachusetts-the cultural heart of the Berkshires. Enjoy high Ceilings, beautiful wood floors, large windows, and abundant natural light throughout. The spacious layout features a gas fireplace, granite countertops, and a gas stove in the modern kitchen. The inviting living room opens to a private balcony, perfect for relaxing outdoors. the primary suite includes an ensuite bath. Additional highlights include in unit washer and dryer, on-demand hot water, natural gas heat, and a large storage unit, your own parking space behind the building and access to a beautiful Exercise room for all condo owners. New HVAC in 2026! You will have convenience in one of the Berkshires most desirable towns!

Set in one of Southeast Pittsfield's most desirable neighborhoods, this very sunny and impeccably maintained home offers the perfect balance of gracious living, flexible space, and effortless entertaining. Lovingly cared for by its current owner, the home unfolds with elegant formal rooms, hardwood floors, and a warm wood burning fireplace anchoring the living room. The heart of the home is an open concept kitchen and family room with cathedral ceilings, where sliders lead seamlessly to a large rear deck overlooking a spacious, flat, and fenced backyard; ideal for gatherings, play, or quiet relaxation amid mature landscaping and beautiful gardens.

Investors zoom in on this property, we have an income producing property. 3 of the 4 units are rented and all tenants are all current. The 4th unit is open for one more tenant. Property has been remodeled, we have a new roof with warranty, foundation work to reinforce this property, new floors in all the units, bathrooms are renovated, the entire interior has been repainted, Kitchen remodel, New stove and refrigerator, New heating circulator pumps installed for all units, necessary plumbing upgrades throughout.

8 Unit investment opportunity! Located just outside of downtown Pittsfield and within walking distance to shops, restaurants, schools, and parks. Low maintenance exterior with loads of off street parking. All units feature one bedroom with separate heat and electricity. Coin-op laundry located on site for additional income.

Must see offering in Indian Lake Estates! This contemporary truly has it all! Enter into the great room with vaulted ceiling, woodstove for chilly evenings, wood floors, and featuring natural woodwork and built-ins in the dining area. Open kitchen, guest bedroom/full bath on the main level along with den/office that leads to the primary suite. Stairway leads to an open loft and private third bedroom/full bath. Nature surrounds you here! Year-round sunroom w wall of windows; then entertain in style on the screened porch that opens to rear deck. Stay-cation on one of the three beaches at Indian Lake, non-motorized with canoe/kayak storage. Tennis courts and play area. Location on a paved road for easy access to Jacob's Pillow, and other nearby Berkshire attractions.

Situated in the finest location in a quiet neighborhood of very nicely kept homes, this three bedroom, two bath home offers the discerning buyer an abundance of privacy, especially with the adjacent 1.33 acre wooded parcel included in the sale. The property also abuts state land to the south, providing additional protection and enhancing the peaceful aura of the surroundings. Stately and spacious, the residence has a wonderful array of living and entertaining areas both inside and out. A lovely kitchen with granite counters and gleaming white cabinetry opens to a two story deck, with al fresco dining and leisure opportunities both up and down. Below is an expansive four season sunroom with access to the decking and to the large fireplaced family room. With a kitchenette close by,

Set on a hilltop, the end of a cul-de-sac in desirable Lanesborough, 56 Victoria Lane offers the perfect blend of privacy, space & functionality. This 3-bedroom, 2-bath home features over 2,600 square feet of living space & a versatile layout designed to fit a variety of lifestyles. The first floor offers 2 bedrooms & a full bath, ideal for guests, one-level living, or a convenient home office. The main living areas are filled with natural light & offer a comfortable flow for entertaining. Upstairs offers a spacious primary en-suite complete with a walk-in closet and a jetted tub. Outside, enjoy the wrap-around deck and peaceful atmosphere. There is also a detached garage and an electric car charger. Just minutes from outdoor recreation, lakes and skiing.

Tucked into the rolling hills of Great Barrington, The Turning Point has been welcoming travelers for more than two centuries. In the 1800s, stagecoaches once paused here--horses rested, stories were traded, and journeys quietly shifted direction. That spirit of arrival still lingers.Now spanning 3,600 square feet, this historic Berkshire retreat has lived many lives: a bustling inn, a beloved home, a place where people gathered, stayed a while, and never quite forgot how it made them feel. With 7 bedrooms and 6.5 baths, the house unfolds with an ease that invites connection and retreat in equal measure.The bones are here--wide-plank floors, glowing fireplaces, generous rooms, and a layout designed for connection. What it needs is someone who sees beyond what it is today and imagines