Move right into this stunning single-family home at highly desirable Berkshire Country Meadows. Nearly new and impeccably maintained, this spacious home offers the ease of condominium living with the feel of a private residence. The open-concept design features a beautiful kitchen, dining area, and living room with a cozy gas fireplace, perfect for entertaining or everyday living, and a separate first floor office with French doors for privacy. The first-floor primary suite boasts a walk-in closet and en suite bath while the walkout lower level expands the living space with a generous family room, two additional bedrooms, full bath and private patio. With 4 bedrooms, 4 full baths, and exceptional space throughout, this home is simply gorgeous and ready to enjoy. Clubhouse, pool, tennis.

These are the Berkshire views you've been dreaming of. Meadow, mountains and enormous sky surround you in nearly every direction, with stunning westerly views across preserved fields to the lower Taconic Mountains. Morning light moves across the meadow; evenings end with the sun dropping behind the ridgeline. Spring brings wildflowers and returning birds, summer fills the fields with native plants and pollinators, autumn moves across the mountains in color, and winter transforms it all to snow-covered meadow and white-capped peaks. Perhaps your greatest pleasure will be getting out into it--walking the fields, cross-country skiing after fresh snow, watching the birds and wildlife, or discovering what has changed in the meadow from one day to the next.

Originally built in the 19th century, this Egremont schoolhouse has undergone a radical,''down-to-the-studs'' transformation, and has been thoughtfully designed to create a high-performance home for modern living, while honoring its historic character. Sound structural integrity, with state of the art insulation, custom engineered windows, a new HVAC system, and a solar array for near zero energy overhead make this home immensely comfortable and sustainable for decades to come. The Great Room features dramatic vaulted ceilings anchored by original exposed beams and a new, high-efficiency propane free standing stove. The chef's kitchen has custom cabinetry topped with honed marble counters. The bath features custom tile work and radiant heated floors.

Discover this spacious and impeccably maintained, privately sited home spanning three levels, designed for both everyday living and effortless entertaining. The open-concept living, dining, and kitchen area features a soaring wood vaulted ceiling, handsome stone fireplace, lots of glass, screened porch and a newly renovated deck overlooking a peaceful backyard with historic stone walls and woodlands. A newer addition offers a generous office or den above the attached garage. The first or lower level provides a private retreat for guests or children. Located in the sought-after Harrington Woods community, residents enjoy a shared pool, tennis and pickleball court, and a welcoming neighborhood, all just minutes from Great Barrington, Otis Reservoir, Monterey Town Beach, and Jacob's Pillow.

Investment opportunity near downtown Pittsfield. This renovated 7,904-square-foot commercial building is situated on approximately 0.72 acres in the Downtown Creative District and is currently leased to an established daycare/school operator through August 2031. The property generates an annual base rent, plus documented reimbursements for real estate taxes, insurance, and water/sewer expenses. The building offers approximately 3,952 square feet on each of two levels, with an open, adaptable layout suitable for educational, nonprofit, institutional, professional, or community-oriented uses. Improvements include central HVAC, replacement windows, sprinkler and fire-alarm upgrades, and extensive interior renovations. An elevator provides convenient access between floors.

Some homes feel as though they belong in the pages of a novel. Here, life unfolds at a gentler pace, with mornings spent listening to Tophet Brook, afternoons beneath the trees, and evenings gathered around the warmth of a brick fireplace. This inviting countryside home offers room to welcome family and friends, whether baking together in the kitchen during the holidays or lingering over conversations long after dinner. A private first-floor primary suite and thoughtfully arranged guest quarters provide a balance of togetherness and personal retreat, while the deck and fenced backyard invite you to enjoy the changing Berkshire seasons. More than a house, this is a place to leave the rush behind, find joy in the everyday, and make room for what matters most.

Former North Adams Country Club property - 87 Acres, extensive frontage on River Rd, with partially renovated 7,196 sq ft. clubhouse (see floor plans) and a 900 sq ft two-bay commercial garage. Solar array and carports bring in annual lease income, could help offset debt service for a financed purchase. Sewer manhole precast chambers installed by clubhouse and road, not connected. See floor plan images for preliminary small home development - stalled due to pandemic, needs reconfiguration due to subsequent cell tower installation (Verizon service). Capacity for one additional cell carrier. Well drilled and capped in northwest corner of land at end of shared driveway.

Former North Adams Country Club property - 87 Acres, extensive frontage on River Rd, with partially renovated 7,196 sq ft. clubhouse (see floor plans) and a 900 sq ft two-bay commercial garage. Solar array and carports bring in annual lease income, could help offset debt service for a financed purchase. Sewer manhole precast chambers installed by clubhouse and road, not connected. See floor plan images for preliminary small home development - stalled due to pandemic, needs reconfiguration due to subsequent cell tower installation (Verizon service). Capacity for one additional cell carrier. Well drilled and capped in northwest corner of land at end of shared driveway.

ARRIVE FRIDAY NIGHT, UNLOCK THE DOOR & ENJOY THE WEEKEND! Turnkey Berkshire get-away in an exceptional location. Beautifully maintained and ready for immediate enjoyment, this inviting Egremont home requires no updates and offers comfort, privacy, and convenience. Features include a two-car attached garage and generator for effortless year-round living. Ideally positioned near skiing, scenic hiking, exceptional dining, and the vibrant villages of Great Barrington & Egremont, with easy access to New York and Connecticut. Egremont's attractive property taxes add to the appeal. A rare opportunity to simply arrive, settle in, and enjoy all that the Berkshires have to offer

Your own sports compound and sanctuary tucked away on a quiet Great Barrington road: this private four-acre retreat centers around an in-ground heated swimming pool and a dedicated tennis/pickleball court framed by natural landscape. Inside, clean mid-century architectural lines deliver remarkable flow, highlighted by two fireplaces, four bedrooms, three baths, space to work from home, and a sunroom overlooking the grounds. Substantial energy upgrades include a high-output ground-mount solar array and an updated heating system that keep operational costs remarkably low, offering a turnkey private playground just minutes from downtown dining, skiing, and cultural landmarks.

A rare opportunity to become the next steward of a remarkable piece of Sheffield history. Dating to 1819 and prominently situated on South Main Street in Sheffield's Historic District, this extraordinary antique is filled with the character, warmth, and craftsmanship of another era. Currently configured as a four-family residence, the property includes three beautiful apartments in addition to the spacious main portion of the home, allowing an owner to enjoy gracious historic living while rental income helps offset expenses. Alternatively, rent all four residences and take advantage of a distinctive investment opportunity. Gorgeous grounds and an exceptional historic setting make this a truly special Sheffield property.

A rare opportunity to become the next steward of a remarkable piece of Sheffield history. Dating to 1819 and prominently located on South Main Street in Sheffield's Historic District, this extraordinary antique is filled with the character, warmth and craftsmanship of another era. 16 rooms, 5 bedrooms, multiple baths and 4 fireplaces, the home features beautiful wide-board floors, period details, sun-filled rooms and gracious proportions. A large three-season porch and welcoming front deck extend the living spaces and add to the home's timeless village appeal. With its rich history, wonderful scale and multipurpose zoning offering intriguing possibilities, this is a property ready for its next chapter--an opportunity to preserve its past while creating a home for generations to come.

Situated on just over 1.6 acres in Southfield, this charming property offers access to a private tennis court, and pool through the homeowners'' association. It has been meticulously updated and is ready for immediate occupancy. The beautiful screened porch and newly constructed terraced stonework establish the home as a genuine indoor/outdoor Berkshire retreat. Enjoy views of a striking gully and stream from your farmhouse sink and natural soapstone countertops, complemented by oak flooring throughout. During the cooler months, relax by the fireplace in the living room, which has been modernized to enhance the flow between the kitchen and porch, thereby maximizing the sense of space and expanding the home''s footprint.

A premier commercial development opportunity awaits at 185 State Road. Positioned directly on the bustling Route 7, this property guarantees maximum brand exposure with a daily traffic count exceeding 16,000 vehicles. Superior site logistics include two oversized curb cuts for easy ingress and egress, along with ample space for on-site parking. This versatile property is engineered for success, with a generous footprint that supports two distinct building envelopes. The dual-envelope design is ideal for a synergistic development: imagine a high-volume drive-through (QSR, bank, coffee) complemented by a prime location for retail or professional offices. Leverage the robust, year-round economy of the Berkshires, a premier destination for tourists and residents.

A premier commercial development opportunity awaits at 185 State Road. Positioned directly on the bustling Route 7, this property guarantees maximum brand exposure with a daily traffic count exceeding 16,000 vehicles. Superior site logistics include two oversized curb cuts for easy ingress and egress, along with ample space for on-site parking. This versatile property is engineered for success, with a generous footprint that supports two distinct building envelopes. The dual-envelope design is ideal for a synergistic development: imagine a high-volume drive-through (QSR, bank, coffee) complemented by a prime location for retail or professional offices. Leverage the robust, year-round economy of the Berkshires, a premier destination for tourists and residents.

A rare Williamstown investment opportunity just moments from WilliamsCollege. 181 & 183 North Street combines a substantially renovated two-family residence with a newly constructed detached ADU, creating three distinct residences on one property. 181 North Apt. A offers 2 bedrooms/1 bath; Apt. B offers 4 bedrooms/1 bath; and the detached 183 North ADU offers 3 bedrooms/2 baths. All three residences feature fully applianced kitchens and in-unit laundry, with modern updates and off-street parking. The ADU is currently leased through the end of the 2026-27 academic year, providing established rental income. An exceptional opportunity for an investor seeking multiple rental streams or an owner-occupant looking to live in one residence while generating income from the others.

Berkshire ridge views and ten private acres set the scene for this distinctive log contemporary on George Carter Road in Becket. Set on a quiet country road just beyond Jacob's Pillow Dance Festival and within easy reach of Lee and Lenox, the home offers generous gathering spaces, a private guest suite, and a wonderful setting for a four-season Berkshire getaway. At the heart of the home is a dramatic great room with soaring cathedral ceilings, massive exposed log beams and trusses, and a floor-to-ceiling brick fireplace. A wall of windows rises to the roofline, filling the space with natural light and framing the Berkshire ridges beyond. Generous living and dining areas offer plenty of room to gather, while glass doors open directly to a wraparound deck overlooking the grounds and pool

Well-maintained seven-unit investment property in a convenient Southeast Pittsfield location. This handsome brick building features spacious apartments, classic architectural character and practical layouts. Six units offer two bedrooms and one bathroom, while the additional basement-level apartment includes one bedroom and one bathroom that needs remodeling. Each unit features a fireplace mantel, rear porch with both interior and exterior access, along with a flexible front room that can be opened to the dining room. Additional improvements and amenities include replacement windows, on-site laundry, private off-street parking, individual basement storage areas for each apartment and a rear interior egress staircase serving all units. Heat and hot water are included in the rents.

Dreaming of your own private sanctuary? 30+ acres await exploration! Enter between two stone pillars and the long winding driveway will take you past woodland glades, open spaces, mature tree stands, manicured lawns and a magnificent spring-fed swimming quarry! Acres of open cleared land afford additional usage options. Cedar log home, one-owner custom built. Large wrap-around deck and long covered porch; great for summer entertaining! Inside you'll enjoy over 2000 sf of relaxed country living. Great room with vaulted ceiling, massive stone fireplace. Open kitchen w. granite counters and island w seating. Two first floor bedrooms and full bath. Upper level with spacious primary suite and an open loft with fireplace. Finished walk-out lower level w. 2 car garage. Truly one-of-a-kind!

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!