Tucked away on a quiet country road just minutes from the heart of historic Stockbridge, this 3.49-acre property pairs timeless New England charm with modern comforts. The star of the show is a beautifully updated red farmhouse with 3 bedrooms and 2.5 bathrooms, set on a sunny, bucolic lot that feels worlds away--yet is moments from downtown.The main house has been thoughtfully renovated, blending original character with contemporary upgrades. Post and beam construction adds warmth and architectural texture, while a sleek gas fireplace anchors the open living and dining areas. The updated kitchen is ideal for gatherings both casual and festive. The first-floor primary suite includes a walk-in closet and private bath. Upstairs, two additional bedrooms and a full bath complete the

Exceptional custom-built home on 3.81 private acres in Pittsfield, offering the perfect blend of luxury, comfort, & privacy. Built in 2003, this well maintained 4-bedroom, 4.5-bath residence features a thoughtfully designed floor plan, driveway alarm, gas fireplace, home theatre system, 2-car heated attached garage with central vac. A private in-law suite, ideal for multigenerational living. An IMPRESSIVE 3,500 sq ft outbuilding providing endless possibilities for contractors, hobbyists, car enthusiasts, storage, or home-based business use. Equipped with a backup generator for added peace of mind. Enjoy peaceful outdoor living with a beautiful koi pond, private surroundings and trails for hiking, ATV's and snowmobiles. A rare opportunity to own a truly unique property in the Berkshires.

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, BUpstreet 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 caregiver

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

Enchanting 55-Acre Country Estate Along Mill Brook Discover a true rural refuge where historic charm meets masterful modern design. Set on 55 breathtaking acres alongside the dramatic geological beauty of Mill Brook complete with swimming hole, this lovingly maintained 5-bedroom estate offers an unparalleled sanctuary. At the heart of the property is a circa 1830 Cape, beautifully preserving its original character with stunning wood floors, classic moldings, and cozy fireplaces. Over the years, the home has been thoughtfully expanded for modern living. A masterfully designed kitchen and den serve as the ultimate gathering hub, while the first-floor primary suite boasts dramatic cathedral ceilings. Sip your morning coffee in the sun-drenched three-season porch, complete with a coz

Set on just over seven acres between Lee and Stockbridge, this c.1850 Greek Revival delivers classic Berkshire character with real scale. Nearly 4,700 square feet with a gracious flow, tall windows, and preserved period details. Every bedroom offers an en suite, creating an easy setup for hosting family and friends. Common spaces include a welcoming foyer, two living rooms, a formal dining room, a library, and a large cook's kitchen with eat-in area and pantry. Three period fireplaces add warmth and charm. Outside, mature trees frame open meadow, with room for gardens, games, and long summer evenings. The setting is remarkably convenient. Tanglewood, Lenox, Stockbridge, and downtown Lee are a short drive, and access to Route 7 and the Mass Pike keeps weekend trips simple.

Sitting right on the Lenox-Lee line, Katydid Cottage is one of the few freestanding homes at Fox Hollow - your own house, your own private patio, with Lenox and Tanglewood just up the road. It feels like a single-family home but comes with the ease of condo ownership, so your weekends go to the lake instead of the upkeep. The main floor is where this one really works. The kitchen is bright and open to a big dining room, and the living room has a gas fireplace for the cold months. The primary suite is on the first floor too, so you can live on one level if you'd prefer.

Set within one of the Berkshires most coveted communities, 9 Eastbrook Lane is a masterclass in refined living, where thoughtful design meets impeccable care. Beautifully and intentionally sited, this distinguished residence offers 5 bedrooms, 3 full and 2 half baths across a gracious, light-filled layout designed for both elegant entertaining and everyday comfort.The stunning kitchen showcases rich maple cabinetry, a premium Viking range, dual refrigerators and exceptional workspace, perfectly suited for the discerning cook. The renovated primary bathroom evokes a true spa experience, blending luxury and serenity with timeless finishes. Every detail has been meticulously maintained, from the seamless indoor-outdoor flow to the expansive Trex decking ideal for al fresco gatherings.

Rarely does a property emerge with this much soul, style, and built-in momentum. Nestled on 5.14 expansive acres along the high-visibility Route 23 corridor, Hy's Fried is the definitive Berkshire success story--a masterful ''roadhouse revival'' that has captured the imagination of the Brooklyn-to-Berkshires set. Originally the iconic Old Egremont Club, this site has been meticulously reimagined into a ''hallucinatory chicken shack'' and late-night vinyl lounge, offering a rare turn-key opportunity that includes both a thriving, high-margin business and the underlying real estate. By day, the venue is a stylized destination for the region's best gluten-free fried chicken--a 6-hour brined, hormone-free masterpiece that earned the Rural Intelligence Reader's Choice award.

Rarely does a property emerge with this much soul, style, and built-in momentum. Nestled on 5.14 expansive acres along the high-visibility Route 23 corridor, Hy's Fried is the definitive Berkshire success story--a masterful ''roadhouse revival'' that has captured the imagination of the Brooklyn-to-Berkshires set. Originally the iconic Old Egremont Club, this site has been meticulously reimagined into a ''hallucinatory chicken shack'' and late-night vinyl lounge, offering a rare turn-key opportunity that includes both a thriving, high-margin business and the underlying real estate. By day, the venue is a stylized destination for the region's best gluten-free fried chicken--a 6-hour brined, hormone-free masterpiece that earned the Rural Intelligence Reader's Choice award.

Welcome to one of Southeast Pittsfield's most coveted neighborhoods, where this exceptional Colonial seamlessly blends timeless elegance with modern luxury. Offering 4 bedrooms and 3.5 baths, the home showcases a simply stunning interior highlighted by a chef's kitchen with Omega cabinetry and commercial-grade appliances. Expansive windows bathe every room in natural light, creating effortless indoor-outdoor flow. Outside, unwind to unforgettable sunsets from the private backyard abutting Canoe Meadows, complete with a large wraparound deck, in-ground swimming pool, and pool house. The finished walkout lower level features a second kitchen, full bath, home gym, and generous recreation space ideal for teens, guests, or extended stays. A truly rare offering in an irreplaceable setting.

Welcome to this newly remodeled 4,298 sq. ft. luxury residence, perfectly set on 1.53 acres of beautifully landscaped grounds. Built in 1998 and thoughtfully updated, this home blends timeless elegance with modern sophistication. Inside, the open and airy floor plan features 4 bedrooms and 3 ½ bathrooms, designed for both comfort and style. The chef's kitchen boasts a Sub-Zero refrigerator, Wolf appliances, and a built-in Miele coffee machine, while the dining room is enhanced with custom-built-in fridge and freezer drawers—perfect for hosting. From the attached two-car garage, a custom mudroom with built-in shoe storage leads into a finished home gym outfitted with state-of-the-art equipment.

A Stunning Three-Story Residence with Breathtaking Views for an Easy Care Lifestyle in the Berkshires.Majestic and magical perfectly describe this exquisite three-story mountain top home, designed to capture the stunning and distant views of the Berkshire skyline. With over 5,000 square feet of expansive living space, this centrally located residence offers the perfect opportunity to either escape, join a quaint community or work at home with glorious views of the Berkshire Hills.Prime Location for Nature and Culture.Nestled in a charming small-town neighborhood, this home is bordered by beautiful woodlands, providing direct access to hiking trails and the nearby Appalachian Trail. Its central location places you at the heart of the area's vibrant culture and great outdoors.

Open House June 13, 1-2:30. Striking and sophisticated riverfront condominium in superb location, with close proximity to restaurants, shops and theater on Spring and Water Streets, the Taconic Golf Club, Williams College, and the Clark Art Institute. One of only 6 recently built town house units on the river in the handsome Cable Mills complex, number 8 has benefitted beautifully from the discerning taste and style of its owner, with elegant yet understated lighting fixtures, and enchanting touches of color and texture throughout. Light-filled with an abundance of large windows, it offers as well two terraces and two upper decks providing opportunities for al fresco dining and fresh air relaxation. A sleek suite of Thermador appliances graces the kitchen/dining area which includes

Open House June 13, 1-2:30. Striking and sophisticated riverfront condominium in superb location, with close proximity to restaurants, shops and theater on Spring and Water Streets, the Taconic Golf Club, Williams College, and the Clark Art Institute. One of only 6 recently built town house units on the river in the handsome Cable Mills complex, number 8 has benefitted beautifully from the discerning taste and style of its owner, with elegant yet understated lighting fixtures, and enchanting touches of color and texture throughout. Light-filled with an abundance of large windows, it offers as well two terraces and two upper decks providing opportunities for al fresco dining and fresh air relaxation. A sleek suite of Thermador appliances graces the kitchen/dining area which includes

Rare opportunity to own a commercial store front on the iconic Railroad Street in downtown Great Barrington. Great investment property with two filled store fronts. Options available to increase a larger footprint.

Just up the road from the world-renowned Jacob's Pillow Dance Center, this stunning architect-designed sanctuary sits on 14 sprawling acres with panoramic views of Greenwater Pond and the rolling valley beyond. At the heart of this masterfully crafted 1998 home is the great room with soaring vaulted ceilings centered on a magnificent oversized stone fireplace. This spectacular space is banked by a wall of glass windows and doors leading to an impressive 60-foot deck for a front row seat to dazzling sunsets. The great room flows seamlessly into a sleek and thoughtfully appointed kitchen, and a spacious dining room perfect for entertaining a crowd. The primary suite serves as a personal haven, featuring its own stunning vistas, dual primary baths, and a small office. The lower level...

Completed in 2022 and set atop one of North Berkshire County's most scenic country roads, this architecturally striking contemporary residence was thoughtfully designed to embrace natural light, energy efficiency, exceptional indoor-outdoor living, and panoramic views of the Mount Greylock Reservation. Positioned along sought-after Bailey Road in Lanesborough, the property offers a rare combination of modern design, privacy, and breathtaking Berkshire mountain scenery just minutes from Williamstown, Jiminy Peak, Mass MoCA, and the region's renowned cultural destinations.

Originally built with classic 19th century detail, this 6 bedroom, 3.5 bath Colonial/Victorian has been thoughtfully expanded and renovated, carefully embellishing its original character with today's sought-after conveniences. Elegantly spacious rooms with high ceilings and tall windows lead to the well-designed kitchen, where you'll find 2 copper sinks, Wolf double ovens, pot filler, warming drawer, built-in Miele coffee maker, and even a dumb waiter! In addition, a large sunroom was added, with radiant floor heat for year-round enjoyment. Other modern upgrades include a sophisticated central A/C system, back-up generator, and water filtration system. Most recently a gorgeous, heated in-ground pool was installed on your private 2.35 acres. Historically named ''Hilltop,'' this gracious

A custom built home set on 16 private acres, offering 5-bedrooms, 5 full baths, 1 half bath with over 4,000 square feet of living space. Surrounded by natural beauty and peaceful scenery, the property provides the perfect balance of privacy, space, and comfort. Inside, you'll find generously sized rooms, multiple living and entertaining areas, and a flexible floor plan ideal for both full-time living and weekend retreat use. The spacious primary suite, ample guest accommodations, and thoughtfully designed layout make this home well-suited for hosting family and friends. An unfinished area in the basement allows for an additional room made to your liking. A short drive to Otis ridge and the Otis Reservoir, making outdoor activities right in your backyard!