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.

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.

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!

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 Productions, 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.

Discover a peaceful retreat in Alford with this charming 4-bedroom, 2.5-bath Contemporary Cape set on more than 8 acres. Relax on the spacious screened-in porch while listening to the birdsong and the gentle flow of Scribner Brook. Offering an upscale cabin feel in every season, this inviting home provides the perfect escape from the pace of everyday life. Enjoy privacy, natural beauty, and the tranquility of your own wooded retreat.

Rare opportunity to own a spacious four-bedroom, four-and-a-half-bath end-unit town home with three finished levels, a two-car garage, and multiple outdoor, screened in living spaces. Tucked into a quiet cul-de-sac and set back from the road, this inviting home enjoys a peaceful, wooded backdrop, abundant natural light, and convenient access to the community pool--an ideal setting for relaxed everyday living and entertaining. The main level centers around a sun-filled living room with vaulted ceilings, transom windows, and a gas fireplace. A french- door opens to an enclosed screened deck overlooking the woods, creating an easy connection between indoor and outdoor living. The kitchen features granite countertops, stainless

Stunning Contemporary Home in Great Barrington - Perfect Blend of Privacy and Convenience Discover 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.

Perched on Mount Hunger is this lovely, private, contemporary four-bedroom, three-bath home located near Lake Garfield, of which there are winter views. The current owners added a huge, beautiful living/dining room with a fieldstone fireplace, cathedral ceiling and huge windows. The renovated kitchen has granite counters with a Viking cooktop and Bosch double wall ovens. A first floor primary suite is complimented by a den and a three-season porch. The second floor holds two guest bedrooms and a guest bath, while the lower walk-out level has a fourth bedroom, a family room, laundry and utility room and a storage room with built-in shelving. Located well off the road with air conditioning, an outdoor shower and fiber internet. A true Berkshire country home with the best town beach nearby.

Stunning architect designed space with soaring ceilings, floating staircases and numerous high-end features. Ideally situated on nearly ¾ acre abutting an 18-acre nature reserve. Just a short walk to downtown Lee shops and restaurants. Lots of room for a pool, tennis court, and/or pickleball court. Minutes from the best places in the Berkshires. Great investment opportunity with the nearby $100 million Eagle Mill development. Lots of room with 4,000 square feet of living space plus a separate 2,500 square foot area with large stained glass windows to create a second dwelling unit, studio, chapel, gym, office, or entertainment extravaganza. Combining the best of new construction with old charm, you need to view this amazing space to experience its magnificence!

Mixed use property located just 7 miles south of Gt Barrington on Route 7. Two commercial units and two residential units. Solar on roof and in back of property bring in additional lease revenue. Long term tenants in each apartment. Anchor commercial tenant, Berkshire Fence & Accessories, to sign long term lease with new owner. Second commercial unit vacant, perfect for owner occupied buyer.

Just around the corner from world-renowned Tanglewood, this exceptional Richmond property offers a truly prime Berkshires location -- where music, culture, and natural beauty meet. Set on just over five picturesque acres with shared ownership in a charming small pond, the setting is as special as the home itself. Beautiful open landscaping creates an inviting approach, with sweeping lawns and thoughtfully maintained grounds that enhance the sense of privacy and serenity. The home itself is bright and airy, filled with natural light and designed for both comfortable everyday living and gracious entertaining. The kitchen is the heart of the home, seamlessly open to a sunny breakfast nook and a sun-filled family room -- perfect for gathering with friends and family.

Privately set on just under 7 acres, this beautifully renovated home offers the perfect combination of tranquility, privacy, and convenience. A meticulously paved circular driveway leads through elegant, iron fencing to the level, beautifully landscaped property. The home offers approximately 2,800 square feet of thoughtfully updated living space, with 3 to 4 bedrooms and 2 full baths across two spacious levels. Natural light fills the interior, highlighting beautiful wood floors throughout and adding to the warm, inviting atmosphere. Skylights bring even more light into the home, while the oversized deck provides an ideal setting for outdoor entertaining, relaxing, and enjoying the peaceful surroundings. An oversized two-car garage offers generous parking and storage.

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...

A private Berkshire lodge with room for everyone. Set on 4.89 acres in Becket Woods, this five-bedroom, four-bath home offers more than 4,000 square feet of living space across three finished levels. It is an ideal retreat for gathering family and friends, with ample space for everyone to spread out. At the center of the home is a dramatic two-story great room, where a massive stone fireplace rises through the soaring wood-paneled space. Large arched windows fill the room with natural light and views of the surrounding trees, while the open loft above adds to the lodge-like scale and character. The bright kitchen opens directly to the great room and features a Viking range, butcher-block island, generous workspace, and an eat-in area.

Live, Love, & Play in Blythewood Estates priced favorable $250,000 less than assessed value for a quick sale to allow you enjoyment this beautiful Berkshire season. A private enclave near premier Lake Onota to experience idyllic living in the Berkshire hills while creating lasting memories. This stunning 6000+ sf, 5 Bedroom, 5.5 bath colonial is thoughtfully designed and beautifully set on 3.42 manageable acres with sweeping meadow views nestled perfectly to create peace in nature while centrally located minutes to the culture, arts, museums, eclectic dining and central to Tanglewood and The Clark Art. Three levels of living create a blend of fun and entertainment with a degree of separation on levels. First floor offers one level easy living with a dramatic two story primary bedroom suit

Nestled on over 3 private acres with an extraordinary 650 feet of frontage on Hayes Pond, this exceptional waterfront retreat offers sweeping elevated views, a private dock, sandy beach, and direct access to swimming, kayaking, and fishing. Designed to embrace its stunning natural setting, the home features expansive windows and multiple outdoor living spaces, including a wraparound deck, waterside gazebo, and screened porch with hot tub connection--perfect for entertaining or relaxing in every season. The bright open-concept interior includes 4 bedrooms and 3 full baths, highlighted by a dramatic great room with knotty pine ceilings, a wood-burning stove with stone hearth, and direct deck access overlooking the water. The spacious primary suite also opens to the deck and features its own

Contemporary home built in 2012 on over 11 acres walking distance to Stockbridge center. Original house was taken down and this sun-drenched home was built on the saved footprint. Main floor has a small living area off the entry open to large kitchen and dining with sliders to the deck, primary suite with walk-in closet and deck access, 1/2 bath and access to the oversized garage. Second floor has vaulted ceilings, a large landing, second living area, 2 guest rooms with a hall bath and another primary suite. There are two porches off the second floor, one small off the primary and the other flanking the East side - covered for protected enjoyment. The Konakpot Brook winds through the back of the 11+ acres giving access to fishing and just relaxing by the water.

Some spaces change the way you imagine living. Loft 306 is one of them. 1,985 SF inside. Another 1,615 SF of private terrace outside. South-facing Berkshire mountain views. Suddenly there is room for long summer dinners, a garden in pots, friends for the weekend, morning coffee in the sun--and an entire outdoor room under a very big Berkshire sky. Conceived by celebrated architects LATENT Productions, Greylock WORKS is a highly considered transformation of a historic Berkshire mill, respecting what was here rather than erasing it.

Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a warm and inviting escape. Two additional en-suite guest bedrooms occupy the second floor with sitting area between. Residents enjoy exclusive access to a resort-inspired amenity suite—pool, fitness center, clubhouse, and tennis—all just minutes from the cultural and culinary heart of Lenox. A rare blend of privacy, comfort, and sophistication. This is a truly outstanding home, must see.

Uncommonly Superb View -- A Vermont Meadow Retreat Tucked quietly into a broad meadow and surrounded by lush Vermont landscape, this property enjoys one of those rare, completely unspoiled western vistas: a full, harmonious sweep of the Taconic Mountain ridgeline, framed perfectly within human scale. The almost 40 acre setting--meadow bordered by deep woodland--creates a sense of arrival, privacy, and permanence that is difficult to replicate. The architect designed home blends natural materials inside and out, offering a calming, organic environment that feels inseparable from the land around it. One of the sellers' guiding goals the architect skillfully interpreted, was harmony with the landscape, expressed most beautifully in the roofline: ... (see more)