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.

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)

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 !

Dreamy river Colonial: tucked away on 4 beautiful acres, 1361 feet of river frontage, offering privacy and a quiet sanctuary for wildlife viewing. Main floor features an updated classic chef's kitchen that flows into a spacious Great Room w/ wood-burning fireplace, dining area, 1/2 bath, and direct access to the sun deck with sparkling river and dramatic sunset views. A breezeway connecting the 2-car garage is a sunny space for all of your seasonal gear. Upstairs, the large primary bedroom includes a 2nd wood-burning fireplace and en suite bath, while two additional bedrooms share a full bath. Main floor office and a finished lower level currently serves as guest accommodations, media room, fitness, laundry, and a variety of additional uses. New landscaping! 4 bed Title V, completed 4/26.

Gorgeous contemporary ranch home built in 2001, ideally situated on the North Adams/Williamstown line with breathtaking mountain views from every window. Sited on a 14 acre pastoral parcel, of which 6.9 acres are being placed in a conservation restriction, the home and landscape reflect the unique beauty of the Berkshires.This thoughtfully designed home offers convenient one-level living with three first-floor bedrooms, including a cozy primary suite featuring its own charming balcony. The main level also includes a large living/dining space with radiant heat and a beautiful fireplace, featuring an open, light-filled layout perfect for everyday living and entertaining. The lower level provides excellent flexibility with ample storage rooms, a two-car garage, and a finished bonus living

A DRILLED WELL, A COMPLETE 6 BEDROOM SEPTIC SYSTEM, A HORSE BARN AND A SHED COMES WITH THIS FABULOUS 42 PLUS ACRE PARCEL. BEAUTIFUL STONE WALLS SURROUND THE BUILDING SITE AND ACROSS FROM PROTECTED LAND

Beautifully maintained home set on a private one-acre lot on a quiet cul-de-sac in one of Lenox's most desirable neighborhoods. This thoughtfully designed residence offers four bedrooms and 5.5 baths, including a spacious main-level primary suite with a luxurious en-suite bath. The inviting floor plan is ideal for both everyday living and entertaining. Step outside to a beautifully landscaped backyard featuring a built-in grill, hot tub and plenty of space to relax or gather with family and friends. A rare opportunity to enjoy privacy, comfort, and an exceptional Lenox location.

Historic 9-Unit Bed & Breakfast | ±10,560 SF on ±0.33 Acres Exceptional opportunity to own a beautifully maintained three-story historic bed & breakfast offering approximately 10,560 square feet on a ±⅓-acre lot. Within walking distance to the downtown theater/business district. This well-appointed property features nine unique guest suites, each with private baths and kitchenettes, blending classic charm with modern amenities. Large parking lot in the rear of the property also offers a separate right of way directly onto East Housatonic St. Guests are welcomed through an elegant entry foyer, leading to inviting common spaces including a parlor, formal dining room, and fully equipped common kitchen. The first floor also includes two spacious guest suites.

Beautifully maintained 4-bedroom, 4.5 bath home located in one of Lenox's most desirable neighborhoods. Thoughtfully designed floor plan featuring a spacious living room with vaulted ceiling and abundant natural light. The well-appointed kitchen offers granite countertops, stainless steel appliances, and comfortable dining area overlooking the private backyard. Generous first-floor primary suite provides convenience and privacy, while three additional bedrooms and well-appointed baths offer ample space for family and guests. A versatile den/home office and finished lower-level family room add flexibility for today's lifestyle. Enjoy outdoor living from the screened porch and stone patio surrounded by mature landscaping. Conveniently located just minutes from downtown Lenox and Tanglewood.

Great Barrington A masterful rebuild with reverence for Great Barrington's past and a bold reimagining for modern living. This 5-bedroom, 4-1/2 bath colonial sits in-town and blends historic charm with contemporary luxury for effortless, years-long comfort. Property Highlights 5 Bedrooms | 4 Full Baths + 1 Half Bath** Complex rebuild from the ground up** - preserved nod to the town's heritage with a fresh, modern interior Chef's Kitchen** - high-end appliances, ample prep space, and thoughtful layout for entertaining Radiant Floor Heating** - in entry Dual Fuel Heat throughout High Velocity Central Air Conditioning** - efficient, quiet climate control Solid Heavy Doors with Emtek Hardware** - substantial, timeless feel with premium finishes 4-Season Porch**

Discover this breathtaking timber-frame home sited on a peaceful and private 10-acre park-like setting central to the Berkshires. Redesigned by architect Pam Sandler, who added a vaulted great room ceiling, a welcoming front porch, a spacious screened porch, and a 3-car garage. Featuring a first-floor en-suite primary bedroom, a generous living & dining area anchored by a commanding fieldstone fireplace, and a well-planned kitchen with all stainless appliances. Three upstairs bedrooms have ample closet space, and the basement family room with a wood-burning stove offers a cozy winter retreat. This eco-friendly home features a newly built barn, solar panels, and heat-pump climate control. There is so much to experience in this beautifully updated home, just 10 minutes from Tanglewood.

Set in the heart of the Berkshires of Lee, Mass, this beautifully maintained 4-bedroom home captures the essence of Berkshire living with panoramic, elevated views for all 4 seasons that will leave you speechless; particularly in Autumn, when views in the Berkshires explode with color. A 4th oversized garage below the house is the perfect place for all of your toys. Inside, the home offers 3 finished levels of flexible living space designed with an open concept. The 1st floor primary suite provides the ease of one-level living and features a newly renovated bathroom with walk-in shower, creating a spa-like retreat with tasteful tile finishes.

Special Berkshire retreat on 25 private acres in Harrington Woods with beautiful views. Offering 5,400 sq ft, this 4-bedroom, 4-bath home features oversized rooms and high ceilings. The main level includes a recently renovated chef's kitchen, expansive primary suite with walk-in closets, guest room/office, library with built-ins, dramatic living room and a 400 sq ft screened porch. The walkout lower level offers two additional bedrooms, exercise room, family room, professional pool table, sauna and steam shower. Additional highlights include an oversized 2-car garage with Level 2 EV charger, 12x24 storage shed, and a 30-panel solar array with a transferable utility credit. HOA amenities include tennis, pickleball and a heated seasonal pool. Minutes to Otis Ridge and Great Barrington.

Experience the beauty of Berkshire lakefront living on beautiful Pontoosuc Lake, where breathtaking sunrise views, peaceful waters, and exceptional privacy create the perfect year-round retreat. Nestled in the heart of the Berkshires, this beautifully remodeled home blends luxury, comfort, and thoughtful design, ideal for both everyday living and entertaining by the lake.

Set across 30+ pristine Berkshire acres, this property offers sweeping westerly mountain views, gently rolling fields, and Cone Brook running the length of the land to Shaker Mill Pond. With approximately 2,000 feet of frontage on Swamp Road, the possibilities are wide open: farming, equestrian use, a private estate, or potential subdivision into 6+ buildable lots.Two substantial barns, both equipped with electric and water, are already in place, offering immediate utility and flexibility. The setting is both scenic and convenient & just minutes to the village of West Stockbridge. A short drive to Tanglewood and Lenox, and within easy reach of ski areas.Additionally, a 1950s four-bedroom, two-bath home with a heated basement sits along the road frontage, ready for

A rare opportunity to own one of the most extraordinary parcels in the region. High Meadows Farm encompasses sweeping open meadows, mature woodlands, and truly breathtaking 360-degree views stretching from Mount Greylock to the south, Mount Anthony to the north, the Taconic Ridge to the west, and Dome and Pine Cobble to the east. Wander a secluded birch-lined pathway, discover a magnificent century-old oak tree, and follow the gentle brook that borders the property. This remarkable landscape offers a rare combination of privacy, natural beauty, and accessibility. Create an incomparable estate overlooking the mountains, or take advantage of the property's three ready-to-build lots to establish a family compound nestled among meadows and woodland. Whether envisioned as a private retreat,

Tucked away at the end of a private cul-de-sac on 1.22 acres, this 4-bedroom, 4-bathroom contemporary home delivers sophisticated Berkshire living just minutes from downtown Great Barrington. Offering the perfect footprint for full-time remote professionals, weekend escapees, or downsizers, this property pairs a spacious layout with the effortless lifestyle of a premier community association. The heart of the home is a dramatic, light-filled great room anchored by soaring cathedral ceilings and a brick fireplace paired with charming built-ins. The main level is designed for entertainment and ease, featuring a lavish first-floor primary suite with walk-in closets and a spacious ensuite bath. Upstairs, three additional guest bedrooms are complemented by a private, separate bonus studio

Located in a ''hidden'' neighborhood behind a stonewall entrance, this newly built home offers tranquil living just 5 minutes from the heart of Great Barrington. The spacious farmhouse front porch is the perfect spot to enjoy quiet mornings or gather in evenings with family and friends. Light-filled and open, the main level features an elegant living and dining area framed by French doors, a gas fireplace, and a chef's kitchen designed for effortless entertaining. Also on the 1st floor, a guest bedroom suite enjoys a private bath with shower and soaking tub. On the 2nd floor the generous primary suite offers dual walk-in closets as well as an luxuriously oversized shower and soaking tub.

Well maintained and set in a prime Egremont location, this home is perched above the Egremont plain with open views. Quiet and private, yet just minutes to downtown Great Barrington, Egremont and everything the Berkshires has to offer. The main level is bright and welcoming, with an open living space centered around a wood-burning fireplace. A first-floor library adds a quiet, separate space; ideal for a home office while the kitchen connects directly to the deck, creating an easy flow for indoor/outdoor living and a perfect spot to take in the views. The upper level features three bedrooms, including a primary ensuite, along with a full bath and an additional den that can easily serve as a lounge or office. The lower level offers a full in-law apartment complete with it

Situated at the top of vibrant Railroad Street, this property offers exceptional visibility in a bustling location, making it an ideal spot for retail stores, restaurants, cafes, or office spaces. The building features two spacious stories and a full basement, providing ample room for various business operations. With high ceilings that create an airy atmosphere and windows on three sides that flood the interiors with natural light, the space feels open and inviting. This is a remarkable opportunity to establish your business in the heart of Great Barrington, surrounded by the excitement and energy of a thriving community.