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

Nestled in a peaceful, wooded setting, this exceptional home offers the perfect blend of comfort, style, and natural beauty. Sunlight fills the open floor plan through expansive windows, creating bright, inviting living spaces and showcasing scenic views year-round. A soaring stone fireplace anchors the great room, while beautiful hardwood floors flow throughout. Enjoy the screened porch, accessible from both the great room and the first-floor primary suite, for quiet mornings or relaxing evenings. The main level also features a spacious primary suite and convenient first-floor laundry. Upstairs, a generous loft provides flexible living space, along with three additional bedrooms and two full baths, including one en suite. . . . .

Easy living Ranch home on beautiful Onota Lake. Fantastic views of the Lake and Distant Berkshire Hills. Enjoy westerly sunset views from your expansive, manicured lawn and almost every room in the house. A quiet setting with comparable homes and easy access to all the Berkshires has to offer. Needs a little TLC, but well worth it for this sought after location and lifestyle. Hardwood floors refinished and interior recently painted.

Tucked away at the end of a long driveway and perched atop its own private hill, this stunning 3-bedroom, 2.5-bath post-and-beam home offers complete privacy and breathtaking mountain views. The open floor plan is centered around a dramatic floor-to-ceiling fieldstone wood-burning fireplace, with soaring ceilings, exposed beams, and beautiful pine floors throughout. The primary suite includes a private bath, while two additional vaulted-ceiling bedrooms share a full bath. Enjoy central AC, a metal roof, board-and-batten siding, portable generator hookup, and a large dry basement for storage. Outside, relax on the expansive rear deck, swim in your spring-fed pond, fish on a lazy Sunday afternoon, and enjoy spectacular sunsets and incredible stargazing from your own hilltop retreat.

Perfectly positioned on the border of Hancock and Williamstown, this striking Post & Beam contemporary estate offers a rare blend of architectural sophistication and rustic elegance. Spanning approximately 27 acres of meadows and woodlands, this property serves as a secluded sanctuary with views of countryside, mountains, and it is 3.5 miles to Jiminy Peak Ski Resort. The home's interior unfolds across three expansive levels defined by windows, views, soaring ceilings, and rich hardwood flooring. The main living areas include a cozy living room with a Mansfield model wood-burning stove, media/music areas, and a 3-season sunroom that flows seamlessly onto a spacious trex deck. The chef's kitchen is a masterpiece of function and style, complete with a walk-in pantry and dining area.

Set on a desirable tree-lined dead-end street in the heart of Lenox, this beautifully restored 1937 Cape blends timeless character with exceptional craftsmanship. Featured in Berkshire Magazine, the 3,740 sq. ft. home offers original heart pine floors, a wood-burning fireplace, and extensive updates including new plumbing, electrical, Pella windows, roof, and central AC. The three-level layout features 3 bedrooms, 4 full baths, two upper-level suites, and a finished lower level with a guest suite, office, and workshop. French doors open to a wraparound veranda overlooking Goshen stone terraces, fruit trees, and a fire pit. Enjoy sidewalk access to downtown, and Tanglewood is just minutes away.

In the Berkshires, the rarest luxury isn't simply a beautiful home--it's finding a place that makes you want to stay a little longer. Welcome to 130 East Dugway Road. As you arrive, the pace of life begins to slow. Morning coffee lasts a little longer, evenings linger beneath Berkshire skies, and weekends become treasured family traditions. Thoughtfully designed for both elegant entertaining and quiet retreat, this exceptional home blends timeless architecture, refined craftsmanship, and inviting living spaces that feel as welcoming as they are beautiful. Just minutes from Lenox, Tanglewood, and the region's finest cultural attractions, this is more than a remarkable residence--it is the place where generations gather, memories are made, and the Berkshires truly feel like home.

An incredible opportunity to surround yourself with privacy and exceptional views of Mt. Greylock. This amazing contemporary with detached guest house is sited on 4.5 acres. The main house offers 4 bedrooms, 2.5 bathrooms, kitchen with butler's pantry, granite countertops and modern appliances. The kitchen flows into the formal dining room w/wood burning fireplace and access to a covered deck. The living room with vaulted ceilings is enhanced by a floor to ceiling fieldstone propane fired fireplace and access to a large inviting deck. A hexagon barn was completely renovated into a delighful guest house with private deck, kitchen, bathroom, 1st floor bedroom and additional sleeping area on the 2nd floor. The property is enhanced by beautiful professional landscaping. Many Upgrades.

Custom contemporary home built in 1996 with thoughtful gathering spaces. Main floor has a vaulted ceiling living room with fireplace, open to dining and the eat-in-kitchen. Down a hall to the south end there is the primary suite, a powder room, laundry, the den with vaulted ceiling and a woodstove and access to the garage. On the north side of the main living room is a large entry foyer, a great room with woodstove and 3/4 bath. Upstairs there are two bedrooms, a hall bath and ample closet space. The lower level has a walkout section with a large bedroom, hall bath and a hall that takes you into the below grade finished area with office, play space and extra room. The screened porch off the entry foyer leads to a very large deck on the east side of the property angled southeast with views

This Stockbridge home has it all...privacy, protected view, river frontage, plenty of room for all washed with natural light and location, location, location!! Down a town maintained country lane, this special property welcomes you to this spacious home with living rm, great room w/fp, den/office, open kitchen/dining w/wall of glass leading to the wonderful screened porch & spacious decking, mud room off 2 car garage, laundry & half bath complete the main level. Upper level has generous primary en suite with balcony overlooking the serene yard and two guest bedrooms and bath. Centrally located for easy access to restaurants, theater, shopping, museums, skiing, cultural venues and only ,minutes to the Village of Stockbridge!

Just minutes from Tanglewood on the sunny side of Lenox Mountain, this lovely five-bedroom, five-bath home is privately set on almost eleven acres of rolling lawn and woodland. A welcoming foyer opens to a light-filled great room where a striking two-sided stone fireplace creates distinct living and dining spaces, all flowing to decks, a terrace and a screened porch. The main level also features a library/den, a primary suite, laundry room, powder room, and an attached two-car garage. Upstairs are three guest bedrooms and two full baths, one being en suite. The walk-out lower level offers a fully self-contained one-bedroom apartment along with extensive storage. Outside, the expansive pastoral grounds provide ample space for a pool, while Lenox Mountain Brook meanders through the propert

A significant price reduction has just been made on this terrific revenue opportunity property in Stockbridge. The historic General Williams House (circa 1795) has been restored and updated. Featuring 6 bedrooms, 5.5 bathrooms, 6 beautiful wood burning fireplaces, large dining and living spaces and 2 kitchens. THIS PROPERTY HAS AN EXCELLENT HISTORY OF RENTAL INCOME. The ''Ice House'' features its own kitchen and bath, for family gatherings or as Artist Studio. A sparkling in-ground pool for your summer pleasure. All this and more exists close to Main Street Stockbridge, Norman Rockwell Museum, Tanglewood, and all the most important cultural amenities. Rental income? This property has a very nice history of rental income! Who could ask for anything more? Call for a showing today

Paradise Found! Exquisite Hidden Vermont Retreat. Follow the gravel road to the end and you will discover this amazing wonderfully protected and private home on 37 acres in the peaceful town of Stamford. The best of Vermont skiing, boating, hiking, winter and summer recreation as well as the shopping, dining, art, and culture of the Berkshires of Massachusetts are also just a short drive away. Stepping into the bright contemporary entry one is immediately impressed. The first floor includes a kitchenette, guest bedroom, large bedroom immaculately furnished for children, and full bath. The large utility room and oversized two car garage complete this level. Ascending to the second level the first impression is WOW.

IMMACULATE, LIKE-NEW DESIGNER CONTEMPORARY HOME tucked away on a quiet country cul-de-sac just minutes from downtown Great Barrington. Thoughtfully planned for effortless luxury living, this exceptional residence is part of an HOA community that allows you to simply arrive, enjoy, and leave with peace of mind knowing your home will remain impeccably maintained. The open-concept floor plan is highlighted by soaring 12-foot tray ceilings, stunning wood floors, a dramatic linear fireplace, and beautifully designed living spaces filled with natural light. An oversized screened porch overlooks the lush green lawn, mature plantings, and serene backyard setting, creating the perfect extension of the home for relaxing or entertaining. A spectacular chef's kitchen: see supplement:

Discover this custom-built home, thoughtfully crafted by an architect trained builder. Generously sized rooms, a chef's kitchen, and detailed trim work throughout create a truly distinctive residence. The main level features a spacious living room, family room, and a primary suite with a private en-suite bath. Upstairs, you'll find two large bedrooms, additional bonus rooms, along with an full bathroom. The finished walkout lower level offers exceptional flexibility an can serve as an in-law suite or comfortable guest quarters. Complete with own kitchen, bedroom, and bathroom, it provides privacy and convenience, Enjoy a short walk to the center of South Egremont, while being just minutes from the shops, restaurants, and attractions of Great Barrington and Sheffield.

Just 3 miles from Tanglewood and moments from the heart of Lenox, this 36+ acre estate offers rare scale, privacy, and flexibility in one of the Berkshires' most sought-after settings. A long, tree-lined driveway creates a strong sense of arrival, unfolding into two separate residences surrounded by woods, open land, and long-range possibility. The acreage offers both seclusion and the ability to selectively open views toward October Mountain State Forest. The main residence is thoughtfully configured for multi-generational living. The first floor centers around a large living and dining room anchored by an oversized stone fireplace, an eat-in kitchen with oak cabinetry and granite counters, and multiple access points to the outdoors.

A striking modern retreat where architecture and landscape exist in complete harmony. Designed by internationally noted architect Alfredo Brillembourg, the home blends clean contemporary lines with warm natural materials and dramatic connections to the outdoors. Expansive walls of glass frame seasonal Berkshire views while filling the interior with changing light throughout the day. The living spaces feel both refined and deeply livable -- soaring ceilings, open gathering areas, and thoughtfully composed volumes create an atmosphere that is at once sophisticated and relaxed. A sleek modern kitchen flows effortlessly into the main entertaining spaces, while private 1st & 2nd floor bedroom suites offer quiet separation and a sense of retreat.

Total privacy. Surrounded on three sides by Nature Conservancy-protected land, 173 Hillsdale Road is one of the most private and extraordinary estates in the Berkshires -- a handcrafted sanctuary where the wilderness is literally your backyard. Moose, deer, bear, fox, and turtles roam master-gardened grounds tended with rare care; fruit trees, a garden pond, mature perennial beds, and lush native plantings make every season a revelation. Custom-built in 2000 from timber milled directly on the property, this 4,842 sq ft home carries an irreplaceable provenance that announces itself at every turn. A native stone fireplace anchors the soaring vaulted great room. An ash sapling banister curves to the interior balcony above. Antique leaded glass casts dappled light across wide-plank floors.

Just a half mile beyond New Marlborough village, this architectural gem offers 5,653 square feet of superior craftsmanship in an enchanting private setting along the Umpachene River. Distinctive circular towers, flowing curved walls, and graceful arched windows are in perfect harmony with the surrounding natural landscape. Custom millwork and premium natural finishes offer a balance of warmth and luxury in this elegant but comfortable 5-bedroom 4.5 bath home. Enter through the grand foyer into the expansive kitchen, living & dining areas, anchored by a striking Scandinavian Soapstone wood stove and a marble wood burning fireplace. A sunny breakfast room off the kitchen leads to a greenhouse atrium and an impressive indoor pool pavilion, fully heated for year-round enjoyment.

Welcome to The Black Mountain House, a meticulous reimagining of a 1976 home, owned and renovated by a design/build husband and wife duo. Up a winding gravel road through the Jug End Preserve, it sits perched at the heart of the Berkshires in the Taconic Mountains. Surrounded by 3,000+ acres of protected wilderness with waterfalls and hiking trails. Picture windows and glass doors pull the greenery inside this multilevel forest retreat. Entirely electric, spring-fed mountain water, brand new baths and Miele kitchen. Five bedrooms, room for the whole crew. Gather by fires, indoors and out. Screening lounge for movie nights. Cedar hot tub and Finnish sauna, perfect après-ski post Catamount, only 8 minutes away. Option to purchase furnished. There is simply nothing like it on the market.