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

Views, privacy, and frontage on Mill Pond. This custom built classic Gilligan house is the perfect home for hosting family and friends with plenty of space both inside, and out. There are 4 plus bedrooms and 5 baths, including a generous primary suite on the first floor, a large den, and a bonus room above the 2 car garage. The property includes a fenced, in- ground pool, extensive flat lawn, perfect for soccer or croquet, and a private dock for paddle boats, fishing and watching out for the resident Bald Eagle! The house sits on 4.49 acres and also includes 4 additional lots for a total of almost 13 acres.

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:

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.

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.

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.

Own a Living Masterpiece. Meticulously curated by the current stewards since 2006. This Colonial Revival offers rare fusion of 18th-century authenticity and cutting-edge modern comfort. Designed for both grand-scale entertaining and intimate family life, this c1930, 7,894 sq. ft., Colonial Revival offers 6-bdrms & 4.5-baths. The interior is a treasure of artisan craftsmanship from the formal dining room with its magnificent shell-carved cove, to original cabinetry with rare wood inlays, hand-carved bookshelves, a classic butler's pantry, multiple stately fireplaces anchor the formal living spaces. Enjoy panoramic views and privacy from the grand porch overlooking 4 pristine acres. a state-of-the-art kitchen featuring Wolf and Sub-Zero, and no expense spared Geo-Thermal heating/cooling.

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.

Experience refined Berkshire living at Coldbrooke East, where timeless elegance meets exceptional privacy. Perfectly sited at the end of a quiet cul-de-sac and abutting the golf course, this extraordinary six-bedroom, 5.5-bath residence offers luxurious single-level living with a thoughtfully designed 1,000-square-foot addition. Custom designer finishes, exceptional craftsmanship, and substantial built-ins create a sophisticated yet comfortable interior. Outside, magnificent perennial gardens, complete privacy, outdoor showers, and courtyard provides a serene retreat. Enjoy access to the nearby Wyndhurst Club and Manor pool, tennis courts, reduced-rate fitness membership, and more. A rare offering combining luxury, lifestyle, and one of Lenox's most coveted settings.

Nestled in the center of Williamstown, just steps from Williams College, this stunning two-story Colonial stucco home offers timeless charm and modern comfort. Built in 1907, this 4,100 sq. ft. residence features five spacious bedrooms, three full baths, and one half bath. Set on 1.35 picturesque acres, the property boasts a large post-and-beam barn, a beautifully covered stone patio, and breathtaking western views of the Taconic Mountains. The expansive, level backyard is adorned with mature gardens and majestic old-growth trees, creating a serene and private retreat. Don't miss this rare opportunity--call today for your private showing!

Welcome to this Berkshire Waterfront Paradise! With amazing lake and sunset views this home has it all. Five bedrooms all with lake views. Your family and friends will find the total relaxation the Berkshires can offer. Whether it's a swim, paddle, fishing or a water ski on the lake it's all just steps out the door. The beautiful stone fireplace sores to compliment this open space and provides a warm cozy touch. Come and start to relax as you enter into paradise.

Located on one of Columbia County's finest roads in the town of Spencertown, this impeccably-maintained private 2922 sq ft. colonial home on 7.4 acres has all of the modern amenities! A fabulous setting with stunning distant views, the home features an open chef's kitchen and great room plan, which was expanded and redesigned in 2021, with Sub Zero refrigerator, Wolf gas oven and Miele dishwasher stainless steel appliances, subway tile backsplash and separate island. The home features a central hallway with an elegant living room and working fireplace, dining room, home office/den, washer/dryer units on both the first floor and basement, central AC and full-house generator. In addition, there is a second driveway entrance with RV/EV electric, which leads to a park-like meadow with walking

A lovely, winding approach to this gorgeous 21-acre estate ensuring serenity, privacy, and the beauty of living in the country. There's an impressive architect-designed guest house with 2 ensuite bedrooms, balconies, dramatic exposed beams and vaulted ceilings. The guest house is an extraordinary place for rentals, or hosting family and friends both winter and summer.The main house is 3-4 bed, 2 1/2 bath, views of Tom Ball mountain, the property is a combination of gardens, fields, forest, and offers several outdoor living spaces, including a stone patio off the kitchen. A short jaunt to No. Six Depot, The Foundry performing arts, and Tanglewood. Central to Gt. Barrington, Lenox and Stockbridge for theatres, boutiques, skiing, golfing, museums and so much more at your fingertips

Stunning contemporary nestled in tranquility. The main level boasts a gracious great room with cathedral ceilings, fireplace and walls of windows that wash the common spaces with natural light and bring nature in. Gourmet chefs kitchen with ample storage and dining room with direct access to the oversized porch that features a gas stove for the chillier days. First floor primary en suite with walk in closet, direct access to your deck and primary bath with beautiful textures throughout. The second level has three guest bedrooms and two full baths. Lower level features a large family room walkout, additional guest bedroom and full bath. Two car oversized garage with studio space above that gives flexibility in its use. Private setting with expansive lawn and professionally

Welcome to your ultimate country retreat, where the charm of history meets the ease of modern living. Here, timeless beauty and serenity reign--an escape where silence is broken only by the wind in the fields and the song of birds.The 1828 brick colonial, a masterpiece of its era, has been exquisitely restored to showcase spacious, light-filled rooms that draw the outdoors in, framing views of meadows, a sparkling pool, and the stately barn. The barn itself is a wonder, waiting to be reimagined--perhaps as a guest house, an artist's studio, or a setting for unforgettable gatherings.Surrounded by farms and opening to distant hills, the landscape feels both boundless and intimate. The pool, perfectly placed, invites leisurely afternoons and is graced with its own elegant pool house.

Spectacular Homestead! Gather year-round with family and friends on this one-of-a kind estate, including 2 houses, 4 historic barns and maintenance building. 161 pristine acres with stunning views, mountain paths, and stunning giant stonewalls throughout. Gorgeous New England marble stone farmhouse built in 1780, with modern addition featuring vaulted ceiling and massive windows which flood the dining and kitchen area with light. Enormous custom built hearth and fireplace, mahogany full bar, artisan-made bookcases, wrap-around deck. Close to Williams College and Jiminy Peak. The property offers swimming in two private ponds, 6 bay carriage barn with second floor for offices, studios., or storage.

A RARE BEAUTY ON HISTORIC YALE HILL! Discover an historically significant gem in this perfectly renovated home! Peacefully tucked away from it all, yet close enough to enjoy a stroll to town, tennis, Library, golf & restaurants. Chef's Kitchen, large flexible living spaces, 4 Bedrooms, 4 Baths, tall ceilings and charm galore. The Mill House, transformed into a cozy Guest quarters, with 3 Bedrooms,, 3 Baths, has a lovely brookside courtyard w/Pergola, rustic charm maintained. Quiet your mind and embody perfect country living. Overlook the Kampoosa Brook, with private swimming area from your backyard! Cultural & recreational activities nearby. Great income potential. Solar powers Main house, car charger & Mill House. A MUST SEE!

Set just off the shoreline of Onota Lake and accessed by a private bridge, this approximately 1.25-acre island offers a kind of ownership that is seldom available in the Berkshires.Surrounded by water, the property creates a natural sense of separation and calm, with broad lake views and a level of privacy that is difficult to replicate without sacrificing accessibility. Here, the experience is distinctly your own, yet the mainland is always within easy reach.The existing residence is positioned to take full advantage of the setting. A vaulted living space with a loft above, two fireplaces, and expansive windows and sliders bring in light and water views throughout the day. A covered porch extends directly toward the lake, offering a simple, immediate connection to the outdoors.

Iconic Lenox home: very rarely does a home with this historic integrity come on the market...now is your time to continue its legacy . Built in 1915 as one of the focal points of Cliffwood Street, this charming home has been updated for today's life style without sacrificing its significant architectural details. Beautiful common rooms including a dream kitchen with marble counters, formal Dining Room with French doors to the enclosed porch and onto the new deck and acre of land; formal Living Room with fireplace, family room and welcoming foyer off the front porch. The 2nd floor is home to all 5 bedrooms plus an inviting ''summer porch'' off one! Updated baths, kitchen, roof, utilities...and add to that: crown moldings, pocket doors...this home is truly a rare find in today's market

Sited at the highest point in Hillsdale this modern home captures the world around while being incredibly private. Main house has tall ceilings tremendous natural light and doors bringing you outside from every space. Music room on the east side captures the Berkshire hills with doors out to the breakfast patio. Office with en suite is off the entry. Second floor is the primary suite; everywhere you look you stop to take in the view, large bath with walk-in closet and laundry. The inner courtyard has a heated pool, sunken jacuzzi, outdoor shower, screen porch with fireplace and beautiful perennial gardens. Hidden off the drive is a guest cottage with open living area, bedroom and full bath.