A luxurious home on one of the most scenic roads in The Berkshires, surrounded by 15 pastoral acres, with picturesque mountain views. Enter a sun-drenched living room with a soaring cathedral ceiling and an elegant fireplace centerpiece. Enjoy an expansive 3-season porch, with panoramic windows and classic mahogany floors. A recently updated eat-in kitchen features Sub Zero appliances and a beautiful butler's pantry. Relax in the newly renovated family room with wall-to-wall casement windows. This 5 bedroom home offers a bonus game room and home office equipped with fiber internet and a spacious private master bedroom with ensuite bath. An additional wing features a separate guest suite with living room, kitchen, dining area, full bathroom and 2 bedrooms. In Alford, renowned for low taxes

HISTORIC BERKSHIRE FARM Best bargain in the Berkshires! Gather year-round with family and friends on this one-of-a kind estate, including 2 houses, 4 historic barns and maintenance building. 161 acres with stunning views, mountain paths, and Jim Kelly's 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.

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.

BERKSHIRE LAKE FRONT WITH BEAUTIFUL WESTERN VIEWS ACROSS THE LENGTH OF LAKE BUEL. Premiere motor boat lake. With 6 bedrooms and 3 full baths there is room for your extended family or friends. Walls of windows allow lake views from most rooms. Open plan for relaxing after a long day swimming, boating, fishing or relaxing on the water. Lovely out door areas include a deck, patio and steps to your dock. Under 10 minutes to downtown Great Barrington and a short drive to Berkshire County culture, dining and entertainment.

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!

Nestled in a secluded, serene setting and surrounded by lush gardens, fruit trees, wildlife and Nature Conservancy on 3 sides, custom-built home offers extraordinary privacy and tranquility. Crafted using wood milled directly from the property, this rustic yet contemporary home boasts a wealth of unique details that highlight exceptional craftsmanship. Moose, deer, bear, turtles, fox and more visit mature grounds tended by master gardener. Incorporates a native stone fireplace, ash sapling banister, antique leaded glass accents, & reclaimed 18th-century tavern doors from historic Egremont Tavern. These elements blend seamlessly with the open-concept floor plan, highlighted by soaring vaulted ceilings and oversized windows. 5 Brs, 5BA w/ attached separate apartment w/ balcony.

The Nine- Square house is, at its core, an authentic country house. On the ground floor are the double living room, dining area, & kitchen, all flowing into each other & anchored by a marble fireplace & 3 large glass doors opening to the exterior terrace with a breathtaking view. A kitchen, office/painting studio, a washroom, a dry bar, & laundry room complete the main level.The central architectural piece of the home is the solid white oak staircase leading up to the second floor. The 4 bedrooms upstairs, though spacious, are much more private & intimate, each with large windows on 2 sides, communing with the serene & quiet landscape outside.

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 on a quiet country road w/ private driveway, this charming 3 BR, 2.5 BA home sits on 8 picturesque acres just minutes from Tanglewood, Stockbridge Bowl & the villages of Stockbridge, Lenox & West Stockbridge. Perfect for outdoor enthusiasts, culture lovers or anyone seeking a peaceful Berkshire retreat. The location offers hiking, yoga & wellness centers, boating, skiing, & convenient access to dining & shopping. Inside, bright & inviting spaces include living room w/ cathedral ceiling, fireplace, & is filled w/ natural light. Primary suite with vaulted ceiling & balcony w/ stunning mountain views. Renovated kitchen opens to a cozy den & breakfast nook connecting seamlessly to the pantry, laundry & mudroom. Lower level with flexible bonus space for family room, gym, office or

Nestled on the top of a hill overlooking rolling meadows, this exceptional property boasts over 30 acres of stunning natural beauty, with panoramic 360-degree views that will take your breath away. A true oasis of tranquility, this estate offers the ultimate in luxurious country living. The grand foyer invites you into this warm, inviting home. With over 6,000 square feet of living space, it offers plenty of room to entertain and relax. The large cook's kitchen is perfect for preparing meals for large gatherings, while the heated sun room provides a cozy spot to enjoy your morning coffee and take in the stunning views of the surrounding fields. This home also features 5 spacious bedrooms (primary with en-suite, four jack-and-jill), each with their own unique charm and character.

BREATHTAKING 360 DEGREE VIEWS Rarely does such a magical property come along with so much to offer. A well built and spacious home with Pickle Ball, Tennis, Swimming Pool, Gazebo, Lake frontage, Lush Green Lawn, Pastures, A Three Car Garage, Outbuildings, VIEWS FROM EVERY ROOM. Kitchen has Sub-Zero refrigerator, Wolf cooktop, large center island and a wall of windows overlook the gorgeous gardens and view. Formal dining room with wet bar and 500 bottle temperature controlled wine storage. A formal living room w/ a fireplace, a spacious family room for watching movies, a gym with a wall of windows looking to Mt Greylock, It is one of the most beautiful properties in the Berkshires. Equidistant to north & south Berkshire County. Close to all the Berkshires has to offer. Land conserved.

An Unrivaled 8-Acre Sanctuary of Beauty, Privacy & SophisticationNestled in the cultural heart of the Berkshires, just steps from downtown Lenox, this extraordinary property offers a rare and coveted blend of seclusion and sophistication set on an unheard-of 8 acres of wooded, professionally designed, and maturely landscaped grounds.Inside, the home has been completely reimagined, with every detail thoughtfully curated. Sunlight pours into the open-concept floor plan, seamlessly connecting the gourmet kitchen, grand great room with a striking stone fireplace, and elegant dining area. French doors on either side of the stone fireplace open to a spacious sunroom, where multiple sliding glass doors lead out to a Trex deck overlooking beautifully terraced gardens.

Hawks Nest Ridge. Quiet privacy on 8.6 acres. Decks, patio, screened porch and pool all enjoy the view and the natural setting. Dramatic open floor plan with walls of windows to the views, soaring stone wood burning fireplace spanning three stories. Cook's kitchen with walk-in pantry. First floor primary suite with gas fireplace and dressing room all abutting library and office. 4 private bedroom suites in total each with their own sitting areas and additional sleeping options. Family room with wet bar and gas fireplace. Exercise room with steam shower. 3-bay garage. A very special retreat with plenty of room for guests and entertaining. Just a short jaunt to dining, shopping, recreational and cultural venues in West Stockbridge, Lenox, Stockbridge and Great Barrington.

Set on over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire leisure.Inside, the home is thoughtfully designed to host both family and guests in complete comfort, offering five well-appointed bedrooms, six full bathrooms, and a half bath, providing privacy and ease for all. The first-floor primary suite serves as a true sanctuary, complete with two separate full bathrooms for an elevated sense of luxury.

Perched dramatically on a 18 acre very private mountainside, this brand-new modern home overlooks the sweeping beauty of the Berkshire Hills. A long, winding driveway builds anticipation as it ascends, ultimately revealing striking contemporary architecture framed by panoramic sunrise views. Designed to embrace the natural landscape at every turn, this residence delivers a serene, elevated living experience unlike anything else on the market.The first floor features an impressive great room with soaring timber beams, an elevated Malm fireplace, and floor-to-ceiling glass that captures the surrounding vistas. A gourmet kitchen imported in its entirety from Germany anchors the main living space with exceptional craftsmanship and modern sophistication. Radiant heat throughout the main

Introducing 
FREE QUARTER FARMNearly 1,500 Acres | Sandisfield, the Southern Berkshires | $4,500,000Miles of private trails for hiking, hunting, fishing, horseback riding - your own wilderness preserve134+ acres not in conservation with 1,489 feet of road frontage - craft your legacy5BR/5BA timeless home built for this wildly beautiful placeStand between your home, overlooking your private lake, and your barns, Turn 360 degrees--everything you see you could own. Pure sanctuary in the highest possible sense.Nearly 1,500 acres where Thorp Brook winds through marshlands, Seymour Mountain rises to 1,682 feet, and miles of trails beckon for every outdoor pursuit. The kind of American dream that exists now only because someone saved it, after they assembled this dream.

Brooke Astor's COBBLE HOUSEWhere Land, Light, and Legacy ConvergeTYRINGHAM VALLEY BERKSHIRE COUNTY MASSACHUSETTS$4,600,0005,885 square feet7 bedrooms8.5 bathrooms27.9 private acres1909 Harrie T. Lindeberg design2,321 +/- feet road frontageThe Valley That Time ForgotThe drive through Tyringham Valley never fails to quiet the soul. Past stone walls that have marked these fields for centuries, through meadows where The Shakers once pastured their sheep, toward the ancient drama of the Cobble--206 acres of exposed bedrock thrust skyward by tectonic forces that shifted the very bones of the earth millions of years ago. Here you find what Tyringham Valley has always offered--that profound quiet that restores and renews.MORE OF THE STORY BELOW

STUNNING LONG VIEWS, RARE 330+ ACRE PARCEL, ABUTS CONSERVATION LAND! Total seclusion and privacy, bucolic countryside with some open meadows and wooded hillside. Once a grand Berkshire estate, the property is comprised of the main Tudor style residence with indoor pool, shingled barn, Dutch colonial multi family dwelling, a guest house & several smaller sheds and workshop. The buildings are all in need of upgrades, but restoration to former glory, a most worthwhile project. Indoor heated pool room opens to beautiful sunken gardens with Contemplation Bench , Stone Walls and perennial gardens. A unique and wonderful opportunity, within close proximity to Gedney Farm, Old Inn on the Green, Southfield Store, and just minutes to ski Butternut and Great Barrington. Being sold AS-IS.

Welcome to an extraordinary lakefront estate on the shores of Pontoosuc Lake, an offering that sets a new benchmark for luxury living in the Berkshires. With over 18,700 square feet of total space, including exceptional garage capacity ideal for car collectors or hobbyists, this remarkable property offers unparalleled scale, versatility, and setting.The main living area showcases a thoughtfully designed open floor plan that flows seamlessly toward the water, ensuring the views are always front and center. Enjoy sweeping northern-facing vistas of Pontoosuc Lake, Mount Greylock, and the surrounding Berkshire hills. Whether relaxing on the expansive deck, swimming in the in-ground pool, or departing from your private dock, the connection to nature and water is ever-present.

Pine Needles.Built circa 1900 as a Berkshire ''cottage'' in the era of grand summer estates, this historic property blends the dignity of Colonial Revival architecture with the relaxed elegance of an Italian villa and the artisanal detail of the Arts & Crafts movement. Sited on 80 private acres just minutes from the heart of Lenox, the estate offers breathtaking southern views, rolling forest, and a rare level of privacy and provenance.Arrival.Approached via a long private drive, the property unfolds gradually--passing a sun-kissed meadow, through a grove of majestic pines, past a stunning carriage house, before arriving at an inviting courtyard. The house itself is beautifully sited to capture natural light and frame the sweeping mountain and pastoral views.