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

Steeped in the timeless elegance of historic Stockbridge, this exceptional Colonial captures the enduring charm of a bygone era, evoking the quintessential New England scenes made famous by Norman Rockwell. Beautifully sited just moments from the heart of town, this distinguished four-bedroom residence blends classic architectural details with gracious, comfortable living. Inside, three fireplaces anchor inviting gathering spaces filled with warmth and character, while three spacious ensuite bedrooms offer exceptional comfort and privacy. Rich period details, handsome proportions, and abundant natural light create a home that is both sophisticated and welcoming. Beyond the main residence, a separate guest cottage provides the perfect retreat for visitors, extended family, a home office,

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!

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.

Welcome to Camp Mohawk, a pristine lakefront property in the heart of the Berkshires. Set on Cheshire Reservoir--a serene, largely uninhabited lake--the property offers both privacy and convenient access just off Berkshire County's main north-south route. Once a summer camp, the estate features an existing main house and barns listed on the National Register of Historic Places, dating back to the late 1700s. There are also numerous sleeping cabins that could be restored. Ideal as a private family compound or for development as a spa or resort, corporate or wellness retreat, or condominium, single-family, or retirement community--the possibilities are truly endless. Can be subdivided.

37-acre, ROCK RIDGE FARM, with early mid 20th century roots. Built in 1785, steeped in local history, Property has remained a working and residential farmstead today and reflects the regions long tradition of working farms. Offering a blend of local heritage and timeless New England character. Along with the main house there are several outbuildings that could be renovated, repurposed or redesigned to your vision. Original house boasts multiple living quarters. Continue this as a working farm, wedding venue, country inn or primary residence. Frontage on Dublin Rd and State Rd. Close to Tanglewood, Bousquet Ski-Sport and other cultural attractions. Easy access to routes in and out of the Berkshires. 37 acres that offer a rare freedom to build, invest or preserve something truly lasting.

COMMANDING VIEWS OVER LAKE GARFIELD WITH A STUNNING MOUNTAIN BACKDROP, this beautifully updated home offers charm with modern refinement. Original architectural character has been thoughtfully preserved, while expansive windows fill the home with light and frame the breathtaking scenery. Recently renovated chef's kitchen, first floor primary bedroom, and loads of closet space address today's needs. And could there be any better spot to watch sunsets than the expansive front porch? What's more, a well-appointed suite in the separate carriage house offers flexible space for guests, a home office, or artist's studio. Features include eight private acres, high speed internet, low Monterey taxes, and proximity to the Monterey bathing beach and the incomparable tomatoes at Anna's farm stand.

Experience the best of Berkshire living in this stunning contemporary waterfront home on Stockbridge Bowl. Thoughtfully designed, this 4 BR, 3 full bath year 'round home offers a seamless blend of modern comfort and natural beauty! Sunlight pours through expansive windows, framing breathtaking water views from nearly every room. The open concept living space is anchored by a striking double sided fireplace, creating a warm and inviting atmosphere for both every day living and entertaining. The kitchen flows effortlessly into dining and living areas, all oriented to capture the lakefront setting. The deck is the perfect place for dining or simply soaking in your surroundings and a private dock provides direct access for boating or swimming. Your opportunity to own a turnkey retreat!

Beautifully restored historic Colonial on a very lightly traveled, town-maintained road with stone walls, fruit trees, open meadow, wooded acreage, a barn and garage. Three quarters of a mile of its own road frontage, bordering protected land. Home to author Simon Winchester for twenty-five years. .. c.1760 and 1840. 4 bedrooms, 3 baths. Library, keeping room with original crane fireplace, Aga kitchen, vaulted living room, screened-in porch. A c.1812 granary rebuilt as a writing studio with loft and full bath. .. Orchard, meadow, vernal stream, quiet forest. 60 acres. A genuine Berkshire country place with a sky that still delivers. Located in Sandisfield, in the Southern Berkshires. Two and a half hours to the city. Two centuries of history on 60 acres. Read the whole story. 'Click'

Luxurious, fully-modernized 1850s Victorian in the heart of Great Barrington. Elegant, four-story 3600 sq. ft. newly renovated clapboard and shingle house with covered porch. Meticulous renovation features chef's kitchen, four+ bedrooms, 4.5 bath, second floor and basement laundry, walk-out finished basement with private entrance and bathroom, perfect for guest suite or professional office. High-end appliances, including 6-burner Wolf stove and Bosch French door refrigerator with two freezer drawers, Bosch dishwasher, wine cooler and microwave in the island. Full-size prep sink in the kitchen island, 36'' farmhouse sink in the main counter. Cabinets are all-wood with soft-close drawers and doors; vented whole-house A/C and heat pump with propane back-up; primary bath with heated floor

Originally built in the 1700s, this historic post-and-beam barn has been thoughtfully renovated over time while maintaining its unique character and charm. A recently installed solar energy system allows for highly efficient living with the potential for an off-grid lifestyle. The home features an open floor plan filled with natural light from numerous oversized windows. A chef's kitchen adjoins the dining area, creating an ideal space for entertaining. With three full floors of living space, the home offers four ensuite bedrooms plus an additional bedroom, providing comfort and privacy for family and guests. Enjoy seamless indoor-outdoor living with a screened porch off the main level leading to spacious decks and a hot tub. The lower level includes a media room and sauna for relaxation

ENJOY STUNNING VIEWS FROM EVERY ROOM OF LAKE GARFILED, THE CONNECTICUT HILLS AND THE CATSKILL MOUNTAINS. THIS BRIGHT SUNFILLED HOME SITUATED HIGH UP ON MT HUNGER RD HAS OVER 700 ACRES OF LAND TRUST LAND DIRECTLY ACROSS THE ROAD TO ENJOY MANY HIKES. A FOUR BED ROOM HOME WITH MORE STORAGE SPACE THAN YOU COULD WISH FOR COMES WITH FIVE FULL BATHROOMS, ONE OF WHICH IS IN THE GUEST APARTMENT ABOVE THE HEATED TWO CAR GARAGE. THE LOWER LEVEL OFFERS MANY OPTIONS FOR OFFICES, STUDIO, GYM OR JUST A LARGE GREAT ROOM FOR AN OVERFLOW OF FRIENDS. WITH A WIDE SPANNING DECK, ENJOY YOUR SUMMER EVENINGS WITH FRIENDS WATCHING THE SUNSET OR BOATERS ON THE LAKE. SO WHY NOT COME SEE 169 AND BE WOWED BY A VIEW THAT WILL TAKE YOUR BREATH AWAY FROM THE MOMENT YOU STEP INSIDE THE FRONT DOOR.

Nestled in the rolling foothills of the Berkshire Hills, this beautifully designed contemporary home offers the perfect blend of warmth, comfort, and modern living. The heart of the home is a chef's kitchen with a sunny breakfast nook that opens seamlessly to the living room, where a dramatic floor-to-ceiling stone fireplace creates an inviting focal point. Just beyond, a screened porch provides the perfect setting for relaxing summer evenings and enjoying the surrounding landscape. The thoughtfully designed first floor also features a formal dining room ideal for entertaining, a spacious laundry room, and a mudroom that connects directly to the attached two-car garage. A handsome office with its own fireplace offers a quiet retreat for work, reading, or simply unwinding.

Welcome to Treetops. A long private driveway passing a large pond sets the scene for this impressive hilltop retreat with 6,000 square feet across three levels and seasonal views of the Taconic Hills. Built with wood hewn from trees on the property, including the distinctive stairway, the home offers a huge open-plan main level ideal for gatherings, along with an indoor pool, hot tub, sauna and a dramatic two-story primary suite. Five bedrooms and five baths provide ample space for guests, with additional bedrooms on the upper and lower levels plus a family room downstairs. A second home may be built on a conserved, included, second parcel. Expansive decks, a three-car garage, sold fully furnished, and abutting the Appalachian Trail conservation lands complete the offering.

Experience the luxury of gracious proportions, impeccable details, and stunning design in this exquisite classical villa that would be as at home in Italy as it is in the Berkshire landscape. Protected views of mountains, rolling hills, and meadows surround the 6.9-acre estate. The atmosphere of sophisticated luxury begins with the approach through an allee of willow trees and in the front courtyard, edged with stately Bradford pear trees and arbor vitae and anchored by the 2716sf, single-level residence and a matched pair of outbuildings--a two-car garage and a garden house. (See MORE)

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.