WHISPERING PINES. This tranquil property will call to you as you wind your way through the tall pine-lined driveway. It is a very private setting and just minutes to Butternut, town, and everything else the Berkshires have to offer. Beautiful mature gardens, Gunite Pool, screen porch, and 3600 sq ft of living space to dwell. This 4 bedroom home has 2-Primary en-suite, a large den over the 2-car attached garage. First floor office space or overflow room for guests. A newer first floor Primary Suite wing added in 2017 boasts a very large walk-in closet, steam shower and an ample-sized bedroom. The expansive screen porch looks out on the yard, pool, yard and gardens. Partially finished will easily help you expand upon this magnificent home. A second 2-car garage for enhanced storage space.

This impressive Italianate residence, dating back to 1880, has been meticulously restored for modern, turn-key living. This coveted location with a private backyard and off-street parking neighboring Talbot & Arding - offers a rare sense of quiet just a few blocks from the restaurants, galleries, and shops of the exciting city. Spanning three thoughtfully renovated stories, the turn-key property includes a large eat-in kitchen, sunny, and bright living and dining room, and a large mudroom. The top two floors contain bedrooms and bonus spaces ideally suited for year-round living and guest suites. The showcase of the home is the gorgeous staircase with a curved banister that enhances all three floors. Outside, there is a private backyard and side patio and a staircase to lower Hudson.

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!

Western-facing sunset views over the Catskill Mountains--the coveted vistas everyone is looking for. Set on 12 beautiful, private acres complete with a tranquil pond, this gorgeous post-and-beam home is expertly designed to take full advantage of its spectacular surroundings.Tucked away on serene Charlie Hill Road, the property immediately welcomes you with sweeping sights of the rolling meadow and water. The moment you step inside, you are struck by the dramatic, two-story living room, where a magnificent wall of windows and French doors perfectly frame the mountain vistas. A massive floor-to-ceiling chimney with a double-sided fireplace beautifully divides the living space from the kitchen and dining area, creating an atmosphere that is both open and incredibly cozy.

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.

The equestrian elegance of this 55 acre property starts at the gated driveway. Perched on the hilltop is a fully equipped custom build multi use barn entirely heated by radiant floor heat and includes 8 14x14 stalls w/ autowaterers perfect for the breeder or veterinarian. Includes kitchenette, office, laundry and bathroom. Also included is a heated equipment shed and workshop, a heated drive through aisle for large trucks, washstalls and more! The grounds include 8 paddocks with waterers, an exercise track, 3 large pastures. A second barn offers 12 additional stalls. The meticulously kept grounds is professionally landscaped and a covered wrap around porch greets guests into the home. Kitchen has quartz counters, GE profile appliances and a slider out to a large patio

A rare opportunity awaits! Own a developable mountain top in the Berkshires! Your 4B/2.5Bath home is 10 years young with custom kitchen and baths. An unobstructed view of Goose Pond and beyond, it's a 56 acre sanctuary mostly comprised of Oak and Mountain Laurel forest with trails. Enjoy a 40 mile view to Mt. Greylock and views of October Mt. State Park, and boating on Goose Pond (@1/2 mile to the the boat launch). Also viewable is Tyringham Valley, South Lee and Bear Town State Forest. Build another home on the property (ADU or a larger home and keep this as your guest house). Possibilities are endless here! Already in place is a 28'X48' building with 14' ceilings with it's own electric service, (could also be used for horses) and a small barn near the house. A one of a kind offering.

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.

A lovely, winding approach to this gorgeous 21-acre estate ensuring serenity, privacy, and the beauty of living in the country. The main house includes 3-4 bed, 2 1/2 bath. An impressive architect-designed guest house has 2 ensuite bedrooms with balconies, dramatic exposed beams and vaulted ceilings. The guest house is an extraordinary place to host family and friends both winter and summer. With views of Tom Ball mountain, this 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!

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.

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.

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.

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 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

This historic farmhouse, originally built in the 1790s, underwent a complete renovation in 2012, including a new foundation, septic system, roof, updated plumbing and electrical, 5-zone heating, central air, and other modern systems. In 2022, a new well and a boiler for radiant heat were also added. Step inside to find timeless Colonial charm--exposed beams, three original fireplaces, and gorgeous antique floors--seamlessly paired with an expansion which added a large family room with a fourth fireplace, finished basement storage, mudroom, and partially screened wraparound porch.

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.

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.