William Pitt Sotheby's International Realty
306 Main Street, 01230 Great Barrington (United States)
Listings of the agency
Listings for sale: 1 to 20 / 62
- 49
Farmhouse Sandisfield (United States)
At the end of a quiet dead-end road in Sandisfield, this c.1892 four-bedroom farmhouse sits less than twenty feet from the wild and scenic West Branch of the Farmington River, a federally protected, free-flowing trout river. Four bedrooms. Two full baths plus a half. 2,516 sq ft. 4.61 acres. Beautifully transformed interior: a granite-island kitchen rebuilt from the ground up, wide softwood floors, working brick fireplace, cast-iron clawfoot tub, first-floor primary opening through French doors to a stone patio, stairs to lawn and river. Kitchen and dining open to a deck over the water. Quarry-granite three-car garage, studio cottage with grandfathered footprint, and a second river parcel with 19th-century mill history included. Flood Zone A12, elevation certificate available. The river is twenty feet from the back door. Not a view of the river, not near the river. The river, close enough that you fall asleep to it in summer and wake to it in winter, when the ice shelf forms along the near bank and the hawks work the open water downstream. This is the thing about 14 Roosterville Road that no description fully prepares you for: the Farmington is not an amenity. It is the address. The sellers transformed the interior thoughtfully and well. Wide softwood floors, exposed ceiling beams, and a working brick fireplace anchor the living room, which easily holds two seating areas. The kitchen was rebuilt from the ground up with a granite island, slate-grey open cabinetry, and windows on three sides that keep the hills and water present while you cook. It is the heart the house always deserved. The kitchen and dining room open onto a deck over the river. The first-floor primary bedroom opens through French doors to a stone patio, with stairs down to the lawn and the Farmington just beyond. Up the painted black-and-white staircase: three more bedrooms, a family room, and a full bath. Two full baths total, one with a classic cast-iron clawfoot tub, one newly tiled. Propane hot water heat through a Viessmann boiler. High-speed internet. Spring means trout stocked at the Clark Road Bridge, right at the property's edge, while hawks and bald eagles work the calm flat water below the house. Nights belong to the fire pit and the sound of the river under a sky without light pollution. Across the road, a neighbor's hay fields roll toward a long mountain view. The property abuts Army Corps of Engineers land on the river side, no development possible, ever, and connects without crossing private land to an old stagecoach trail and the climbing ledges of Hanging Mountain. This stretch of Roosterville Road exists because of two floods. The first came in 1938, the second in the twin hurricanes of 1955. Together they buried the old road that once ran through here and left this place at the end of a quiet dead-end, closer to the river than to the rest of the world. It is one of those rare cases where a natural disaster produced something worth keeping. The outbuildings are exceptional. The three-car garage is built of hand-cut quarry granite, the feather marks of the quarrymen's tools still visible in the stone. The Little House, a sweet clapboard cottage with a grandfathered footprint, has served as a painting studio. What it becomes next is entirely up to you: guest suite, Airbnb, home office, art studio, or something not yet imagined. Included in the sale is a second parcel just north of the Clark Road Bridge, once the site of a Trip Hammer Shop and Saw-Mill advertised in the Connecticut Courant in 1833. The old mill channels and stonework are still legible in the earth. It is a remarkable piece of history to walk, and a beautiful private place to sit by the water. This property is located in FEMA Zone A12. Flood insurance is required for mortgaged purchases and advised for all. An elevation certificate is available. In 1918, a young Italian immigrant named Dominic Campetti, who had once sailed back across the Atlantic to find his sweetheart Caterina Consolati and convince her to begin a life with him in America, purchased the old Elizur Deming Farm on this stretch of the Farmington River. Their descendants farmed it for years after. In the cellar, beneath a trap door in the corner of a first-floor closet, hard cider barrels once kept company with a 50-gallon press and loyal customers from miles around. The state police came. The Berkshire Evening Eagle covered it with evident local enjoyment. The trap door is still there. The river is still there. The next chapter is yours. Reach out to learn more about this historic and unique property! Read more about the area, the history, and its stories.
…$695,0004bedrooms3bathroomsland 1.9haBy William Pitt Sotheby's International Realty
- 34
Apartment Lenox (United States)
Experience elevated wellness living in this exceptional Canyon Ranch penthouse in Lenox. This 3,300+ sq. ft. residence offers three spacious ensuite bedrooms, a powder room, an expansive great room, a chef's kitchen and three fireplaces that create a warm, inviting atmosphere. A private patio provides the perfect retreat to relax and enjoy the natural beauty of the Berkshires. Ownership includes a requisite annual resort membership with full access to Canyon Ranch's world-renowned wellness amenities. Just minutes from the Berkshires' acclaimed cultural attractions, fine dining and outdoor recreation, this is a rare opportunity to enjoy luxury, wellness and timeless design in one extraordinary home.
…$4,150,0003bedrooms4bathroomsBy William Pitt Sotheby's International Realty
- 48
House with pool Richmond (United States)
This architectural gem has been carefully restored and enhanced to exceptional standards, preserving its storied heritage while seamlessly integrating contemporary conveniences. The exceptional property features an elegant Main House, inviting Guest Cottage, Potting Shed/Studio and Barn. Framed by breathtaking panoramic vistas, the estate showcases classic stone walls, a serene spring-fed pond and a heated saltwater pool. The impeccably maintained lawns and expertly designed grounds establish a pristine country retreat. Premium upgrades include superior rock wool insulation throughout. Perfectly positioned just minutes from Tanglewood's celebrated performances, fine dining and thriving cultural attractions in the Berkshires.
…$3,495,0005bedrooms7bathroomsland 2.3haBy William Pitt Sotheby's International Realty
- 24
Farmhouse Lenox (United States)
2 bed, 2 full bath Berkshire retreat. The bright, airy living room features warm wood floors that lead into a cozy eat-in kitchen. With a heated sunporch and 1st floor full bath, the home offers multiple inviting spaces to relax or entertain. Step outside to a brand new back deck, an ideal setting for summer evenings. 2 bedrooms on the second floor, with a full bath and dreamy tub. Meticulously-maintained home with a new 200-amp electrical service, this turnkey retreat ensures total peace of mind. Expansive back yard with basketball court and shed. Whether you're enjoying the classic rocking-chair porch or exploring nearby trails and boutiques, this sweet sanctuary is a rare find in the heart of Berkshires.
…$449,0002bedrooms2bathroomsland 5,423m²By William Pitt Sotheby's International Realty
- 27
House Great Barrington (United States)
Step into effortless Berkshire living in this design-forward mid-century ranch. Perfectly positioned on a quiet downtown dead-end road, this 3-bedroom, 1-bathroom home seamlessly blends crisp, modern style with classic architectural character. Inside, original hardwood floors guide you through a bright, fluid one-level layout. The living room serves as a comfortable anchor for cozy mountain evenings, featuring a striking wood stove that pairs perfectly with the home''s fresh, stylish aesthetic. Outside, the generous 0.41-acre level lot offers a private, shaded yard surrounded by mature trees-a fantastic feature for a property this close to the action. Beyond its residential charm, this property boasts coveted Business zoning, making it perfect for an ideal live-work lifestyle. Antonio M Segalla [email protected] 413-329-4075 WILLIAM PITT SOTHEBY''S - GT BARRINGTON
…$415,0003bedrooms1bathroomland 1,659m²By William Pitt Sotheby's International Realty
- 4
Land Egremont (United States)
Perched atop a breathtaking ridgeline with some of the most extraordinary panoramic views in the Berkshires, this remarkable almost 18-acre estate parcel is one of only seven exclusive homesites within this private enclave. With the most recent neighboring estate having changed hands for $5.6 million, the property's exceptional pedigree and enduring value are unmistakable. Surrounded by more than 220 acres of permanently protected conservation land, the property offers unparalleled privacy, timeless natural beauty, and direct access to a protected greensward ideal for hiking, cross-country skiing, and year-round outdoor enjoyment. A handcrafted stone bridge spanning a tranquil woodland stream welcomes you to an expansive, level building site with coveted southeastern exposure, perfectly positioned to capture dramatic sunrises, rolling hills, forested vistas, and ever-changing Berkshire skies. The entrance, approach, dwelling site, and selective clearing have all been thoughtfully completed, providing an exceptional canvas for a world-class estate. The property spans two of the Berkshires' most desirable low-tax towns--11.2 acres in Egremont and 6.8 acres in Alford and borders New York State, offering the perfect blend of Berkshire culture, Hudson Valley charm, and convenient access to major metropolitan destinations. Perfectly situated in the heart of the Berkshires--home to Tanglewood, Jacob's Pillow, exceptional farm-to-table dining, boutique shopping, renowned cultural institutions, and endless outdoor recreation--the location balances complete privacy with remarkable accessibility. Hudson, New York, with direct Amtrak service to New York City, is nearby, while Manhattan's Upper West Side is approximately two hours away. Boston is just 2½ hours, Albany one hour, and Hartford 1½ hours. With an existing well, roughed-in driveway, excellent percolation, and permanently protected unobstructed views, much of the essential groundwork has already been completed. Opportunities of this caliber are exceedingly rare--a chance to create a legacy estate in one of the Berkshires' most coveted and thoughtfully planned settings.
…$995,00072,722m²By William Pitt Sotheby's International Realty
- Contract pending23
House Stockbridge (United States)
Light-filled contemporary Cape built in 2020, this Stockbridge home features an open floor plan anchored by a great room with a gourmet kitchen, dining area, and living room. Two spacious first-floor bedrooms share a full bath, while the expansive second-floor primary suite offers a luxurious spa bathroom and a balcony overlooking the living area. The four-season sunroom (heated and cooled for year-round use) opens to the level backyard. Lovely front entrance with Bluestone steps into an ample mudroom. Enjoy year-round comfort with zone-controlled mini-splits. Close to vibrant Great Barrington, Stockbridge, and Lenox. A quick drive to Tanglewood, cultural venues, and abundant outdoor recreation including hiking and lakes, this modern retreat blends style, comfort, and an exceptional Berkshires location.
…$699,0003bedrooms2bathroomsland 4,087m²By William Pitt Sotheby's International Realty
- 50
House with garden Great Barrington (United States)
Rare, renovated Berkshire investment compound on 0.59 acres in pedestrian-friendly Housatonic. This turnkey property features two separate legal duplexes (4 units total) offering stellar cash flow. The front home (392 Park St) features a 5BR/2BA unit, a sleek 2BR flat, and a prominent street-front walk-out lower level with incredible commercial/addition potential. The rear Swiss-Gothic home (394 Park St) hosts two updated 2BR units. Enjoy a sprawling backyard with mountain views, a community garden, and fruit-bearing trees. Fully insulated and optimized for easy management with 4 separate heating/electric systems, town sewer/water, and off-street parking for 10+ cars. Moments from Berkshire Mountain Bakery; minutes to downtown Great Barrington and Tanglewood. A rare, turnkey find!
…$985,00011bedrooms7bathroomsland 2,388m²By William Pitt Sotheby's International Realty
- 37
House Egremont (United States)
This new-construction Craftsman Contemporary on private Terra Ferma Drive delivers sharp lines and bright living spaces. Anchored by vaulted ceilings and custom details, the open-concept layout flows directly to an expansive deck overlooking serene wooded wildlife. The five-bedroom, three-bath footprint provides a highly flexible layout for remote work, hosting, and modern living, supported by an attached two-car garage and a large yard, perfect for outdoor summer entertainment. Situated on a premier South Egremont cul-de-sac, the roadway connects directly to the Karner Brook Wildlife Management Area for instant trail hiking access, while keeping you minutes from Catamount skiing, Great Barrington, and low Egremont taxes. Clean, current, and highly efficient.
…$875,0005bedrooms3bathroomsland 4,532m²By William Pitt Sotheby's International Realty
- 50
House with pool Sheffield (United States)
Welcome to Serenity Hill. This 1994 Cape style home captures the timeless charm of the Berkshires from the moment you arrive. At the entrance, stately stone pillars and a classic stone wall offer a graceful welcome, setting the tone for the calm, natural beauty that defines life in the Berkshires. Located on the border of Great Barrington, this Sheffield home is on a peaceful, quiet country road. Less than a mile from Wyantenuck Country Club and just five minutes from downtown Great Barrington. This home offers a peaceful sense of seclusion without ever feeling far from the heart of the Berkshires. Inside, you'll find an airy, open layout with natural flow from room to room, designed with both comfort and connection in mind. The vaulted ceiling in the kitchen adds a sense of light and openness, while seamless transitions between the kitchen, dining area, and living room create a space that feels both cohesive and welcoming. A cozy wood-burning fireplace anchors the living room, adding warmth and charm to the heart of the home. With 3 bedrooms and 2.5 baths, every space feels intentional, comfortable yet refined rendering this home ideal for both everyday living and effortless entertaining. Thoughtful design choices enhance the home's warmth and inviting atmosphere. From the living room, multiple doors open onto a private back deck, creating a natural extension of the home's inviting flow. Beyond the deck, you'll find your own private sanctuary: a peaceful koi pond, an inviting in-ground pool, and a hot tub perfect for unwinding under the stars. Whether you're savoring quiet mornings in nature or hosting lively summer gatherings, this property offers the perfect balance of serenity and connection. This is more than just a home, it's a true Berkshire retreat, where timeless style shines in one of the area's most desirable settings.
…$1,195,0003bedrooms3bathroomsland 8,094m²By William Pitt Sotheby's International Realty
- 45Video
House Alford (United States)
Offered with Seller Financing, this Majestic Tudor Berkshire Estate sits on 71 Acres atop Tom Ball Mountain in quaint Alford, MA. Privacy and Breathtaking views. Formal Entry and Foyer. Stately Living Room and Dining Room. Great Room with Gourmet Kitchen. Den, Family Room, Gym and Massage Room. 5 en-suite Bedrooms in the Main House. 2 Bedroom Tudor Guest House w beamed ceilings and full amenities. Manicured grounds, infinity Pool and Hot Tub, Pool House with full Bath, Tennis Court and Pickleball Court. 7 Garages and additional Barn. Exquisite architectural touches, state-of-the-art home technology and security, in the most peaceful of surroundings. Easy access by road, rail and private Airport. Close to Tanglewood and Berkshire attractions. *Fully Furnished and ready to enjoy.
…$9,500,0007bedrooms9bathroomsland 29haBy William Pitt Sotheby's International Realty
- 39
House with pool Egremont (United States)
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. The front entry of architect-designed residence leads to a luminous interior with tall ceilings, reflective white walls, generous windows and 19 screened French doors that welcome sunlight and breezes and provide for ideal interior-exterior living. To the left of the entry are a living room with a wood-burning Rumford fireplace and hallway to the primary suite with an airy, comfortable bedroom, refined, restorative bath, and walk-in closet/dressing room. To the right, a spacious dining room, well-appointed kitchen, screened porch, and hallway to two bedrooms and full bath. The U-shaped floor plan embraces a secluded formal garden, reflecting pool with fountain, patio with pergola, and 40' lap pool. Completed in 1998, every element of the residence attests to architectural intelligence, superior craftsmanship, and love for the bucolic landscape. The high level of quality is evident in the visually commanding millwork, true stucco exterior, lath-and plaster walls in the principal rooms, east and south pergolas, west-facing screened porch, and sensitive choreography of space. With roots in the classical architecture of ancient Rome, this is a thoroughly modern dwelling replete with whole-house fan, air conditioning, generator, security system, 630-foot drilled well, and chef-ready appliances. The result is a home that feels both sculptural and deeply connected to its setting. With protected views, total privacy, and proximity to South County amenities (7 minutes to Guido's), this is a rare Berkshire offering -- serene, architecturally stunning, and eminently livable.
…$2,450,0003bedrooms2bathroomsland 2.8haBy William Pitt Sotheby's International Realty
- 46
House Stockbridge (United States)
Set on six picturesque acres in Stockbridge, this beautiful contemporary home offers privacy, comfort and stunning views. The thoughtfully designed layout features five bedrooms and 4.5 baths, including a spacious main-level primary suite with a luxurious en-suite bath. The chef's kitchen is equipped with premium Wolf and Sub-Zero appliances, perfect for entertaining or everyday living. An oversized three-car garage and finished lower level provide ample storage, while expansive windows showcase the surrounding landscape. Available furnished. This exceptional property is move-in ready and an ideal Berkshire retreat.
…$3,495,0005bedrooms5bathroomsland 2.5haBy William Pitt Sotheby's International Realty
- Contract pending39
Property Lenox (United States)
Beautifully maintained home set on a private one-acre lot on a quiet cul-de-sac in one of Lenox's most desirable neighborhoods. This thoughtfully designed residence offers four bedrooms and 5.5 baths, including a spacious main-level primary suite with a luxurious en-suite bath. The inviting floor plan is ideal for both everyday living and entertaining. Step outside to a beautifully landscaped backyard featuring a built-in grill, hot tub and plenty of space to relax or gather with family and friends. A rare opportunity to enjoy privacy, comfort, and an exceptional Lenox location.
…$1,200,0004bedrooms6bathroomsland 4,047m²By William Pitt Sotheby's International Realty
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House West Stockbridge (United States)
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 floor for year round comfort. The first-floor primary suite offers a private retreat with a spacious spa-like bath, featuring a large shower, soaking tub, and generous walk-in closet. An impressive entry foyer sets the tone with a sleek architectural staircase, powder room, and coat closet. A two-car attached garage provides ease and convenience. Upstairs, a dramatic loft overlooks the great room and sits adjacent to a second bedroom suite, perfect for guests or family. Separate from the two main suites, a private guest wing includes two additional bedrooms, a large sitting room, and a shared full bath, offering a comfortable and flexible space for visitors. Despite its very quiet mountain-top privacy, the property is ideally situated just 10 minutes from Tanglewood and downtown Lenox. Enjoy effortless access to I-90, making trips to Boston or New York City remarkably convenient. Nearby West Stockbridge offers a charming village atmosphere with boutique shops, a local marketplace, wine store, café, inviting restaurants, and even an old-fashioned hardware store—everything you need within a short and scenic drive.
…$2,975,0004bedrooms4bathroomsland 7.4haBy William Pitt Sotheby's International Realty
- 27
House Stockbridge (United States)
Have you been dreaming of year round fun on Stockbridge Bowl? The time is now! Built in 2011, this lovely home is directly across the street from the beloved town beach and affords water views from most windows. Offering single-level living, 3 BR, 1 full BA, a well appointed kitchen and gracious living spaces. The unfinished walk-out lower level is the perfect place to store your kayaks, and could be finished to offer more living space. There is plenty of off-street parking above and below the home. You are mere moments to Tanglewood's Lions Gate and the very best of the Berkshires. Would make a great rental, or a wonderful family retreat to make memories for years to come. Town sewer, private well, radiant heat, and energy efficient construction, all in a location that can't be be beat!
…$549,0003bedrooms1bathroomland 931m²By William Pitt Sotheby's International Realty
- Contract pending24Video
Farmhouse Lenox (United States)
Beautifully renovated historic farm house available in Lenox, Massachusetts. A charming 1840s clapboard house located on the estate of ''Brookhurst,'' one of the famed Berkshire ''cottages,'' this former guest house has 3 or 4 bedrooms and 2 full baths spread over three floors (primary bedroom and bath on main floor). It has a private gated driveway and an attached 2-car garage. Luxurious traditional decor throughout the home but with all the modern conveniences including AC, wifi, whole house generator and more. A flagstone terrace overlooks the lush backyard and fully planted walled garden. The house benefits from the rolling landscaped vistas of the beautifully maintained estate property it abuts. Minutes to the town of Lenox and to Tanglewood!
…$835,0004bedrooms2bathroomsland 4,047m²By William Pitt Sotheby's International Realty
- 50
House Richmond (United States)
Set on 4.7 beautifully landscaped acres with distant views. This impeccably maintained home offers generous space, thoughtful craftsmanship, and remarkable indoor-outdoor living. Located just minutes from so many of the Berkshires' most beloved attractions, including only 15 minutes from the main gate at Tanglewood, this Richmond property also boasts easy access to major traffic routes connecting you conveniently to both New York and Boston. Your ability to enjoy the region's culture, adventure, and cuisine starts right here.
…$1,495,0004bedrooms5bathroomsland 1.9haBy William Pitt Sotheby's International Realty
- 45
Property Adams (United States)
Welcome to the historic Simmons Cottage located at 2 Melrose Street in Adams, MA. This Victorian gem, completed in 1901, perfectly blends its 19th-century character with modern convenience. Situated on a .24-acre lot in the heart of Adams, the 2,406-square-foot residence features 4 bedrooms, three bathrooms, office, and full attic. The home's historic elegance shines through its preserved curved front porch, original woodwork, stained-glass windows, and rare Lincrusta ceilings. This home has been updated to provide efficiency, including a new roof, upgraded heating system, and a modernized kitchen. A standout feature is the unique historic carriage barn, relocated and repurposed into an incredible five-car detached garage for your vehicles and hobbies!
…$550,0004bedrooms3bathroomsland 971m²By William Pitt Sotheby's International Realty
- 42
House Great Barrington (United States)
Move right into this beautifully renovated mid-century Cape, where modern updates blend seamlessly with timeless charm. Designed for easy single-floor living, this bright and airy home features an open-concept kitchen, dining, and living area that creates an inviting space for both everyday living and entertaining. The living room is highlighted by a soaring cathedral ceiling and abundant natural light, enhancing the home's spacious feel. The thoughtfully designed layout includes a private primary suite with an en suite bath,offering comfort and convenience. French doors open from the living room to a rear deck overlooking a fire pit area, creating the perfect setting for outdoor gatherings, relaxing evenings, and enjoying the surrounding landscape. Ideally located just minutes from downtown Great Barrington, Ski Butternut, and the public boat launch at Lake Buel, this move-in-ready home provides easy access to the best of the Berkshires, from outdoor recreation to dining, shopping, and cultural attractions. Excellent rental history.
…$665,0003bedrooms2bathroomsland 1.1haBy William Pitt Sotheby's International Realty
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