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luxury houses for sale Berkshire County, United States

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Contract pending
42

House Lenox (United States)

Tucked away on 4 acres of wooded and partially cleared land, this lovingly maintained 1960 cape-style home offers the perfect blend of privacy, character, and opportunity. Set back from the road by a long driveway, the property creates a peaceful retreat just minutes from the heart of Lenox and outdoor destinations like October Mountain State Forest and Kennedy Park. Inside, the home is ready for its next chapter with spacious and inviting living areas including a formal living room, dining room, kitchen, and a cozy family room with gas fireplace and slider access to the private backyard. A sunroom off the kitchen is perfect for seasonal enjoyment. The first-floor primary bedroom features a connected full bath with convenient hall access, while upstairs offers two additional bedrooms, an office space, and another full bathroom. A two-car garage located under the home provides direct access to the basement and additional storage or workshop potential. Full of warmth and well cared for through the years, this property is ready for its next owners to reimagine and make it their own.

… 
$550,000
3bedrooms
2bathrooms
land 1.6ha

By William Pitt Sotheby's International Realty

46

Property Great Barrington (United States)

Tucked into the rolling hills of Great Barrington just minutes from downtown and the slopes of Ski Butternut, The Turning Point is a storied 3,600-square-foot Berkshire landmark operating as an active short-term rental. Steeped in history dating back to its 1800s stagecoach tavern roots, the property showcases an enduring dual-facade of classic New England brick and weathered clapboard. Inside, original period charm takes center stage with wide-plank wood floors and glowing fireplaces, perfectly paired with a rare, substantial footprint featuring 7 generous bedrooms and 6.5 bathrooms. Designed for effortless hosting, this expansive retreat offers an incredible canvas for a lucrative rental investment, a boutique bed-and-breakfast, or a magnificent private country compound.

… 
$575,000
7bedrooms
7bathrooms
land 4,047

By William Pitt Sotheby's International Realty

25

House Becket (United States)

Tucked into the woods of Sherwood Greens and just a short walk to Long Bow Lake's private beach, this home is the kind of Berkshire retreat you have been looking for. Set on 2.35 acres with privacy on both sides, it offers the peaceful, tucked-away feeling of a cabin in the woods while remaining just minutes from Lee and the Berkshires' renowned cultural attractions, including Jacob's Pillow, Tanglewood, and the area's vibrant restaurants, shops, and hiking trails. One of the community's greatest attractions is Long Bow Lake itself, a quiet non-motorized lake enjoyed by kayakers, canoeists, paddleboarders, and those seeking a more peaceful pace. Inside, cathedral ceilings, warm pine walls, and a wood stove create an inviting atmosphere that feels instantly welcoming. Offering 1,764 square feet, the spacious living room opens to the dining area, creating a comfortable gathering space filled with natural light and character. Sliding glass doors lead to a brand new deck overlooking the surrounding woods, while a cozy den, kitchen, and half bath complete the first floor. Upstairs, the primary suite features a private bath with a soaking tub, while two additional bedrooms share a full guest bath. Whether you're spending the day at the community beach, paddling across the lake, exploring nearby Berkshire attractions, or relaxing by the fire after a day outdoors, this home captures the laid-back lake lifestyle that makes Sherwood Greens so special. Private, peaceful, and full of charm, 410 Long Bow Lane is the kind of place where weekends turn into entire summers.

… 
$425,000
3bedrooms
3bathrooms
land 9,510

By 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.

… 
$449,000
2bedrooms
2bathrooms
land 5,423

By William Pitt Sotheby's International Realty

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31

House Lee (United States)

Welcome home to this sweet and petite one level easy living ranch style home. Sun-filled bright spaces invite you to relax and enjoy the end of each day in this thoughtfully planned layout. Boasting a king size bedroom, two other bedrooms, and an updated full bath. The galley style kitchen is comfortable for baking and creating all the dinner gatherings you wish. Comfortable everyday dining is open to living and a lovely added sunroom for extra living space and enjoyment. French doors lead to a generously sized back yard with perennial plantings and a shade tree for an outdoor cool evening escape and playtime. Central to all that is Berkshire and Lee with a quaint downtown, shopping, schools, dining, and antiques. Close to parks, playgrounds and October Mountain State Forest for fun!

… 
$269,900
3bedrooms
1bathroom
land 688

By William Pitt Sotheby's International Realty

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.

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$695,000
4bedrooms
3bathrooms
land 1.9ha

By 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.

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$3,495,000
5bedrooms
7bathrooms
land 2.3ha

By 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

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$415,000
3bedrooms
1bathroom
land 1,659

By William Pitt Sotheby's International Realty

Contract pending
40

Farmhouse Pittsfield (United States)

Set on an oversized corner lot at the end of a quiet dead-end street, this bright renovated 3-bedroom, 2-bath home offers an impressive amount of outdoor space in a neighborhood setting. The expansive yard is the standout feature, with established gardens, mature trees, a firepit area, open lawn space, and a fenced section for pets. Inside, the home has been thoughtfully updated throughout. The bright eat-in kitchen features new appliances, stylish finishes, and a generous pantry. The main level also includes a living room, first-floor bedroom, full bath, and a three-season porch. Upstairs you'll find two additional bedrooms, a home office, a renovated full bath, and a covered porch overlooking the neighborhood. The lower level provides laundry and storage space, while the detached garage offers additional room for tools, equipment, and seasonal items. The established gardens, firepit, and oversized yard are what make this property special, creating a home that feels welcoming and well-loved.

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$269,900
3bedrooms
2bathrooms
land 1,862

By William Pitt Sotheby's International Realty

Contract pending
15

House Pittsfield (United States)

Welcome to this well maintained 3-bedroom, 1-bath home tucked away at the end of a quiet side street, offering privacy, convenience, and a beautiful connection to nature. Inside, hardwood floors run throughout most of the home, reflecting years of attentive care and pride of ownership. Step outside to a spacious, fully fenced backyard featuring a deck with a remote-controlled retractable awning, perfect for relaxing or entertaining. Abutting protected land through Berkshire Natural Resources Council, this property offers easy access to hiking trails leading to The Boulders and beyond. A move in ready home in a peaceful setting that you'll love coming home to.

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$272,500
3bedrooms
1bathroom
land 971

By 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!

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$549,000
3bedrooms
1bathroom
land 931

By William Pitt Sotheby's International Realty

Contract pending
41

Farmhouse Great Barrington (United States)

Step back in time and discover the timeless charm of this classic 19th-century New England home, ideally situated on a generous .66-acre corner lot on a quiet street just minutes from the heart of downtown Great Barrington. Rich in character, this antique home retains many of its original architectural details, offering an exceptional opportunity for restoration and reimagination.The inviting, old-fashioned front porch welcomes you to a home filled with history and potential. A classic barn adds versatility for storage, hobbies, or future creative use, while recent updates--including a new boiler and barn roof in 2025 and the convenience of natural gas--provide a solid foundation for your vision. Whether you're looking to restore a beloved antique or create your dream Berkshire retreat, this property offers endless possibilities in an unbeatable in-town location. Bring your imagination and breathe new life into this historic gem. Property is being sold as is.

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$349,000
3bedrooms
1bathroom
land 2,671

By William Pitt Sotheby's International Realty

Contract pending
26

Property Stockbridge (United States)

Embrace the ease of single-level living in this enchanting 3-bedroom, 2-full-bath cottage nestled in historic Stockbridge. Perfect as a year-round residence or a peaceful weekend getaway, this home perfectly blends cozy charm with modern convenience.

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$595,000
3bedrooms
2bathrooms
land 6,070

By William Pitt Sotheby's International Realty

28

House Great Barrington (United States)

Tucked away on 3.6 serene acres, this bright and airy single-level home is the perfect year-round escape. This completely renovated home offers an open concept main living area including the dining room, efficient eat-in kitchen with stainless steel appliances, and family room with wood stove, perfect for relaxation and entertaining. Two additional guest rooms and a den. The newly-completed primary suite boasts a beautiful bathroom and an oversized walk-in closet versatile enough for a home office. Outside, the private grounds feature a dining patio, fire pit, gazebo, and shed. Located just minutes from the slopes of Ski Butternut and downtown Great Barrington, this turnkey property also features a proven track record as a short and long term rental. Propane has been added with additional plumbing to set up gas-powered cooking if desired and possibility to convert wood stove to a gas option. House plumbed for forced air system. The primary suite features radiant floor and a heated towel bar, as well as a new mini split system in 2021. High efficiency tankless Rinnai water heater. Close cell spray foam insulation throughout the house, all exterior walls, crawlspace, and foundation walls. Whole house water filtration system with three stage filter and water softener. Roof replaced in 2021. Ring security system with camera. Whole house dehumidifier in crawl space.

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$599,000
3bedrooms
2bathrooms
land 1.5ha

By William Pitt Sotheby's International Realty

Contract pending
12

House Pittsfield (United States)

Completely renovated in 2021, this thoughtfully updated 2-bedroom, 1-bath home offers easy, low-maintenance living with a fresh, modern feel throughout. With 747 square feet of efficiently designed space, every inch has been maximized for comfort and functionality. The interior features updated finishes, an inviting layout, and abundant natural light, creating a warm and welcoming atmosphere. The kitchen and living areas flow seamlessly, making the home feel open yet cozy--perfect for everyday living or entertaining. Ideally located just minutes from downtown Pittsfield and the vibrant Cultural District, you'll enjoy convenient access to local dining, shopping, arts, and entertainment. Whether you're looking for a primary residence or an investment opportunity, this property offers value and accessibility in a central location.

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$169,900
2bedrooms
1bathroom
land 283

By William Pitt Sotheby's International Realty

Contract pending
50

House Otis (United States)

Whether you're seeking a peaceful country retreat or a full-time residence, this beautifully renovated home offers the perfect blend of rustic elegance and modern comfort. Privately situated on nearly 5 acres and set well back from a quiet country road, the property enjoys expansive yard space, distant views, and a truly bucolic setting. Move-in ready and thoughtfully updated, the open and airy floor plan features 3 bedrooms and 2 full bathrooms. The dramatic great room boasts soaring ceilings, warm wood floors, a cozy wood stove, and an upper-level balcony overlooking the living space below. Large windows invite natural light and showcase the surrounding landscape.The walk-out lower level includes a finished family room and a separate workshop, providing flexible space for recreation, hobbies, or remote work. Outdoors, relax on the open deck or enjoy the seasonal screened in porch while taking in views of the rolling countryside. Additional highlights include a newer roof, carport, and a full solar array that virtually eliminates electric bills. Ideally located just minutes from Otis Ski Ridge, Otis Reservoir, Big Pond, hiking trails, local restaurants, and charming general stores, GB and Lenox an easy drive away, this property offers year-round recreation and the tranquility of country living at its finest.

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$499,000
3bedrooms
2bathrooms
land 2ha

By William Pitt Sotheby's International Realty

Contract pending
44

House Pittsfield (United States)

Pride of ownership shines throughout this beautifully updated ranch situated on a corner lot in a walkable, sought-after neighborhood, close to bike trails, hiking and shopping. This well maintained 3-bedroom, 2 full bath home features central air, a bright modern kitchen with Instaview refrigerator, double oven, 2 filtered water sites and a spacious dining area with cathedral ceiling. The beautifully renovated main bath features a spa style rain shower with dual heads, heated fan, tiled flooring and generous storage. This home offers hardwood floors and cedar closets throughout its comfortable, well-designed space. The private backyard features a pebble epoxy finished patio, a convenient electric awning and a charming stone fire pit for cool evenings, and entertaining. The newly installed HVAC system with central air--along with a new roof, new vinyl siding, new windows and new insulation--ensure year-round comfort, efficiency, and low maintenance. The finished lower level boasts a large family room with exercise area as well as dedicated work and laundry rooms, a cold storage room, and an attached 2 car garage with an additional storage extension.

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$398,500
3bedrooms
2bathrooms
land 971

By William Pitt Sotheby's International Realty

50

House Otis (United States)

Nestled on over 3 private acres with an extraordinary 650 feet of frontage on Hayes Pond, this exceptional waterfront retreat offers sweeping elevated views, a private dock, sandy beach, and direct access to swimming, kayaking, and fishing. Designed to embrace its stunning natural setting, the home features expansive windows and multiple outdoor living spaces, including a wraparound deck, waterside gazebo, and screened porch with hot tub connection--perfect for entertaining or relaxing in every season. The bright open-concept interior includes 4 bedrooms and 3 full baths, highlighted by a dramatic great room with knotty pine ceilings, a wood-burning stove with stone hearth, and direct deck access overlooking the water. The spacious primary suite also opens to the deck and features its own and features its own wood-burning stove and en suite bath. The walkout lower level offers additional living space with a family room, full bath, and two bedrooms ideal for guests or extended family. Additional features include solid wood floors throughout, an attached two-car garage with EV charging, and easy access to the very best of the Berkshires. Located just minutes from Lee and Lenox, with nearby hiking, skiing, dining, Tanglewood, and year-round cultural attractions, this is a rare opportunity to enjoy the ultimate Berkshire waterfront lifestyle. Sale includes lots 34 and 35.

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$1,100,000
4bedrooms
3bathrooms
land 1.2ha

By William Pitt Sotheby's International Realty

50

House Otis (United States)

Completed in 2010 and thoughtfully maintained since, this inviting log home offers a blend of warmth, functionality, and connection to its natural surroundings. A wraparound front deck welcomes you in, setting the tone for the home's relaxed feel. Inside, the main living and dining areas flow comfortably together, anchored by a spacious eat-in kitchen with radiant heat flooring, ideal for both everyday living and gathering. The main level features three bedrooms and two full baths, including a primary suite with its own en-suite. Upstairs, a flexible lofted space can serve as an office, entertainment area, or whatever best fits your needs. Out back, a peaceful setting unfolds with a wildlife pond and frequent visits from local birds and animals, best enjoyed from the rear deck. The lower level adds even more versatility with additional living space, a wood stove for added comfort, and a full in-law apartment complete with kitchen, bath, and walkout access to a private deck, ideal for extended family or rental potential. Recent updates include a new roof (2024), boiler (Dec 2025), high-efficiency water heater, well pump, updated plumbing, and a new sink. The home also features leased solar panels, Pella windows, and wiring for an electric vehicle. Conveniently located near Jacob's Pillow and all that the Berkshires have to offer.

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$729,900
3bedrooms
3bathrooms
land 1.3ha

By William Pitt Sotheby's International Realty

Contract pending
23

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.

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$699,000
3bedrooms
2bathrooms
land 4,087

By William Pitt Sotheby's International Realty

37

Farmhouse Becket (United States)

Tucked against hundreds of acres of protected forest, this beautifully preserved late 1700s Berkshire homestead offers a rare blend of historic New England character, thoughtful modern upgrades, and direct access to the outdoors. Rich in period detail, the home showcases authentic craftsmanship, including hand-hewn beams, wooden pegs, and square nails, timeless elements seldom found beyond true historic farmhouses. Beneath it all, a fieldstone foundation with an insulated rim joist has been professionally sealed, while recent improvements such as a fully insulated roof and comprehensive air sealing enhance comfort and efficiency throughout. Modern systems have been carefully integrated to support year-round living, including an energy efficient mini-split heat pump system providing both heating and air conditioning, a heat pump water heater, and a new 100-amp electrical panel. Hydronic heat remains in place as a reliable backup, offering peace of mind during colder Berkshire winters. The outdoor setting is equally compelling. A fully fenced yard opens through a rear gate directly onto an expansive network of woodland trails, offering immediate access to hiking, biking, snowshoeing, and year-round exploration right from your own backyard. A standout feature is the 12' x 30' off-grid solar-powered barn, fully wired for electricity and lighting and complete with a propane heater and full loft. Currently used as a private fitness studio, this versatile space lends itself equally well to a workshop, studio, or home office--ideal for today's flexible lifestyle needs. Ideally located in the heart of the Berkshires, this property offers a unique balance of privacy and accessibility, equally suited as a full time residence, weekend retreat, or remote work escape surrounded by nature. A truly distinctive offering for those seeking historic charm, modern efficiency, and an immersive Berkshire lifestyle.

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$299,000
2bedrooms
1bathroom
land 1,335

By 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!

… 
$985,000
11bedrooms
7bathrooms
land 2,388

By William Pitt Sotheby's International Realty

30

Property Stockbridge (United States)

Quitessential 1831 side hall Colonial. Charming home located in the village of Interlaken in the town of Stockbridge, MA. Just minutes to Lenox, downtown Stockbridge, and the Berkshire Botanical Center. Listen to the babbling water from the Larrywaug Brook and visit the nearby town park. Sit on the deck or around the firepit to soak in the atmosphere of privacy and peace. This 3 bedroom, 1.5 bath house has been meticulously updated. These updates include: roof, windows, deck, painting, kitchen, baths, cement clapboard, wood flooring, laundry on main level. Full walkout basement, oil heat, central air, town water, town sewer. Garage is partitioned for a workshop but can easily be converted to a one-car garage again.

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$752,000
3bedrooms
2bathrooms
land 486

By 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.

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$1,195,000
3bedrooms
3bathrooms
land 8,094

By William Pitt Sotheby's International Realty

45
Video

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.

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$9,500,000
7bedrooms
9bathrooms
land 29ha

By 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.

… 
$875,000
5bedrooms
3bathrooms
land 4,532

By William Pitt Sotheby's International Realty

Contract pending
50
3D visit

House with pool Lee (United States)

Set on just under an acre along one of Lee's most desirable roads, this beautifully maintained home combines timeless design, quality craftsmanship, and exceptional outdoor living. Overlooking peaceful meadows with stunning sunset views, the setting offers the perfect balance of privacy and natural beauty. Designed for both entertaining and everyday living, the backyard is truly the centerpiece of the property. A tiered bluestone patio creates multiple spaces to gather and relax, featuring a built-in outdoor kitchen, gas fire pit, and a heated saltwater plunge pool by Soake Pools. Mature landscaping, professionally designed landscape lighting, and a charming storage building complete the outdoor space, creating a backyard that feels like your own private retreat. Inside, the home is warm, inviting, and thoughtfully designed. The eat-in kitchen is the heart of the home with a large center island, custom cabinetry, premium JennAir appliances, and direct access to the patio for seamless indoor-outdoor living. Just off the kitchen, the family room offers a comfortable place to unwind, while the formal living and dining rooms provide the perfect setting for holidays and entertaining. A powder room and first-floor laundry add convenience to the main level. Upstairs, the spacious primary suite offers a walk-in closet and a beautifully appointed en-suite bathroom featuring a soaking tub and walk-in shower. Two additional bedrooms share a full bath, while the oversized bonus room provides incredible flexibility. Filled with natural light from a dramatic picture window overlooking the backyard and rolling meadows with distant mountain views, it's the perfect space for a media room, playroom, home office, or fourth bedroom/guest suite. A second staircase offers easy access and enhances the home's thoughtful layout. Additional features include a new roof in 2022, an attached two-car garage and a full basement with radiant heat, providing ample storage and endless potential for future finishing. From the quality craftsmanship and thoughtfully designed floor plan to the incredible outdoor spaces and picturesque setting, this is a home that has been exceptionally cared for and is ready to be enjoyed for years to come.

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$995,000
4bedrooms
3bathrooms
land 3,723

By William Pitt Sotheby's International Realty

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