luxury real estate for sale Berkshire County, United States (page 3)

Convenient one-level ranch in a prime location close to town. This well-maintained home offers four bedrooms and two full bathrooms, ideal for comfortable living. The updated kitchen features modern finishes and plenty of workspace. Enjoy energy efficiency with owned solar panels that significantly reduce utility costs, plus a pellet stove for supplemental heating. A generator ensures uninterrupted power during outages--peace of mind year-round. Situated on a private road, the property provides tranquility while remaining minutes from shopping and dining. Additional highlights include ample storage, a functional layout and move-in-ready condition. Whether you're downsizing, seeking your first home, or looking for a smart investment, this turnkey property delivers.

Welcome home! This magnificent 13.3-acre estate is rich in history and brimming with enchanting features. Nestled in a county setting, this property offers a connection with the outdoors for nature lovers and recreational activities. A low-maintenance wild garden of perennial flowers and shrubs produces a kaleidoscope of colors during the spring and summer seasons. A large, private office area with high-speed internet provides a productive ''work from home'' environment. The first floor features an eat-in country kitchen with an antique Glenwood stove. The formal living room, with its wood-burning fireplace, is ideal for cozy evenings. The sitting room, complete with built-in bookshelves, is perfect for a home library or study. A large addition boasts vaulted ceilings, adding grandeur and space to the home with versatility for a home office, first-floor primary bedroom, family room or guest quarters. The formal dining room, featuring built-in cabinetry, is perfect for hosting dinner parties. The sunroom, featuring a fountain pond, is bathed in natural light and offers a serene setting. Additionally, the first floor includes a laundry room and a full bathroom, as well as an enclosed four-season porch. The second floor includes four bedrooms, offering peaceful retreats for family members or guests. A full bathroom serves the upstairs bedrooms, and a hobby room provides an ideal space for crafts, projects, or as an additional study area. The large barn is perfect for storage, farming, hobbies, or even transforming into a creative space. The two-car detached garage includes a finished space above, providing a perfect spot for a potential home office, studio, or guest accommodations. Further enhancing the property is a brand-new heating system, new septic and a whole-house generator. Steeped in history and surrounded by beautiful gardens and pastoral views, this property is more than just a home--it's a lifestyle.

At $375,000, it's rare to find this kind of space, condition, and flexibility in the heart of Pittsfield. Set just off North Street, 84 Elizabeth Street offers 2,788 square feet of recently updated living space with a layout that actually works. The first floor flows effortlessly from room to room, with a bright, updated kitchen, formal dining area, two connected living spaces, and the kind of details you don't often see at this price point, including original pocket doors that bring character without sacrificing openness. A mudroom and first-floor laundry add everyday convenience right where you want it. Upstairs, the bedrooms are all generously sized, and the bathrooms have been thoughtfully renovated with a clean, modern feel. The updates here aren't surface level, they've been done throughout the home in a way that makes it feel move-in ready from day one. A spacious pantry, multiple storage options, and two outbuildings give you flexibility beyond the main house. One includes a private garage bay with additional storage, while the second is a larger barn-style structure shared with the neighboring property, ideal for equipment, hobbies, or overflow. Prepaid solar panels add real long-term value, helping offset future utility costs. If you've been looking for true square footage, updated interiors, and a walkable in-town location without stretching your budget, this is a standout opportunity.

Built in 2004, this exquisitely-crafted historic reproduction home seamlessly blends old-world charm with contemporary comfort. Set on 1.82 acres with sweeping mountain views, this 3-bedroom, 2.5-bathroom home features meticulous hand-crafted details throughout, honoring traditional design while offering the conveniences of modern construction. The welcoming gourmet eat-in kitchen is perfect for everyday living and entertaining. Step out to the inviting covered porch--an ideal spot to savor morning coffee and evening sunsets with mountain vistas. The primary suite captures stunning views, while the expansive yard provides additional room to roam. 2-car oversized garage. Secluded setting just minutes to downtown Great Barrington and other Berkshire attractions.

Set within one of Pittsfield's most established and desirable neighborhoods, this beautifully maintained Colonial blends timeless character with carefully curated updates. From the moment you enter, a gracious living room sets the tone--anchored by a gas fireplace, framed by classic built-ins, and finished with gleaming hardwood floors that carry throughout. The formal dining room offers an elegant setting for entertaining and transitions seamlessly into the thoughtfully renovated kitchen. Designed with both style and function in mind, it features quartz countertops, updated appliances, and a clean, sophisticated aesthetic. A versatile first-floor room, currently used as an office, offers flexibility for a fourth bedroom. A well-appointed half bath adds a touch of personality with its distinctive, design-forward wallpaper. Upstairs there are three well-proportioned bedrooms including one with a delightful sleeping porch--an inviting nod to the home's classic New England roots. A full bath serves the second floor, while the finished third-floor attic presents exceptional bonus space, ideal for a private studio, playroom, or creative work-from-home space. Additional highlights include a newer roof on both the main house and garage, updated electrical systems, a one-car garage, a thoughtfully designed patio for outdoor entertaining, and an additional half bath in the basement. A rare offering in Southeast Pittsfield--where classic architecture, modern updates, and attention to detail come together in a location that remains consistently in demand.

Located in Stockbridge, this historic General Williams House (circa 1795) has been restored and updated. Featuring 6 bedrooms, 5.5 bathrooms, 6 beautiful wood burning fireplaces, large dining and living spaces and 2 kitchens. The ''Ice House'' features its own kitchen and bath, for family gatherings or as Artist Studio. A sparkling in-ground pool for your summer pleasure. All this and more exists close to Main Street Stockbridge, Norman Rockwell Museum, Tanglewood, and all the most important cultural amenities. Who could ask for anything more?

The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental. The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests and has been a strong performer for weddings, corporate retreats, and multi-generational stays. The grounds feature open lawns, established gardens, and west-facing views. Fully ADA compliant and walkable to Lenox's restaurants, shops, and cultural venues. A rare opportunity to own a large-scale, income-producing property in one of the Berkshires' most established locations.

Set in one of Southeast Pittsfield's most desirable neighborhoods, this very sunny and impeccably maintained home offers the perfect balance of gracious living, flexible space, and effortless entertaining. Lovingly cared for by its current owner, the home unfolds with elegant formal rooms, hardwood floors, and a warm wood burning fireplace anchoring the living room. The heart of the home is an open concept kitchen and family room with cathedral ceilings, where sliders lead seamlessly to a large rear deck overlooking a spacious, flat, and fenced backyard; ideal for gatherings, play, or quiet relaxation amid mature landscaping and beautiful gardens. A heated sunroom extends year round enjoyment, while the layout offers remarkable versatility with five bedrooms, including two primary suites. The first floor primary features a walk-in closet and en suite bath, while the second floor primary also offers an en suite and double closets, complemented by additional second floor bedrooms. A finished, heated area in the expansive basement adds valuable bonus space, and practical comforts include first floor laundry, three zone natural gas heat, town water and sewer, and a two car attached garage with loft storage above. Thoughtful, inviting, and designed for both everyday living and entertaining, this is a home that truly delivers a lifestyle.

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.

Just around the corner from world-renowned Tanglewood, this exceptional Richmond property offers a truly prime Berkshires location-- where music, culture, and natural beauty meet. Set on just over five picturesque acres with shared ownership in a charming small pond, the setting is as special as the home itself. Beautiful open landscaping creates an inviting approach, with sweeping lawns and thoughtfully maintained grounds that enhance the sense of privacy and serenity. The home itself is bright and airy, filled with natural light and designed for both comfortable everyday living and gracious entertaining. The kitchen is the heart of the home, seamlessly open to a sunny breakfast nook and a sun-filled family room-- perfect for gathering with friends and family. A large pantry provides exceptional storage and functionality. For more formal occasions, enjoy a separate dining room, elegant sitting room, and formal living room. A heated sunroom offers year-round enjoyment, while a dedicated first-floor office/library provides ideal work-from-home flexibility. Upstairs, you'll find four spacious bedrooms and two full bathrooms, offering ample room for family and guests alike. Practicality meets versatility on the main level with a convenient laundry/mudroom and half bath located just off the garage. Above the garage, a finished bonus space with its own full bathroom presents endless possibilities-- whether as a private studio, guest suite, bedroom, or additional family room. In a highly desirable Richmond location near Lenox and all that the Berkshires have to offer, this property combines space, light, and flexibility with an unbeatable address close to Tanglewood. A rare opportunity to enjoy quintessential Berkshires living.

Enjoy outstanding country living in idyllic Monterey with its low real estate taxes and easy access to Lake Garfield and Lake Buel. Butternut Ski Area is only 5 minutes away. 8 minutes to downtown Great Barrington. This timber frame, open floor plan contemporary home features beautiful, wide plank pinewood floors, a cathedral ceiling great room, and a bonus sleeping loft area. A fireplace on the main level and a wood stove on the lower level add warmth and charm. Ready to move right in? With relatively low inventory level, particularly in Monterey, this listing is a lucky strike extra.

Set on just over seven acres between Lee and Stockbridge, this c.1850 Greek Revival delivers classic Berkshire character with real scale. Nearly 4,700 square feet with a gracious flow, tall windows, and preserved period details. Every bedroom offers an en suite, creating an easy setup for hosting family and friends. Common spaces include a welcoming foyer, two living rooms, a formal dining room, a library, and a large cook's kitchen with eat-in area and pantry. Three period fireplaces add warmth and charm. Outside, mature trees frame open meadow, with room for gardens, games, and long summer evenings. The setting is remarkably convenient. Tanglewood, Lenox, Stockbridge, and downtown Lee are a short drive, and access to Route 7 and the Mass Pike keeps weekend trips simple.

This Woodmonte Estates lot offers a builder-ready parcel equipped with on-site utilities, including public sewer, a private well, and underground electric and gas. Tucked away in a premier luxury community, this location provides a serene, private setting while maintaining close proximity to year-round recreation. It is just a short drive to the renowned cultural hubs, skiing, lakes, and numerous outdoor activities of the Berkshires. Please note that home must be minimum 3000 sf, with design and construction of home subject to HOA approval. With additional adjacent lots available to create an expansive, custom estate, this location represents the ultimate destination—privately situated yet perfectly connected to everything the region has to offer.

A stunning three-story residence with breathtaking views for an easy-care lifestyle in the Berkshires. Majestic and magical perfectly describe this exquisite three-story mountaintop home, designed to capture the stunning and distant views of the Berkshire skyline. With over 5,000 square feet of expansive living space, this centrally located residence offers the perfect opportunity to either escape, join a quaint community, or work from home with glorious views of the Berkshire Hills. Prime location for nature and culture. Nestled in a charming small-town neighborhood, this home is bordered by beautiful woodlands, providing direct access to hiking trails and the nearby Appalachian Trail. Its central location places you at the heart of the area's vibrant culture and great outdoors. Quality Craftsmanship, Thoughtful Design, and Energy Star Rated: This quality-built and immaculately maintained two-owner home features an expansive floor plan that enhances three distinct levels of living space. The layout is ideal for those seeking abundant room, making it perfect for multi-generational living options. On the first floor, the spacious living room is thoughtfully planned mid-level, complimenting the dining room, office space, a first floor primary suite option, and a first floor laundry room, all providing one-level convenience. Gourmet Kitchen with Scenic Views: The oversized gourmet kitchen invites you to prepare homestyle recipes while enjoying panoramic mountain views. Granite counters top timeless-style maple cabinetry with an island that expands over 10', built-in breakfast bar, and computer station for two cooks to comfortably create, laugh, and live. Luxurious Private Suites and Modern Conveniences: Upstairs, you'll find two additional primary suites plus two guest bedrooms, offering privacy and comfort, making them perfect retreats for guests, including a laundry area for added functionality on each level. Versatile Lower Level for Entertainment and Relaxation: The lower walkout level expands your living possibilities, featuring a second fireplaced living room, a second kitchen, a movie theatre media room, an exercise room, a sixth bedroom, and a fourth full bath. This versatile space is ideal for entertaining, wellness, and accomodating guests. Ample Garage Space for Adventure and Everyday Living: A four-car garage provides ample shelter for both everyday vehicles and sports or all-terrain vehicles, supporting a lifestyle full adventure as you explore everything mountaintop living has to offer. Easy Care Homesite: Creating lasting experiences with this unique, tiered homesite. Live an easy-care lifestyle and and creating lasting experiences on this low-maintenance property. Enjoy a hike through Wahconah Falls National Park, join the CSA of Holiday Farm, mountain bike at The Boulders, and discover the history that abounds in Dalton, while residing in this sought-after neighborhood. Move in to a solidly-built home, relax, enjoy, and feel soothed while gazing at mystical skies and mountains from each room. Embrace the beauty of the central Berkshires inside or out.

This Woodmonte Estates lot offers a builder-ready parcel equipped with on-site utilities, including public sewer, a private well, and underground electric and gas. Tucked away in a premier luxury community, this location provides a serene, private setting while maintaining close proximity to year-round recreation. It is just a short drive to the renowned cultural hubs, skiing, lakes, and numerous outdoor activities of the Berkshires. With additional adjacent lots available to create an expansive, custom estate, this location represents the ultimate destination—privately situated yet perfectly connected to everything the region has to offer.

Imagine owning your own secluded sanctuary, where total privacy and tranquility are yours for the taking. This extraordinary property offers the rare opportunity to build your dream retreat on a breathtaking piece of land, untouched by the outside world. With 20-foot-tall mountain laurel trails leading to the top of a mountain with stunning views right at your doorstep, you'll have endless access to nature's beauty, all while remaining completely secluded. The land consists of 6 separate parcels, all being sold together, creating the perfect canvas for whatever you envision. Don't miss out on staking your claim to this hidden gem, an unparalleled escape!

Imagine waking up in a sun-splashed home just steps from Great Barrington's lively Main Street—where every café, bookstore, and gallery feels like an extension of your neighborhood. This second-floor floor-through condo is more than a home; it's a canvas for your life. Over 1,800 sq. ft. of expansive living space unfolds with towering ceilings, oversized windows, and graceful arched doorways that evoke another era. Every detail—from the textured walls to the light pouring in at all hours—creates a sense of romance and possibility. The home is thoughtfully divided: one wing offers a spacious bedroom and lounge with guest alcove, while the other wing hosts a dining area, kitchen, and charming nook for work or rest. A central hall with clawfoot tub bath and laundry ties the spaces together, blending beauty with everyday comfort. Here, you are at the center of it all: Broadway-quality theater, world-class dining, outdoor adventures, all just beyond your front door. Own a piece of Great Barrington's historic soul, and let it inspire your next chapter. Please note: this is a walk-up unit with no elevator, limiting certain commercial applications but ideal for residential or studio use. The property spans the entire second floor of a well-maintained historic building and is located in a B2 mixed-use zone (buyer to verify permitted uses). With a smart division of space across two wings, the condo currently functions as a residence but offers potential for live/work, gallery, or creative studio configurations.

Spacious and adaptable, this Pittsfield home offers exceptional flexibility for today's lifestyle. The first floor features a sun-filled living room with hardwood floors and a bay window, a generous kitchen with an island and large dining area, and a mudroom with convenient first-floor laundry. A full bath and two bonus rooms on the main level provide versatile options for home offices, guest space, or additional bedrooms, allowing for the ease of one-level living if desired. Upstairs, a large landing creates the perfect spot for a home office or play area, while the primary bedroom boasts a walk-in closet and private exterior balcony. Three additional bedrooms and a full bath complete the second floor. Outside, enjoy a fenced-in backyard, one-car garage, solar panels, and a location just minutes from parks, shopping, and dining.

Properties of this magnitude and character are becoming a true rarity in today's market. Brookmede Farm, isn't just a listing; it is a magnificent blank canvas of 22 beautiful scenic acres, defined by sweeping mountain views and a profound sense of quiet serenity. From the moment you arrive, the silence and the scale of the landscape invite you to imagine the unlimited possibilities. Whether you envision a world-class equestrian estate, a sustainable organic farm with cows and chickens, or a sophisticated multi-structure family compound, this land provides the space and the soul to make it a reality. Standing as a centerpiece to this vision is a towering, three-story Timber Frame barn. With its incredible volume and structural presence, it offers a legendary head start for a premier stable, a grand creative studio, or an architectural centerpiece for your new estate. The property is directly abutted by conservation land, ensuring your privacy and pristine views are preserved forever. The location is nothing short of ideal. You are nestled in a peaceful pocket of New Marlborough where complete privacy is guaranteed, yet you remain within touching distance of the Berkshires' most beloved landmarks. You are just two minutes from the world-class culinary experiences at Cantina 229 and The Old Inn on the Green, Gedney Farm and Southfield Store, and only ten minutes from the vibrant shops and culture of Great Barrington. This is the ultimate opportunity for a visionary buyer who wants a quiet, scenic retreat without sacrificing proximity to the best the region has to offer. You truly have to explore these 22 acres in person to feel the energy of the land and see the potential of the barn. Come stand on this ground, take in the mountain vistas, and see how you can transform this rare Berkshire find into your own dream property.

Old Farm Lane, Lot #26 offers the perfect blend of wooded privacy and neighborhood community, while being tucked away on a quiet cul-de-sac. Utilities are in place with public sewer, private well, underground electric and gas. This lot borders the Pittsfield State Forest and offers close proximity to other year-round activities. It is also a short drive to the cultural hubs of Lenox, Williamstown, and North Adams. Privately located with access to everything.

This recently renovated 1890 Colonial offers four bedrooms and two full bathrooms on 38 private acres in Otis. The home features a wood-burning fireplace, updated kitchen and bathrooms, and a first-floor bedroom addition with vaulted ceilings. It is connected to town sewer and has a private well. A detached garage and several outbuildings provide extra space for storage or projects. This home awaits your finishing touches. The property combines historic character with modern updates and plenty of outdoor space for year-round or seasonal living.

Lenox in-town condo.....ready for a new owner, need a close location to Tanglewood, Shakespeare and Company, The Mount, Venfort Hall, Kennedy Park, Pleasant Valley Wildlife Sanctuary? Well this is the perfect location! 2 bedrooms, 1 full bath, wood floors and carpeted bedrooms, great light, fully applianced kitchen. Easy to show!

OWN THE ENTIRE NORTH SHORE OF a 10 ACRE POND. Tucked into the quiet SE corner of the Berkshires, this is a property where the pace of the world seems to slow. 21.3 acres in all, with nearly the entire north shore of Ida Pond—and actual ownership of the pond, historically known as Morley Swamp Reservoir, a tributary of the Buck River that flows to West Lake in Sandisfield State Forest. With approx. 1,200 feet of shoreline, mature woods, colonial-era stone walls, and deeded rights for quiet recreation—no motorboats permitted—this land offers profound privacy and connection to nature. A place to walk alone to the water at sunrise, where the world feels untouched. Just 7 minutes to Monterey, 20 to Great Barrington. A legacy property for those who value peace, nature and possibility. Tucked into the quiet southeast corner of the Berkshires, this is a property where the pace of the world seems to slow. A rare and elemental beauty: 21.3 acres in all, with nearly the entire north shore of Ida Pond, and actual ownership of the 10-acre waterbody historically known as Morley Swamp Reservoir, a tributary of the Buck River that flows to West Lake in Sandisfield State Forest. With approx. 1,200 feet of shoreline, mature woods, colonial-era stone walls, and deeded rights for quiet recreation, no motorboats permitted, this land offers profound privacy and connection to nature. A place to walk alone to the water at sunrise, where the world feels untouched. Build, preserve, or hold. Just 7 minutes to Monterey, 20 to Great Barrington. A legacy property for those who value peace, nature, and possibility.

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.

High on a hilltop in the Southern Berkshires stands East Hill Farm. 227 cultivated acres encompassing pristine forest, a spring-fed pond, a striking barn, verdant pastures, formal and vegetable gardens, a pool, and a tennis court. The centerpiece: a 1798 Georgian home, 5,000 SF with 5 bedrooms. Ready for private living, entertaining, horses, farming, a bespoke destination, or simply: tranquility. Includes a reimagined 6,000+ SF guest house, once an Arabian horse barn. 2½ hours to both NYC & Boston, yet a world apart. East Hill Farm offers what money rarely can buy: authenticity at scale. A 227 year-old house expanded, refined for 21st century life. Land, privacy, history, and a place of peace, which has endured through every chapter of American history. The next chapter begins with you. Reach out! Where The World Falls Away--227 acres. 227 years. One extraordinary hilltop farm. Drive up East Hill Road through Southfield village, past the store, climbing toward the top of Woodruff Mountain. The dirt road is well-maintained and lightly traveled. Sugar maples line your approach--massive, ancient trees that have watched over this land since before the house was built. Behind them, set back from the road, stands the kind of barn that makes photographers stop their cars. Three and a half stories of hand-hewn timber, painted proper New England red, moved here piece by piece from Amherst, Massachusetts, because the sellers understood that a farm needs a real barn. Not a replica. The real thing. The House Stops Your Heart--Federal period, 1798, when John Adams was president. This wasn't just another farmhouse. When Thomas Shepard commissioned John Collar to build this, he was making a statement. 8 rooms. 5 fireplaces. Ceilings higher than any farmer needed. Those distinctive 12-over-12 windows with hand-blown glass that turns the morning light liquid. A facade with sidelight windows and dentil cornice that announced to every traveler: here lives a person of substance. Walk through that front door and the wide center hall opens before you. Original wide-plank floors--King's boards, they called them, because timber this wide was supposed to be reserved for the Royal Navy's masts. Twin parlors flank the entrance, flooded with southern light. To your left, the original keeping room, now the dining room, where that massive cooking fireplace with its beehive oven still works perfectly after 227 years. The draft in these fireplaces is extraordinary. The woodwork throughout is original or crafted by hand precisely to match. Chair rails, wainscoting, built-in china cabinets with their original hardware. Those small cupboards tucked around the chimneys--John Collar's signature touch. Five Families in 227 Years--Jesse Hartwell married Thomas Shepard's niece and turned the house into a meeting place for progressive thinkers, and through the 19th century, the Hartwell family made this their home. Then came the Arabian horse breeders in the 1930s who added the newer rear ell and built what's now the guest house. The current sellers bought the house and five acres in 1969, then spent the next five decades not just restoring but thoughtfully expanding it. You'll be only the fifth resident to call East Hill Farm home--and despite its National Register status, free to shape its future as you see fit. That newer section? Radiant heat underfoot, a proper mudroom with laundry, a family room or perfect home office with its own kitchen, and an elevator up to a sun-filled library with built-in shelves and an ensuite bedroom and bath. A luminous sunroom framing year-round sunsets, with sweeping views across the formal gardens, horse pastures, and the shimmering pond below. Upstairs in the original part of the house, an additional four bedrooms, each with its own character. The canopy bedroom with its blue and white toile--that's not staging, that's how the family lives. Wide hallways, deep closets, and in that large upstairs hall above the front door, a perfect spot to sit and read while gazing out the neoclassical window over your barn, fields and forest, mountains in the distance. 5 full and 1 half baths in all--some original 1930s with their good bones, others from the 1980s restoration. The kitchen? Also 1980s, completely functional with good counter space, and a working wood-fired stove alongside modern appliances. Morning light streams in from the east, and sunset views are to the west, opening onto fieldstone patios on either side. Everything works: oil heat from a Viessman German boiler, cedar shake roof (much replaced in 2021), private well water so good they've bottled it up for guests, backup generator, fiber internet. The bones are so good and the mechanicals so solid that you can move in tomorrow or update to your taste--the house won't fight you either way. 227 Acres: A Complete World--East Hill Farm is more than the sum of its parts. From the original five-acre homestead, the current owners lovingly reunited land to create the breathtaking 227-acre estate it is today. 154 acres stretching across the north side of East Hill Road, and 73 tranquil acres to the south. To the north, a substantial portion of the property borders Sandisfield State Forest and thousands of acres of protected land. To the south, you have a section along Hotchkiss Road that is part of the New Marlborough Land Trust. Each acre is part of a dream fulfilled, a landscape that invites endless exploration and inspiration. Walk west from the kitchen patio between the formal gardens. Brick paths wind through perennial beds: heritage roses, peonies, iris. A long row of prolific blueberry bushes. In the vegetable garden, established asparagus and rhubarb come back stronger every year. Passing that perfect garden shed with its slate roof, as mist rises off the pond, becomes part of your morning coffee stroll. The pond--almost four acres, brook-fed, crystal clear. The family created it, and for decades it's been their private swimming hole, sailing spot, fishing paradise. Circle the pond and you'll find the big fishing rock on the west side, the perfect swimming spot on the east. Or head into the forest. Miles of trails, including a loop road that connects to Sandisfield State Forest. In spring, Lee Brook, the largest of several on the farm, roars with snowmelt. Up where the brook crosses the trail, it forms a waterfall after a hard rain. These are the headwaters of the Whiting River, and you own it. This isn't just acreage - it's a complete ecosystem. Meadows, forests, water, gardens, pastures, each flowing naturally into the next. Built for Whatever You Dream--That magnificent barn across the country road--3,550 SF on a full stone foundation, electricity, running water, lower level for equipment, main floor with stalls and work rooms, massive hay loft. Four pastures with water sources, run-in barns with power and water, and additional smaller outbuildings. The infrastructure is thoughtfully designed, whether your dreams include horses, alpacas, heritage sheep, a flourishing market garden, an orchard, festive celebrations, a tranquil retreat center, or simply savoring the seasons as they change across your land. The guest house tells its own story. Built as stables for those 1930s Arabians, it's now 6,668 SF divided into four independent residences, with cathedral ceilings and fireplaces. Some would use this for multi-generational living. Others might see a writers' or artists' retreat, a wedding venue, or wellness center. The bones are spectacular--soaring spaces and abundant light. Morning swims in the sparkling gunite pool with its serene fieldstone waterfall. Afternoons spent on the newly resurfaced tennis court. Evenings wandering down to the pond, soaking in the tranquility. Or embrace the rhythm of nature: January mornings breaking ice on water troughs, February afternoons tapping maples for syrup, and March evenings tending seedlings in the greenhouse, dreaming of summer tomatoes. The possibilities are manifold; life on East Hill Farm is generous and abundant. History You Can Touch--Walk these 227 acres and feel it: the weight of continuity. Five families in 227 years. Thomas Shepard, who helped found New Marlborough. The Hartwells, who held it for a century. Arabian horse breeders who landed their plane in the pasture. The current family, who pieced the scattered acres back together, whose daughters gathered eggs, boiled sap into syrup, grew the gardens that still bloom today. Some things do endure. That which matters can be preserved. In a disposable world, permanence is possible. The next chapter begins with you. The Berkshire Life, Perfected--Twenty minutes to Great Barrington's restaurants and shops. Less than ten to the Southfield Store. Tanglewood for summer concerts, Jacob's Pillow for dance, Butternut for winter skiing. Bradley Airport an hour away, Manhattan and Boston each two and a half hours. But honestly? Once you're here, leaving becomes the hard part. Mornings at East Hill Farm start with the mourning doves' lullaby that sounds like memory itself. The Sandhill Cranes return each spring to the lower pastures, their distinctive call announcing another season. Summer evenings, you'll sit on the west porch watching the sunset over your pond while fireflies rise from the meadows, and emerge from the woods. Winter nights, you'll build fires in those perfect fireplaces and be grateful they built that beehive oven so large. Everything here has been cared for with a deep knowledge of history and respect for nature and tradition. The heritage roses still bloom. The stone walls still stand true. The forest trails lead to hidden waterfalls and forgotten cellar holes. The gardens produce abundance. The pastures are ready to graze horses. Or you could simply walk your 227 acres knowing that in a world of constant change, you've found something real, something lasting, something irreplaceable. At $5.8 million, East Hill Farm offers what money rarely can buy: authenticity at scale. A genuine 18th-century house that works for 21st-century life. Land enough that you own your own hilltop. Buildings that tell the story of America. Privacy without isolation. History without the museum ropes. And beyond price, a place of profound peace that has endured through every chapter of American history, a hilltop sanctuary. Wake each morning in that otherworldly, untouchable tranquility that settles over the hilltop, where the rest of the world falls away, to watch the sun set where generations have watched it set, to be part of something larger than yourself, while making it entirely your own. 227 acres. 227 years. Some things are meant to be. Come see.