luxury real estate for sale Great Barrington, 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.

Modern comfort meets timeless New England farmhouse charm in this beautifully maintained 3BR/2BA home on 3.2 peaceful acres in Egremont. Filled with natural light, the open-plan kitchen, dining and living spaces feature hardwood floors throughout, updated kitchen and baths, and a warm, inviting flow ideal for everyday living or weekend retreat. Enjoy a spacious primary suite with en suite bath, family room with wood-burning fireplace, full covered front porch, oversized attached 2-car garage, and a large dry basement ready for expansion. Bucolic setting on a quiet country road just minutes to Great Barrington, with exceptionally low Egremont taxes

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.

Majestic 71 acre Tudor Estate atop Tom Ball Mountain in the quaint hamlet of Alford, MA. Enjoy total privacy and breathtaking views from nearly every room. The main house features 5 en-suite bedrooms, a gourmet kitchen, formal living and dining rooms, den, family room, gym, billiard room and massage room. A separate 2-bedroom guest house offers beamed ceilings and full amenities. Manicured grounds include an infinity pool, hot tub, pool house with full bath, tennis and pickleball courts, 7 garage bays, and a barn. State-of-the-art lighting, whole-house generator, smart tech, and security. Fully furnished and ready to enjoy.

Discover a rare blend of modern functionality and classic charm in this meticulously-maintained Cape, ideally situated on over 3.5 private acres in the sought-after, low-tax town of Egremont. With a serene woodland backdrop, this bright and airy home offers an elevated living experience with open-concept flow and seamless indoor-outdoor integration. Thoughtfully designed with wheelchair accessibility at the forefront, this home features expansive, light-filled spaces including a chef's kitchen and open dining area, and a screened porch. Beyond the main living quarters, the lower level hosts a versatile apartment, perfect for guests or multi-generational living. Just moments from French Park and the cultural heartbeat of Berkshire County, this 4-bed, 3-bath home provides a private sanctuary without sacrificing proximity to the region's premier attractions.

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.

Renovated modern country retreat near Prospect Lake and Catamount Mountain Ski Resort. This stylish home blends contemporary comfort with natural surroundings. The open living and dining room features a wood-burning fireplace, while the eat-in kitchen boasts high-end appliances, stone countertops and laundry. Two bedrooms and two full baths provide comfortable accommodations. The primary suite offers a brand-new full bath and walk-in closet. Glass doors open to a spacious deck overlooking the private backyard and gentle stream--ideal for morning coffee or evening relaxation. Additional highlights include a detached garage, garden shed, efficient heating and central A/C. New roofs on both the house and shed ensure peace of mind. Available fully furnished and equipped for turnkey enjoyment.

Exquisite private Tudor-style stucco estate set on more than 18 breathtaking acres with panoramic views and a winding approach that creates an extraordinary sense of arrival. Bright, airy, and thoughtfully designed, this 5-bedroom, 5-bath residence blends timeless architecture with modern comfort and exceptional indoor-outdoor living. The heart of the home is a stunning great room featuring soaring ceilings, a majestic fireplace, abundant natural light, and hardwood floors throughout. An open-concept layout flows seamlessly into the generous chef's kitchen, complete with a professional-grade gas range, spacious dining area, and direct access to the expansive deck overlooking the rolling landscape. The main-level primary suite offers privacy and convenience with a spacious bath and serene views. Upstairs, a second-floor family room overlooks the great room below and is complemented by two additional en suite bedrooms. A separate guest suite includes its own bedroom, bath, and workout area, ideal for visitors or extended stays. Additional highlights include a sunroom, seasonal screened porch, custom-built freshwater swimming pond, and a full walk-out basement ready to be finished for additional living space. Enjoy deeded rights to Prospect Lake, just minutes from downtown Great Barrington, all while benefiting from low Egremont property taxes.

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.

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 to Foxleigh Estate, a designer residence perched high on over 14 private acres on a quiet dead-end road in prime Hillsdale, with sweeping Catskill and Berkshire Mountain views. A long, pea gravel drive framed by stone walls leads to this 3,666-square-foot, four-bedroom, three-bath residence that has been transformed through a full designer renovation. A new heated saltwater gunite pool and spa sanctuary with a sauna, hot tub, and cold plunge are positioned to capture breathtaking views, completing a property that sets a new standard for country living at the border of the Hudson Valley and the Berkshires. This luxurious home was built for entertaining and unwinding, just minutes to skiing and hiking, with easy access to both Hudson and Great Barrington.The home's character is clear from the threshold: a new Dutch door finished in high lacquer opens into interiors where every detail has been considered. Walls dressed in grass weave wallcovering, Hudson Company reclaimed white oak floors, and custom lighting create an ambiance of quiet luxury. The living room is warmed by a wood-burning fireplace and flows directly onto a new bluestone patio and cedar-fenced outdoor entertaining terrace. Off the kitchen, a sunny dining room has walls of windows offering panoramic views, with French doors that lead to the patio. A refined library with custom built-in cabinetry offers a quiet retreat for work or contemplation.The kitchen anchors the home. Calacatta marble countertops and a double-width farmhouse sink with high-end fixtures set the tone, while a Wolf range beneath a custom stucco hood with Waterworks tile backsplash brings professional-grade performance to the space. Paneled appliances, including a Liebherr refrigerator and Miele dishwasher, sit alongside a wine fridge and custom built-in cabinetry, creating a kitchen equally suited to a quiet weekday morning and a large dinner party. A built-in bar station with wine cooler and ice maker serves the adjacent dining area. The primary suite features a Juliet porch capturing the mountain views, a custom dressing room, and a spa-caliber bathroom with freestanding tub and walk-in shower. Two additional bedrooms feature custom millwork, and a snug room with built-in bed offers additional sleeping space. A custom mudroom with bench and closet, a laundry room with LG washer and dryer, and retractable screen doors round out the interior.The grounds, designed by Wagner Hodgson, include a heated gunite saltwater pool surrounded by stone walls and fencing, with pea gravel paths and stone steps connecting to the broader landscape. A spa sanctuary set into the woods features a WiFi-enabled sauna, a gunite hot tub and cold plunge with app controls, and custom ipe decking, creating a resort-quality wellness retreat. A built-in Lynx Sedona grill connected to the house gas line, a new ipe deck, a cedar outdoor shower, and a remotely controlled irrigation system for garden beds complete the outdoors. A serene pond adds to the property's natural character, and old-growth trees line the quiet road that borders the estate.The lower level gym with direct outdoor access overlooks the pond through a wall of glass, and is equipped with a Pilates reformer and treadmill. Infrastructure upgrades include a new well pump, hot water tank, and water filtration system, a 22KW Generac generator, a 1,000-gallon in-ground propane tank capable of powering the home for up to a week, new HVAC upstairs, and a new front portico at the main entrance. Interiors and architectural updates by celebrated designer Louise Copeland of L.B. Copeland, including a reconfigured floor plan, new kitchen, flooring, lighting, and front portico. Offered with the option to purchase furnished. At this level of design, setting, and privacy, Foxleigh Estate is without peer in the region.

Imagine never tiring of your own backyard. Nestled on one of the prettiest roads in Hillsdale, this beautiful single-level home is a front-row seat to rolling meadows, distant hills, and the quiet magic of the changing seasons. This sun-drenched, single-level home offers an effortless lifestyle framed by stunning, panoramic views. Inside, an expansive open floor plan invites the outside in. The thoughtfully appointed, updated kitchen flows seamlessly into a generous living area anchored by custom built-ins and a cozy wood-burning fireplace. Wall-to-wall windows grace the formal dining room, ensuring every meal is accompanied by breathtaking scenery. Both the living and dining rooms offer direct access to a sprawling rear deck, perfect for entertaining. A tranquil sun-room provides a versatile space, ideal for a home office or a quiet retreat. Down a private hall, the sleeping wing awaits. The primary suite is a true haven, featuring a second fireplace, a charming window seat for reading, a large walk-in closet, and an en-suite bath. Two additional well-proportioned bedrooms with ample closet space share a pristine hall bathroom. A generous two-car attached garage and a full basement offer abundant storage and convenience right off the main entry.Outside, the 8.3-acre grounds are a serene blend of manicured lawn, wild meadow, and mature plantings. The location is truly stellar: less than five minutes to Catamount Mountain Resort for year-round adventure, and just moments from

Lots of preparation work went into this building lot with a handsome meadow and dramatic ledge formations with large pockets of cool ferns. Some western views and a north east field stone wall. Almost 2 acres. Old well in place. Excellent percolation test results with 1 inch per min. Curb cut. Ready to build.

Welcome to a newly built modern farmhouse estate set on 11.7 private acres in the heart of Hillsdale. Arriving via a sweeping driveway, rolling lawns unfold into cultivated fields and far-reaching pastoral and mountain views in every direction. Designed for indoor-outdoor living, this 4-bedroom, 4-bath residence blends modern architecture with the warmth and ease of Hudson Valley living. Clean architectural lines are softened by natural materials, soaring vaulted ceilings, and expansive walls of glass that fill the home with changing light throughout the day. At the center of the home, the dramatic great room rises to a 20-foot vaulted ceiling anchored by a wood-burning fireplace clad in earthy, chestnut-toned marble. Large Arcadia custom glass doors open seamlessly to over 540 square feet of covered outdoor living space, creating an effortless connection between indoors and out—ideal for entertaining, quiet mornings, or long sunset evenings overlooking the landscape. The kitchen was designed as both a gathering space and a functional centerpiece, featuring custom walnut cabinetry handcrafted by a Brooklyn cabinetmaker, integrated Fisher & Paykel and Bosch appliances, an oversized monolithic island, and a 48-inch double-oven gas range. A generous butler’s pantry and bar area adds additional prep space, storage, a second dishwasher, prep sink, and microwave drawer—allowing the main kitchen to remain clean, open, and entertaining-ready. The primary suite is a private retreat with vaulted ceilings, a custom dressing room, and a spa-like bath finished in dramatic Calacatta Violetta marble with soaking tub, oversized shower, and fluted glass steel-framed doors. Upstairs, a second primary suite offers a walk-in closet and marble-appointed bath, alongside an additional en-suite bedroom. A versatile fourth bedroom on the main level offers flexibility as a guest suite, office, wellness room, or media space with direct patio access. Thoughtfully engineered for high-performance living, the home features spray foam insulation, high-performance windows, forced-air heating and central air conditioning, on-demand hot water, Lutron lighting controls, remote-access thermostats, generator hookup readiness, and a heated detached 26x26 two-car garage. Just minutes from Catamount Mountain Resort and the Hamlet of Hillsdale, and within easy reach of Great Barrington and Hudson, the property offers a rare combination of architectural refinement, rural privacy, and access to the Hudson Valley and Berkshires’ celebrated farm-to-table dining, local markets, cultural destinations, and year-round recreation. A modern farmhouse of quiet confidence, architectural clarity, and elevated rural living. (listing agent has a financial interest in the property)

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.

Discover a truly singular retreat: a 1,700-square-foot, octagonal contemporary barn residence designed and built by a noted architectural designer. Set deep within more than four acres of pristine woodlands on one of Columbia County’s most coveted roads, this home offers the rare combination of modern architecture, privacy, and effortless living. Expansive pivoting picture windows invite a constant play of light throughout the interior and frame the surrounding landscape as living art. Inside, the soaring cupola-topped ceiling and radiant-heated polished-concrete floors create a calming, loft-like atmosphere, anchored by a dramatic floating propane fireplace. The designer kitchen integrates seamlessly into the open living and dining spaces, making the home equally suited for quiet evenings or stylish entertaining. Two airy, loft-style sleeping areas, and two sleek glass-and-steel baths complete the thoughtfully curated layout. Every element of the home blends sophistication with simplicity—ideal for a buyer who values design, nature, and ease. Tucked away yet minutes from Hillsdale, Hudson, Egremont, and Great Barrington, the location offers instant access to the region’s best culture, dining, and outdoor recreation. With NYC and Boston a little over 2 hours away, this property is the perfect full-time escape or effortlessly luxurious weekend base. A rare architectural and design statement, this steel-and-glass modern barn redefines country living for the buyer seeking something truly unique. Plans are available for a one or two bedroom addition.

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.

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.