luxury house with terrace for sale Sheffield, United States

Hidden off a private Egremont drive, this Adirondack retreat is crafted for quiet mountain living. Soaring cathedral ceilings elevate the main floor, centered by a freestanding hearth that warms the open layout. An intimate loft bedroom perches above, while the finished walk-out lower level offers flexible bonus space suited for a media room, home office, or guest overflow--including two finished rooms currently utilized for sleeping (note: larger egress windows needed for official bedroom status). Outside, the large screened porch creates a secluded open-air lounge in total privacy. A South County haven minutes from downtown dining, cultural hubs, and Catamount Skiing and recreation.

Versatile mixed-use property pairing a sophisticated second-floor apartment with a flexible first-floor residence that doubles as an ideal commercial or gallery space. Overlooking a tranquil year-round brook and a private backyard, the offering sits right downtown Egremont and includes the convenience of an ample garage. | Property Highlights | Second-Floor Apartment: Sophisticated, charming living quarters featuring high-quality finishes, total privacy, and serene views of the brook and grounds. First-Floor Mixed-Use Space: Currently configured as a comfortable residential apartment while offering incredible potential for an art gallery, retail boutique, or commercial enterprise. Ample Garage: Generous garage space providing excellent storage, parking, or workshop potential. Exceptional Septic Infrastructure: Robustly engineered system designed to service a 35-seat restaurant. First floor has been a restaurant, bookshop, and now a residence.

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.

Tucked away at the end of a private cul-de-sac on 1.22 acres, this 4-bedroom, 4-bathroom contemporary home delivers sophisticated Berkshire living just minutes from downtown Great Barrington. Offering the perfect footprint for full-time remote professionals, weekend escapees, or downsizers, this property pairs a spacious layout with the effortless lifestyle of a premier community association. The heart of the home is a dramatic, light-filled great room anchored by soaring cathedral ceilings and a brick fireplace paired with charming built-ins. The main level is designed for entertainment and ease, featuring a lavish first-floor primary suite with walk-in closets and a spacious ensuite bath. Upstairs, three additional guest bedrooms are complemented by a private, separate bonus studio above the den--offering an ideal, quiet space for an executive home office or fitness room. Outdoor living is built for relaxation, featuring an expansive wrap-around deck with scenic views, a stone patio, and a spectacular 3-season screened porch overlooking mature perennial gardens. Modern mechanicals include central air and a full backup generator system for ultimate peace of mind. As a resident of this coveted neighborhood, you'll enjoy exclusive access to the heated community pool. Simply lock up, leave, and enjoy nearby Tanglewood, local ski mountains, and Main Street dining.

The Cub House Located in the coveted Twin Lakes area of Salisbury, The Cub House is all about possibility. Set on nearly six acres along a quiet gravel road, this property offers an ideal address, beautiful natural surroundings, and the chance to either improve the existing It features a functional layout with a comfortable kitchen that opens into a large living and dining room with a fireplace. The primary has an ensuite bath and the second bedroom and hall bath complete the main floor. There is also a covered porch and an open deck. The lower level has an additional semi-finished room, plus ample storage, laundry and a garage. The home offers a solid foundation for updates. Whether you're looking to modernize the existing structure, create a custom country getaway, or expand your footprint on the generous acreage, the possibilities are endless. Enjoy total seclusion surrounded by nature, while still being just minutes from lake recreation and town conveniences. Bring your contractor and your design ideas. Properties with this much land and privacy in this location do not come along often! Imagine crisp mornings on your porch, afternoons on the water, and evening walks in this coveted lake community. Dive into lake life, and never look back. Offered as-is.

OUTSTANDING COUNTY 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 contemporary features an open floor plan with 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. Move in ready! With a relatively low inventory level, particularly in Monterey, this listing is a rare gem.

This beautiful modern farmhouse in the Twin Lakes community enjoys shared access on Lake Washinee. The home's minimalist design melds simplicity with sophistication. First floor en-suite bedroom, light filled rooms all have seamless vantage points to take in the natural beauty of the out-of-doors. Fresh timbered beams, two story windows, solid white oak floors, solid hemlock & mahogany doors, Carrara countertops, just some of the finishing's. Energy efficient building standards in a new home and an energy savings HVAC system provide for lower energy costs. Whether entertaining or the desire for quietude there are spaces to accommodate everyone's needs..an Adirondack room off the kitchen, an intimate patio setting off the dining room, huge deck off the great room.The lower level has a delightful entertainment room with fireplace & walk out to a large patio with swing chairs & hammock, a nudge to relax. The great room has a 28ft ceiling, stone surround wood-burning fireplace and a ton of ambiance. Paneled walls and a gas fireplace in the library/bedroom add a a level of comfort and warmth. The primary bedroom has a beautiful ensuite bath. Open the double doors to its charming balcony, sun rays & soft breezes. Private schools, train, hospital, shopping, all within minutes. Hiking and biking trails, kayak, play and fish in our many lakes, rivers and streams. Less than 2 hrs & 1.25 hrs to NYC and Bradley Int airports respectively.

Exceptional design and craftsmanship distinguish this stunning home. The single-level interior is warm, sophisticated and filled with natural light, with the kitchen, dining and living areas flowing together in one open space surrounded by specialty windows and French doors. Set on four private acres amid the highest peaks in South County, the home offers immediate access to premier hiking and protected lands. Locally sourced Massachusetts walnut floors, Scavolini cabinetry, Miele and Sub-Zero appliances, extensive custom woodwork, shoji-inspired glass sliding doors, and a dramatic stone fireplace wall speak to the quality and attention to detail throughout. A two-sided gas fireplace connects the living room and primary bedroom, which features rich woodwork and an en-suite bath with an oversized walk-in shower. Two additional bedrooms share a second full bath with a soaking tub. Downstairs, a large heated recreation room provides flexible additional space. A wraparound deck and screened porch extend the living space outdoors. Just beyond, a stream babbles year-round, and a private trail leads out from the home. An oversized heated two-car garage, radiant heat, central air, a whole-house generator and fiber internet add comfort and convenience, including the ability to work easily from home. The Appalachian Trail, Mount Everett, Bash Bish Falls and Alander Mountain are all nearby, with miles of protected land and exceptional hiking just outside the door. Quiet roads, spectacular dark skies and Mount Washington's low property taxes add to the appeal, while Great Barrington and New York City remain within easy reach.

Tucked away on a peaceful private drive, this custom Craftsman home (built 2022) combines timeless architectural character with effortless modern living. Designed with accessibility and everyday ease in mind, the main level features zero-step entry and true single-level functionality. At the heart of the home is a bright, spacious cook's kitchen that flows seamlessly into welcoming living spaces. Outdoor living shines with both a classic front porch to take in quiet sunsets and a stunning screened porch designed for bug-free Berkshire evenings. The versatile 4-bedroom layout features a private primary suite alongside an attached in-law apartment-ideal for multigenerational living, long-term guests, or rental potential. A dedicated home office makes remote work a breeze, while an upper-level bonus room easily transforms into a serene yoga studio, creative workspace, or media lounge. Included is an oversized 3 bay garage and a whole home generator for ease and comfort. Pristine modern construction in an unbeatable Egremont location, just minutes to Great Barrington dining, Catamount skiing, and a trailhead just steps from your door.

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.

Charming in-town Cape on a spacious lot with inground pool. Located in a delightful neighborhood close to town, this inviting home built in 1951 offers 5 bedrooms and 2 full baths. Inside, the residence seamlessly balances ample room to spread out with warm, light-filled spaces tailored for everyday living and entertaining. Timeless architectural details throughout bring character and charm, including a wood-burning fireplace, graceful arched doorways, and custom built-in cabinetry. Outdoors, a private in-ground pool is set within a large, sunny yard, creating a wonderful oasis. Turn-key peace of mind is provided by recent upgrades, including a newer furnace, water heater, and pool filter. Town water, town sewer, and natural gas from the street. Close to everything; a must see!

Welcome to Meadow Wood This elegant property on a secluded reach of the Green River epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lily pond, terraces, pastoral views, and privacy. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage w/ potting room and a studio space. The Gunite pool is surrounded by an espaliered apple tree fence & generous stone terrace. The large screened pool house includes 1/2 bath, outdoor shower, kitchenette & massive fireplace. Further from the house is the barn complex consisting of a 2 bedroom apartment with yard & patio, separate studio apartment and 4 garage bays, a barn, and cutting gardens. The custom home, built by one of the region's premiere builders, has been featured in design magazines, garden tours & has received a Garden Club of America award for its ethos & thoughtful use of building materials. The house was constructed using sustainable & recycled low maintenance building materials designed to last a lifetime. Hidden from the road, the main house is approached by a long drive lined with mature Scarlet Oaks & daffodils. A courtyard filled with specimen crabapple trees, stone walls & walkways creates the welcome entry to this 1 level home. The exterior walls are planted w/ climbing hydrangea that blur the lines between structure & nature-a common motif throughout the property. The setting is both well designed and peaceful. The grand entry foyer sets the tone for the house. It connects to an enfilade of rooms filled w/ southern sun that run the length of the house.Large windows and french doors that welcome both the light and warmth from the sun on a winter's day & open to exterior terraces in the fair months. All the rooms have extensive garden & pastoral views. The east side of the entry is the living room with high, coffered ceilings & a fireplace made with grand tour columns. Adjacent to the living room is the primary suite w/ doors to a private terrace, shower, & lawn. The velvet covered walls create perfect silence, a jewel box of a room. Dual bathrooms and closet areas w/ steam shower & large soaking tub with views complete the suite. West of the entry hall is the large eat-in kitchen w/ coveted AGA range. The doors open onto a patio with lily pond, field views, & cherry trees. The kitchen/service area includes a butler's pantry, & mudroom. The far west end of the house, with perfect evening light, has a cozy sitting room. Adjacent to this is an office/library spaces, another library is located between the guest room and the larger office/sitting room. Both library areas have custom floor to ceiling bookshelves. The larger office has french doors that open to a private and romantic courtyard garden w/ espaliered peach trees & blooms to attract pollinators. Western windows have views of a fenced field and plantings. Majestically on a small rise, is the Parthenon-like pool house, a focal point of the outdoor areas. The adjacent heated Gunite pool is a place of refuge and serenity. Step into a world of enchantment and be transported to a realm of natural beauty and tranquility. The intimate spaces and thoughtfully curated common areas throughout the property create an environment that is as classic and timeless as it is fun and whimsical. It is truly a home that seamlessly integrates its beautiful interior with the curated natural beauty and tranquility. The intimate spaces & thoughtfully curated common areas throughout the property create an that is as classic and timeless as it is fun and whimsical. It is truly a home that seamlessly integrates its beautiful interior with the curated natural beauty that surrounds it.

This 70s Modern home has been revamped to a 21st century Contemporary. Perfectly situated between the spectacular east and west lakes in the Twin Lakes region of Salisbury, it's an easy walk to the lake to enjoy part ownership of the beach/lake access point, or relax in the back yard by the pool, relishing in the privacy and beauty of your surroundings. The upper level features an open floor plan with vaulted ceilings, lots of light, and wood beams. Walk out right onto the expansive deck, or enjoy the private balcony off the Master bedroom suite. The lower level has two additional bedrooms, an office, a full bath, a laundry area, and a central family room. Other features include a whole house generator, an owned solar electric system, mini-splits for climate control (heat & AC), and professionally maintained grounds. This is a clean, well kept home and property in the middle of a lake community in one of the most desirable areas in the Berkshires. Close to Salisbury, Hotchkiss, Berkshire, and Indian Mountain schools, and less than 30 minutes to the Wassaic train station.

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.

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.

Tucked away on five private acres in Monterey, this singular handcrafted Berkshire cottage feels as though it emerged from a storybook. Natural-edge wood siding, steep rooflines, a massive fieldstone chimney and a tower-like upper level rise from a landscape of hydrangeas, woodland and a grape-covered arbor. Inside, the house is an irresistible mix of rustic character and thoughtful updates. Original wood floors, reclaimed hand-hewn beams, paneled walls, arched doors and unexpected architectural details give each room its own identity. The dramatic great room is the heart of the house, where soaring volume, exposed beams, richly paneled walls and an immense fieldstone fireplace create a space that feels far removed from everyday life. French doors open to a stone patio, while an open staircase rises through the room to the upper level, adding to the home's storybook quality. A sun-filled pink living room offers a dreamy contrast - soft, light-filled and wrapped in windows overlooking the hydrangeas and surrounding woods. A pleasing counterpoint to the darker, more rustic great room, it is an inviting place to read, relax or gather. A remodeled kitchen combines form and function, with white cabinetry, stone counters, a farmhouse sink, center island and a stunning commercial-style range beneath a stainless-steel hood. The adjoining dining room creates an easy flow for entertaining. Four bedrooms are arranged in two separate wings, offering privacy and flexibility. The south wing begins with a first-floor bedroom and bath, continues upstairs to a second bedroom with a newly added bath, and culminates in a third-floor office tucked beneath the peaked roof. On the opposite side of the house, in the north wing, two additional bedrooms each enjoy their own bath. Thoughtful bathroom updates, including the addition of the upstairs bath, bring modern comfort while remaining true to the character of the home. The story continues outdoors. Hydrangeas spill across the front of the house, mature grapevines climb the arbor, and lawns fade into woods and wild garden areas. The west-facing hillside brings seasonal mountain views through the trees, along with places to dine outdoors, wander, garden or simply enjoy the quiet. Private and quietly tucked away, yet only about 15 minutes from Great Barrington, with access to Monterey's Lake Garfield town beach and close to the lakes, trails, and outdoor recreation that make this part of the Berkshires so appealing. Low Monterey taxes and high speed internet on site.

Enchanting Egremont! Positioned on a beautiful 5.3 acre lot in Egremont, this solidly built home offers a rare combination of privacy and accessibility. A tree lined driveway leads to this peaceful Berkshire retreat, conveniently located with quick access to the Taconic State Parkway. Inside, you'll find over 2,500 square feet of living space highlighted by a dramatic living and dining room featuring a soaring two-story ceiling, skylights, an interior balcony, and a wonderful wood-burning fireplace. The spacious kitchen is complemented by a separate breakfast room with slider access to the outdoors, offering an ideal setting for everyday dining and entertaining. The home offers three spacious bedrooms and two full bathrooms, along with a versatile first floor den that can easily serve as a home office, guest room, or potential fourth bedroom. All three bedrooms feature slider access to the rear deck, creating a seamless connection to the surrounding landscape. Generous closet space throughout adds to the home's functionality. Enjoy front and rear decks, a beautiful natural setting, and seasonal mountain views. The property provides exceptional privacy while remaining close to Great Barrington and the area's amenities, recreation, dining and cultural attractions. A rare opportunity to own a private Berkshire retreat in one of Southern Berkshire County's most desirable locations.

Set on over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire leisure. Inside, the home is thoughtfully designed to host both family and guests in complete comfort, offering five well-appointed bedrooms, six full bathrooms, and a half bath, providing privacy and ease for all. The first-floor primary suite serves as a true sanctuary, complete with two separate full bathrooms for an elevated sense of luxury. The main level of the home includes a generous living room, a formal dining room featuring a custom four-wall mural by noted (formerly local) artist Laurel Tewes, a cozy library or den, a well-appointed kitchen with three refrigeration units including a side-by-side Sub-Zero, two Miele dishwashers, a six-burner Viking range with double ovens, and two large pantries. There are two screened porches: one informal and accessible from the living room, and a larger one off the kitchen vestibule, currently used for outdoor dining. A guest powder room completes the main level. The second floor includes a second primary suite, along with three additional spacious guest bedrooms, each with its own private bathroom to ensure comfort and privacy for family and visitors alike. A well-equipped gym provides a dedicated space for fitness and wellness, while a large laundry room with two washers and dryers adds everyday convenience. A generous corner office, with windows facing east, south, and west, offers a quiet and functional workspace, complete with a dumbwaiter to easily transfer items between floors. The grounds are a nature lover's retreat, featuring a network of walking trails, including approximately half a mile of cut grass perimeter paths, and strategically located perennial gardens. A fenced backyard encloses roughly three-quarters of an acre, perfect for pets or recreation. Along the southern side of the home, a slightly elevated patio spans the kitchen, dining room, and living room, with direct access from French doors and a single kitchen entry. Part of the patio is shaded by mature, 20+ year-old wisteria growing over a trellis, while another section is covered by a motorized awning, creating an ideal setting for outdoor dining and entertaining. Throughout the home you will find six functioning fireplaces, wide-plank wood flooring, oversized windows, and exceptional craftsmanship in every detail. An oversized three-car garage adds functionality to the home's many luxury features. Ideally located just minutes from the vibrant center of Great Barrington, the property also offers quick and scenic back-road access to Taft Farm, Catamount, Tanglewood, and the surrounding cultural and recreational attractions that make the Berkshires so desirable. This is a rare opportunity to own a one of a kind estate in the region's most sought-after settings, where refined living meets timeless natural beauty.

Moments from Lake Mansfield and Main Street, this turnkey contemporary offers clean lines, natural light, and effortless Berkshire living. The main level features an open-concept floor plan anchored by a show-stopping Duvemåla tiled stove, serving as a striking centerpiece for gatherings and cozy evenings by the fire. Enjoy the convenience of a first-floor bedroom alongside one of the home's three well-appointed full baths. Upstairs, an expansive primary suite impresses with vast cathedral ceilings. The finished lower level adds a versatile bonus room, providing extra square footage for a home gym or game room. Outside, relax and entertain on the sun-soaked deck overlooking the oversized grounds of this rare double-sized parcel.

Welcome to NEWGRANGE, a grand 1920s Manor House capturing the golden age of lakeside country living. This historic estate echoes the effortless elegance of an early 20th-century summer retreat. Imagine hosting lavish gatherings in the formal dining room, or retiring by original, roaring stone fireplaces after a leisurely day on the water or the slopes. Encompassing over 10,000 sqft, the sprawling residence boasts ten spacious bedrooms, a classic country kitchen, and sweeping living areas. Stroll the 7.7-acre grounds--past the guest house, pond, and gardens originally designed by Frederick Law Olmsted--down to your private dock on Lake Garfield. Ideally located near Tanglewood and premier skiing, and low Monterey taxes, this Berkshire gem is a rare invitation to reclaim a masterpiece.

Welcome to Forest's Edge. Set along a quiet country road traveled only by those with a reason to be there, this 1950s farmhouse presents that rare, elusive balance: complete sanctuary without isolation. Following a comprehensive, top-to-bottom renovation in 2021, every surface has been lovingly reimagined with an emphasis on quiet luxury and timeless craft. Arrival begins along a classic peastone driveway edged in Belgian block. A deep, welcoming front porch sets the scene generously scaled for classic Adirondack chairs, crisp afternoon breezes, and effortless entertaining. Inside, the main floor unfolds with natural light with windows surrounding the space. The living room serves as a cozy anchor, centered around a focal stone fireplace with a convenient propane insert and flanked by windows that invite sunlight to stream through all day. Just beyond, the dining area catches lovely views of the side porch stretching toward the pool. The kitchen is a beautiful balance of form and function: custom-paneled appliances, elegant marble countertops, a center island with an integrated breakfast bar, and a six-burner Wolf range equipped with a griddle and double ovens. Completing the main level is a powder room and a flexible front office that could seamlessly transition into a mudroom or playroom. The second floor hosts three spacious bedrooms, a full bath, and a dedicated laundry room that makes daily routines feel entirely luxurious. The entire third floor is devoted to the primary retreat, elevated high in the treetops for ultimate privacy. This sanctuary includes an expansive walk-in closet-easily tailored as a quiet reading lounge or private office-and a spa-inspired bath complete with a walk-in shower and deep soaking tub. Outdoors, the landscape honors the property's natural contours. Professionally designed perennial beds weave around a dramatic rock formation, while hydrangeas dot the open lawn. Tucked discreetly away from the main house, a tranquil pool and sun deck offer the ultimate private retreat for warm summer afternoons. A seamless blend of character and modern convenience, where no detail was too small to consider, and no expense was spared. Proven academic year and summer rental income property.

There is no doubt that Copake Falls, NY is a sweet spot for the Upstate, located near the wild and wonderful New York and Massachusetts border and situated in the heart of the Bash Bish watershed in the Taconic range of mountains. This turn-key cottage enjoys the deepest level of privacy, reached through a private road that traverses uphill into some local altitude and coupled with seasonal views of ridge lines for which the area is famed. This Miller Brook Lane house features 3 bedrooms and 2 full bathrooms with the option to add another bath in the daylight finished basement with the plumbing already in place. The open floorpan upstairs is friendly to a dinner party with room for a dining table and a wood burning fireplace enhanced by a covered porch to extend the entertainment. Pick dinner sides from your raised garden and grill out of doors in complete serenity, high above the valley below. Take advantage of the cedar log construction; not only do these homes blend nicely with upstate forest scenery, the construction offers great natural insulation against cold winters, high resistance to rot and insects in humid areas, a pleasant wood scent, and a stable structure that settles well. Copake Falls is super convenient to both Hillsdale, NY, with its diners and breweries and groceries or head into Great Barrington for sushi and shopping at nearby Guidos grocery.

Set on just under six acres along one of Salisbury's most scenic roads, The Bunker Hill House is a true one-of-a-kind property. A seasonal haven for accomplished artists since its construction in the late 1970s, the three-bedroom, two-bathroom home is defined by imaginative architecture and thoughtful design. Originally constructed using repurposed metal Agway barns, the home itself is an expression of creativity. At its center, a light-filled entry way connects the home's two wings. Skylights overhead fill the space with natural light, while French doors open to a private dining porch nestled among seasonal gardens. The south facing wing is split between two levels. Downstairs, a welcoming living room features a custom bow window, wall-to-wall bookshelves, and a wood-burning fireplace. Upstairs, the primary suite offers its own fireplace and an ensuite full bathroom. The northern wing centers around a bright kitchen with high ceilings, an eat-in dining area, and a window bench. Beyond, the library is one of the home's defining spaces, with custom floor-to-ceiling bookshelves lining three walls and a large picture window overlooking the front gardens. Across the hall, an octagonal bedroom opens onto a private porch, while an adjoining office leads to the home's third bedroom. Rising above it all is the octagonal viewing tower, where expansive windows frame sweeping views of the gardens, surrounding hills, and distant mountain ranges. Outside, the landscape has been carefully cultivated over decades. A fenced-in garden with raised garden beds, fruit trees, fern groves, and established perennial gardens makes the property both beautiful and functional throughout the seasons. As a final expression of the property's playful and creative spirit, a staircase climbs to the summit of "The Big Rock," revealing a new point of view- in many ways, perhaps. Offering exceptional privacy just minutes from the center of Salisbury, the property is within walking distance of the Lion's Head Trail and provides easy access to the area's celebrated lakes, dining, and shopping. Equal parts home, retreat, and creative sanctuary, The Bunker Hill House is a special home in a special part of the world. Offered As-Is.

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!