luxury properties for sale Berkshire County, United States

Situated on one of the finest lots on the street, offering backyard privacy and distant mountain views, is this thoughtfully renovated Colonial-style home with an in-law suite. From the properties landscape and pool to the in-law suite addition, this owner has thought through every detail updating and making a more sustainable home for someone to enjoy for many years to come! The first floor of this center hall colonial includes a formal living room; formal dining room; eat-in kitchen with breakfast nook; and cozy den with new wood floors and slider to the screened porch. Off the kitchen, a new mudroom expansion with a laundry room connects to the in-law suite addition. The in-law suite with expansive views of the backyard boasts a large vaulted open room with a walk-in closet, full bathroom, radiant heated floors and mini-split air conditioning. The second floor features a large primary suite with walk-in closet and renovated bathroom with soaking tub and separate glass shower. Finishing out the second floor are three spacious bedrooms and a full bathroom. The lower-level accessible through the house or the garage, has been recently remodeled with a full bathroom added. Ample storage and space allows for a family room and separate storage/work space. Outside, an inground salt water pool is surrounded by sustainable landscaping perfect for pollinators and bird watching. Recent updates on this 5-bedroom, 5 bathroom home include a new roof and windows (2021), in-law addition (2022), heating system (2022), exterior painted (2022), screen porch addition (2022), owned solar system (2023), pool salt water filtration system (2023), A/C split system (2024), remodeled basement with full bathroom (2023), and new garage doors (2022). Do not miss out on this spectacular home!

Sited on a large lot on one of the loveliest streets in Pittsfield, this gracious, one of a kind home exemplifies classic elegance and sophistication. Step into the grand main hallway with impressive staircase, soaring ceilings, ornate crown moulding and exquisite hardwood flooring throughout.The main floor with generous rooms is perfect for large gatherings with formal dining room, an expansive living room with a fireplace with carved wood mantel, a stunning kitchen with endless cabinets and counter space with professional range, two dishwashers and breakfast nook. Relax and take in the large back yard from the reimagined sun room and screened porch. Climb the majestic staircase to the dramatic second floor landing with 4 comfortable guest bedrooms and a wonderful primary bedroom with en suite bath. Convenient, private, close to all. Just a few minutes to Guidos, Berkshire Medical Center, Barrington Stage, downtown Lenox, etc.

Welcome to historic North Adams, where culture, charm, and character meet! Nestled just a stone's throw away from the renowned MASS MoCA art Museum, this 3-bedroom, 3-bathroom includes a primary suite with its own private bath, and sun porch. This must-see property includes new electric and plumbing throughout, you can enjoy peace of mind knowing that this historic beauty has been carefully updated for modern living. Original hardwood floors grace the spacious living areas, creating an inviting ambiance that's perfect for both relaxing evenings and lively gatherings.

Discover the charm of yesteryear with this enchanting 6-bedroom, 2-bathroom antique home nestled in the vibrant town of Lee. Accompanied by a large two-story stone barn, this residence offers a blend of historical elegance and modern potential. Original features such as wood floors, Dutch door, and classic stairway railing are complemented by a dining room with beamed ceilings, built-in china cabinets, and bay window with marble seat. Stained glass windows and pocket doors add to the home's unique character, while a marble fireplace graces the front parlor. The sizeable retro kitchen, complete with Geneva cabinets, awaits your personal touch. Set on a corner lot with mature plantings, the property boasts a private, quiet backyard. The property acts as a warm welcome to the picturesque and culturally vibrant Berkshires region. Call today for your private showing!

Tyringham is arguably the most beautiful place in the Berkshires. The majestic east-west valley has retained its historic character, with antique homes nestled among rolling farm fields and gently sloping hills. Just off Main Rd, on a quiet lane known as Church Road, sits the NorthRUP/ROP-Wilson House. Built in the late 1700s in the Georgian-Federal period, the home underwent a Greek Revival update in the 1830s, giving it a grander, yet timeless appeal. Having had few owners, the home has fortunately retained its original detail and character. Nestled in the middle of the valley, with views of the old school house and hillside cemetery, time seems to stand still here. Imagine the stories told around the grand fireplace, the family dinners, and the generations that have called this place home. A short stroll out the front door is wonderful Tyringham Cobble, miles of hiking trails and views. The first floor features a spacious eat-in kitchen that opens to a stone patio perfect for outdoor lounging and firefly spotting. Gather in the formal dining room for dinner with friends, below a vintage metal chandelier. A wide central hall with powder room separates the kitchen and dining areas from two additional living spaces. The Green Room offers stunning views of Church Rd, while the Yellow Room boasts a grand fireplace. Upstairs, one finds four more bedrooms - two with picturesque valley views - and a full bathroom. Pass through the Yellow Room to another grand room with a fireplace, an adjoining back room, and an upstairs area with two more rooms perfect for extra space during the summer or perhaps an artist studio. This home is truly for the antique lover - preserve the home's original charm or elevate it to new heights. The house is in good mechanical and structural condition. The rear of the home would require updated HVAC and electric to become four-season living space. Only 5 minutes to grocery shopping, 7-14 min to the great eating scenes in Lenox and Lee, and less than 20 min to downtown Great Barrington.

Welcome to sweet colonial comfort in Lenox! This 4-bedroom, 2-bath home is perfectly situated near many Berkshire attractions, blending convenience with charm. Step inside to find a spacious kitchen that flows seamlessly into the dining and sunroom. Both the sunroom and family room open to a large deck, where the soothing sounds of Yokun Brook await. The family room features lovely built-ins, perfect for both lounging and a home office setup. The main level hosts the primary bedroom with a cozy wood fireplace and an en-suite three-quarter bathroom with laundry. Upstairs, you'll find three more bedrooms sharing a modern, renovated bathroom. The third level boasts two large finished attic rooms, offering endless possibilities. A walk-out lower level and fenced-in yard provide extra space and privacy. With natural gas, public water, and sewer, this well-thought-out home ensures ease and comfort. Plus, it has a fantastic rental income history. Discover your new favorite spot in Lenox. Don't miss out!

Watch the sunrise and set from your Berkshire Home. This four bedroom, 3 1/2 bath colonial with modern renovations, is nestled at the end of a cul-de-sac on a quiet street, within walking distance to the middle and high school and on a bus route for the elementary school. The house features four bedrooms with wood flooring. The Primary Bedroom has vintage hickory floors, ensuite bath, California closets, three head shower and soaking tub to watch the sunrise and bathe under the moon. The main floor has an open renovated kitchen with a Wolf stove, two dishwashers, center island, marble and granite counters, handmade cabinets and cherry floors. Open dining area for your dinners and large gatherings.

A true MUST-SEE 6 bedroom, 3 bath for those who value history, character, and modern living within a classic setting. With its preserved character and timeless elegance meticulously maintained and significantly updated throughout the years. As you enter, you are greeted by expansive rooms with soaring ceilings, hardwood floors, and original built-ins that tell a story of artisan craftsmanship. The intricate stained glass windows create a kaleidoscope of light, adding to the home's enchanting ambiance. Featuring traditional fireplaces and so much more, this residence offers warmth and charm in every corner. Offering ample space for guests. The screened sun porch and rear deck extend the living space outdoors, perfect for entertainment or quiet contemplation. Nestled close to the heart of downtown Pittsfield, this property is a stone's throw from a vibrant cultural scene, making it an ideal candidate for a potential Airbnb venture. This historic residence is not just a home; it's a legacy of Pittsfield's architectural heritage, awaiting its next steward. Call to book your private showing today!

Enjoy every season in this 4 bedroom 3.5 bath Victorian farmhouse with wrap-around porch. Updated in 2017 this home is conveniently located 3 miles from Great Barringtons Main Street and a short walk to the Berkshire Waldorf School and the Green River. The eat-in country ''chef's'' kitchen features an English AGA cooker, Subzero fridge, soapstone countertops and cherry cabinets. Views from the kitchen take in the treed backyard and bucolic views. Main level includes a living room with Jotul gas stove, den , powder room. There are 3 bedrooms on the second level 2 baths with claw foot tubs.

Breathtaking Views from this Stylish and Pristine Home! A home can be a sanctuary, a retreat, and even a source of inspiration. Such is the case at 20 Brewer Hill. Perched atop a small knoll in beloved New Marlborough, with sweeping southerly views into Connecticut, 20 Brewer Hill exudes positivity and warmth. Sitting on the front porch, one can track the ever-changing horizon as the sun moves from dawn to dusk. Morning mist, rainbows, and pink skies are not uncommon. The grounds extend over three acres, with show-stopping perennial gardens, a meandering paved driveway, and a mix of lawn and meadow. The views continue as you step inside, from the updated eat-in kitchen, dining room, light-filled office, and spacious primary suite with renovated en-suite bathroom. Enjoy winter coziness by the living room's gas stove, and summer evenings from the pretty stone patio. Three guest bedrooms and a full bath offer ample guest quarters. This home is in truly pristine condition. Thoughtfully remodeled and meticulously kept, with major improvements made inside and out by the current owners over the past seven years. Amenities include a laundry room, pantry, attached two car garage, mudroom, full basement with storage space, whole house generator, and solar panels that provide a low energy bill and transferable power credits. Located only 2.25 hours from NYC, 2.5 hours from Boston, and 20 minutes from bustling Great Barrington, 20 Brewer Hill is ideally situated in beautiful emerald-green New Marlborough. Just far enough from the busier thoroughfares and crowds, but short drives to the area's many natural and cultural attractions.

For the first time in 64 years, this beautifully maintained center hall colonial is available for a new family to create lasting memories. At the end of a quiet street, in a highly sought-after neighborhood, this expansive home sits on a flat lot with mature landscaping which offers privacy and shade for summer enjoyment. Upon entering the gracious foyer, you are greeted by a warm and inviting living room featuring a wood-burning fireplace and built-in cabinetry. Across the hall is a formal dining room, perfect for hosting gatherings and dinner parties. The eat-in kitchen offers plenty of space for casual meals with ample storage and room for holiday gatherings. Next to the kitchen there is a convenient half bathroom and a versatile den or office space with built-in cabinetry which provides a quiet retreat for work or relaxation. The second floor offers a primary bedroom with double closets and en-suite bathroom, three additional bedrooms and a full bathroom. The finished third floor offers two additional bedrooms and a half bathroom, offering flexibility for guests. The basement boasts a cozy family room with a fireplace and built-in bookshelves, ideal for movie nights or game days. An attached two-car garage provides convenience and additional storage. Outside, the spacious yard offers endless possibilities for outdoor activities and gardening. This beloved family home combines timeless charm with modern conveniences, making it a rare find in this desirable location. Don't miss the opportunity to make it your own and continue its legacy of cherished moments.

Bright, Beautiful, and Pristine - 2019 Build on Wonderful Melville Court! Located just 1 mile from downtown Lenox on a lovely cul-de-sac of high end homes, 1 Melville is a sparkling contemporary home with colonial era flair. Well crafted with high end finishes, this ''like new'' 4400+ sq ft 2019 build boasts all of today's amenities. A living room with double-height ceilings, large picture windows, and fireplace is the home's inviting core. It opens to a light-filled chef's kitchen with a large island, 36'' range with hood, wall ovens, and two sinks. The kitchen further connects to a relaxing private deck and a dining room that fills with evening light. A first floor bedroom and full bath allow for one level living. A grand, yet understated, staircase leads to the second floor landing. To the right one finds the primary suite, which dazzles with a luxurious soaking tub, walk-in shower, double vanity, and extra large walk-in closet. A spacious laundry room sits outside the bedroom door. Cross over the walkway overlooking the first floor and arrive at two guest bedrooms and a full bath. A walk-out lower level hosts a fun rec room, additional guest sleeping quarters, and a full bath. Outside, a sweet side yard abuts wooded land for privacy and connects to the lower level in the back yard. Superbly located! Stroll to downtown Lenox in 20 min or a mere 3 min by car; bustling Great Barrington is only 20 min away, and Pittsfield is a mere 10 min commute. Immaculately kept, great value, and completely turnkey - make an appointment before it's gone!

On the Water in Monterey! This one owner Colonial styled residence is now on the market for the first time in 27 years. As part of the Steven's Lake private association, you can enjoy swimming and kayaking without the constant noise and the disruption of power boats. Although listed as a 3 bedroom home, there are 5 distinct sleeping areas and the screened porch and open area deck are idyllic for your own relaxation or for entertaining guests. With a little updating here and there, the investment in this home will pay very handsome dividends. Opportunities like this one do not come along very often.

On the crest of Woodruff Mountain, moments from The Southfield Store, York Lake, and area amenities, a classic country estate awaits. Its centerpiece is a stately 5BR, 5000sf, c. 1798, Georgian-Federal home, set on a 232-acre property encompassing a 3,550sf historic barn, smaller barns & run-ins, gardens & green house, Gunite pool & pool house, tennis court, fields, pastures, stream, mile-long trail abutting Sandisfield State Forest, and 5-acre spring-fed pond, all arranged for maximum livability and delight. You'll be pleased with the elevator, generator, & other mod cons, and charmed by historic details, stunning vistas, & untrammeled view of the star-studded night sky. Not enough? A 6,000sf guest house with four apartments suggests myriad uses for guests or income. Perfectly beautiful. The origins of East Hill Farm date to the 1740s, when New Marlborough was first settled, and Thomas Shepard came from Cambridge, Massachusetts, to establishe a home in Southfield. In 1798, he built a grander residence signifying his prosperity and stature in the community. Shepard's new home boasted a facade and interior details in the latest neoclassical style, eight rooms including four bedrooms, five fireplaces, and expansive views across pasture and fields to the south. Now on the market for the first time in 55 years, East Hill Farm awaits a new steward to write a new chapter in its rich history. Throughout its 226-years, the now 232-acre property has been enhanced and adapted to meet the needs and wishes of many generations. The property's new owner will benefit from a classic vision of what a gracious country home should be, with tennis court, Gunite swimming pool, pool house, green house, spring-fed pond and streams, historic three-story barn, two smaller barns, woodlands and trails, perennial gardens, pastures, run-in sheds, and an expansive guest house with four apartments and totaling nine bedrooms. A three-bedroom caretaker's house, set on five acres, though not part of this listing, is being offered separately to the buyer of East Hill Farm. Classic, too, is the landscape design: gardens near the house lead the eye to pasture, hedgerow, and pond, and, beyond that, to a distant west view. Sight lines are punctuated by towering sugar maples, stone walls. The property abuts both Sandisfield State Forest and New Marlborough Land Trust acreage, connecting the two. About 2.5 hours drive from New York and Boston and 60 minutes from Bradley International Airport, East Hill Farm offers privacy as well as unparalleled access to culinary, recreational, and cultural amenities, including Sandisfield State Forest, York Lake, 1,000-acre Pond, Southfield Store, Old Inn on the Green, Butternut ski resort, and Great Barrington's shops, restaurants, and performance venues. Tanglewood, five Equity theaters, Jacob's Pillow Dance Festival, and amenities in northwest Connecticut are within easy reach. New Marlborough is a low-tax town of artists, writers, craftspeople, and second-home owners, attracted by its laid-back, sophisticated rural atmosphere. Its meeting house is the venue for the Music & More series and exhibits by painters, sculptors, ceramicists, and photographers, while its village green is the setting for a vibrant Saturday morning farmers' market. The Thomas Shepard House Listed in the National Register of Historic Places, the Thomas Shepard House was built by Connecticut housewright John Collar who did many homes in the southern Berkshires; one of his design trademarks was the creation of passages and closets next to the chimneys between rooms. In 1798, the Georgian architectural style was transitioning into the lighter, brighter Federal fashion; for instance, the home's fireplace surrounds feature both Georgian bolection moldings and Federal mantels. One unique detail is its enclosed staircase, which is thought to be original and reflect an early use of the house as a meeting place for a progressive Christian community. Subsequent owners have honored the home's original features: millwork and chair rails, chimney cupboards, hardware, wide-board flooring with original T-nails, the dining room's cooking fireplace with oversized beehive oven, and 12-over-12 window sash crafted of dense, durable first-growth wood, containing hand-blown 18th-century glass, and fitted with storms for maximum R-value. Subsequent owners have also added features for comfortable modern living. In the 1930s, a rear ell was added. The sellers enlarged this, bringing the home's size to an estimated 5,000sf and allowing for radiant heat, modernized kitchen, five bathrooms, large mudroom with laundry, family room with kitchenette and full bath, four-car garage, plus a second-floor sunroom, library, and additional bedroom. An elevator connects the library to the family room, a generator keeps things running whatever the weather, and the basement incorporates a wine cellar. The home's cedar shake roof was put on in 2021, there is high-speed Internet, a security system, a drilled well, and the heating fuel is oil. The National Register report is available upon request. Lifestyle Amenities On the north side of East Hill Road, the current owners created a tennis court, 20'x40' Gunite swimming pool, pool house, greenhouse, and 1,960sf barn. Behind it, a mile-long woodland loop road connects the main compound with the guest house to the east and pond to the west. Just west of the home's roofed flagstone patio and ancient apple tree, parterre gardens brim with perennials, annuals, and herbs, blueberry bushes, irises, peonies, and heritage roses. A picturesque 280sf garden shed provides a sweet focal point there, while a broad, mowed path leads to a stone wall and rustic gate, pasture, large spring-fed pond, estimated to be five acres in size for boating, fishing, and swimming. On the road's south side are pastures and woodlands, a stream with charming footbridge, and two barns. The current owners brought in a three-story, 3,550sf, 18th-century barn, dismantled in Vermont and reconstructed on site; this contains a number of large bays and two work rooms. They also built a smaller barn near the stream. Each of the pastures has a water source. In addition, there are two run-in sheds with electricity and running water, and three utility sheds. A portion of the property is in Massachusetts Chapter 61A, which provides for reduced taxes on agricultural properties. The Guest House The guest house is a 6,000sf structure, built in the 1930s as a barn for Arabian horses. Reimagined circa 1990, it contains four duplex apartments, each with radiant heat, independent exterior entrance, living/dining room with fireplace and cathedral ceiling, workable kitchen, first- and second-floor baths, generous closet space, and garage and storage space. It has a new oil/wood furnace, a fire security system, and a shared laundry room off the hallway that connects the apartments to the garage. Apartment 1: Spacious first-floor living/dining room with fireplace and French doors opening to a large, private terrace, den with built-ins, full bath; kitchen, and gracious good-morning staircase leading to the upper floor, which has three bedrooms with one en suite and one shared bath. Apartment 2: Spacious first-floor living/dining room with fireplace and doors onto a large, private terrace, den with built-ins, half bath, and kitchen, and staircase leading to two bedrooms with shared bath. Apartment 3: Spacious first-floor living/dining room with fireplace and French doors to the lawn, den with built-ins, kitchen, half bath, and staircase leading to the two bedrooms and shared bath on the second floor. Apartment 4: Spacious first-floor living/dining room with fireplace and built-ins, den with built in shelving, full bath with claw-foot tub, kitchen, and staircase to two bedrooms and shared bath on the second floor.

Newly renovated family compound offers an abundance of living spaces across 2 distinct houses. The main house impresses with 6 ensuite bedrooms, a grand living room with a fireplace and an ambiance steeped in 1800s charm. The revamped kitchen and large dining room provide a perfect setting for cooking and gathering. Beautiful wide plank, vintage wood floors throughout main and cottage houses. The main house has a first floor primary and office area. Upstairs there are 5 more ensuite bedrooms and an additional sitting area. Connected by a stone courtyard with trellis, the separate cottage has a mudroom entry with half bath and laundry. Step into a sweet kitchen with stylish breakfast nook. The back of the cottage has a sizable area for lounging and dining. Upstairs are two bedrooms and one shared bath. Set on 0.4 of an acre, there is a flat, side yard for kicking around the soccer ball. The outdoor space features a hot tub, sauna, solo stove, as well as a spacious stone patio for year round outdoor enjoyment. This turn key home has a successful rental history, low taxes, and is close proximity to skiing and downtown Great Barrington.

''A Perfect Place Farm'' - a Berkshires Masterpiece on 17+ Acres The one you've been waiting for...a preeminent build in a premier location. 37 Main Rd checks off the wish list: sweeping views, modern comforts, privacy, location, and colonial era character, but in an immaculately kept turnkey 2002 home. Located in Tyringham valley, one of the Berkshires' most majestic locations, 37 Main Rd is idyllically sited on the northern slope of Tyringham valley, and faces to the southwest. The expansive front porch, sunroom, and living and sleeping quarters all are positioned to track the sun's daily arc across this picturesque east-west valley. Built in 2002 by Lou Boxer, a name known locally for quality and craftsmanship, the main house is 5092 square feet, plus 1594 square feet of guest/rec space in the three-bay carriage house. The highest quality materials are found throughout. A stunning great room opens to the front porch, and features a wood burning fireplace, high ceilings, plaster finished walls, and beautiful cherry flooring. The adjacent chef's kitchen connects the great room and a striking sunroom. Cooks will enjoy the 48 Viking double oven range, Sub-Zero refrigerator and wine fridge, two sinks, a warming oven, and a butler's pantry. The sunroom is the perfect light-filled, yet cozy area to take in the four seasons. And the wood-paneled library is a show stopper, with fireplace, wet bar, Sub-Zero fridge, coffered ceiling, and dramatic mill work. An office sits conveniently next door. The upstairs features the primary bedroom and ensuite bath, a second en suite bedroom, two more guest bedrooms with a third full bath, and a sweet den tucked away in the rear of the home. A bright and spacious gym, rec/billiards room, and guest sleeping quarters are found in the stylish carriage house. Three oversized garage bays allow for multiple cars and storage. Outside, the landscaping captivates. A perfectly executed driveway meanders up from Main Rd, through two stone pillars, up the gently sloping lawn, passing stately stone stairs, and arriving at a beautifully designed circular drive, with exquisitely placed perennials and specimen trees. 37 Main is superbly located, close to all the Berkshires attractions and amenities. Only 5 minutes to grocery shopping, 7-14 min to the great (and expanding) eating scene in Lenox and Lee, and less than 20 min to downtown Great Barrington. Tanglewood, Jacob's Pillow, and numerous theater and live entertainment venues are all nearby. Pristinely kept, high speed Internet, and low Tyringham taxes.

Welcome to Blue Spruce Farm, a magnificent 23-acre estate rich in history and brimming with enchanting features. Nestled in a serene setting, this certified wildlife habitat offers a sanctuary for nature lovers and a retreat from the bustle of everyday life. Enjoy leisurely walks on the maintained trails that meander through the 23 acres, offering tranquil views and a connection with nature. A low-maintenance wild garden of perennial flowers and shrubs produce 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. Originally built in 1770, this home harmoniously blends historic charm with modern conveniences. 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 that offers a comfortable space to enjoy the beauty of the property year-round. The second floor includes four bedrooms, offering peaceful retreats for 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 are a brand-new heating system and a whole-house generator. Blue Spruce Farm is more than just a home; it's a lifestyle. Steeped in history and surrounded by beautiful gardens, pastoral views, wooded trails and wildlife, it is the property you have been waiting for and do not want to miss out on!

Back in the day when an abundance of Land was the custom, this recently renovated Colonial home, which is set on 139 acres, provided its homeowners then and now the perfect country setting to enjoy life as it should be. The beautiful Deerfield River and all that it provides is directly across the road, so if fishing or kayaking is your preference, then it is an easy wish fulfillment. On the other hand, if you prefer a stroll in the woods along the many hiking trails around the property, this wonderful home is an open door to the life you want to enjoy! Seeing is believing; call for a showing today.