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46 Photos
GILCREST PROPERTIES
$807,500
3 BD | 3 BA
Residential - Single Family

Welcome to 326 Pratt Hill Rd., a tranquil retreat just outside the Hamlet of Spencertown. This exquisite property spans two parcels totaling 8.1 acres, ensuring complete privacy on a quiet country road. The 3-bedroom, 2-bathroom home also features an outdoor shower, perfect for embracing nature. Inside, enjoy the warmth of two gas fireplaces and a wood stove, with central AC for year-round comfort. The incredible chef's kitchen is a culinary dream, boasting top-of-the-line appliances. Outside, beautifully maintained gardens and a stunning bluestone patio create a picturesque landscape, ideal for outdoor entertaining or relaxation. This unique property is a true sanctuary, blending rustic charm with modern amenities, making it the perfect retreat for peace and comfort. Call today!


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BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY
$849,000
4 BD | 3 BA
Residential - Single Family

Welcome to Breezy Acres, a private retreat located just 2 hours from Boston and 12 minutes to the Mass Pike. This meticulously maintained property offers an abundance of natural light and picturesque views that are sure to captivate. Upon entry, you are welcomed by soaring ceilings that span all three levels of living space. The first floor includes a lovely kitchen with solid cherry cabinets, typhoon Bordeaux granite counters, a powder room, a laundry room, mini-splits for heat & A/C, and a Rumford-style fireplace made with locally sourced stone - perfect for cooler evenings. The radiant heated kitchen seamlessly connects with spacious living areas on both sides of the home.


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WILLIAM PITT SOTHEBY'S - LENOX
$850,000
3 BD | 3 BA
Residential - Single Family

Let's begin with the location which is nestled high in the hills of Spencertown. Some may say it's the crown jewel of Columbia County, given its knockout country charm, quaint town square, ten minute drive to Chatham's well curated main street, and easy access to the Berkshires, skiing and the great outdoors.With the stage set you can now focus on a choice 10-acre setting, graced with boundless mountain views and picture-perfect sunsets, a massive star gazing sky, privacy, peace, quiet, plus a pond and stream. Focus in a bit closer and you now take in the classic, warm, gracious, well built, modern log home paired with a generous, finished three car garage. Upon entering you will be captivated by the stunning stone fireplace, open floor plan with gourmet kitchen, great room


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$869,000
4 BD | 5 BA
Residential - Single Family

Sunny Contemporary Home with 60' Pool on 1.3 Beautifully Landscaped Acres!Sunlight, privacy, and style. This architect-designed house is exceptionally located in a light-filled lot with a wonderful pool and impeccably kept gardens. This home is move-in ready and allows for one-level living. Relax in the stunning screened porch that overlooks mature gardens and a private backyard. The modern and updated kitchen, with stone countertops opens, marble floor, stainless steel appliances, opens to a spacious living room with fireplace, dining area, vaulted ceilings, skylights, and a large deck. The first floor primary bedroom features an ensuite bath, large soaking tub, skylight, and fireplace.


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DIGRIGOLI REAL ESTATE
$874,000
4 BD | 4 BA
Residential - Single Family

Enjoy total peace and quiet in a park like setting yet a few minute drive to Main St GB. Property sits high on the hill with mountain views. Perfect flow for entertaining and easy living. 1st floor primary bedroom with en suite bath & jetted tub, central A/C, living room fireplace, screened-in porch off of eat-in kitchen, vaulted ceilings, hardwood floors, and ceramic tiles. New carpeting throughout and a large cedar closet in one of the bedrooms. In-home office with separate entry, large dry basement with high ceilings perfect for in home gym. Insulated garage with long paved driveway. If your looking for a solid newer built home this is it! The average home price in this location is in the million dollar plus range


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COLDWELL BANKER REALTY WESTFIELD
$874,000
3 BD | 2 BA
Residential - Single Family

Welcome to Colesbrook Manor, an ash timber frame construction masterpiece set alongside lively Coles Brook on 4.4 acres in the southeastern slopes of Crane Hill. Built in 1984 and solely occupied by joiner, carpenter and Heartwood School (of timber framing and energy-efficient house design) co-founder Andy Inganni, this home takes advantage of the microclimates of its setting and the energy and lifestyle benefits of traditional craftsmanship and construction. Beyond 3 bedrooms and 2 full bathrooms, this home features an expansive open floor plan on its main level, inclusive of a living room, dining room, kitchen, indoor raised garden bed with symbiotic drainage, and a screened entry porch. The split level features an in-law suite with bedroom, bathroom, sauna, and screened back porch.


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WILLIAM PITT SOTHEBY'S - LENOX
$919,000
4 BD | 3 BA
Residential - Single Family

Incredible Berkshire Mountain Home - Frank Lloyd Wright inspired architecture capturing Berkshire mountain views. Its magical set on a hilltop enveloped in mature landscape, secret gardens with waterfalls and a coy pond surrounding the inground pool. Grandiose two story stone pillared entry welcomes you into the stain glassed door dramatic entry. Notice soaring ceilings, archways curved flooring to the sunken living room with walls of glass framing the beautiful outdoors. Formal dining open to this light filled entry. Central air makes the yearround sunroom perfect for relaxation, pool and bird watching. Thoughtful and easy one level floorplan flows to everyday dining, kitchen and floor to ceiling stone fireplaced family room. Saunter to the stone patio for outside dining, wade in


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STEEPLEVIEW REALTY - ADAMS BRANCH
$995,000
5 BD | 6 BA
Residential - Single Family

This unique property has everything you can imagine.It really needs to be seen to appreciate. There are multiple levels. The main living area (which can be accessed via the elevator from the heated garage) is open with gleaming wood floors, natural woodwork & stunning views. There are french doors leading to the huge wrap around screened deck which has water, a stone fireplace and multiple gas hook ups for grilling or heaters. The living room has vaulted ceilings an inviting stone fireplace and wonderful views. The kitchen is well laid out with 2 pantries, upgraded appliances and a wet bar compete with a dishwasher and wine cooler. Enjoy dining in front of the brick fireplace or in the cozy breakfast area.


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ALTON & WESTALL REAL ESTATE AGENCY, LLC
$1,000,000
4 BD | 3 BA
Residential - Single Family

Stylishly updated for modern living, this 4 bedroom 2.5 bath home is a dream come true. Set on 1.6 acres of park-like lawn and mature trees it commands a quiet spot on a cul-de-sac in the center of town. The kitchen has been renovated with quartz and granite countertops, stainless steel appliances and spacious center island with butcher block counter and vegetable sink. The living room with fireplace is the heart of the home and opens to the dining room. The bedrooms and baths are all on the main floor. The lower level offers two finished rooms. There is a 2 car garage, a stone patio and separate heated studio 19' x 19', and the 1.6 acres includes excess acreage enough for 2 building lots with frontage on West Main Street.


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EXp REALTY
$1,100,000
5 BD | 4 BA
Residential - Single Family

Open, light airy 5BR contemporary & only a 5 minute drive to downtown Great Barrington! Loads of sunlight throughout with open floor plan. Floor to ceiling windows & cathedral ceiling in kitchen & great room. The main bedroom also has floor to ceiling windows & cathedral ceiling. State-of-the-art chef's kitchen opens to a huge deck overlooking the beautifully landscaped, level property. Home also features a den, living room, family room plus a lower level recreation room. Property is surrounded by majestic hardwoods & evergreens, with fenced dog run, creating serenity & privacy. Perfect for entertaining also has an outstanding short term rental history. Recently added generac full generator with 1000 gl propane tank. NEW Mitsubishi HVAC Splits. Sq ft includes 756 sq ft basement spac


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$1,250,000
5 BD | 5 BA
Residential - Single Family

Nestled in a peaceful corner of the South Berkshires, between Sandisfield and Otis, lies a 4,645 sq ft home with 16 beautiful acres. This 5-bedroom, 4 1/2-bath property isn't about opulence; it's about creating a welcoming space for gatherings. Built by the sellers with the intention of hosting frequent guests, this home has been lovingly maintained & thoughtfully designed.Inside, you'll find a range of inviting living spaces. The 4-season sunroom lets you enjoy the changing scenery all year round. The great room, with its high ceilings adjoins the huge eat-in kitchen, the heart of the home, ideal for cooking and sharing meals. The family room, game room, and wet bar provide plenty of options for relaxation and entertainment. Radiant heated floors throughout the home! (see supplement)


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PREFERRED COUNTRY PROPERTIES
$1,350,000
4 BD | 3 BA
Residential - Single Family

This c.1770 Federal protected by 27 acres retains much of the elegance and charm of 250 years ago.. set in a protected valley with other historic buildings, you experience the past while enjoying the present .. enter the maple lined driveway until the classic buildings greet you .. 3,415 sq-ft home plus 4-stall 2-story horse barn, corn crib, garden house, 2-car garage .. to delight the senses a heated inground pool surrounded by meadowy fields, paddocks and a winding brook by shade trees .. spend your days walking your evergreen woods, sitting by the brook, dining in the outdoor room with its bluestone floor surrounded by ancient barn foundation walls. In addition to the restful serenity of this exceptional property, you will enjoy nearby Berkshire Cty attractions. 1st time avail 52yrs.


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STONE HOUSE PROPERTIES, LLC
$1,395,000
6 BD | 5 BA
Residential - Single Family

A Magnificent 6 bedroom stucco residence less than a mile to the center of Stockbridge. Enjoy views of the golf course and mountains in the distance. Five fireplaces, a beautiful eat in kitchen, stunning butlers pantry with a cozy nook to sit in, and a sun filled spacious dining room. Read a good book in the beautiful library next to one of the five fire places throughout the house. Step out beautiful French doors to your screened in patio which leads to a well lit and heated pool. A 20 ft hallway wall of built in cabinets and closets leading to the primary bedroom. Three en suite bedroom areas for guests and family. Electric car charger in the heated garage. Majestic stonewalls. Not far to all attractions Tanglewood, Norman Rockwell, ski areas etc. A must see!


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$1,495,000
1 BD | 2 BA
Residential - Condo/Townhouse

Enjoy Canyon Ranch Living, the ultimate in luxury in this gated community, that offers gracious living with a focus on health and wellness. This turn-key, this one bedroom condo with home office has a half-bath and en-suite bedroom. A chef's kitchen with marble counters opens onto the great room with marble gas fireplace. The private balcony is lovely for morning coffee or to catch the evening sunsets. A home office is a flex space that can serve as a den or extra guest space.The principle bedroom is en-suite with spa amenities in the upgraded marble bathroom and generous customized walk-in closet. Marble gas fireplace sets a peaceful tone. Ask to see list of amenities.


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ROBERTS & ASSOC. REALTY, INC
$1,650,000
4 BD | 5 BA
Residential - Condo/Townhouse

Prepare to be wowed when you visit this luxury condo at Stockbridge Terrace! The details, custom features and craftmanship are second-to-none! Seeking one-level living? Literally just bring your suitcase as furnishings can be available in this well-appointed one-owner home. Entertain in style with open floor plan. The living/great room's centerpiece is the stone fireplace, oversized windows and cherry floors. Enjoy the formal dining room or savor summer dining on the spacious screened porch. Bedrooms are thoughtfully placed to ensure maximum privacy. Primary suite is on the first floor with jetted tub and oversized shower. along with custom outfitted walk-in closet. On the upper level you'll find two additional bedrooms each with ensuite baths. The family room includes custom


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WHEELER & TAYLOR REALTY CO., INC.
$1,700,000
3 BD | 3 BA
Residential - Single Family

Expansiveness & spectacular views into CT! This contemporary cedar home is an idyllic setting in a dream location featuring a hilltop swimming pool w/ stone patio, 36' x 60' horse barn with plenty of room for horses, koi pond w/ bridge, mature landscaping, and beautiful stonework throughout. The spacious interior of this light-filled home with soothing earth tones & warm woods includes 3 BRs, 2.5 bathrooms, open concept floor plan, private office space, central A/C, jetted tub, screened porch, gas fireplace, skylights, and incredible views both inside & out. Gather year-round with friends & family at this spectacular retreat!


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ALTON & WESTALL REAL ESTATE AGENCY, LLC
$1,750,000
2 BD | 3 BA
Residential - Single Family

Maya Lin Masterpiece. Evoking the serenity and simplicity of the Japanese courtyard aesthetic, this extraordinary home, Maya Lin's first residential conception, stuns in the purity of its design and materials, in the singular curvilinear articulation of its roofline, and in the liberal use of fieldstone, slate, cherry, maple and ash in restrained architectural elements yielding a rich yet exquisitely understated ambience. The graceful rooflines reflect the swells and hollows of the distant hills, and define as well the interior spatial configuration and elevations. Upon entering through the front door a glimpse of the lovely central courtyard hosting Japanese maples and koi pond lies ahead. The main living area opens both to this intimate courtyard and to a deck with the inspiring view.


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PIRETTI REAL ESTATE
$1,795,000
5 BD | 5 BA
Residential - Single Family

Custom built 5 BR Contemporary home with beautiful architectural features to match the beautiful October Mt. views! Open floor plan with family room and kitchen/eating area all accessible to the deck and pretty yard, first floor guest suite and more formal rooms too... DR and LR with French doors to the front porch. The arched doorways, tray ceilings and stunning built ins surrounding the FP make this home unique. There are 4 additional Bedrooms and 3 full baths on the 2nd floor with a 2 room Primary Suite (sitting room and bedroom) with gorgeous full bath. Conveniently located near the High School and close to all the culture the Berkshires has to offer. Enjoy the pristine condition, the beautiful views from both the front porch and the rear patio, and the great Lenox schools!


87 Photos
FAIRGROUND REAL ESTATE, INC
$1,850,000
4 BD | 4 BA
Residential - Single Family

Location, location Location heated pool and tennis courtPerched on one of Hillsdale's most bucolic and quiet roads, everything about this 1800s cedar shingled property says, Welcome home.'' Its owners painstakingly transformed the center hall colonial, bringing more brightness to the first floor. The airy kitchen has granite counters, and includes a Viking stove and Miele dishwasher, and opens to a three-season porch with a Vermont Casting propane stove. The four bedroom home has 3.5 baths (including a 5x6' Whirlpool tub in primary bath, conveniently located on main floor with a door that leads to a quiet patio). The stately living room has a working fireplace, as does the primary bedroom. The meticulously maintained property includesd tennis court and heated swimming


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MAPLE AND MAIN REALTY, LLC
$1,850,000
4 BD | 5 BA
Residential - Single Family

An outstanding rarity in Northampton - an exquisitely designed and built Contemporary hilltop residence with sweeping southeasterly views. With over 6000 sq. ft, 6+ acres of land with trails abutting 17 acres of conserved land, this property has it all - from a luxurious 1st floor primary bedroom suite with 2 walk in closets, jacuzzi tub and private deck overlooking the vista, to the gourmet kitchen that opens to the living room & masonry fireplace. Other features include a 2nd en-suite bedroom on the main level, a sun room and private office plus a loft used as an artist's studio. Downstairs there are 2 bedrooms with a bathroom suite, media room, game room, indoor Endless lap pool with state of the art ventilation system. The 3-car garage has an exercise room above. Outside you'll find

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