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57 Photos
THE KINDERHOOK GROUP - PITTSFIELD
$2,100,000
4 BD | 4 BA
Residential - Single Family

''High Meadows'' is a grand and luxurious 20 acre estate with spectacular sweeping views of October Mountain. Set high upon a private knoll, the chic and newly renovated 4 bedroom contemporary home features a towering sun filled great room, wine cellar, 3 fieldstone fireplaces and new outdoor bar/kitchen to mention just a few.There are meticulous specimen landscaping with master gardens, pear and apple orchards, groomed walking trails and perhaps best of all, not only a lovely gunite pool/spa area, but an extraordinary crystal clear swimming and trout pond! This is an ideal home and property for ENTERTAINING friends and family! Call for a private tour.


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BROCKMAN REAL ESTATE, LLC
$2,200,000
8 BD | 7 BA
Residential - Single Family

MORNINGSIDE, TYRINGHAM A spectacular estate dating back to the Tyringham Shakers. This is an extraordinary, & unique opportunity to own a part of Berkshire history. Overlooking Tyringham valley, Morningside is set on 44 acres with a circa 1800 Manor House originally constructed by the North Family of the Tyringham Shakers. Pool, pool house, swim pond, & stunning gardens. The permanently protected U.S. Appalachian Trail borders the land to the south & east. 16 rooms include a huge kitchen, 7 bedrooms, one a palatial master suite, and 4 full and 2 1/2 baths. A large 3-car carriage barn has a large vaulted room & full bath above. The setting is both spectacular & quiet, without being isolated. You are in the heart of the Berkshires with staggering views. Add'l land & homes available.


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STONE HOUSE PROPERTIES, LLC
$2,250,000
3 BD | 4 BA
Residential - Single Family

A chance to own an exquisite federal Colonial with charming eyebrow guest house and gorgeous antique barn. On over 100 acres and only 6 miles to Hudson. Property filled with mature perennial gardens, beautiful stone and brick patios, and an abundance of wildlife. The house flooded with natural light and with gleaming wood floors. Cook for family and friends in a state of the art chef's kitchen with glass surrounded breakfast nook. Enjoy your coffee in the year round sunroom or curl up with your favorite book in front of one of the many wood burning fireplaces. The master suite: an oasis complete with fireplace, light filled sitting area and master bath with large soaking tub. Other features include: media room, wine cellar, home gym, office and craft room.


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LANDVEST, INC.
$2,300,000
4 BD | 5 BA
Residential - Single Family

Windy Ridge Farm is an elegant country estate on 140 acres with views to Mt Greylock and the valley to the south. The location off a 1/4 mile long tree lined drive offers privacy in a bucolic setting, yet is only a 15 min drive to Williamstown, 8 minutes to Jiminy Peak, and 25minutes to Tanglewood.. There is so much to enjoy at home! The fabulous gunite pool with water fountain and surround sound, and the tennis court are favorites for the summer. The wine entertaining area is used for pre-dinner cocktails and dining is either seasonally in the 3-season gazebo with 360-degree views or the formal dining room with a roaring fire. The sunken living room with 20' ceiling, fireplace and balcony is ideal for entertaining. Open fields suitable for Agriculture, horse farm.


48 Photos
STONE HOUSE PROPERTIES, LLC
$2,395,000
5 BD | 6 BA
Residential - Single Family

Prominently sited on 18 acres to offer views, privacy, and dramatic sunsets.A gentle sprawling lawn and private wooded background surround this custom brick estate home. The open layout and attention to detail make it ideal for casual country living allowing dramatic views from most all rooms. The floor plan is comfortable with perfectly proportioned rooms that flow seamlessly.The impressive entrance is framed by a beautiful spiral staircase. Sun filled gourmet kitchen with oversized center island. Multiple fireplaces throughout give the home a cozy feeling and the custom millwork gives each room a finishing touch. Spacious first floor master suite with fireplace. Finished lower level was designed as an in-law suite and has a private entrance. Desirable West Stockbridge address.


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STONE HOUSE PROPERTIES, LLC
$2,400,000
0 BD | 2 BA
Residential - Single Family

This unique and majestic property has been originally erected in 1853 as a residence for a local doctor Clarkson T. Collins. The American Gothic Revival style home has been converted many times since and it is currently the home of a renowned local jeweler. It consists of 1940 sq. ft of the first floor and 1680 sq. ft of the second floor. With the right mix of creative vision and passion, it can be turned back to that ''one of a kind'' home. Situated right in the heart of Great Barrington, within walking distance to downtown, it is also only 2+ hours travel from Boston or New York. Come take a look, bring your architect and decorator and this incredible property could be yours.See also MLS 230288


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BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY
$2,400,000
4 BD | 4 BA
Residential - Single Family

RARE WATERFRONT OPPORTUNITY: A SUMMER PARADISE FOR YOUR FAMILY. Build your dream home. There are beautiful renderings of possibilities on this nearly 5 acres on the beautiful Stockbridge Bowl. Over 300 feet of pristine lake frontage. Amazing mountain and water views in every season.Shared driveway in place. Rare opportunity to have your dream home within 71 feet of the lake. Minutes to Tanglewood, Kripalu, and Canyon Ranch.


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BERKSHIRE PROPERTY AGENTS, LLC
$2,450,000
3 BD | 4 BA
Residential - Single Family

Amazing opportunity to own a large parcel of land in one of the most desirable towns in Columbia County. With frontage on four picturesque roads less than 10mins to great barrington this 1850s barn offers so much; Main house has a great room with fireplace and loft above, large dining room off eat-in kitchen and laundry room with ample storage and separate entry, 3 guest rooms all with en suite. the post and beam structure allows for the entire main space to be opened up with southern exposure. lower level pool area, tower structure ideal for studio and it just keeps going; A 20 acre pond, tennis court, original concrete pool and trails taking you back to the frontage along the Roe Jan.Organically Farmed.


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COHEN & WHITE ASSOCIATES
$2,500,000
5 BD | 6 BA
Residential - Single Family

Applegate Farm...Country residence with both formal and informal common spaces to accommodate a few or many with five fireplaces, two master suites and guest wing with tennis court all overlooking your own lake with a western mountain view for backdrop. 100 + acres of very special land located on the border of Egremont and Sheffield on a back country road.


36 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$2,550,000
5 BD | 4 BA
Residential - Single Family

Spacious 1800's Colonial tastefully updated on 8 acres of land with 296 ft of waterfront on Stockbridge Bowl! A private dock for your boat. A secluded flat grass area for picnics and sunbathing. Swim from the sandy water front. The house offers 4 or 5 bedrooms, 4 updated baths, expansive eat in kitchen with butcher block counters, an island, stainless appliances and walk in pantry/laundry room. The kitchen opens to the cozy family room with French doors to a covered porch and views of acres of fields. The living space includes a 25 ft living room with fireplace, large dining room currently being used as a pool room! Time for a game? Enjoy out door living in style; porches, decks, gardens, stone walls, gorgeous lawn and basketball court. More than enough space for pool and or tennis!


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BERKSHIRE HOMES AND CONDOS
$2,600,000
10 BD | 10 BA
Residential - Single Family

Proudly presenting this newly refurbished 10 Bedroom, 9 and half bath, privately owned, walk to town, historic Lenox ''Cottage''. Lovingly named Osceola after the dramatic view of Osceola Mountain on the Yokun Ridge experienced upon entering the columned and balustraded front porch. Osceola Mansion was designed by world renowned architects Rotch and Tilden in 1889 and commissioned by Sarah Pollock Livingston. Today, this comfortable and beautifully appointed home features an entry foyer with a fireplace to warm your hands and toes after a winter's sleigh ride. Enter the Grand Hall which invites you into the Living Room to your right or draws your attention to the unique Oval Dining Room to your left. Straight ahead is the picturesque outdoor covered 80 feet in length Veranda


60 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$2,600,000
7 BD | 10 BA
Residential - Single Family

Magnificent country contemporary gently sited on 145 +/- acres offering enchanting forest woodlands, open meadow and wonderful awe-inspiring views. The main residence offers expansive spaces with the highest degree of finishes. Designer kitchen with a massive center island has an open concept to cozy spaces for entertaining or simply life as you wish. Your retreat style grounds vary from large timber tracts with hiking, biking and snowshoe trails, to your custom designed Gunite pool with Pool House.. Planning a reunion or guests for the weekend? The separate rustic refined guest barn is the ultimate experience. Paradise found equidistant to The Berkshires and Northampton. 3 1/2 hrs from the NYC and Just over 2 hrs from Boston. Minutes to Skiing, Rafting and Fly Fishing


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ELYSE HARNEY REAL ESTATE
$2,600,000
3 BD | 4 BA
Residential - Single Family

CIRCLE Z 348 plus acres, stunning home, stable with 5 stalls, garages, acres of pasture, VIEWS, forest, streams, trails with endless possibilities for a private estate, Equestrian facility, private club, upscale housing, energy farm and more. The home is beyond stunning, with the finest craftsmanship, solid oak floors, doors and trim. Indoor pool with steam shower, multiple bedrooms and baths, 2 massive stone fireplaces, a rare Massive KACHELOFEN stove fills a wall. Covered porch with views of estate.


38 Photos
COHEN & WHITE ASSOCIATES
$2,650,000
4 BD | 5 BA
Residential - Single Family

We all know it: we have one life to live; one home of our heart; one family retreat in which all may thrive...YOURS may be available now for you in Williamstown! A Home of comfort, harmony and created with an unprecedented level of thoughtful attention to every detail from the perfectly aligned and matched Brazilian cherry flooring to the unsurpassed stone mason's craftsmanship of fireplace design; the Lazure hand painted walls; and perfection-achieved quality evident in every niche and corner of every room. Set perfectly on 27 private acres of lawns, patios and pool; woodlands, and extensive all season gardens opening onto magical views of hills and sky beyond. This is a home where life is inspired. This is a home for a most-fortunate family....perhaps it's yours! See Supplement....


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REAL LIVING REALTY PROFESSIONALS
$2,699,000
5 BD | 5 BA
Residential - Single Family

Welcome to Big Pond - The hidden gem of waterfront living! Your family and friends will find themselves in awe from sunrise to sunset. As you approach the winding circular driveway, you soon realize the placement and fine quality construction of detail left no stone unturned. See Supplement.


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BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY
$2,850,000
5 BD | 8 BA
Residential - Single Family

A unique mountain top estate with 180 degree views of Vermont, Williamstown and Mount Greylock. This meticulously curated sanctuary intimates simple luxury by combining the best materials with an inspired concept. The design and stunning architecture marry to create energy and flow for this 5 bedroom estate. The home itself benefits from a commitment towards precision engineering. Noted Jackson Hole architect shipped hand hewn beams from Montana to create this vision. Only minutes to Williams College you can gather with family and friends with formal and informal spaces. 72 Unspoiled acres afford privacy, Soaring ceilings, large fireplaces, in-ground pool, gourmet kitchen, open plan and views from almost every room. This home is awaiting its next chapter, let it be part of yours.


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BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY
$2,895,000
6 BD | 7 BA
Residential - Single Family

ONCE IN A LIFETIME IT COMES ALONG: a modern renovation. Every detail is thoughtful, the rooms offer height and grace, its magnitude gives space without being overwhelming. Built on the top of Great Barrington's Hill. Peering down on the town, within walking distance on 3 +acres. Built by a local craftsman and designed with easy living in mind. The open kitchen/great room, has a soaring ceiling, will gather you with family and friends in front of the stone fireplace or relaxing at the granite island while meals are prepared in the chef quality kitchen with Calcutta marble counters. Clean modern lines, meticulously chosen materials, two master suites, a modern open stairway concept with metal balusters, outdoor kitchen, spa pool. Light and Bright in law/Nanny suite. Kosher Kitchen.


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LENOX CANYON REALTY
$2,950,000
4 BD | 6 BA
Residential - Single Family

Exquisite in every detail, this home graces more than an acre of prime Berkshire property! In a league of it's own as part of the Pinecroft subdivsion of Canyon Ranch, this luxurious haven offers the option of membership to the world class health and wellness facility. A gourmet kitchen, fireplaced living room with wet bar and gracious dining room welcome you home!Numerous exceptional amenities abound including an eight seat hi-def movie theater, climate controlled wine cellar, sauna and soda fountain. Other features include a heated three car garage, heated gunite pool with spa and a fully equipped outdoor kitchen in the pool house!


51 Photos
BERKSHIRE PROPERTY AGENTS, LLC
$3,100,000
5 BD | 6 BA
Residential - Single Family

Cookledge, is a sprawling contemporary compound spread over mountain top glacial outcroppings, with awe-inspiring views south over Connecticut and west to the Taconic Range. Nearby the Southfield Store Cafe, drive up the long romantic winding drive to this sensitively sited and quality built home with huge windows and glass doors that draws one outside from almost every room to the truly stunning views. Large airy rooms with high ceilings, tall doorways, hardwood floors, multiple fireplaces, along with separate master and guest bedroom wings, all with ensuite baths, flow easily throughout the main house. The heated three-car garage has a Tesla charger and a guest or caretaker apartment above, with a fireplace and deck. Total seclusion, trails to a stream gorge, and magnificent serenity.


46 Photos
THE KINDERHOOK GROUP - PITTSFIELD
$3,100,000
4 BD | 4 BA
Residential - Single Family

Rare opportunity to own this private, 32-acre estate in the center of Alford. Built in 1875, the historic post-and-beam home was completely renovated by famed director Dick Schneider to create this spacious and comfortable country house perfect for relaxing with friends and family. The main part of the house features a light-filled, eat-in kitchen which leads out to the deck overlooking nature. The living room has a wood-burning fireplace and an adjacent den with attached full bath. Upstairs are 3 bedrooms including a large master suite. The breezeway off the downstairs atrium leads to a 2-car garage above which are located the guest quarters with full bath and which is also ideal for use as an office or home gym. The grounds are simply gorgeous, with the Alford Brook running through

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