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48 Photos
LANCE VERMEULEN RE, INC
$875,000
5 BD | 3 BA
Residential - Single Family

1780's colonial set on over 12 beautiful acres. Few like this left in the Berkshires. Originally a Stagecoach stop between Hartford and Albany, this spacious home has those special details not found in modern buildings today. Built in cabinets, wide plank floors and fireplaces, one complete with bread ovens and usable hanging cooks pot. Dutch door looking out to lovely view. Recently updated kitchen leads into a greenhouse with fountain and radiant floors for year round use. Dining room table is the original to the home & is included in the sale to be passed onto the next family to make their own memories. There is a separate guesthouse with a full open kitchen, LR, bath, laundry room & loft. Several outbuildings including Tack room, chicken coop/playhouse, & much more. Can be sub-divided.


52 Photos
WHEELER & TAYLOR REALTY CO., INC.
$899,000
4 BD | 2 BA
Residential - Single Family

THREE HOUSES FOR SALE ON 11.6 PARK LIKE ACRES .1910 CONVERTED ANTIQUE BARN is now a warm and welcoming MAIN HOUSE with 4+ bedrooms, 2 full baths, large stone fireplace, cherry wood paneling, lots of windows, 2+ car garage .TWO ADDITIONAL RANCH STYLE HOUSES have a separate driveway and privacy. Perfect GUEST COTTAGE and CARETAKERS properties. Unique opportunity in a desirable area in Stockbridge.


55 Photos
WHEELER & TAYLOR REALTY CO., INC.

THREE HOUSES FOR SALE ON 11.6 PARK LIKE ACRES . 1910 CONVERTED ANTIQUE BARN is now a warm and welcoming MAIN HOUSE, with 4 + bedrooms and 2 full baths, cherry paneling, large stone fireplace and 2+ car garage with storage. TWO ADDITIONAL RANCH STYLE HOUSES are included with separate driveway and privacy. The perfect GUEST HOUSE AND CARETAKERS properties. Unique opportunity in an ideal location.


4 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Build your perfect home on this land sited along one of the most prestigious roads in Stockbridge.The property encompasses the entire corner running along Prospect Hill, Larrywaug and to North Church St. or divide into three lots. Four acre zoning and this property has enough frontage and acreage for three building lots. With clearing there is the possibility of views from different sites on the property.


38 Photos
HELEN MULLANY REAL ESTATE, LLC
$995,000
6 BD | 3 BA
Residential - Single Family

Gracious 1890 residence with carriage barn income property, graces the charming main street of Stockbridge. The main house is comprised of 4 bedrooms, double parlors w/fireplace, formal dining room, country kitchen and the most delightful screened porch. An attached 2 bedroom apartment with separate entrance, is ideal for extended family and guests. Distanced from the main house by a circular drive, the converted carriage barn sets behind, housing three apartments. Mature landscaping, perennial gardens, stone patios, and a 3 bay garage complete this idyllic compound. Red Lion Inn, Stockbridge Golf Club and theatre nearby.


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HELEN MULLANY REAL ESTATE, LLC
$995,000
4 BD | 3 BA
Multi-Family

A gracious Main Street property with four rental apartments, a main house with four bedrooms, double parlors, country kitchen, two full baths, a wonderful screened porch and a three bay garage. The yard has wonderful out door spaces for the residents, and all a short walk to everything the town offers. Perfect for an investor owner occupier.


38 Photos
COHEN & WHITE ASSOCIATES
$998,500
7 BD | 7 BA
Residential - Single Family

What a beautiful home for TODAY! Set in the heart of Stockbridge -- that most gracious and iconic of Berkshire towns -- ''Seasons'' is a New England classic, a lovingly detailed, superbly renovated 1862 Greek Revival mansion, warm and welcoming. From the restful length of its shady porch to the elegantly appointed front parlor, from the serene formal dining room to its secluded bedroom retreats, ''Seasons'' manages to both welcome the world, while offering friends and family a perfect refuge. This spectacular all-season ''Getaway'' home, part 19th century, part 21st, generously arranged, with elegantly designed public rooms, and the pleasures of a spacious modern chef's kitchen with Multi-zone air conditioning throughout. In perfect order, it's waiting for YOUR fortunate family!


35 Photos
COHEN & WHITE ASSOCIATES

Rated #2 in the country in 2018 and #16 in the world, Seasons on Main is a nationally recognized top rated 1862 Greek revival B&B in the center of Stockbridge and has been lovingly restored to its original grandeur and maintained with the utmost care.This is your opportunity to own a turnkey business with a proven record of success, or to have as your own exquisite homestead.


32 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$1,295,000
4 BD | 4 BA
Residential - Single Family

Magnificent contemporary in spectacular setting. This move-in ready home has it all! Sun filled living room w/ double height, cathedral ceilings & floor to ceiling windows, great room that opens to a 4 season, enclosed, heated porch plus a large outdoor deck, perfect for entertaining friends. 1st floor also includes large first floor master suite w/ luxurious master bath & a state-of-the-art, open chef's kitchen. 2 spacious bedrooms upstairs plus an office. Fully finished, walk-out lower level w/ bedroom & full bath. Beautifully manicured grounds w/ mature plantings, lush lawns & waterfall. Deeded access to pvt. dock on Stockbridge Bowl, just across the road - perfect for a kayak or paddleboard. Plus, additional deeded rights to private Beachwood beach, just a short walk away.


36 Photos
LANCE VERMEULEN RE, INC
$1,450,000
14 BD | 15 BA
Residential - Single Family

Perfect for large family or other looking to utilize10,000 sf plus of space for dwelling or other mixed-use purposes. Current configuration has 13 guest suites plus the owners' apartment. Full commercial-level kitchen with large dining spaces, bar/tavern area and other spaces for offices, etc.


36 Photos
LANCE VERMEULEN RE, INC

Thornewood Inn (13 guest rooms plus owners' apartment) with a full restaurant is available for its next owner for the first time in nearly 40 years. Greatly expanded and upgraded by the current owners to be a successful inn as well as reception setting for weddings, family celebrations and more. Situated at the junction of Rtes 7 & 183, many views of Berkshire hillsides are to be enjoyed. The restaurant with dance floor can seat 125. There is additional seating of 30 on a breakfast porch. Fully-equipped commercial kitchen and cozy tavern/bar complete this versatile offering. Liquor License conveys with this sale subject to nominee approval by Town of Great Barrington.


53 Photos
COHEN & WHITE ASSOCIATES
$1,495,000
7 BD | 9 BA
Residential - Single Family

Stunning Circa 1850's renovated with seven bedrooms and nine full baths. Classic Greek Revival with strong lines and lovingly preserved details; three period fireplaces, generous gourmet eat-in cook's kitchen and the comfort and style of today's living in the perfect location just a short drive to Tanglewood and in between Stockbridge and Lenox!! This property offers gracious common spaces and six en-suite guest bedrooms. New first floor guest suite with separate entrance


16 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$1,500,000
3 BD | 2 BA
Residential - Single Family

Rare opportunity to own a Berkshire Landmark. Known as ''the Antique Shop'' in Norman Rockwell's Main Street Painting, this iconic Building is famous worldwide. Classic Victorian Style with acres of charm. 3 Stories with on-site Parking. 3 'Main Street' Retail Spaces, a large (and vacant) Second Floor Residential / Office space and an income producing Third Floor. Owned and well-maintained by the same family since the 1960's and steps away from The Red Lion Inn and former ''Alice's Restaurant''. Minutes to Tanglewood and all Berkshire Attractions. Ideal for Investment, Office, Residential or Retail use. A true 'once in a life-time opportunity' to be part of Stockbridge History.


16 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Rare opportunity to own a Berkshire Landmark. Known as ''the Antique Shop'' in Norman Rockwell's Main Street Painting, this iconic Building is famous worldwide. Classic Victorian Style with acres of charm. 3 Stories with on-site Parking. 3 'Main Street' Retail Spaces, a large (and vacant) Second Floor Residential/Office space and an income producing Third Floor. Owned and well-maintained by the same family since the 1960's and steps away from The Red Lion Inn and former ''Alice's Restaurant''. Minutes to Tanglewood and all Berkshire Attractions. Ideal for Investment, Office, Residential or Retail use. A true 'once in a life-time opportunity' to be part of Stockbridge History.


6 Photos
MACCARO REAL ESTATE

Prime Commercial Building ,Outstanding location on busy Route 7 next door to Price Chopper/Marshall's Shopping Center in Great Barrington Business District. Formerly a auto dealership the over 8,000 square foot building includes display area, office space, and work area with high ceiling and overhead doors.


12 Photos
BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

RARE BUILDING LOT ON THE BEAUTIFUL STOCKBRIDGE BOWL: Beautiful open water frontage with views across the deep section of the Bowl. Very special parcel. Building site perched above the lake to build your dream lake front home. There could be two homes on this site. Swimming, canoeing, boating, fishing from your waterfront. Very few parcels such as this will ever be available. Watch the Josh Billings from your own home. See concept schematics with the photos which are site specific for this lovely parcel. Over 100 feet of water frontage. More land available. Could be a lovely family compound.


19 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$2,200,000
2 BD | 6 BA
Residential - Single Family

Main Street Stockbridge Historic Property - Home to Williams & Sons Country Store and the picturesque shops in ''The Mews'', this building is an adored piece of Stockbridge's historic downtown landscape, and one of the few featured in Norman Rockwell's world renowned 1967 painting - Stockbridge Main Street at Christmas. With a total of 10 units, including a well established restaurant, six retail spaces, two apartments, and one office, this property provides consistent and profitable income with a flexible layout. Two of the retail spaces have Main Street entrances, while the other four and the restaurant are accessed from The Mews. With direct access from the Mews to the courtyard of the Red Lion Inn, these retail shops have plenty of foot traffic throughout each season.


19 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Main Street Stockbridge Historic Property - Home to Williams & Sons Country Store and the picturesque shops in ''The Mews'', this building is an adored piece of Stockbridge's historic downtown landscape, and one of the few featured in Norman Rockwell's world renowned 1967 painting - Stockbridge Main Street at Christmas. With a total of 10 units, including a well established restaurant, six retail spaces, two apartments, and one office, this property provides consistent and profitable income with a flexible layout. Two of the retail spaces have Main Street entrances, while the other four and the restaurant are accessed from The Mews. With direct access from the Mews to the courtyard of the Red Lion Inn, these retail shops have plenty of foot traffic throughout each season.


7 Photos
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.


32 Photos
BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

This property is a great opportunity for any investor. Currently being run as a twenty-four lane bowling alley with a bar, an arcade, a food stand, a Uhaul center and a mini golf course. You could easily add eight more bowling lanes to this property. Centrally located in Great Barrington so it is easy to get to CT, NY, the Turnpike, and all of Berkshire County. There is so much upside to this property. There is parking for 89 cars and a very high traffic count daily. This is the price for both the real estate and the business.

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