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Stockbridge, Massachusetts: Country Homes, Houses, and Rural Real Estate

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$7,900,000 33 acres 8 Beds | 10 Baths | 10971 sqft
2 Glendale Middle Rd, Stockbridge, MA 01262 - Berkshire County

33 acres Stockbridge, MA

SOUTHMAYD FARM Gilded Age at its finest in Stockbridge. This 1870 Berkshire estate has been fully restored & is privately sited on 33+ acres within walking distance of town. Adjacent to the Stockbridge Golf Club & the Norman Rockwell Museum, the view includes a mile of Housatonic River frontage. The 8500' main house w/ 8 bedrooms is complemented by a carriage house, greenhouse/studio, pool,
Private Lake
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$5,885,000 11.84 acres
82 Interlaken Rd, Stockbridge, MA 01262 - Berkshire County

11.84 acres Stockbridge, MA

Rare opportunity to build your dream lake front home(s) on 11+ acres on Stockbridge Bowl. 373 ft of lake frontage. Property is 3 separate tax lots & 3 separate homes can be built. Ideal family compound. All of this, just a stone's throw from Tanglewood & very close to downtown Lenox, Stockbridge, Great Barrington, many cultural attractions & fun outdoor activities. Your lake front paradise awaits!
Private Lake
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$3,150,000 4.86 acres
Interlaken Rd, Stockbridge, MA 01262 - Berkshire County

4.86 acres Stockbridge, MA

Rare opportunity to build your dream lake front home on approximately 5 acres on Stockbridge Bowl. 315 feet of lake frontage. Only a stone's throw from Tanglewood & very close to downtown Lenox, Stockbridge, Great Barrington, many cultural attractions & fun outdoor activities. Your lake front paradise awaits!
Private Lake
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$2,900,000 36.4 acres 4 Beds | 7 Baths | 5952 sqft
79 Hawthorne St, Stockbridge, MA 01262 - Berkshire County

36.4 acres Stockbridge, MA

Spectacular 36-acre estate steps from Tanglewood's Hawthorne Gate. Enjoy the relaxed elegance of the impeccable New Traditional brick manor house, which combines 21st-century conveniences with exquisite top-quality custom details and graceful elements of another era. In a jewel-like setting with beautiful landscaping and views of emerald lawns and hills. Custom furnishings available separately.
Private Lake
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$2,350,000 4.2 acres
Interlaken Rd, Stockbridge, MA 01262 - Berkshire County

4.2 acres Stockbridge, MA

Rare opportunity to build your dream lake front home on 4 + acres on Stockbridge Bowl. Only a stone's throw from Tanglewood & very close to downtown Lenox, Stockbridge, Great Barrington, many cultural attractions & fun outdoor activities. Your lake front paradise awaits!
Private Lake
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$2,295,000 3.78 acres 7 Beds | 9 Baths | 7750 sqft
75 Main Road, Stockbridge, MA 01264 - Berkshire County

3.78 acres Stockbridge, MA

For the discerning buyer looking for a unique and eclectic private estate, the historic Santarella beckons. With roots woven deep into the heart of the Berkshires in Western Massachusetts, this is a magical fantasy getaway unlike any other. Set on 4 acres in the breathtaking Tyringham Valley, the property consists of four separate living structures, with the earliest built in the 1750's. The four buildings, totaling approximately 8,000 square feet include: an 1880's barn turned into The Gingerbread House, a 1750's Colonial 4-bedroom home, a 1900's post-and-beam sickle shed converted to a charming cottage, and the Honeymoon Silo, a romantic wooden structure boating views across the valley from its arched ceiling bedroom. The current own
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$1,995,000 3.78 acres 7 Beds | 9 Baths | 7750 sqft
75 Main Road, Stockbridge, MA 01264 - Berkshire County

3.78 acres Stockbridge, MA

For the discerning buyer looking for a unique and eclectic private estate, the historic Santarella beckons. With roots woven deep into the heart of the Berkshires in Western Massachusetts, this is a magical fantasy getaway unlike any other. Set on 4 acres in the breathtaking Tyringham Valley, the property consists of four separate living structures, with the earliest built in the 1750's. The four buildings, totaling approximately 8,000 square feet include: an 1880's barn turned into The Gingerbread House, a 1750's Colonial 4-bedroom home, a 1900's post-and-beam sickle shed converted to a charming cottage, and the Honeymoon Silo, a romantic wooden structure boating views across the valley from its arched ceiling bedroom. The current own
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$1,700,000 20.57 acres 6 Beds | 5 Baths | 4580 sqft
1 Mahkeenac Rd, Stockbridge, MA 01262 - Berkshire County

20.57 acres Stockbridge, MA

Extraordinary contemporary Shingle-Style residence on 20 acres with deeded rights to a private beach on Stockbridge Bowl. The design concept of four cabins connected by stone and glass passageways allows for private and public spaces for friends and family with lofty gathering rooms, a master with two bathrooms, multiple en-suite guest bedrooms, a bunk room, and a large screened porch summer room.
Private Lake
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$1,695,000 4.2 acres 5 Beds | 5 Baths | 4247 sqft
5 Stone Hill Rd, Stockbridge, MA 01262 - Berkshire County

4.2 acres Stockbridge, MA

Stunning 5BR Contemporary with sensational westerly views. Set on over 4 acres in a prestigious neighborhood, the casual elegance & gracious floor plan make this home the perfect Berkshire getaway. The well-designed great room, large country kitchen, & mahogany screened-in porch make for easy entertaining. Impeccably maintained & in move-in condition. Within walking distance of downtown Lenox.
Private Lake
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$1,489,000 8.4 acres 4 Beds | 4 Baths | 3100 sqft
Dugway Rd, Stockbridge, MA 01262 - Berkshire County

8.4 acres Stockbridge, MA

Secluded & private, yet conveniently located in scenic Stockbridge, w/in minutes drive of the Berkshires' premier cultural attractions. Magnificent setting offers tranquil retreat in stunning landscape. Beautiful natural features create an intimate sense of connection with nature & the seasons. Over 30 conservation acres & pvt walking trails ensure this beauty & tranquility will remain forever.
Private Lake
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$750,000 5.53 acres 3 Beds | 3 Baths | 1 sqft
Westdale Rd, Stockbridge, MA 01262 - Berkshire County

5.53 acres Stockbridge, MA

Custom Built by Waller Building Contractors, STONELEIGH COTTAGE, 3 BR, 2.5 bath, 1,975 sq' home on 5.53 acres, a seldom traveled country road, in the village of STOCKBRIDGE. 1st fl master BR suite, family room, kitchen, dining, attached garage, AC,BRAND NEW. Other designs are available on the Web at FrankBetzAssociates.Com. This enables buyer other custom choices to select.
Private Lake
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$749,000 2.5 acres 3 Beds | 3 Baths | 2742 sqft
6 Brookside Ln, Stockbridge, MA 01262 - Berkshire County

2.5 acres Stockbridge, MA

This shingle style contemporary with deeded access to STOCKKBRIGE BOWL was designed by Benjamin Hicks Stone in the Frank Lloyd Wright tradition. Located on a quiet lane with a private boat DOCK on the inlet. Features: chef's kitchen, exposed beams, 3 fireplaces, spacious great room , huge master bath w\ sauna, Zema tub. All bedrooms w/ French doors to balconies.
Private Lake
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$679,900 4.09 acres 3 Beds | 2 Baths | 2348 sqft
1 Old Tree Farm Rd, Stockbridge, MA 01262 - Berkshire County

4.09 acres Stockbridge, MA

Stockbridge gem! Craftsman quality home on 4+ peaceful/private acres. Top of the line appliances in the kitchen, with double ovens, granite counters. Separate side entrance leads to a mudroom/laundry/pantry space. Fireplace, oak floors throughout. Large screened porch overlooks forest and singing bird habitat! Bonus: above the 2C garage is a loft studio apartment with kitchen/bath, and skylights.
Private Lake
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$599,000 12.7 acres
9 Dugway Rd, Stockbridge, MA 01262 - Berkshire County

12.7 acres Stockbridge, MA

Secluded & private, yet conveniently located in scenic Stockbridge, w/in minutes drive of the Berkshires' premier cultural attractions. Magnificent setting offers tranquil retreat in stunning landscape. Beautiful natural features create an intimate sense of connection with nature & the seasons. Over 30 conservation acres & pvt walking trails ensure this beauty and tranquility will remain forever.
Private Lake
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$595,000 7 acres 3 Beds | 2 Baths | 2006 sqft
12 North Church St, Stockbridge, MA 01262 - Berkshire County

7 acres Stockbridge, MA

NEW PRICE..ACREAGE DOUBLED...With views to the West, this unique contemporary has the feel of a tree house. Living room with two-sided fireplace, dining room, updated kitchen, den and full bathroom are on the upper level. Three bedrooms & full bath on lower level with direct access to a patio. In a most convenient location minutes from Stockbridge and Tanglewood...a must see at this price!!
Private Lake