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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,
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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.
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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
$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.
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$1,695,000 3.2 acres 6 Beds | 5 Baths | 9477 sqft
29 Prospect Hill Rd, Stockbridge, MA 01262 - Berkshire County

3.2 acres Stockbridge, MA

Magnificently restored 18th century colonial in spectacular setting w/ awesome mountain views. 1st floor is graced by double parlors, multiple fireplaces, loads of sunlight, spacious living room, game room, 3-season enclosed porch plus 3 bedroom in-law suite w/ separate kitchen. Spectacular, level grounds w/ gunite pool, fruit trees & beautiful landscaping & stone work. Property also includes a
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$1,650,000 4.26 acres 3 Beds | 3 Baths | 2278 sqft
10 Train Hill Rd, Stockbridge, MA 01262 - Berkshire County

4.26 acres Stockbridge, MA

Commanding 4+ acres of manicured lawns, professional landscaping, privacy, heated gunite pool, wonderful stonework & tennis court surround this country Contemporary located within minutes to Tanglewood. Great Room w/vaulted ceiling & wall of glass, dramatic stone fireplace, open loft,gourmet kitchen, bedrooms w/stunning baths..a David Lanoue renovation with quality materials....a must see!!
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$1,489,000 8.4 acres 4 Beds | 4 Baths | 3100 sqft
7B 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.
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$895,000 25.99 acres 4 Beds | 4 Baths | 2900 sqft
4 Madisons Way, Stockbridge, MA 01262 - Berkshire County

25.99 acres Stockbridge, MA

This very private, warm and cozy contemporary on over 25 acres with views of Beartown State Forest is centrally located between Great Barrington and Stockbridge. Master bedroom and bathroom are on the first floor with two large bedrooms and bathroom on the second floor and a fourth bedroom and bathroom on the lower level. A three car garage with storage space above complete the renovations.
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$799,000 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.
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$750,000 5.53 acres 3 Beds | 3 Baths | 1 sqft
lot 2 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.
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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.
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$640,000 3.55 acres 3 Beds | 2 Baths | 2006 sqft
12 North Church St, Stockbridge, MA 01262 - Berkshire County

3.55 acres Stockbridge, MA

At the top of a grassy slope, nestled in the woods with wonderful 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.
$595,000 2.14 acres 4 Beds | 5 Baths | 3342 sqft
18 Lukeman Ln, Stockbridge, MA 01262 - Berkshire County

2.14 acres Stockbridge, MA

Ideal STOCKBRIDGE location....meticulously renovated, surrounded by 2+ usable flat park-like acres of landscaped privacy w/in-ground pool minutes from the Village & just a short drive to Tanglewood. Generous common living spaces, hardwood flooring, 2 fp's, eat-in country kitchen w/Viking appliances, master br en suite w/sitting rm, 3 guest br, stunning stone work, screened porch & AC..GREAT PRICE
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$525,000 16 acres 4 Beds | 2 Baths | 1654 sqft
13 Hill Rd, Stockbridge, MA 01262 - Berkshire County

16 acres Stockbridge, MA

Classic mid-century 1950's gem in a convenient Stockbridge location minutes from Main Street. Sleek lines, hard wood flooring, open staircase, eat in kitchen, masonry fireplace, interesting windows that let the outdoors and natural light in. First floor master bedroom, three guest bedrooms, open loft family room.....great house for family and entertaining!
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$345,000 2.1 acres 3 Beds | 2 Baths | 1130 sqft
58 Interlaken Rd, Stockbridge, MA 01262 - Berkshire County

2.1 acres Stockbridge, MA

CLOSE TO STOCKBRIDGE BOWL,in a quiet neighborhood, is this spacious charming 3 BR embanked ranch with master bedroom on main floor. Eat in kitchen with wooden cabinets and living room with fireplace.