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Homes for sale in Stockbridge Massachusetts

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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,
$2,500,000 70.87 acres
49 & 51 Interlaken Rd, Stockbridge, MA 01262 - Berkshire County

70.87 acres Stockbridge, MA

Located across from the Stockbridge Bowl are 70 plus acres on picture perfect scenic land. Right on the Lenox/Stockbridge border, this property boasts absolute privacy all within walking distance to Tanglewood, Kripalu and many other cultural attractions. Walk across the street to the Stockbridge Bowl boat ramp. Build your dream house on a southern exposure hill surrounded by private hiking trails
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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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$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
$2,250,000 9.4 acres 5 Beds | 6 Baths | 4194 sqft
21 Prospect Hill Rd, Stockbridge, MA 01262 - Berkshire County

9.4 acres Stockbridge, MA

Exquisitely renovated late 1700 antique home w/ perfect proportions & amazing grounds. High ceilings, multiple fireplaces & historic details, flooded with light. Beautifully sited on over 9 acres on one of the most prestigious roads in the county. Barn, apple orchard, specimen trees, masterful stonework. Secluded and private heated Gunite pool w/ classic pool house & adventurous boardwalk.
$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.
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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.
$1,250,000 0.5 acres 3 Baths | 4806 sqft
48 Main St, Stockbridge, MA 01262 - Berkshire County

0.5 acres Stockbridge, MA

Known for generations as the Old Corner House this spectacular 1790s property is now available. The former home of The Norman Rockwell Museum this historic house has been converted to a beautiful office building. House features 13 separate offices, a large conference room, three bathrooms, an elevator and is handicapped accessible. Wonderful historic details have been maintained.
$825,000 25.99 acres 4 Beds | 4 Baths | 2536 sqft
4 Madison Way, Stockbridge, MA 01262 - Berkshire County

25.99 acres Stockbridge, MA

Over twenty five scenic acres with beautiful mountain views abound this newly renovated 4 bedroom cape. Located minutes from Great Barrington and Stockbridge this immaculate home has three levels of living. Enjoy the spacious open deck for outdoor grilling or your screened-in deck for dining with picturesque sunny views. Large three car garage with room above to finish for extra living quarters.
$750,000 24 acres
Westdale Rd, Stockbridge, MA 01262 - Berkshire County

24 acres Stockbridge, MA

This beautiful 24 arce lot would be great for you to build your dream home. It has been subdivided in 5 separate lots which could be a very good investment as well.
$599,000 10.6 acres 3 Beds | 3 Baths | 2018 sqft
5 Larrywaug Rd, Stockbridge, MA 01262 - Berkshire County

10.6 acres Stockbridge, MA

Paradise in Stockbridge! Looking for turn-key living on acreage? The original ranch has been transformed into a contemporary with quality materials inside and out! Spacious rooms, hardwood floors, cook's kitchen with stainless and granite; main floor master w bath, two guest bedrooms/bath, a/c, lower level in-law/office suite. Roof, windows, heating all updated. Ten acres, in-ground pool, too!
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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!!
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$584,000 20.2 acres
7 Dugway Rd, Stockbridge, MA 01262 - Berkshire County

20.2 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.
$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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$499,000 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.
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$489,000 8.4 acres
3A 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 and tranquility will remain forever.
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$479,000 14.9 acres
3E Dugway Rd, Stockbridge, MA 01262 - Berkshire County

14.9 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.
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$449,000 11.5 acres
3C Dugway Rd, Stockbridge, MA 01262 - Berkshire County

11.5 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.
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$439,000 5.06 acres 3 Beds | 3 Baths | 2444 sqft
9 CASTLE HILL Rd, Stockbridge, MA 01262 - Berkshire County

5.06 acres Stockbridge, MA

Take a Circa 1800's Farmhouse, attach a 20th Century apartment above a heated two-car garage, surround it with 5+ acres of manicured lawns and mature specimen trees and you have a situation perfect for a family compound, extended family or a private guest suite to enjoy year round or seasonally, minutes from the Main Street of Stockbridge. The original porch was converted to year round living
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$359,000 10.5 acres
3 Dugway Rd, Stockbridge, MA 01262 - Berkshire County

10.5 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.
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$339,000 6.8 acres
3D Dugway Rd, Stockbridge, MA 01262 - Berkshire County

6.8 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.
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$329,000 5 acres
3F Dugway Rd, Stockbridge, MA 01262 - Berkshire County

5 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.
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$319,000 7.1 acres
3B Dugway Rd, Stockbridge, MA 01262 - Berkshire County

7.1 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.
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$300,000 2 acres
Old Tree Farm Road, Stockbridge, MA 01262 - Berkshire County

2 acres Stockbridge, MA

Wooded, two-acre lot in an established Stockbridge neighborhood. Has sewer line, underground electric and cable; well site established. Close to Tanglewood and Stockbridge Bowl.
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$259,000 3.62 acres 2 Beds | 1 Bath | 1064 sqft
13A Glendale Middle Rd, Stockbridge, MA 01262 - Berkshire County

3.62 acres Stockbridge, MA

PRICED BELOW ASSESSMENT: Looking for a small place in the Stockbridge to call your own? This is it! Built in 2001 this two bedroom, one bath home is bright and easy to maintain. It has a full basement that could be finished and an oversized one car garage. Close to Tanglewood, Berkshire Festival, and Jacob's Pillow.
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$249,000 22 acres
6 Bean Hill Rd, Stockbridge, MA 01262 - Berkshire County

22 acres Stockbridge, MA

Tranquil setting on a quiet country road located between Stockbridge and Lenox. Within walking distance to Tanglewood and Stockbridge Bowl. Town sewer available on the road. Desirable area with beautiful homes. The listing price of this 22 acre parcel is below the assessment by the town.
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$165,000 2.12 acres
15 LAKE Dr, Stockbridge, MA 01262 - Berkshire County

2.12 acres Stockbridge, MA

A lightly wooded sloping two acre parcel with frontage on a gravel road off route 183. Recent successful perc. Potential water views. A short walk to deeded access to Stockbridge Bowl. Seller's are offering an excellent opportunity to purchase this lake area parcel with outstanding owner financing terms with ''no interest'' for three years...please call for details.
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$125,000 1.01 acres
46 Glendale Rd, Stockbridge, MA 01262 - Berkshire County

1.01 acres Stockbridge, MA

Beautiful acre+ land parcel with Easterly Mountain Views; cleared, level, easily accessible and within a short drive from Great Barrington or Stockbridge. Easy to build-on, the Perc Test and Soil Evaluation are in place.
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$80,000 1.07 acres
Rt 102 --, Stockbridge, MA 01262 - Berkshire County

1.07 acres Stockbridge, MA

Five SEPARATE lots! Lots #19,20,21,22 asking $80,000 EACH. Lot #24 asking $100,000. Lot #24 has water, slab and sewer accessibility. Lots can be sold together or separately. Lots 19, 20, 21, & 22 abut one another. Lot 24 is one lot away from the other four lots. See photo. Down Main St. Stockbridge, onto Church St., onto West Stockbridge Rd., (Rt. 102), Land will be on your right.