CountryHomesofAmerica.com
#1 in Rural Real Estate Online

Stockbridge Massachusetts Homes for sale - Page 1 of 2

24 photos
$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,
7 photos
$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!
7 photos
$3,150,000 4.86 acres
82B 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!
8 photos
$2,350,000 4.2 acres
82C 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!
36 photos
$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
30 photos
$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
23 photos
$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

STOCKBRIDGE BOWL PRIVATE BEACHWOOD BEACH MEMBERSHIP with this extraordinary contemporary Shingle-Style residence on 20 acres. 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 2 bathrooms, multiple en-suite guest bedrooms, a bunk room, and a huge screened porch.
27 photos
$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.
9 photos
$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.
$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.
8 photos
$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.
$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!
20 photos
$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!!
6 photos
$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.
21 photos
$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!
34 photos
$525,000 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
$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!
8 photos
$499,000 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.
7 photos
$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.
7 photos
$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.
7 photos
$459,000 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.
31 photos
$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
7 photos
$390,000 11.5 acres
4 Meadow Rd, Stockbridge, MA 01262 - Berkshire County

11.5 acres Stockbridge, MA

Major Price reduction!! This exceptional parcel of land will make a most desirable spot for your home minutes from Tanglewood and the Stockbridge Bowl. Gently sloping with distant western view...lightly wooded with some clearings. This acreage can be subdivided for a second house site if desired. Will build to suit, house plans available...call for details!!
7 photos
$389,000 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.
1 photos
$385,000 2.05 acres
82D Interlaken Rd, Stockbridge, MA 01262 - Berkshire County

2.05 acres Stockbridge, MA

Prime opportunity to build your dream home on 2 + acres in beautiful Stockbridge. Just a stone's throw from Tanglewood & Stockbridge, very close to downtown Lenox, Stockbridge, Great Barrington, many cultural attractions & fun outdoor activities.
7 photos
$379,000 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.
6 photos
$369,000 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.
1 photos
$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.
11 photos
$269,000 3.62 acres 2 Beds | 1 Bath | 1064 sqft
13A Glendale Middle Rd, Stockbridge, MA 01262 - Berkshire County

3.62 acres Stockbridge, MA

Looking for a small place in the Berkshires to call your own? This two bedroom, one bath home is bright and easy to maintain. It has a full basement that could be finished off and an oversized one car garage.
11 photos
$269,000 3.62 acres 2 Beds | 1 Bath | 1064 sqft
13A Glendale Middle Rd, Stockbridge, MA 01262 - Berkshire County

3.62 acres Stockbridge, MA

Looking for a small place in the Berkshires to call your own? This two bedroom, one bath home is bright and easy to maintain. It has a full basement that could be finished off and an oversized one car garage.
/* */