Luxury Homes

Search the latest luxury homes for sale in Stockbridge, MA with McLean Realtors, the Berkshires’ local real estate experts. Discover a variety of listings for sale, and feel free to contact us with any questions or to schedule a showing. Save your favorite listings when you register with us, and we can send you email updates when properties that match your criteria are posted.

2 Glendale Middle, Stockbridge, MA 01262

Price$6,875,000

Est. Mortgage: $/month

Pending

MLS Number 215244

  • Listings Residential
  • Address 2 Glendale Middle Rd
  • Bedrooms 8
  • Bathroom 10
  • Square Feet 10971

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, , 3 bedroom guest house, barn complex and paddocks, a magnificent maze, and additional formal gardens. See documents file for detail of each building, room and floor plan.

Listed by Cindy Welch and Keith Ross of LANDVEST, INC.

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McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

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$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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79 Hawthorne, Stockbridge, MA 01262

Price$2,750,000

Est. Mortgage: $/month

MLS Number 219710

  • Listings Residential
  • Address 79 Hawthorne St
  • Bedrooms 4
  • Bathroom 7
  • Square Feet 5952

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.

Listed by Gladys Montgomery and Maggie Barry of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

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$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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21 Prospect Hill, Stockbridge, MA 01262

Price$2,250,000

Est. Mortgage: $/month

MLS Number 217160

  • Listings Residential
  • Address 21 Prospect Hill Rd
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 4194

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.

Listed by Christian G Deckert of BERKSHIRE PROPERTY AGENTS

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McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

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$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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8 Stone Hill, Stockbridge, MA 01262

Price$2,240,000

Est. Mortgage: $/month

MLS Number 220955

  • Listings Residential
  • Address 8 Stone Hill Rd
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 4476

Living is easy in this impressive Stockbridge contemporary located on a fantastic plot of land with western view, blazing sunsets and heated pool all minutes from Tanglewood. Three levels of thoughtful living spaces with soaring two level Great Room open to informal dining and gourmet kitchen make the perfect gathering space around the fireplace on cool fall days while taking in the view from the walls of glass. Wander out to the extensive decking on those warm fall days that overlook the heated pool and look forward to making memories of Berkshire summers. The master bedroom, with "His & Her" baths, are on the main level; guests have their own floor. Lower level family room with fireplace and galley kitchen with bar make this wonderful family space most convenient for exercising,

Listed by Mary Jane White and Brandon White of COHEN & WHITE ASSOCIATES

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McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

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$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1 LAHEY CROSSROAD, Stockbridge, MA 01262

Price$1,895,000

Est. Mortgage: $/month

MLS Number 215909

  • Listings Residential
  • Address 1 Lahey Crossroad --
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4847

Total privacy on 22 acres with back country roads for strolling. Within a couple of miles you will find fresh baked bread, a pub, the Norman Rockwell Museum, the Berkshire Botanical Garden and Chesterwood. And within 6 or 7 miles you will find the boat ramp at Stockbridge Bowl, Kripalu Yoga Center and Tanglewood. Wonderful setting with mature trees, landscaped gardens, extensive stonework and in-gorund pool. Beautifully designed home with dramatic two-story foyer, spacious living room, exceptional library, dining room and porch each with fireplace, country kitchen. Great wall space to display art. A covered colonnade joins the main house to the guest house with 2 bedrooms, bath and gathering room plus a large office/studio and a garden workshop. A FABULOUS place to live! A winding driveway through dappled sunlight and mature trees leads to the picturesque setting for this exceptional home. The house is surrounded by expansive landscaped gardens, with seasonally blooming perennials, rock garden plants, rare species, and extensive stonework. Enter the gracious spacious two-story foyer. Step down into the sun filled living room with fireplace. The exceptional library is lined with bookshelves. Dining room has its own fireplace as does the adjacent dining porch. The large eat-in country kitchen has a wall of windows looking out to the gardens. The butler's pantry and the large back mudroom provide terrific work spaces for household activities and entertaining. Complete with wine cellar in the basement. The flow of spaces is excellent and there are multiple accesses to the outdoors. On the second floor is the master suite with a sunny southern exposure, his and her walk-in closets with custom cabinetry, and a grand European styled bath. Two other bedrooms, one with a fireplace, open onto an open balcony porch overlooking the gardens. The rooms are beautifully sized and have a dedicated bath. Two more bedrooms with a sitting area are easily available just steps away in the charming guesthouse reached by a covered stone colonnade. This building also contains a large open office space that could be used as a family game space or studio. On the lower of the three levels is a garden studio/workshop. Through the gardens and stone paths is the in-ground swimming pool for summer enjoyment. Take walks on the country back roads, stroll to Chesterwood. Terrific location near the Norman Rockwell Museum and the Berkshire Botanical Garden. 7 miles to Great Barrington and 6 miles to Tanglewood.

Listed by Martha Piper and Sheila Thunfors of STONE HOUSE PROPERTIES, LLC

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McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1-A Bean Hill, Stockbridge, MA 01262

Price$1,750,000

Est. Mortgage: $/month

MLS Number 220949

  • Listings Residential
  • Address 1-A Bean Hill Rd
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3719

Exquisite home with winter views. Walk to the town beach to your stored kayaks from this open, bright and beautiful contemporary home. Wide open plan with bamboo flooring, two fireplaces, a beautiful first floor master bedroom and glorious master bathroom. Top of the line materials, a gourmet kitchen with a center island, beautiful granite counters and stainless steel appliances. Sit on the peaceful screened porch and listen to the music from Tanglewood just minutes away. Minutes to the downtowns of Stockbridge, Lenox, Great Barrington, and West Stockbridge This is a perfect home in a perfect Stockbridge location. Please see supplement for specifications.

Listed by Maureen White Kirkby of BARNBROOK REALTY, INC.

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McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

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Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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11 Wheatley, Stockbridge, MA 01262

Price$1,690,000

Est. Mortgage: $/month

MLS Number 212585

  • Listings Residential
  • Address 11 Wheatley Dr
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 4345

Quiet, serene and beautiful - a retreat or a place for magnificent entertaining - it's your choice. One of a kind home, built by the current owners in 1994 & lovingly maintained. Enter the foyer & take in a view across the great room through two stories of windows to the gunite pool, Lily Pond and views beyond. Living room, 1st floor master bedroom, atrium dining all take in the view. A custom paneled office is nestled away for privacy. The second floor offers three more bedrooms & 2 full baths. The lower lever has spacious media & game rooms & extra all purpose rooms with a full bath. Your dock on Lily Pond is great for canoes & kayaks. Less than 5 minutes to Lenox and Stockbridge. Deeded rights to private beach on Stockbridge Bowl.

Listed by Anthony C Blair and Suzanne Crerar of STONE HOUSE PROPERTIES, LLC

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McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5 Stone Hill, Stockbridge, MA 01262

Price$1,595,000

Est. Mortgage: $/month

MLS Number 219969

  • Listings Residential
  • Address 5 Stone Hill Rd
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4247

Set on 4.2 acres in a prestigious neighborhood, this 5 bedroom contemporary has sensational pastoral views overlooking a farm and two mountain ridges. A spacious, open floor plan, large country kitchen, privately placed ensuite guest rooms and expansive patio and porch facing unending views, make this home perfect for entertaining. Within walking distance to Lenox for shopping and dining.

Listed by Sheila Thunfors of STONE HOUSE PROPERTIES, LLC

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McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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7B Dugway, Stockbridge, MA 01262

Price$1,489,000

Est. Mortgage: $/month

MLS Number 219084

  • Listings Residential
  • Address 7B Dugway Rd
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3100

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.

Listed by Marc Bachman of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2 Lincoln, Stockbridge, MA 01262

Price$1,275,000

Est. Mortgage: $/month

MLS Number 220671

  • Listings Residential
  • Address 2 Lincoln Ln
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2971

''A Merchants Home'' The Best of New World and Old. Inspired French Country Estate this exceptional home tells a story. A private driveway leads to this remarkable residence. The first floor of this lovely house includes a Chef's kitchen with Separate eating area, Office, Library with Fireplace, Laundry Room, Powder room, Mud room, Screen Porch, with a Formal Living Room with Fireplace. Temperature controlled master wine cellar. The second floor offers the Master Bedroom with sitting area, large bath and River views, 2 guest rooms with en suite bath, one large fireplace.2 Lincoln Lane is truly an address of prestige, located within walking distance to many restaurants and cultural attractions. Separate charming guest house. Private entrance. The grounds features a landscape plan thoughtfully designed by Windy Hill. This beautiful home and grounds make this property a must see. The privacy, space, and proximity to both river and main street Stockbridge make it a one-of-a kind opportunity. This location is secluded and quiet as though living in the country yet close enough to walk to town and get a cup of coffee. 2.5 hours to NYC and 2 hours to Boston . 45 minutes to Hartford Int'l Airport or Albany Int'l Airport.

Listed by Maggie C Merelle of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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McLean Realtors
68 Main Street
Lenox MA, 01240
Office: 413-637-9070

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details