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Berkshire County, Massachusetts Vacation Homes For Sale: Showing 1-15 of 159 .

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House in Otis, Berkshire County, Massachusetts,
$765,000

Set privately back from 200 feet of unspoiled shoreline, and commanding a spectacular westerly view ... View Details   Visit Website

House in Lenox, Berkshire County, Massachusetts,
$850,000

this new William Poole designed home has classic detailing with a flexible, modern floor plan.... View Details   Visit Website

House in Sandisfield, Berkshire County, Massachusetts,
$424,900

GREAT VACATION HOME- 5BR/2.5B contemporary salt-box. Spacious open plan with room for all, yet... View Details   Visit Website

Condo in Lee, Berkshire County, Massachusetts,
$325,000

Original Owner -- 1st time on market. A very upscale and unique unit (not at all typical). Wood... View Details   Visit Website

House in West Stockbridge, Berkshire County, Massachusetts,
$1,950,000

This fabulous new home has been exceptionally well planned and executed. Beginning with the great... View Details   Visit Website

Condo in Pittsfield, Berkshire County, Massachusetts,
$509,000

Public Remarks: Beautiful western mountain views. End unit with large wrap around deck and... View Details   Visit Website

House in Pittsfield, Berkshire County, Massachusetts,
$2,200,000

Fabulous lake front compound. Gorgeous mountain and lake views. Beautifully landscaped. Dock,... View Details   Visit Website

House in Sandisfield, Berkshire County, Massachusetts,
$269,500

Comfortable chalet style vacation home. Cozy w/ wood paneled walls and wood stove. 3 BR, +loft, 2... View Details   Visit Website

House in New Marlboro, Berkshire County, Massachusetts,
$1,950,000

Fabulous country estate on 100 +/- acres. In quite setting. Views, lake front, swimming pool,... View Details   Visit Website

House in Monterey, Berkshire County, Massachusetts,
$895,000

This well-designed home is sited for maximum privacy on 7.7 beautifully landscaped acres with... View Details   Visit Website

House in Southfield, Berkshire County, Massachusetts,
$419,000

Just an ideal summering - wintering - vacationing Berkshire retreat...perfect for the weary city... View Details   Visit Website

House in West Stockbridge, Berkshire County, Massachusetts,
$599,900

PRICED BELOW ASSESSMENT!!!Newly constructed custom designed luxury 'open floor plan' style home... View Details   Visit Website

Condo in Lee, Berkshire County, Massachusetts,
$325,000

Original Owner -- 1st time on market. A very upscale and unique unit (not at all typical of other... View Details   Visit Website

House in West Stockbridge, Berkshire County, Massachusetts,
$795,000

This light and bright, architect designed contemporary is ideally located near the top of Lenox... View Details   Visit Website

House in Pittsfield, Berkshire County, Massachusetts,
$239,900

Waterfront property on Onota Lake.Priced below assesed value. Enjoy one level living in this ranch... View Details   Visit Website

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