Home Buying

8 homes in the Berkshires for your ideal winter getaway

From Great Barrington to Williamstown, we've got you covered.

1554-north-pittsfield-ski-berkshires
This lake home at 1554 North St. in Pittsfield is on the market for under $400,000 and 7.1 miles from Bousquet Mountain Ski Area in Pittsfield. Apex Virtual Media

If you’re longing to hit the slopes without crossing state lines, the Berkshires are calling.

We have curated a list of eight Berkshire County homes where you can sit back and relax with your loved ones après ski:

9253 Mountainside Drive, Hancock

-Jessica Kahn
-Jessica Kahn
Jessica Kahn
-Jessica Kahn

$579,000

3 bedrooms, 2 full baths, 1 half bath 

1,666 square feet

Pets Unknown

Parking 2 spaces

Fee $653

⛷️1 mile from Jiminy Peak Mountain Resort in Hancock

***

37 Egremont Plain Road, Great Barrington 

Sam Backhaus Photography
Sam Backhaus Photography
Sam Backhaus Photography
Sam Backhaus Photography

$875,000

4 bedrooms, 2 full baths

3,284 square feet

1-acre lot

⛷️5.6 miles from Butternut Ski Area and Tubing Center in Great Barrington

***

33 Eleanor Road, Pittsfield

-Jessica Kahn
-Jessica Kahn
-Jessica Kahn
-Jessica Kahn

$529,000

4 bedrooms, 2 full baths

2,197 square feet 

0.29-acre lot

4.6 miles from Bousquet Mountain Ski Area in Pittsfield

***

85 E. Main St., Stockbridge

-Gavin Preuss/Home and Property Photography
-Gavin Preuss/Home and Property Photography
-Gavin Preuss/Home and Property Photography
-Gavin Preuss/Home and Property Photography

$875,000

4 bedrooms, 4 full baths

2,668 square feet

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0.80-acre lot

1.7 miles from Holiday Inn Club Vacations Oak n’ Spruce Resort in South Lee

***

1554 North St., Pittsfield

Apex Virtual Media
Apex Virtual Media
Apex Virtual Media
Apex Virtual Media

$399,000

2 bedrooms, 2 full baths

1,152 square feet

0.18-acre lot

7.1 miles from  Bousquet Mountain Ski Area in Pittsfield

***

580 S. Main St., Unit 408, Lanesborough

-Janinne Kuzdeba
Janinne Kuzdeba
Janinne Kuzdeba
Janinne Kuzdeba

$150,000

1 bedroom, 1 full baths

600 square feet

Pets Unknown

Parking 1 space

Fee $311 a month

8.7 miles from Jiminy Peak Mountain Resort in Hancock

***

160 Water St., Unit 209, Williamstown

Courtesy of Streamline Communities (staged)
Courtesy of Streamline Communities (staged)
Courtesy of Streamline Communities
Courtesy of Streamline Communities

$495,000

1 bedroom, 1 full bath

1,296 square feet

Pets Unknown

Parking 1 space

Fee $503 a month

13.5 miles from Jiminy Peak Mountain Resort in Hancock

***

148 Maple Ave., Unit 28, Great Barrington

-Rendering courtesy of Berkshire Hathaway Barnbrook Realty
-Rendering courtesy of Berkshire Hathaway Barnbrook Realty
-Rendering courtesy of Berkshire Hathaway Barnbrook Realty

$798,700

2 bedrooms, 2 full baths

1,141 square feet

Pets Unknown

Parking 1 space

Fee $375 a month

3.9 miles from Butternut Ski Area and Tubing Center 

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