Our mobile site is optimized for smaller screens.

TRY IT NO THANKS

Lenox MA Real Estate

There are things to do, places to go and people to see year-round in Lenox. The historic, walkable town is as happening as it is charming, filled with events, hiking trails, and shopping spots. From the bucolic lawns of Tanglewood (the summer home of the Boston Symphony Orchestra) to world class theatre at Shakespeare & Company to restaurant-lined Church Street, there’s lots to do in Lenox. 

Browse current listings for sale in Lenox, MA. Don't hesitate to contact us with any of your questions.

Search SimplerRegister now to save your favorite listings and custom searches. Best of all, we'll email you when new properties that match your criteria hit the market

Click here to view homes for sale in Lenox.

106 & 114 Cliffwood, Lenox, MA 01240

Price$4,750,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217523

  • Listings
  • Beds 8
  • Baths 8
  • Sq Ft 8500
  • Acres 4.6

Unsurpassed 19th Century Queen Anne Style Berkshire Lenox ''Cottage'' restored and reinvented for today's most discriminating family wishing for an understatedly elegant, 'cool' and comfortable Twenty-First Century lifestyle. See attached document for all details. Shown by advance appointment only.

Listing courtesy of Mary Jane White and Nancy K. Kalodner of COHEN & WHITE ASSOCIATES

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

151 Walker, Lenox, MA 01240

Price$4,250,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 214688

  • Listings
  • Beds 10
  • Baths 10
  • Sq Ft 6934
  • Acres 12.76

Thistlewood - A classic Berkshire Cottage that has been meticulously restored & updated for a modern lifestyle. Designed by noted Boston architects Rotch & Tilden, the main house offers classic proportions and elegant details throughout. The grounds wrap the house with stately gardens, pool & poolhouse.

Listing courtesy of Dan Alden and Nick Geranios of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

51 Walker, Lenox, MA 01240

Price$3,995,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 216168

  • Listings
  • Beds 11
  • Sq Ft 10798
  • Acres 0.69
  • Exterior Features Bus-Public

Gilded Age ''Cottage'' Mansion built for Handel Proctor of Proctor & Gamble. Residence currently an upscale 11 room B&B with full restaurant, bar, Terrance lounge --all is PRISTINE condition. Grossing over $1M annually. Property has a newly built Owner/Manager 3 bedroom home -- elegant presentation in downtown Lenox -- All F, F&E, licenses and client details included in purchase price.

Listing courtesy of Bob Romeo of CENTURY 21 FRANKLIN STREET ASSOC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1 Pinecroft Drive, Lenox, MA 01240

Price$3,950,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218940

  • Listings
  • Beds 6
  • Baths 7
  • Sq Ft 7816
  • Acres 1.14

This exquisite home is in the Canyon Ranch subdivision of Pinecroft, walking distance to the wonderful village of Lenox. Ownership offers the option of membership to the world class health and wellness resort. The home is being offered furnished. Features include a gated and heated driveway and courtyard, heated in ground pool and fabulous fully equipped pool house with outdoor kitchen. The home boasts custom interior design, steam shower, gourmet kitchen and a wet bar in the living room. The lower level offers a sauna, climate controlled wine cellar, hi-def movie theatre and a magically nostalgic soda fountain!

Listing courtesy of Mike Taxter of LENOX CANYON REALTY

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

89 Cliffwood, Lenox, MA 01240

Price$3,950,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217574

  • Listings
  • Beds 6
  • Baths 8
  • Sq Ft 10333
  • Acres 3.17

SUPREMELY WELCOMING...One of Lenox's last 19th century Berkshire''cottages'' that has been meticulously restored and updated.

Listing courtesy of Deborah Levinson of Berkshire Property Agents

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

390&399 Under Mountain, Lenox, MA 01240

Price$3,650,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219053

  • Listings
  • Beds 7
  • Baths 9
  • Sq Ft 10629
  • Acres 106

Magnificent, superbly located 106-Acre Lenox estate property--a once-in-a-lifetime opportunity. At its centerpiece is a baronial Tudor mansion with impressive yet comfortable light-filled rooms, exquisite architectural details, 7 bedrooms, 11 fireplaces, indoor & outdoor swimming pools. The mansion is set on 11 acres. Across the way is an additional 95 acres, providing gorgeous open views of fields & mountains to the south. Abutting future Berkshire Natural Resources conservation land, this parcel contains several buildings: a stable (2BR, 1BA groom's quarters), a barn converted to residences (5BR, 2BA), and a one-story cottage (3BR, 2BA), on a building envelope limited to 10 acres. Minutes to Tanglewood and Lenox village, Shakespeare & Co., restaurants, and shops. See also MLS 213169.

Listing courtesy of Gladys Montgomery and Maggie C Merelle of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

165 KEMBLE, Lenox, MA 01240

Price$2,300,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 216335

  • Listings
  • Beds 2
  • Baths 3
  • Sq Ft 1790

Enjoy the ultimate luxury of the wellness lifestyle in this residence at Canyon Ranch, Lenox, one of the nation's premier spas. One of only 19 units, it features a spacious great room, master suite, kitchen, two fireplaces, private patio. Mandatory annual resort membership affords access to its unparalleled facilities, close to the cultural, culinary, and outdoor amenities in the Berkshires.

Listing courtesy of Gladys Montgomery and Marc Bachman of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

165 Kemble, Lenox, MA 01240

Price$2,300,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 216337

  • Listings
  • Beds 2
  • Baths 3
  • Sq Ft 2060

Enjoy the ultimate luxury of the wellness lifestyle in this residence at Canyon Ranch, Lenox, one of the nation's premier spas. One of only 19 units, it features a spacious great room, master suite, kitchen, two fireplaces, private patio. Mandatory annual resort membership affords access to its unparalleled facilities, close to the cultural, culinary, and outdoor amenities in the Berkshires.

Listing courtesy of Marc Bachman and Gladys Montgomery of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

9 Cliffwood, Lenox, MA 01240

Price$2,295,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217903

  • Listings
  • Beds 6
  • Baths 6
  • Sq Ft 5102
  • Acres 0.7

This gracious home exemplifies New England village living at it's best. Impeccably restored in 2008, this c.1805 center hall Colonial is just steps from every convenience. An extensive landscaping plan has created a completely private backyard oasis. Rare combination of privacy and in-town living. There are high ceilings in every room, wood floors throughout, 4 fireplaces & 6 spacious bedrooms

Listing courtesy of Suzanne Crerar of STONE HOUSE PROPERTIES, LLC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

165 Kemble, Lenox, MA 01240

Price$2,050,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 216336

  • Listings
  • Beds 2
  • Baths 3
  • Sq Ft 2060

Enjoy the ultimate luxury of the wellness lifestyle in this residence at Canyon Ranch, Lenox, one of the nation's premier spas. One of only 19 units, it features a spacious great room, master suite, kitchen, two fireplaces, private patio. Mandatory annual resort membership affords access to its unparalleled facilities, close to the cultural, culinary, and outdoor amenities in the Berkshires.

Listing courtesy of Gladys Montgomery and Marc Bachman of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

165 KEMBLE, Lenox, MA 01240

Price$1,950,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 216334

  • Listings
  • Beds 2
  • Baths 3
  • Sq Ft 1790

Enjoy the ultimate luxury of the wellness lifestyle in this residence at Canyon Ranch, Lenox, one of the nation's premier spas. One of only 19 units, it features a spacious great room, master suite, kitchen, two fireplaces, private patio. Mandatory annual resort membership affords access to its unparalleled facilities, close to the cultural, culinary, and outdoor amenities in the Berkshires.

Listing courtesy of Gladys Montgomery and Marc Bachman of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

165 KEMBLE, Lenox, MA 01240

Price$1,900,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 216332

  • Listings
  • Beds 2
  • Baths 3
  • Sq Ft 1790

Enjoy the ultimate luxury of the wellness lifestyle in this residence at Canyon Ranch, Lenox, one of the nation's premier spas. One of only 19 units, it features a spacious great room, master suite, kitchen, two fireplaces, private patio. Mandatory annual resort membership affords access to its unparalleled facilities, close to the cultural, culinary, and outdoor amenities in the Berkshires.

Listing courtesy of Gladys Montgomery and Marc Bachman of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.