Lenox Real Estate

Lenox is the perfect place to live the life you want, where city culture meets country living. The county’s longest-held center for culture, Lenox in central Berkshire County is home to Tanglewood, The Mount, Shakespeare and Company, and several world-class resorts and restaurants amidst many lakes, rivers, and hiking trails. There are real estate options for everyone in Lenox, from those looking to relocate – maybe buy a vacation home – or perhaps find a gracious retirement community in a peaceful surrounding Lenox has it.

Search new real estate in the Berkshire town of Lenox, MA. Discover hundreds of current listings, including beautiful antique properties and single-family homes. Like what you see? Register with us to save your favorites, and receive notifications with similar properties are listed. Contact us today to see any of the homes below!

36 Pittsfield Rd Lenox MA 01240

MLS Number 228146

  • Commercial
  • Village Berkshire - South
  • Square Feet 24253
  • Year Built 1900

This unique property along route 7 in lenox lends itself to development with a combination of retail, entertainment, office and residential spaces. Its location has high visibility, two dedicated curb cuts including a signaled intersection and high traffic count (35,198 aadt in 2018). Property is within the gateway mixed use development overlay district which encourages intensive mixed use development approaches. It abuts the recently built courtyard marriott hotel and is directly across the street (at a signaled intersection) from the lenox commons - a successful development of retail and office with condominiums. The property totals 68+ acres, ~25 acres are in the c3a (commercial) zoning district + overlay above the balance (~43 acres) is in r1a (residential, 1 acre minimum).

Listed by STONE HOUSE PROPERTIES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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

36 Pittsfield Rd Lenox MA 01240

Price$3,800,000

Est. Mortgage: $/month

MLS Number 228149

  • Land
  • High School Lenox Memorial
  • Village Berkshire - South
  • Acreage 68.87
  • Square Feet 2,999,977

This unique 68 acre property along route 7 in lenox lends itself to development with a combination of retail, entertainment, office and residential spaces. Its location has high visibility, two dedicated curb cuts including a signaled intersection and high traffic count (35,198 aadt in 2018). Property is within the gateway mixed use development overlay district which encourages intensive mixed use development approaches. It abuts the recently built courtyard marriott hotel and is directly across the street (at a signaled intersection) from the lenox commons - a successful development of retail and office with condominiums. The property totals 68+ acres, ~25 acres are in the c3a (commercial) zoning district + overlay above the balance (~43 acres) is in r1a (residential, 1 acre minim

Listed by Aldrich Blair Team of STONE HOUSE PROPERTIES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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

106 Cliffwood St Lenox MA 01240

Price$3,600,000

Est. Mortgage: $/month

MLS Number 217523

  • Single Family
  • Bathroom 8
  • Address 106 Cliffwood St
  • Village Berkshire - South
  • Square Feet 8500

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.

Listed by COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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

89 Cliffwood St Lenox MA 01240

Price$3,350,000

Est. Mortgage: $/month

MLS Number 227001

  • Single Family
  • Bathroom 7
  • Address 89 Cliffwood St
  • Village Berkshire - South
  • Square Feet 10371

Best of the berkshires. Truly one of the most gracious homes exquisitely restored for modern life with family and friends. Designed by boston architects in the 1880's the unparalleled flow and understated charm of this home function as beautifully today as then. In superb condition, with excellent systems throughout. Large, caretaker apartment or home office too. Beautifully sited gunite swimming pool and mature gardens add to the sense of elegance, ease and privacy. , ideally located in lenox one can walk to town, tanglewood or hike in kennedy park and the numerous preserved woodlands. See documents for additional information and details.

Listed by STONE HOUSE PROPERTIES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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

1 Pinecroft Dr Lenox MA 01240

Price$3,250,000

Est. Mortgage: $/month

MLS Number 222383

  • Single Family
  • Bathroom 6
  • Address 1 Pinecroft Dr
  • Village Berkshire - South
  • Square Feet 7816

Enjoy the ultimate berkshire luxury lifestyle in this turn-key residence, with a preferred membership to canyon ranch resort, which is just steps away. This extraordinary home features a beamed great room with stone fireplace, formal dining room, gourmet eat-in kitchen, main-level master with fireplace & two walk-in closets, main level guest suite, four additional bedrooms, a lower level with vintage soda fountain, screening room, wine room & sauna, a deck & patio, heated swimming pool, & pool house containing a guest suite & full kitchen for outdoor entertaining. Impeccable details throughout, including a heated courtyard parking area; offered fully furnished. Ideally located near lenox village & the cultural, culinary & recreational amenities for which the berkshires are renowned.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

51 Walker St Lenox MA 01240

Price$2,995,000

MLS Number 225629

  • Commercial
  • Bathroom 13
  • Village Berkshire - South
  • Square Feet 10798
  • Year Built 1912

Iconic masterpiece in the heart of lenox village!Built in 1912 as a summer ''cottage'' for harley procter, of procter & gamble, the inn has hosted everyone from john williams, arthur fiedler and yo yo ma to paul newman and norman rockwell.The historic mansion is a centerpiece and crown jewel of the town located in the heart of lenox village.The 5 star rated inn boasts 11 luxurious bedrooms with private bathrooms, a full restaurant, bar and the only piano lounge in town. Expansion potential.3 bedroom owner home included. Turnkey and awaiting your fresh energies and ideas!

Listed by THE KINDERHOOK GROUP - PITTSFIELD

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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

51 Walker St Lenox MA 01240

Price$2,995,000

Est. Mortgage: $/month

MLS Number 225630

  • Single Family
  • Bathroom 15
  • Address 51 Walker St
  • Village Berkshire - South
  • Square Feet 10798

Iconic masterpiece in the heart of lenox village!Built in 1912 as a summer ''cottage'' for harley procter, of procter & gamble the home has been the site of some of the berkshires most lavish celebrations hosting everyone from arthur fiedler and yo yo ma to paul newman and norman rockwell.The elegant 5 star 11 bedroom mansion is a centerpiece and crown jewel of the town. A rare opportunity to enter the rich cultural heritage of lenox and the berkshires. Turn - key and awaiting your fresh energies and ideas! Expansion potential.Newly built 3 bedroom guest home included.

Listed by Natalie Weissbrod and James Nugent of THE KINDERHOOK GROUP - STOCKBRIDGE

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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

114 Main St Lenox MA 01240

Price$2,695,000

MLS Number 223816

  • Commercial
  • Village Berkshire - South
  • Square Feet 9986
  • Year Built 1790

Meadow place, a historic 9,986 square foot building in the lenox village was built in 1790 by col. Elijah northrup. This property is located on 3.2 level acres in lenox center and has 242 feet of frontage on main street. An incredible opportunity to own this property for redevelopment. Lots of possibilities for residential and/or commercial build-out. Truly, a rare opportunity.

Listed by LANCE VERMEULEN RE, INC., LENOX

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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

25 Cliffwood St Lenox MA 01240

Price$2,600,000

Est. Mortgage: $/month

MLS Number 228145

  • Single Family
  • Bathroom 10
  • Address 25 Cliffwood St
  • Village Berkshire - South
  • Square Feet 7393

Proudly presenting this newly refurbished 10 bedroom, 9 and half bath, privately owned, walk to town, historic lenox ''cottage''. Lovingly named osceola after the dramatic view of osceola mountain on the yokun ridge experienced upon entering the columned and balustraded front porch. Osceola mansion was designed by world renowned architects rotch and tilden in 1889 and commissioned by sarah pollock livingston. Today, this comfortable and beautifully appointed home features an entry foyer with a fireplace to warm your hands and toes after a winter's sleigh ride. Enter the grand hall which invites you into the living room to your right or draws your attention to the unique oval dining room to your left. Straight ahead is the picturesque outdoor covered 80 feet in length veranda

Listed by BERKSHIRE HOMES AND CONDOS

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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

194 Pittsfield Rd Lenox MA 01240

MLS Number 225227

  • Commercial
  • Village Berkshire - South
  • Square Feet 21168
  • Year Built 1973
  • Zoning Business

Days inn by wyndham is a 59 unit / 2 floor single structure building in the high traffic commercial zone of route 7&20 in lenox ma. A very attractive 3 acre site set high above the road with gorgeous westerly mountain views, excellent numbers, and up-to-date pip. There are, as well, 2-1 bedroom manager units and in-ground pool.It is close to all area attractions and is walking distance to kennedy park. A superb value awaiting your fresh ideas.

Listed by James Nugent of THE KINDERHOOK GROUP - STOCKBRIDGE

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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

5 Pinecroft Dr Lenox MA 01240

Price$2,295,000

Est. Mortgage: $/month

MLS Number 225890

  • Single Family
  • Bathroom 7
  • Address 5 Pinecroft Dr
  • Village Berkshire - South
  • Square Feet 5151

Magnificent turn-key, sun filled contemporary close to downtown lenox, tanglewood and the berkshires' world class cultural attractions. Canyon ranch membership is also available, with canyon ranch access via a groomed walking trail behind the property. The gourmet, state-of-the-art, eat-in kitchen & spacious great room make this home ideal for entertaining family & guests. Open floor plan, separate sleeping wing for family & guests, top of the line finishes throughout. The property is beautifully landscaped & the home is on town sewer & water & natural gas. Don't miss this dream opportunity live in the lap of luxury, in the heart of charming lenox!

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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

165 Kemble St Lenox MA 01240

Price$1,850,000

Est. Mortgage: $/month

MLS Number 220572

  • Single Family
  • Bathroom 3
  • Address 165 Kemble St
  • Village Berkshire - South
  • Square Feet 1683

Unit #8. 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.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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