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!

106 Cliffwood St Lenox MA 01240

Price$3,600,000

Est. Mortgage: $/month

MLS Number 217523

  • Single Family
  • Address 106 Cliffwood St
  • Village Berkshire - South
  • Year Built 1883
  • Parking Spaces 3

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

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$
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$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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.

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89 Cliffwood St Lenox MA 01240

Price$3,350,000

Est. Mortgage: $/month

MLS Number 227001

  • Single Family
  • Address 89 Cliffwood St
  • Village Berkshire - South
  • Year Built 1888
  • Parking Spaces 3

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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.

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1 Pinecroft Dr Lenox MA 01240

Price$3,250,000

Est. Mortgage: $/month

MLS Number 222383

  • Single Family
  • Address 1 Pinecroft Dr
  • Village Berkshire - South
  • Year Built 2004
  • Parking Spaces 3

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: 3.81% last updated on Jul 18, 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.

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51 Walker St Lenox MA 01240

Price$2,995,000

Est. Mortgage: $/month

MLS Number 225630

  • Single Family
  • Address 51 Walker St
  • Village Berkshire - South
  • Year Built 1912
  • Bedrooms 14

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 THE KINDERHOOK GROUP - STOCKBRIDGE

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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.

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51 Walker St Lenox MA 01240

Price$2,995,000

MLS Number 225629

  • Commercial
  • Village Berkshire - South
  • Year Built 1912
  • Square Feet 10,798
  • Bedrooms 14

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 Natalie Weissbrod and James Nugent of THE KINDERHOOK GROUP - PITTSFIELD

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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.

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114 Main St Lenox MA 01240

Price$2,695,000

MLS Number 223816

  • Commercial
  • Village Berkshire - South
  • Year Built 1790
  • Square Feet 9,986
  • List Date 07/05/2018

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: 3.81% last updated on Jul 18, 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.

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165 Kemble St # 17 Lenox MA 01240

Price$2,300,000

Est. Mortgage: $/month

MLS Number 216337

  • Condominium Residential - Condo/Townhouse
  • Address 165 Kemble St # 17
  • Middle School Lenox Memorial
  • High School Lenox Memorial
  • Village Berkshire - South

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. Now you can live in luxury at Canyon Ranch® in Lenox, Massachusetts, and enhance your life with greater health and vigor and longevity. There are only 19 beautifully appointed residences, currently under construction at the Canyon Ranch Residences at Bellefontaine. By living on the property, homeowners get full access every day of the year to the active, all-healthy environment that is the hallmark of the world's most celebrated wellness resort, Canyon Ranch. The nineteen residences are comprised of six different open floor plans with high ceilings and eco-friendly materials. Depending on the unit, there are beautiful terraces or balconies to enjoy the fresh country air. The residences feature hardwood flooring, gas fireplaces, custom designed cabinetry, spacious closets, and tile and stone baths. Connected to the resort via an enclosed walkway, there is climate-controlled underground parking and 24-hour security with a staffed, gated entrance. About Canyon Ranch in Lenox Make each day as action-packed, leisurely or inspiring as you need it to be. You'll have access to top Canyon Ranch fitness and health specialists, and spend your days surrounded by natural beauty. Plus just outside the gates lay the charming town of Lenox and rich cultural life of the Berkshires. Homeowners must purchase a membership package to the resort, and can customize their services. The Art of Relaxation: With nearly 100 spa services to choose among, booking a Canyon Ranch body wrap, facial, manicure, or your favorite salon service couldn't be easier. From Healing Energy for mind-body balance to massages and neuromuscular therapy to ease aches and pains, the therapeutic offerings will help you de-stress, reenergize and treat your body right. Personalized Medical Care: Pursue your healthiest life with the help of Canyon Ranch professionals right next door. The Canyon Ranch integrative health care approach encompasses your body, mind and spirit. The diverse wellness team inc...

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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.

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194 Pittsfield Rd Lenox MA 01240

MLS Number 225227

  • Commercial
  • Village Berkshire - South
  • Year Built 1973
  • Square Feet 21,168
  • List Date 10/27/2018

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: 3.81% last updated on Jul 18, 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.

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165 Kemble St. #17 -- Lenox MA 01240

Price$2,300,000

Est. Mortgage: $/month

MLS Number 220577

  • Single Family
  • Village Berkshire - South
  • Year Built 2017
  • Parking Spaces 1
  • Bedrooms 2

Unit #17. 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 Gladys Montgomery and Leslie Chesloff of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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.

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5 Pinecroft Dr Lenox MA 01240

Price$2,295,000

Est. Mortgage: $/month

MLS Number 225890

  • Single Family
  • Address 5 Pinecroft Dr
  • Village Berkshire - South
  • Year Built 2004
  • Parking Spaces 2

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: 3.81% last updated on Jul 18, 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.

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165 Kemble St, # 16 Lenox MA 01240

Price$2,100,000

Est. Mortgage: $/month

Pending

MLS Number 226533

  • Condominium Residential - Condo/Townhouse
  • Address 165 Kemble St, # 16
  • Middle School Lenox Memorial
  • High School Lenox Memorial
  • Village Berkshire - South

Imagine yourself in a home that is exquisite in every detail. Situated on the grounds of Canyon Ranch in the Berkshires-in a league of it's own as one of the world's most celebrated health and wellness resorts. One of only 19 units, this residence is being offered furnished and features a luxurious master suite, guest bedroom, spacious great room, kitchen, study/office, 2 fireplaces and a private balcony. The mandatory membership affords access to an extensive world of healthy living, wellness opportunities, outdoor sports and an invigorating, life enriching environment. All this, in the Berkshires of Western Massachusetts where culture, culinary arts and nature abound!

Listed by LENOX CANYON REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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.

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165 Kemble St # 8 Lenox MA 01240

Price$1,850,000

Est. Mortgage: $/month

MLS Number 216331

  • Condominium Residential - Condo/Townhouse
  • Address 165 Kemble St # 8
  • Middle School Lenox Memorial
  • High School Lenox Memorial
  • Village Berkshire - South

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. Now you can live in luxury at Canyon Ranch® in Lenox, Massachusetts, and enhance your life with greater health and vigor and longevity. There are only 19 beautifully appointed residences, currently under construction at the Canyon Ranch Residences at Bellefontaine. By living on the property, homeowners get full access every day of the year to the active, all-healthy environment that is the hallmark of the world's most celebrated wellness resort, Canyon Ranch. The nineteen residences are comprised of six different open floor plans with high ceilings and eco-friendly materials. Depending on the unit, there are beautiful terraces or balconies to enjoy the fresh country air. The residences feature hardwood flooring, gas fireplaces, custom designed cabinetry, spacious closets, and tile and stone baths. Connected to the resort via an enclosed walkway, there is climate-controlled underground parking and 24-hour security with a staffed, gated entrance. About Canyon Ranch in Lenox Make each day as action-packed, leisurely or inspiring as you need it to be. You'll have access to top Canyon Ranch fitness and health specialists, and spend your days surrounded by natural beauty. Plus just outside the gates lay the charming town of Lenox and rich cultural life of the Berkshires. Homeowners must purchase a membership package to the resort, and can customize their services. The Art of Relaxation: With nearly 100 spa services to choose among, booking a Canyon Ranch body wrap, facial, manicure, or your favorite salon service couldn't be easier. From Healing Energy for mind-body balance to massages and neuromuscular therapy to ease aches and pains, the therapeutic offerings will help you de-stress, reenergize and treat your body right. Personalized Medical Care: Pursue your healthiest life with the help of Canyon Ranch professionals right next door. The Canyon Ranch integrative health care approach encompasses your body, mind and spirit. The diverse wellness team inc...

Listed by Leslie Chesloff and Gladys Montgomery of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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