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

Lenox, MA36 Pittsfield Rd

Price$3,800,000

Est. Mortgage: $/month

MLS Number 228149

  • Land
  • High School Lenox Memorial
  • Village Berkshire - South
  • Acreage 69
  • 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 STONE HOUSE PROPERTIES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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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 Aldrich Blair Team of STONE HOUSE PROPERTIES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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106 Cliffwood St Lenox MA 01240

Lenox, MA106 Cliffwood St

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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

Lenox, MA89 Cliffwood St

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: 3.69% last updated on Nov 7, 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

Lenox, MA51 Walker St

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 THE KINDERHOOK GROUP - STOCKBRIDGE

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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

Lenox, MA51 Walker St

Price$2,995,000

MLS Number 225629

  • Commercial
  • Co Listing Office Id 810
  • Bathroom 13
  • 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 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

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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25 Cliffwood St Lenox MA 01240

Lenox, MA25 Cliffwood St

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: 3.69% last updated on Nov 7, 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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115 New Lenox Rd Lenox MA 01240

Lenox, MA115 New Lenox Rd

Price$2,350,000

Est. Mortgage: $/month

MLS Number 228886

  • Single Family
  • Bathroom 3
  • Address 115 New Lenox Rd
  • Village Berkshire - South
  • Square Feet 5870

''High Meadows'' is a grand and luxurious 20 acre estate with spectacular sweeping views of October Mountain. Set high upon a private knoll, the chic and newly renovated 4 bedroom contemporary home features a gorgeous great room, wine cellar, game room, exercise room, billiards room, sun room, 3 fieldstone fireplaces and new outdoor bar/kitchen to mention just a few.A 27 head sprinkler system services meticulous specimen landscaping with master gardens, pear and apple orchards. There are also groomed walking trails and perhaps best of all, not only a lovely gunite pool/spa area, but a crystal clear 2 acre swimming and trout pond with a sophisticated pump system! Call for a private tour.

Listed by James Nugent of THE KINDERHOOK GROUP - STOCKBRIDGE

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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
  • 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: 3.69% last updated on Nov 7, 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 # 14 Lenox MA 01240

Lenox, MA165 Kemble St # 14

Price$2,300,000

Est. Mortgage: $/month

MLS Number 229116

  • Condominium Residential - Condo/Townhouse
  • Address 165 Kemble St # 14
  • Middle School Lenox Memorial
  • High School Lenox Memorial
  • Village Berkshire - South

Discover luxury living and a wellness lifestyle at their finest in this elegant two-bedroom second-floor unit with gorgeous custom details and beautiful westerly views at Canyon Ranch, Lenox. Canyon Ranch Living defines the quintessential luxury lifestyle in the Berkshires. Completed in 2017 to the highest standards, the 19-unit building connects to the main lobby, spa, and dining rooms via an indoor walkway for year-round convenience. As a requirement of purchase, memberships in the Homeowners Association and Resort ensure access to myriad activities and programs, select concierge and spa services, fine dining, and the cultural and recreational offerings for which Canyon Ranch and the Berkshires are so well known. Custom furnishings are available for a turn-key purchase.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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

Lenox, MA5 Pinecroft Dr

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: 3.69% last updated on Nov 7, 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

Lenox, MA165 Kemble St # 8

Price$1,850,000

Est. Mortgage: $/month

MLS Number 216331

  • Condominium Residential - Condo/Townhouse
  • Co Listing Office Id 110139
  • Address 165 Kemble St # 8
  • Middle School Lenox Memorial
  • High School Lenox Memorial

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: 3.69% last updated on Nov 7, 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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