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!

319 Under Mountain Road Lenox MA 01240

Lenox, MA319 Under Mountain Road

Price$13,500,000

Est. Mortgage: $/month

MLS Number 244657

  • Residential
  • Bathroom 6
  • Bedrooms 7
  • Square Feet 13,261
  • Acreage 218.11

Pine needles built in 1903, this very private berkshire cottage epitomizes the area- past and present. Built in the arts and crafts style, surrounded by hundreds of acres of land, with magnificent southern views, one can enjoy nature, sports, and a relaxed lifestyle. Unspoiled, original detailing in place. Settle right in and be transported back to an earlier age. Paneled public rooms overlook the unspoiled views. Logias beckon to the out of doors. Seven bedrooms and 9 baths, two sleeping porches . The eat in kitchen offers space to gather, cook, enjoy the wildlife. This east wing also contains a butler's pantry, formal dining room, a summer dining room and one of the loggias.

Listed by Martha Piper of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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349 Old Stockbridge Road Lenox MA 01240

MLS Number 245298

  • Commercial
  • Acreage 11.9
  • Parking Spaces 100

A rare, once in a lifetime opportunity to own an original berkshire cottage! This spectacular property is situated on a 12-acre campus in lenox, overleigh was built in 1903 by samuel frothingham. Its history is detailed in the popular coffee table book ''the berkshire cottages-a vanishing era'', by carole owens. This property is located just 1.8 mi. From downtown lenox and within minutes to the most popular berkshire attractions. Designed by adams and warren out of nyc and built by joseph clifford's sons, a firm responsible for several cottage era constructions and renovations in berkshire county. A rare find, this property has deep roots in being used as an academic setting for several diverse private residential schools and has been well maintained throughout the years.

Listed by Timothy Gallagher of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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349 Old Stockbridge Road Lenox MA 01240

Lenox, MA349 Old Stockbridge Road

Price$3,100,000

Est. Mortgage: $/month

MLS Number 245369

  • Residential
  • Bathroom 30
  • Bedrooms 32
  • Square Feet 38,415
  • Acreage 11.9

A rare, once in a lifetime opportunity to own an original berkshire cottage! This spectacular property is situated on a 12-acre campus in lenox, overleigh was built in 1903 by samuel frothingham. Its history is detailed in the popular coffee table book ''the berkshire cottages-a vanishing era'', by carole owens. This property is located just 1.8 mi. From downtown lenox and within minutes to the most popular berkshire attractions. Designed by adams and warren out of nyc and built by joseph clifford's sons, a firm responsible for several cottage era constructions and renovations in berkshire county. A rare find, this property has deep roots in being used as an academic setting for several diverse private residential schools and has been well maintained throughout the years.

Listed by Timothy Gallagher of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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813 East Street Lenox MA 01240

Lenox, MA813 East Street

Price$2,995,000

Est. Mortgage: $/month

MLS Number 245332

  • Residential
  • Bathroom 9
  • Bedrooms 7
  • Square Feet 6,578
  • Acreage 4.92

Listed by Mary Jo Piretti-Miller of PIRETTI REAL ESTATE

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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55 Crystal Street Lenox MA 01240

Lenox, MA55 Crystal Street

Price$2,500,000

Est. Mortgage: $/month

MLS Number 244500

  • MultiFamily
  • Acreage 2
  • Year Built 1930

Unique 10-unit school building conversion in coveted lenox!Nestled atop a hill with distant views, this beautiful historic masonry building offers a unique opportunity as a 10-unit rental property + extra spaces.All units are currently rented; hot water and electric are individually metered. Great rental income and cap rate!Renovated apartments boast hardwood floors, spacious rooms, and many have superb views. Conveniently located only minutes from downtown lenox, the property features ample parking, coin-operated laundry, a boiler room, natural gas, and three storage rooms.2 acres of gently sloping lawn in front and a flat back lawn with ample parking.Great appreciation potential in an arguably the berkshires' most sought after town, this is an opportunity not to be missed!

Listed by Jared Kelly and Elle Villetto of WILLIAM PITT SOTHEBY'S - LENOX

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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 Street Lenox MA 01240

Lenox, MA165 Kemble Street

Price$2,300,000

Est. Mortgage: $/month

Pending

MLS Number 245154

  • Condo
  • Bedrooms 2
  • Bathroom 3
  • Year Built 2017
  • Square Feet 1,790

Enjoy canyon ranch living, the ultimate in luxury in this gated community, that offers gracious living with a focus on health and wellness. This two bedroom condo with home office has a split bedroom design with en-suite bathrooms. A chef's kitchen with marble counters and pantry opens onto the great room with a marble gas fireplace. The private balcony is lovely for morning coffee. A home office is a flex space that can serve as a den or extra guest space.The primary bedroom is en-suite with spa amenities in the marble bathroom, generous walk-in closet and marble gas fireplace. Mandatory annual resort membership affords access to its unparalleled facilities, close to the cultural, culinary, and outdoor amenities in the berkshires.

Listed by Leslie G Chesloff of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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751 East Road Lenox MA 01240

Lenox, MA751 East Road

Price$2,050,000

Est. Mortgage: $/month

Pending

MLS Number 244339

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,862
  • Acreage 23.99

This unique contemporary home sited on 24 wooded acres features a frank lloyd wright inspired architectural design and offers a stylish and private berkshire retreat with stunning views. Decks and patios off of every room seamlessly blend indoor and outdoor living to embrace the beautiful natural landscape. The living room features an array of windows w/ built in lighting and treatments, filling the space with natural light that brings out the warm tones of the cherry floors. The unique side roll desk showcases the master craftsmanship in the custom woodwork you encounter throughout the home. Lovely open kitchen with granite counters. The lower level features a sauna, screened porch and secret wine cellar. There is also room for guests in two additional bedrooms, full bath, and an

Listed by Conor Meehan of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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12 Bishop Estate Road Lenox MA 01240

Lenox, MA12 Bishop Estate Road

Price$1,499,000

Est. Mortgage: $/month

MLS Number 244635

  • Residential
  • Bathroom 5
  • Bedrooms 3
  • Square Feet 2,185
  • Acreage 4.31

Discover your dream home in the berkshires! This expansive and luxurious cape has been thoughtfully renovated throughout and offers an immaculate, light and bright home to love. New windows masterfully placed allow the beauty of the berkshires inside while enjoying the comforts of home. Renovations include exquisite porcelanosa tile, open floor plan, 5 full baths, a spectacular kitchen with commercial grade refrigerator, new windows, 400 amp electric and discreet ceiling mounted mini splits for your comfort. Nestled in desirable bishop estate across from canyon ranch, the property offers 4.31 acres of serene privacy while being just a short walk to the heart of the berkshires in downtown lenox. With only 17 homes on the property, you'll enjoy a peaceful and tranquil setting close to

Listed by Heather Gallagher of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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125 Old Stockbridge Road Lenox MA 01240

Lenox, MA125 Old Stockbridge Road

Price$1,499,000

Est. Mortgage: $/month

MLS Number 244280

  • Residential
  • Bathroom 6
  • Bedrooms 4
  • Square Feet 4,800
  • Acreage 4.07

A grand two-story foyer with a beautifully crafted staircase welcomes your entrance to this stately home. The spacious rooms are bathed in natural light. Wonderful details include two fireplaces, french doors, butler's pantry, back staircase, beautiful wood floors. Large eat-in kitchen and formal dining room. Gracious back porch off the family room looks out to the lovely meadow and woods. Impressive second floor balcony with lovely sitting area. Primary suite with office (could be a 5th bedroom). Second floor and lower-level laundries. Finished lower level with 3 additional rooms and full bath. Walk to all that shakespeare and company has to offer. Restaurants, shopping, canyon ranch, miraval, hiking and more are only mere minutes away.

Listed by Timothy Gallagher and Sheila Thunfors of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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22 Walker Street Lenox MA 01240
Pending

MLS Number 243066

  • Commercial
  • Acreage 0.14
  • Parking Spaces 4

3,899 square feet of retail / office space on walker st in the historic center of lenox. Currently comprised of 3 storefronts plus a 700 sq ft apt w/full kitchen, 2 1/2 baths. Upgraded mechanicals & roof. Main thoroughfare offering abundant car and foot traffic. Original details abound in this lovely 1895 structure. Tanglewood is a few minutes away along with all of the great lenox restaurants and shopping. Tremendous potential for multiple uses including restaurant, cafe, gallery,live/work and more!

Listed by Steven J. Weisz and Thom Garvey of WILLIAM PITT SOTHEBY'S - LENOX

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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257 W. Mountain Road Lenox MA 01240

Lenox, MA257 W. Mountain Road

Price$1,290,000

Est. Mortgage: $/month

Pending

MLS Number 244897

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,844
  • Acreage 4.94

Custom designed home for ease of living in a picture perfect setting near mass audobon! Beautifully designed and maintained with an open floor plan, first floor primary suite, great room with access to large trex deck, open dining/kitchen with access to the pretty screened porch, plus 2 additional first floor rooms for whatever your life style wishes...Den, office or music room? Hardwood floors throughout, propane fired gas heat/hot water plus central a/c, lovely architectural details and to top it off there is unfinished space if you need more! This home is priced to sell and in pristine condition, so you can move right in!! Enjoy the country setting and the lenox schools!

Listed by Mary Jo Piretti-Miller of PIRETTI REAL ESTATE

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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22 Woods Lane Lenox MA 01240

Lenox, MA22 Woods Lane

Price$999,000

Est. Mortgage: $/month

MLS Number 244752

  • Condo
  • Bedrooms 3
  • Bathroom 4
  • Year Built 2002
  • Square Feet 3,017

First time on the market this impeccably maintained townhome at fairwynds ii, is set on the grounds of miraval, a luxury wellness resort and spa. It is just off the golf course at the end of a cul-de-soc. Open living plan on the first floor is great for gathering with others or just having a nice airy feel. This home is thoughtfully designed with 3 en suite bedrooms and each guest room having it's own dedicated sitting room as well as access to the second floor deck. Never rented, original owner. Discounts at wyndhurst golf club and the gym/spa are available to fairwynds owners.

Listed by Suzanne Crerar of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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Based on information submitted to BCMLS  as of January 23, 2025 . All data is obtained from various sources and has not been, and will not be, verified by broker or BCMLS.  All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.