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 237753

  • 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 ((413) 528-4192)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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101 & 107 Yokun Avenue Lenox MA 01240

Lenox, MA101 & 107 Yokun Avenue

Price$5,500,000

Est. Mortgage: $/month

MLS Number 241180

  • Residential
  • Bathroom 8
  • Bedrooms 10
  • Square Feet 11,748
  • Acreage 44.88

Modern life in an elegant country houserenowned for its 19th century cottages, the berkshires (known as the inland newport) boasts numerous wonderful homes of the era. It's a rare thing indeed when one has been beautifully restored for modern life and enjoyment; rarer yet that it exists on its original 40+ acres with fantastic views, in the very heart of lenox, ma.The offering, representing the original configuration, includes 101 and 107 yokun ave. As well as mid-century modern, 95 yokun ave. Completed in 1929, the design of the main house reflects the english craftsmen homes of the early 1900's which focused on human-scaled grandeur.Also for sale as commercial property (#241178)

Listed by Selina Lamb of BIRCH PROPERTIES ((415) 515-3750)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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101 & 107 Yokun Avenue Lenox MA 01240

MLS Number 241178

  • Commercial
  • Acreage 44.88
  • Parking Spaces 10

Commercial opportunity renowned for its 19th century cottages, the berkshires (known as the inland newport) boasts numerous wonderful homes of the era. It's a rare thing indeed when one has been beautifully restored for modern life and enjoyment; rarer yet that it exists on its original 40+ acres with fantastic views, in the very heart of lenox, ma.The offering, representing the original configuration, includes 101 and 107 yokun ave. As well as mid-century modern, 95 yokun ave. Completed in 1929, the design of the main house reflects the english craftsmen homes of the early 1900's which focused on human-scaled grandeur. Also for sale as residential (#241180)

Listed by Selina Lamb of BIRCH PROPERTIES ((415) 515-3750)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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2 Kemble Street Lenox MA 01240

MLS Number 241173

  • Commercial
  • Acreage 3

Unlock a prime investment opportunity at the kemble. - located in lenox, ma, a vibrant downtown in the heart of the berkshires. This prestigious property, a renowned great estate, has been expertly transformed into a highly profitable luxury estate destination property. With grand gathering spaces, a well-equipped kitchen, mahogany bar, and 13 en-suite bedrooms, it easily accommodates parties and guests of 20+. Breathtaking views and manicured lawns with multiple terraced areas for outdoor gatherings. According to airdna, the kemble is #1 top grossing vacation rental in the berkshires and beyond. Excellent reviews. Financials available. Fully ada compliant

Listed by Cameron Volastro and Lori J Rose of STONE HOUSE PROPERTIES,LLC ((413) 232-4253)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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2 Kemble Street Lenox MA 01240

Lenox, MA2 Kemble Street

Price$5,485,000

Est. Mortgage: $/month

MLS Number 241190

  • Residential
  • Bedrooms 13
  • Square Feet 9,556
  • Acreage 3

The kemble, a registered ''great estate'' built in 1881 is located in the heart of the thriving downtown lenox business district. This classic colonial revival building has recently been refreshed with modern furnishings and decor, repurposed as a luxury rental property, and is being offered as a turn key operation. With grand gathering spaces, a well equipped kitchen, handsome mahogany bar, and 13 en-suite bedrooms, the property can easily accommodate groups of 20+ and is frequently rented to wedding parties, corporate retreat groups, and multi-generational family retreats. Stays can vary from a weekend to month or longer. Guests can choose to bring in cooks, bartenders, and waitstaff, if desired. Manicured lawns and gardens. Breathtaking views to the west. Fully ada compliant.

Listed by Lori J Rose and Cameron Volastro of STONE HOUSE PROPERTIES,LLC ((413) 232-4253)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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10 Richmond Mountain Road Lenox MA 01240

MLS Number 240440

  • Commercial
  • Acreage 21.4

The apple tree inn is a luxurious 34 room private b&b sited on over 20 spectacular rolling hillside acres with heavenly distant views of the scenic berkshire mountainscape. Ideal for weddings and large events, the main house, built in 1885, hosts 13 guest rooms, a handsome tavern/tap room, and a upscale 100+ seat restaurant. The lodge building was added in 1966 with 21 additional rooms, and the original carriage house is now a lovely 6 bedroom/2.5bath owners home. Unique in its location, guests can walk across the street to tanglewood for a show or simply enjoy the symphonic sounds from the front porch with dinner. Stockbridge bowl is only steps away as well as kripalu yoga center. Connecting to town sewer now. Call for a private tour!

Listed by James J Nugent of THE KINDERHOOK GROUP - PITTSFIELD ((413) 499-7490)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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135 Main Street Lenox MA 01240

MLS Number 237253

  • Commercial
  • Acreage 4.22
  • Parking Spaces 25

The garden gables inn is ideally located in the center of lenox on over 4+ private park-like acres with gardens, patios, mature trees and a heated 70' pool. Beautifully furnished and tastefully decorated, the inn consists of 15 unique rooms all with updated private baths, several with fireplaces and all fully air conditioned. The historic 1780 main building and attached cottage includes 9 guest rooms and 2 spacious suites. The separate orchard cottage includes 4 ensuite rooms with separate entrances, cathedral ceilings and fireplaces. There are 2 charming dining areas in the main building in addition to the library/music room and cozy ''sherry room'' both with fireplaces. The kitchen is well equipped with updated appliances and adjoins the private innkeeper's quarters.

Listed by Katie Soules and C. Randolph Thunfors of STONE HOUSE PROPERTIES,LLC ((413) 232-4253)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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135 Main Street Lenox MA 01240

Lenox, MA135 Main Street

Price$2,600,000

Est. Mortgage: $/month

MLS Number 237252

  • Residential
  • Bathroom 17
  • Bedrooms 16
  • Square Feet 8,722
  • Acreage 4.23

The garden gables inn is ideally located in the center of lenox on over 4+ private park-like acres with gardens, patios, mature trees and a heated 70' pool. Beautifully furnished and tastefully decorated, the inn consists of 15 unique rooms all with updated private baths, several with fireplaces and all fully air conditioned. The historic 1780 main building and attached cottage includes 9 guest rooms and 2 spacious suites. The separate orchard cottage includes 4 ensuite rooms with separate entrances, cathedral ceilings and fireplaces. There are 2 charming dining areas in the main building in addition to the library/music room and cozy ''sherry room'' both with fireplaces. The kitchen is well equipped with updated appliances and adjoins the private innkeeper's quarters.

Listed by C. Randolph Thunfors and Katie Soules of STONE HOUSE PROPERTIES,LLC ((413) 232-4253)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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$2,499,000

Est. Mortgage: $/month

Pending

MLS Number 241458

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

Living in this spacious home is like living in your own private resort....In addition to the stylish contemporary main house with 5 br, 4 full and 2 half baths there is also a lavish pool house with kitchen, living space, and full bath, cathedral ceilings and walls of ship lap, plus a state of the art outdoor kitchen...All under a beautiful pavilion overlooking the in ground gunite pool. Fabulous spaces to enjoy in all seasons with 4 fireplaces in the main house, 3 levels of living space with fully finished lower level (game room, family room bedroom & bath and wine cellar) that walks out to the hot tub , 2 fire pits (one gas, one wood) and spa. Beautifully private setting....Your vacation is in your back yard!

Listed by Mary Jo Piretti Miller of PIRETTI REAL ESTATE ((413) 637-1696x1)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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15 Franklin Street Lenox MA 01240

Lenox, MA15 Franklin Street

Price$2,450,000

Est. Mortgage: $/month

MLS Number 241012

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 4,424
  • Acreage 0.1

A unique opportunity to own two amazing residential units affording 2 bedrooms and full bath each with gourmet kitchens and soaring vaulted ceilings in walking distance to all things central to lenox. Just 2 miles from tanglewood, rentals would be the obvious choice in an already difficult rental market, or take advantage of an owner/operator dream living and working at the same location with an iconic, upscale italian steakhouse below you. Mixed use and turnkey ready to go, the current family owners are retiring after 35 years and are ready for a new start. Its location is in the robust central part of lenox with an extremely large outdoor dining patio and walking distance to most shopping attractions. 3 hours to nyc, 2.5 hours to boston; 30-60 minutes to most berkshire attractions!

Listed by Jeffrey M. Loholdt of WILLIAM PITT SOTHEBY'S - GT BARRINGTON ((413) 528-4192)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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15 Franklin Street Lenox MA 01240

MLS Number 240868

  • Commercial
  • Acreage 0.1
  • Parking Spaces 2

Upscale and updated restaurant of 35 years, owners retiring and ready for a fresh start. Enjoy loyal customers to the lenox area for dining / shopping and the seasonal influx of visitors to enjoy tanglewood. An extremely robust and heavily trafficked new england town located 2.5 hours from boston, 3 hours from nyc, and just 2 miles from tanglewood's main gate. Centrally located in the berkshires of western massachusetts affording an expansive outdoor dining patio in its quaint downtown area. The restaurant and residential spaces were completely renovated in recent years. The two modern apartments/condos on the top floor have 2 bedrooms with 1 full bathroom and souring vaulted ceilings: rental income and/or living space options for the new owners. Call today to preview.

Listed by Jeffrey M. Loholdt of WILLIAM PITT SOTHEBY'S - GT BARRINGTON ((413) 528-4192)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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4 Melville Court Lenox MA 01240

Lenox, MA4 Melville Court

Price$2,300,000

Est. Mortgage: $/month

MLS Number 240105

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 3,907
  • Acreage 0.78

Beautiful and pristine. Every aspect of this home is top-of-the-line. Every room is nicely sized and professionally furnished. And, the good news is, this outstanding property is being sold fully furnished. What you see is what you get...Quality furniture, linens, dishware, etc. Just bring your toothbrush and you are at home. But, there's more; within a mile to the center of lenox, a 10 minute bike ride to tanglewood, located on a cul-de-sac = no traffic. Nice view situations, professionally landscaped lawn and garden areas, 3 car garage, wrap around porch, town water, town sewer, natural gas & 400 amps. Five bedrooms and 4 1/2 bathrooms, 3 fireplaces, wolf appliances, in-home theater, sauna, steam shower, & exquisite library. Seeing is believing! Not many are made this good!

Listed by George Cain of WILLIAM PITT SOTHEBY'S - GT BARRINGTON ((413) 528-4192)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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 TourAsk A QuestionMore Details

Based on information submitted to BCMLS  as of September 30, 2023 . 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.