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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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$5,840,000

Est. Mortgage: $/month

MLS Number 238388

  • Residential
  • Bathroom 14
  • Bedrooms 13
  • Square Feet 9,556
  • Acreage 3

The kemble, a registered ''great estate'' built in 1881 is located within walking distance to the wonderful array of shops and restaurants in downtown lenox. This classic colonial revival building has recently been refreshed with modern furnishings and decor, repurposed as a luxury estate, and is being offered as a turn key property. With grand gathering spaces, a well equipped kitchen, handsome mahogany bar, and 13 en-suite bedrooms, the property can easily accommodate parties and guests of 20+. Property qualifies as a ''great estate'' allowing for special uses in the residential district. When not using the property, enjoy the benefits of short/long term rental. Manicured lawns and gardens, stone walls, breathtaking views to the west, and fully ada compliant.

Listed by Lori J Rose and C. Randolph Thunfors of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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 238371

  • Commercial
  • 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 C. Randolph Thunfors and Lori J Rose of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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$2,750,000

Est. Mortgage: $/month

MLS Number 237252

  • Residential
  • Bathroom 17
  • Bedrooms 16
  • Square Feet 8,688
  • Acreage 4.23

The garden gables, located in the center of lenox on over 4 very private park-like acres with gardens, patios, mature trees and a heated 70' pool, can be the ultimate family compound. Beautifully furnished and tastefully decorated with 16 unique bedrooms all with updated private baths, several with fireplaces and all fully air conditioned.The historic 1780 main building and attached eladesor cottage includes 12 spacious suites. The separate orchard cottage includes 4 ensuite rooms with separate entrances, cathedral ceilings and fireplaces.There are also 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 equipped with updated appliances. An extraordinary opportunity!

Listed by C. Randolph Thunfors and Michael Linden of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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 15

The garden gables inn is ideally located in the center of lenox on over 4 very 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 eladesor cottage includes 9 rooms and 2 spacious suites. The separate orchard cottage includes 4 ensuite rooms with separate entrances, cathedral ceilings and fireplaces.There are also 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 Michael Linden and C. Randolph Thunfors of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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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55 Crystal Street Lenox MA 01240

MLS Number 239181

  • Commercial
  • Acreage 2

Grand former lenox school building conversion ''crystal hill''. Now with 11 units: eleven 1-bedroom apartments. Boiler room, coin op laundry room, 3 storage rooms, updates include 2014 simplex alarm, 2015 re-roof, 2016 re-roof, 2019 apartments updated; 2021 new driveway; 2022 building newly painted. Current gross income $213,300.

Listed by Susan Calkins of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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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55 Crystal Street Lenox MA 01240

Lenox, MA55 Crystal Street

Price$2,700,000

Est. Mortgage: $/month

MLS Number 239066

  • MultiFamily
  • Acreage 2
  • Year Built 1930

Grand former lenox school building conversion ''crystal hill''. Now with 11 units: eleven 1-bedroom apartments. Boiler room, coin op laundry room, 3 storage rooms, updates include 2014 simplex alarm, 2015 re-roof, 2016 re-roof, 2019 apartments updated; 2021 new driveway; 2022 building newly painted. Current gross income $213,300.

Listed by Susan Calkins of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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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165 Kemble Street Lenox MA 01240

Lenox, MA165 Kemble Street

Price$2,400,000

Est. Mortgage: $/month

MLS Number 239487

  • Condo
  • Bedrooms 3
  • Bathroom 3
  • Year Built 2017
  • Square Feet 1,685

Experience the ease and pleasure of the luxury wellness lifestyle in this elegant three-bedroom, second-floor condominium with custom details, and west views--one of only 19 homes at canyon ranch, one of the nation's premier spas. Completed in 2017 to the highest standards, the building connects to the main lobby, spa, and dining rooms via an indoor walkway for year-round convenience. Required memberships in the resort and homeowners' association assure access to myriad activities, programs, select concierge services, and dining. The resort is also within easy reach of the cultural, culinary, and recreational offerings for which the berkshires and lenox are known. Offered turn-key. (seller may wish to exclude some primary suite furniture.)

Listed by Gladys Montgomery of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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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79 Reservoir Road Lenox MA 01240

Lenox, MA79 Reservoir Road

Price$2,265,000

Est. Mortgage: $/month

MLS Number 238752

  • Land
  • Acreage 12

Rare 12 acre lenox parcel with stunning long views extending over conserved land, and parson's marsh. Ready to build! Perfect location for a private estate or high end family compound.This cleared high view parcel has a septic system in place, municipal water and electric on street. Located 2 miles to both tanglewood's main gate and downtown lenox. Hiking/xc skiing, kennedy park with miles of maintained trails is just across the street as is the ma audubon bird sanctuary.Lot 1: $850,000 (5.39 acres +/-)lot 2: $1,650,000 (6.61 acres +/-)both parcels: $2,265,000 (12 acres)

Listed by Nikki Carchedi and Elisha Poirier of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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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13 Cliffwood Street Lenox MA 01240

Lenox, MA13 Cliffwood Street

Price$1,999,900

Est. Mortgage: $/month

MLS Number 239233

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,396
  • Acreage 0.51

In town lenox historical treasure the worthington house circa 1815. Live in one of lenox's most sought after neighborhoods on cliffwood street. Exceptional location is steps to lenox art, shopping and dining district as well as a walk to kennedy park hiking. Just minutes to tanglewood for the ideal berkshire setting. Incredible private retreat is created with mature landscaping surrounding the expansive rear yard and wrap around porch and rear mahogany deck. Experience the charm and history in the federal simple style antique kitchen, den and first of three fireplaces. Enter into formal living and dining fireplaced rooms with bold and vibrant colors. Floor to ceiling original windows fill the room with natural sunlight. Dr wothingtons heir bequest house to the church on the hill.

Listed by Tonia L. Scalise of WILLIAM PITT SOTHEBY'S - LENOX

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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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100 Old Stockbridge Road Lenox MA 01240

Lenox, MA100 Old Stockbridge Road

Price$1,675,000

Est. Mortgage: $/month

MLS Number 239422

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,199
  • Acreage 0.9

Easy access to the lenox village from this charming 1940's cape that's been tastefully expanded and updated while preserving all its character. Beautiful kitchen/great room concept with a playroom (or office or bedroom) above with cathedral ceilings. Formal living and dining rooms, fabulous office with built in desk/tech center (could also be a 1st floor bedroom suite as it has a full bath & closet), cozy den with access to the 3 season porch and trex deck beyond. Wonderfully private yard with goshen stone patio, fire pit, and walls all surrounding the beautiful in-ground pool. This home has been lovingly renovated and cared for and is just awaiting you to love it too!Enjoy the benefits of living in lenox, with land in stockbridge too (use both stockbridge bowl and laurel lake).

Listed by Mary Jo Piretti Miller of PIRETTI REAL ESTATE

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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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79 Reservoir Road Lenox MA 01240

Lenox, MA79 Reservoir Road

Price$1,650,000

Est. Mortgage: $/month

MLS Number 238754

  • Land
  • Acreage 6.61

Rare lenox parcel with stunning long views extending over conserved land, and parson's marsh. Ready to build! Perfect location for a private estate or high end family compound. This cleared high view parcel has a septic system in place, municipal water and electric on street. Located 2 miles to both tanglewood's main gate and downtown lenox. Hiking/xc skiing, kennedy park with miles of maintained trails is just across the street as is the ma audubon bird sanctuary.Lot 1: $850,000 (5.39 acres +/-)lot 2: $1,650,000 (6.61 acres +/-)both parcels: $2,265,000 (12 acres)

Listed by Nikki Carchedi and Elisha Poirier of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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 February 4, 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.