Lenox, MA Homes

• 

  

  

  /7

  $1,800

  Pending

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft

  55 Crystal St Unit 7, Lenox, MA 01240

  Bright and inviting one-bedroom apartment with a spacious open kitchen, dining, and living area. Original wood floors and large windows add warmth, charm, and natural light throughout the space. Conveniently located in Lenox, close to shopping, restaurants, and Tanglewood. Heat and trash removal are included in the rent, and the building offers convenient coin-operated laundry facilities. Listed

  Christian Garner NOCHER REALTY

  55 Crystal St Unit 7, Lenox, MA 01240
• 

  

  

  /26

  $550,000

  Sold Jul 09, 2025

  170 Main St, Lenox, MA 01240

  • 1 Bed
  • 1 Bath
  • 597 Sq Ft
  • Built 1900

  Last Sold Summary

  • 22% Above List Price
  • $921/SF
  • 6 Days On Market

  Current Estimated Value $542,985

  Last Listing Agent Mary Jo Piretti PIRETTI REAL ESTATE

  170 Main St, Lenox, MA 01240
• 

  

  

  /43

  Est $1,034,589

  Not Listed For Sale

  49 Sargent Brook Rd, Lenox, MA 01240

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1973

  49 Sargent Brook Rd, Lenox, MA 01240

  Last Sold Summary

  • 21 Days On Market
• 

  

  

  /50

  $7,975,000

  • 8 Beds
  • 6.5 Baths
  • 9,364 Sq Ft

  399 Under Mountain Rd, Lenox, MA 01240

  Highwick Farm Manor House is a beautifully restored Berkshire Cottage originally built as a gentleman's equestrian estate. After years of meticulous renovation and thoughtful restoration this remarkable property stands now complete, showcasing exquisite craftsmanship and timeless grandeur. Highwick features lead-glass windows framing picturesque views, ten fireplaces, walnut paneling and pocket

  Molly Thomas COMPASS MASSACHUSETTS , LLC GB

  399 Under Mountain Rd, Lenox, MA 01240
• 

  

  

  /48

  $594,000

  Sold Sep 05, 2025

  296 Housatonic St, Lenox, MA 01240

  • 3 Beds
  • 2.5 Baths
  • 1,919 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Above List Price
  • $310/SF
  • 5 Days On Market

  Current Estimated Value $606,474

  Last Listing Agent Victoria Standring Lamacchia Realty, Inc. - Dalton

  296 Housatonic St, Lenox, MA 01240
• 

  

  /16

  Est $299,485

  Not Listed For Sale

  1 Morgan Manor Unit 7, Lenox, MA 01240

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft
  • Built 1968

  1 Morgan Manor Unit 7, Lenox, MA 01240

  Last Sold Summary

  • 39 Days On Market
• 

  

  /41

  $4,690,000

  $160K PRICE DROP

  • 13 Beds
  • 14 Baths
  • 9,510 Sq Ft

  2 Kemble St, Lenox, MA 01240

  The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental. The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests and has been a

  Cameron Volastro WILLIAM PITT SOTHEBY'S - LENOX

  2 Kemble St, Lenox, MA 01240
• 

  

  /24

  $425,000

  Sold Sep 22, 2025

  130 West St, Lenox, MA 01240

  • 3 Beds
  • 2 Baths
  • 1,375 Sq Ft
  • Built 1890

  Last Sold Summary

  • 19% Below List Price
  • $309/SF
  • 45 Days On Market

  Current Estimated Value $447,975

  Last Listing Agent Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  130 West St, Lenox, MA 01240
• 

  

  /17

  Est $514,996

  Not Listed For Sale

  15 Post Rd, Lenox, MA 01240

  • 3 Beds
  • 1.5 Baths
  • 1,439 Sq Ft
  • Built 1958

  15 Post Rd, Lenox, MA 01240

  Last Sold Summary

  • 5 Days On Market
• 

  

  /30

  $795,000

  • 3 Beds
  • 3 Baths
  • 2,218 Sq Ft

  200 Old Stockbridge Rd Unit Vanna 3, Stockbridge, MA 01262

  Welcome to The Vanna Building at Winden Hill. First time to the market in nearly thirty years this is an excuisite example of Period living. The sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three bedrooms

  Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

  200 Old Stockbridge Rd Unit Vanna 3, Stockbridge, MA 01262
• 

  

  /34

  $495,000

  Sold Jun 15, 2026

  31 Saint Ann's Ave, Lenox, MA 01240

  • 3 Beds
  • 2 Baths
  • 1,753 Sq Ft
  • Built 1900

  Last Sold Summary

  • 7% Below List Price
  • $282/SF
  • 85 Days On Market

  Current Estimated Value $539,515

  Last Listing Agent Amy Shufelt BERKSHIRE LISTINGS

  31 Saint Ann's Ave, Lenox, MA 01240
• 

  

  /31

  Est $750,161

  Not Listed For Sale

  17 Taconic Ave, Lenox, MA 01240

  • 4 Beds
  • 3 Baths
  • 2,740 Sq Ft
  • Built 1974

  17 Taconic Ave, Lenox, MA 01240

  Last Sold Summary

  • 2 Days On Market
• 

  

  /21

  $375,000

  Pending

  • 4 Beds
  • 2 Baths
  • 1,968 Sq Ft

  524 Walker St, Lenox Dale, MA 01242

  Come see one of the very few multi families available in Lenox!! One unit is vacant and move in ready. Perfect for owner occupied buyer or an investor looking for a nice multi family in the Berkshires!!

  David Houser NON-MEMBER / RECIPROCAL

  524 Walker St, Lenox Dale, MA 01242
• 

  

  /49

  $627,500

  Sold Sep 12, 2025

  7 Cedar Ln, Lenox, MA 01240

  • 4 Beds
  • 2.5 Baths
  • 2,265 Sq Ft
  • Built 1989

  Last Sold Summary

  • 11% Below List Price
  • $277/SF
  • 94 Days On Market

  Current Estimated Value $670,909

  Last Listing Agent Margaret Apkin WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  7 Cedar Ln, Lenox, MA 01240
• 

  

  /36

  Est $643,118

  Not Listed For Sale

  150 West St, Lenox, MA 01240

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1890

  150 West St, Lenox, MA 01240

  Last Sold Summary

  • 45 Days On Market
• 

  

  /28

  $279,000

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,140 Sq Ft

  74 Holmes Rd, Lenox, MA 01240

  Charming Cape in Lenox! Spacious eat in kitchen with access to a screened porch and large deck overlooking the private backyard, living room with wood flooring, quaint dining area, mudroom that connects to the garage, first floor bedroom and full bath. Second level has two bedrooms and finished family room in lower level walkout. Property has had several improvements made within the last 15 years

  Cortney Dupont COHEN & WHITE ASSOCIATES

  74 Holmes Rd, Lenox, MA 01240
• 

  

  /70

  $950,000

  Sold Dec 30, 2025

  257 W Mountain Rd, Lenox, MA 01240

  • 3 Beds
  • 2.5 Baths
  • 2,844 Sq Ft
  • Built 2002

  Last Sold Summary

  • 26% Below List Price
  • $334/SF
  • 156 Days On Market

  Current Estimated Value $1,009,053

  Last Listing Agent Nicole Moore KELLER WILLIAMS REALTY

  257 W Mountain Rd, Lenox, MA 01240
• 

  

  /18

  Est $340,842

  Not Listed For Sale

  15 Holmeswood Terrace, Lenox, MA 01240

  • 2 Beds
  • 1 Bath
  • 1,272 Sq Ft
  • Built 1957

  15 Holmeswood Terrace, Lenox, MA 01240

  Last Sold Summary

  • 66 Days On Market
• 

  

  /33

  $799,000

  Pending

  • 4 Beds
  • 3 Baths
  • 2,123 Sq Ft

  70 Galway Ct, Lenox, MA 01240

  Beautifully maintained and updated, this charming Cape offers 2 first floor bedrooms and baths, 2 second floor bedrooms with full bath in between, updated cherry kitchen wtih granite counters, formal dining and living and a family room with fireplace, vaulted ceilings and sliders to the large deck. Enjoy this wonderful ''walking neighborhood'', closet to Miraval Resort for pool, golf & fitness

  Mary Jo Piretti PIRETTI REAL ESTATE

  70 Galway Ct, Lenox, MA 01240
• 

  

  /14

  $396,200

  Sold Jul 21, 2025

  5 Morgan Manor Unit 9, Lenox, MA 01240

  • 2 Beds
  • 1 Bath
  • 938 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Above List Price
  • $422/SF
  • 5 Days On Market

  Current Estimated Value $395,638

  Last Listing Agent Mary Jo Piretti PIRETTI REAL ESTATE

  5 Morgan Manor Unit 9, Lenox, MA 01240
• 

  

  /41

  Est $448,260

  Not Listed For Sale

  18 Holmeswood Terrace, Lenox, MA 01240

  • 3 Beds
  • 3 Baths
  • 1,780 Sq Ft
  • Built 1965

  18 Holmeswood Terrace, Lenox, MA 01240

  Last Sold Summary

  • 39 Days On Market
• 

  

  /26

  $1,400,000

  • Land
  • 14.6 Acres
  • $95,890 per Acre

  286 Lee Rd, Lenox, MA 01240

  A once-in-a-lifetime opportunity to build your dream home on a large waterfront parcel in Lenox. This spectacular 14-acre property offers privacy, tranquility, and direct frontage on beautiful Laurel Lake while remaining just minutes from downtown Lenox, Tanglewood, shopping, dining, and all the Berkshires has to offer. Enter through the stone and metal electric gate, cross the stone bridge, and

  Katie Soules WILLIAM RAVEIS - BERKSHIRE

  286 Lee Rd, Lenox, MA 01240
• 

  

  /48

  $277,000

  Sold Jun 16, 2026

  7 Rolling Hills Unit 7-1, Lenox, MA 01240

  • 2 Beds
  • 3 Baths
  • 1,552 Sq Ft
  • Built 1976

  Last Sold Summary

  • 18% Below List Price
  • $178/SF
  • 32 Days On Market

  Last Listing Agent Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  7 Rolling Hills Unit 7-1, Lenox, MA 01240
• 

  

  /34

  Est $1,572,669

  Not Listed For Sale

  125 Old Stockbridge Rd, Lenox, MA 01240

  • 4 Beds
  • 6 Baths
  • 4,800 Sq Ft
  • Built 1989

  125 Old Stockbridge Rd, Lenox, MA 01240

  Last Sold Summary

  • 236 Days On Market
• 

  

  /29

  $299,000

  • 2 Beds
  • 3 Baths
  • 1,552 Sq Ft

  5 Rolling Hills Unit 4, Lenox, MA 01240

  Move right into this beautifully updated, light-filled condo offering the perfect blend of comfort and elevated style. Featuring an open floor plan, tall ceilings, and a beautiful renovated kitchen with newer appliances, this home is designed for effortless living and entertaining. Enjoy flexible bonus space in the finished lower level--ideal for a cozy lounge, home office, or guest retreat, plus

  Laiken Rapisarda Lamacchia Realty, Inc. - Dalton

  5 Rolling Hills Unit 4, Lenox, MA 01240
• 

  

  /58

  $4,000,000

  Sold Jun 10, 2026

  319 Under Mountain Rd, Lenox, MA 01240

  • 7 Beds
  • 8 Baths
  • 13,261 Sq Ft
  • Built 1903

  Last Sold Summary

  • 20% Below List Price
  • $302/SF
  • 167 Days On Market

  Current Estimated Value $5,041,615

  Last Listing Agent Jared Kelly WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  319 Under Mountain Rd, Lenox, MA 01240
• 

  

  /75

  Est $1,865,467

  Not Listed For Sale

  47 Fairwynds Dr, Lenox, MA 01240

  • 5 Beds
  • 5.5 Baths
  • 5,064 Sq Ft
  • Built 2001

  47 Fairwynds Dr, Lenox, MA 01240

  Last Sold Summary

  • 274 Days On Market
• 

  

  /78

  $2,100,000

  • 5 Beds
  • 4 Baths
  • 3,387 Sq Ft

  19 Cliffwood St, Lenox, MA 01240

  Iconic Lenox home: very rarely does a home with this historic integrity come on the market...now is your time to continue its legacy . Built in 1915 as one of the focal points of Cliffwood Street, this charming home has been updated for today's life style without sacrificing its significant architectural details. Beautiful common rooms including a dream kitchen with marble counters, formal Dining

  Mary Jo Piretti PIRETTI REAL ESTATE

  19 Cliffwood St, Lenox, MA 01240
• 

  

  /27

  $382,000

  Sold Feb 17, 2026

  6 Morgan Manor Unit 6-2, Lenox, MA 01240

  • 2 Beds
  • 2 Baths
  • 949 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Below List Price
  • $403/SF
  • 6 Days On Market

  Last Listing Agent Katie Soules WILLIAM RAVEIS REAL ESTATE

  6 Morgan Manor Unit 6-2, Lenox, MA 01240
• 

  

  /28

  Est $2,106,399

  Not Listed For Sale

  15 Blossom Hill, Lenox, MA 01240

  • 6 Beds
  • 4.5 Baths
  • 5,800 Sq Ft
  • Built 1999

  15 Blossom Hill, Lenox, MA 01240

  Last Sold Summary

  • 108 Days On Market
• 

  

  /5

  $385,900

  • Land
  • 15.91 Acres
  • $24,255 per Acre

  2 New Lenox Rd, Lenox, MA 01240

  Opportunity Knocks! Expansive Lenox parcel - currently 2 approved building lots (1.0 acre and 14.91 acres) w/ frontage on East Street and New Lenox Road. Seller has a proposed subdivision that would make it 4 lots (1.0 acre, 3.5 acres, 7.59 acres & 2.98 acres). Build your dream home or take advantage of this unbeatable development opportunity in highly sought after location! Water, sewer & gas on

  Sean Taylor MORESI REAL ESTATE PARTNERS

  2 New Lenox Rd, Lenox, MA 01240
• 

  

  /41

  $185,000

  Sold Sep 15, 2025

  12 Crystal St, Lenox Dale, MA 01242

  • 5 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1900

  Last Sold Summary

  • 7% Below List Price
  • $92/SF
  • 5 Days On Market

  Current Estimated Value $230,418

  Last Listing Agent Derek Greene The Greene Realty Group

  12 Crystal St, Lenox Dale, MA 01242
• 

  

  /23

  Est $324,922

  Not Listed For Sale

  38 Hillside Dr, Lenox, MA 01240

  • 2 Beds
  • 1 Bath
  • 952 Sq Ft
  • Built 1955

  38 Hillside Dr, Lenox, MA 01240

  Last Sold Summary

  • 6 Days On Market
• 

  

  /24

  $12,000

  • 2 Beds
  • 1 Bath
  • 1,032 Sq Ft

  33 Saint Anns Ave, Lenox, MA 01240

  Experience the ultimate August in Lenox! This lovely cottage is available to rent from August 1 - September 2, offering a prime location just steps from Main Street and minutes to Tanglewood. Inside, enjoy a light-filled spaces and cozy proportions. This 2-bed, 1-bath retreat features a first-floor bedroom, bathroom, and washer/dryer. The second bedroom is a loft space. Relax on the deck, grill,

  John Burns WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  33 Saint Anns Ave, Lenox, MA 01240
• 

  /2

  $2,500,000

  Sold May 20, 2026

  250 West St, Lenox, MA 01240

  • 6 Beds
  • 6.5 Baths
  • 4,289 Sq Ft
  • Built 2007

  Last Sold Summary

  • 6% Below List Price
  • $583/SF
  • 212 Days On Market

  Current Estimated Value $2,603,850

  Last Listing Agent Selina Lamb BIRCH PROPERTIES

  250 West St, Lenox, MA 01240
• 

  

  /33

  Est $530,194

  Not Listed For Sale

  17 Westminster Rd, Lenox, MA 01240

  • 3 Beds
  • 2 Baths
  • 1,542 Sq Ft
  • Built 1964

  17 Westminster Rd, Lenox, MA 01240

  Last Sold Summary

  • 64 Days On Market
• 

  

  /23

  $79,900

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft

  405 Pittsfield Rd Unit Lot F2, Lenox, MA 01240

  Totally renovated and move-in ready mobile home in Lenox! This 2-bedroom home is located on a quiet dead-end street in the Berkshire Mobile Park and offers a nice deck along with an ample side yard to enjoy. Shed in the back needs some repairs to the roof.

  Tanya Shepardson Lamacchia Realty, Inc. - Dalton

  405 Pittsfield Rd Unit Lot F2, Lenox, MA 01240
• 

  

  /20

  $210,000

  Sold Sep 29, 2025

  260 Pittsfield Rd Unit B11, Lenox, MA 01240

  • 2 Beds
  • 1.5 Baths
  • 950 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $221/SF
  • 12 Days On Market

  Current Estimated Value $221,471

  Last Listing Agent Amanda Kmetz ROBERTS & ASSOC. REALTY, INC

  260 Pittsfield Rd Unit B11, Lenox, MA 01240
• 

  

  /47

  Est $1,567,564

  Not Listed For Sale

  37 Fairwynds Dr, Lenox, MA 01240

  • 3 Beds
  • 3.5 Baths
  • 3,044 Sq Ft
  • Built 2011

  37 Fairwynds Dr, Lenox, MA 01240

  Last Sold Summary

  • 3 Days On Market
• 

  

  /29

  $359,000

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  37 Holmes Rd, Lenox, MA 01240

  Compare for value in the Lenox market! Sweet, petite, move-in ready ranch. Living room and bedrooms with hardwood floors; two nicely updated bathrooms; eat-in kitchen opens to spacious, private rear deck. Bonus features include the oversized two car garage, Buderus boiler for natural gas heat, and over a 1/2 acre of open sunny lawn. Easy access to shopping, dining and all of the Berkshires'

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  37 Holmes Rd, Lenox, MA 01240

Showing Results 41 - 80, Page 2 of 18