3,261

Lenox, MA Homes

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    • /26

      Est $693,211 Not Listed For Sale

      143 W Mountain Rd, Lenox, MA 01240

      • 3 Beds
      • 2 Baths
      • 1,747 Sq Ft
      • Built 1978
      143 W Mountain Rd, Lenox, MA 01240

      Last Sold Summary

      • 9% Above List Price
      • $363/SF
      • 3 Days On Market
      • Last Sold Price $634,000
      • Oct 18, 2023

      Last Listing Agent Barney Stein LANCE VERMEULEN RE, INC

  • /14

    $358,000

    • 2 Beds
    • 1 Bath
    • 968 Sq Ft

    4 Morgan Manor Unit 4, Lenox, MA 01240

    Lenox in-town condo.....ready for a new owner, need a close location to Tanglewood, Shakespeare and Company, The Mount, Venfort Hall, Kennedy Park, Pleasant Valley Wildlife Sanctuary? Well this is the perfect location!2 bedrooms, 1 full bath, wood floors and carpeted bedrooms, great light ....fully applianced kitchen....Easy to show!

    Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    4 Morgan Manor Unit 4, Lenox, MA 01240
  • /61

    $1,750,000 Sold Sep 24, 2025

    11 Blossom Hill, Lenox, MA 01240

    • 4 Beds
    • 4.5 Baths
    • 4,349 Sq Ft
    • Built 1999

    Last Sold Summary

    • $402/SF
    • 22 Days On Market

    Current Estimated Value $1,753,854

    Last Listing Agent Paula McLean PAULA MCLEAN REALTORS INC.

    11 Blossom Hill, Lenox, MA 01240
    • /58

      Est $1,468,832 Not Listed For Sale

      100 Old Stockbridge Rd, Lenox, MA 01240

      • 4 Beds
      • 3 Baths
      • 3,199 Sq Ft
      • Built 1940
      100 Old Stockbridge Rd, Lenox, MA 01240

      Last Sold Summary

      • 13% Above List Price
      • $406/SF
      • 87 Days On Market
      • Last Sold Price $1,300,000
      • Aug 18, 2023

      Last Listing Agent Mary Jo Piretti PIRETTI REAL ESTATE

  • /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
  • /12

    $577,500 Sold Nov 21, 2025

    30 Walker St, Lenox, MA 01240

    • 4 Beds
    • 2 Baths
    • 2,170 Sq Ft
    • Built 1930

    Last Sold Summary

    • 4% Below List Price
    • $266/SF
    • 5 Days On Market

    Current Estimated Value $585,714

    Last Listing Agent Timothy Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    30 Walker St, Lenox, MA 01240
    • /43

      Est $976,605 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

      • 1% Below List Price
      • $589/SF
      • 21 Days On Market
      • Last Sold Price $989,900
      • Aug 25, 2023

      Last Listing Agent Stacy Chojnowski William Pitt

  • /53

    $449,000

    • 3 Beds
    • 2 Baths
    • 1,720 Sq Ft

    500 Walker St, Lenox, MA 01242

    Charming 3 bedroom, 2 bath spacious New England Farmhouse with wide board pine floors, updated kitchen & baths, natural gas heat & hot water, vinyl replacement windows, home office/den and first floor laundry room/mudroom. New beautiful 20x18 bluestone patio & retaining wall installed in 2022.

    Matt Carlino MACCARO REAL ESTATE

    500 Walker St, Lenox, MA 01242
  • /51

    $715,000 Sold Oct 22, 2025

    19 Hawthorne St Unit Stables 1A, Lenox, MA 01240

    • 2 Beds
    • 2 Baths
    • 1,705 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Above List Price
    • $419/SF
    • 3 Days On Market

    Last Listing Agent Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    19 Hawthorne St Unit Stables 1A, Lenox, MA 01240
    • /16

      Est $301,427 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

      • 3% Above List Price
      • $406/SF
      • 39 Days On Market
      • Last Sold Price $292,000
      • Dec 12, 2024

      Last Listing Agent Molly Gillon COMPASS MASSACHUSETTS , LLC GB

  • /31

    $679,000

    • 4 Beds
    • 3.5 Baths
    • 1,843 Sq Ft

    28 Evergreen Trail Unit 28, Lenox, MA 01240

    Custom designed 4 BR, 3.5 bath Townhome with Kennedy Park in your back yard! A one owner home with many upgrades make this one of the most desirable in Lenox Woods. Open floor plan with gorgeous kitchen, granite countertops, tile floors & high backsplash, stainless, upgraded appliances and walk in pantry; stone fireplace enjoyed by all the common spaces; first floor en-suite BR; screened porch

    Mary Jo Piretti PIRETTI REAL ESTATE

    28 Evergreen Trail Unit 28, Lenox, MA 01240
  • /28

    $475,000 Sold Aug 12, 2025

    127 Housatonic St, Lenox, MA 01240

    • 3 Beds
    • 1 Bath
    • 1,380 Sq Ft
    • Built 1860

    Last Sold Summary

    • 5% Below List Price
    • $344/SF
    • 35 Days On Market

    Current Estimated Value $435,113

    Last Listing Agent Donna DiGrigoli DIGRIGOLI REAL ESTATE

    127 Housatonic St, Lenox, MA 01240
    • /17

      Est $560,510 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

      • 3% Above List Price
      • $380/SF
      • 5 Days On Market
      • Last Sold Price $546,500
      • Aug 26, 2024

      Last Listing Agent Mary Jo Piretti PIRETTI REAL ESTATE

  • /30

    $895,000

    • 3 Beds
    • 2.5 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
  • /39

    $615,250 Sold Jun 25, 2025

    9 Sullivan Ln, Lenox, MA 01240

    • 4 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Built 1963

    Last Sold Summary

    • 5% Below List Price
    • $385/SF
    • 28 Days On Market

    Current Estimated Value $600,736

    Last Listing Agent Erin Candee WILLIAM RAVEIS - BERKSHIRE

    9 Sullivan Ln, Lenox, MA 01240
    • /31

      Est $825,291 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

      • 6% Above List Price
      • $285/SF
      • 2 Days On Market
      • Last Sold Price $780,000
      • Oct 28, 2024

      Last Listing Agent Mary Jo Piretti PIRETTI REAL ESTATE

  • /41

    $4,850,000

    • 13 Beds
    • 13.5 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
  • /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 $532,092

    Last Listing Agent Mary Jo Piretti PIRETTI REAL ESTATE

    170 Main St, Lenox, MA 01240
    • /36

      Est $633,413 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

      • 14% Above List Price
      • $396/SF
      • 45 Days On Market
      • Last Sold Price $555,000
      • Nov 28, 2023

      Last Listing Agent Sheila Thunfors STONE HOUSE PROPERTIES, LLC

  • /34

    $535,000 Pending

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

    31 Saint Ann's Ave, Lenox, MA 01240

    This charming bungalow offers the Lenox lifestyle you've been dreaming of ✨ Located on a quiet dead-end street just steps from downtown, enjoy morning coffee, local dining, or evenings at Tanglewood before strolling home under the stars 🌙Inside, approximately 1,700 square feet blends warmth and comfort--perfect as a second home, weekend escape, or full-time living. There is also

    Amy Shufelt BERKSHIRE LISTINGS

    31 Saint Ann's Ave, 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 $584,585

    Last Listing Agent Victoria Standring LAMACCHIA REALTY, INC

    296 Housatonic St, Lenox, MA 01240
    • /18

      Est $344,438 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

      • 19% Above List Price
      • $228/SF
      • 66 Days On Market
      • Last Sold Price $290,000
      • Nov 01, 2024

      Last Listing Agent Derek Greene The Greene Realty Group

  • /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
  • /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 $443,852

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

    130 West St, Lenox, MA 01240
    • /41

      Est $479,954 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

      • 11% Above List Price
      • $244/SF
      • 39 Days On Market
      • Last Sold Price $434,000
      • Oct 25, 2024

      Last Listing Agent Laiken Rapisarda LAMACCHIA REALTY, INC

  • /28

    $279,000

    • 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
  • /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 $641,841

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

    7 Cedar Ln, Lenox, MA 01240
    • /75

      Est $1,896,924 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

      • 13% Above List Price
      • $331/SF
      • 274 Days On Market
      • Last Sold Price $1,675,000
      • Jan 29, 2024

      Last Listing Agent Paula McLean PAULA MCLEAN REALTORS INC.

  • /33

    $350,000

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft

    16 E New Lenox Rd, Lenox, MA 01240

    OFFER DEADLINE 5PM MONDAY MAY 4THWelcome to this classic 1950s ranch on East New Lenox Road, offering bright, simple living in the Berkshires. This three-bedroom, one-bath home features wood floors, fresh paint, and a clean, functional layout.A three-season porch connects to the attached two-car garage and overlooks a fenced backyard—ideal for relaxing or entertaining. While there is no basement,

    Bresdin Mihlek Coldwell Banker Realty - Western MA

    16 E New Lenox Rd, Lenox, MA 01240
  • /32

    $975,000 Sold May 28, 2025

    7-B Coldbrooke South -- Unit 7B, Lenox, MA 01240

    • 3 Beds
    • 2.5 Baths
    • 2,264 Sq Ft
    • Built 1988

    Last Sold Summary

    • 10% Above List Price
    • $431/SF
    • 2 Days On Market

    Last Listing Agent Lori Rose STONE HOUSE PROPERTIES, LLC

    7-B Coldbrooke South -- Unit 7B, Lenox, MA 01240
    • /69

      Est $767,232 Not Listed For Sale

      93 Hubbard St, Lenox, MA 01240

      • 4 Beds
      • 4 Baths
      • 3,072 Sq Ft
      • Built 1950
      93 Hubbard St, Lenox, MA 01240

      Last Sold Summary

      • 26% Above List Price
      • $199/SF
      • 176 Days On Market
      • Last Sold Price $610,500
      • May 24, 2023

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

  • /48

    $324,500

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

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

    Think spring in the Berkshires and enjoy condo living in Lenox at Rolling Hills. Spacious end unit brings in natural light and offers two bedrooms/two baths on upper level with an additional full bath and family room/office on the finished lower level. In this unit owners have replaced the custom-sized slider and the windows adding to energy efficiency. Central a/c, natural gas. The former golf

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    7 Rolling Hills Unit 7-1, 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 $964,886

    Last Listing Agent Nicole Moore KELLER WILLIAMS REALTY

    257 W Mountain Rd, Lenox, MA 01240
    • /28

      Est $2,079,652 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

      • 8% Above List Price
      • $332/SF
      • 108 Days On Market
      • Last Sold Price $1,925,000
      • Jan 26, 2024

      Last Listing Agent Leslie Chesloff William Pitt

  • /58

    $4,995,000 Under Contract

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

    319 Under Mountain Rd, Lenox, MA 01240

    Pine Needles.Built circa 1900 as a Berkshire ''cottage'' in the era of grand summer estates, this historic property blends the dignity of Colonial Revival architecture with the relaxed elegance of an Italian villa and the artisanal detail of the Arts & Crafts movement. Sited on 80 private acres just minutes from the heart of Lenox, the estate offers breathtaking southern views, rolling forest,

    Jared Kelly WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    319 Under Mountain Rd, 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 $402,022

    Last Listing Agent Mary Jo Piretti PIRETTI REAL ESTATE

    5 Morgan Manor Unit 9, Lenox, MA 01240
    • /33

      Est $534,942 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

      • 11% Above List Price
      • $311/SF
      • 64 Days On Market
      • Last Sold Price $480,000
      • Nov 15, 2024

      Last Listing Agent Paula McLean PAULA MCLEAN REALTORS INC.

  • /36

    $495,000 Pending

    • 3 Beds
    • 1.5 Baths
    • 1,376 Sq Ft

    11 Lawton St, Lenox, MA 01240

    Set just moments from downtown Lenox, this charming New England farmhouse blends classic character with thoughtful modern updates. From the moment you arrive, the home's inviting presence and timeless appeal set the tone for what's inside.The recently renovated kitchen serves as the centerpiece of the home, beautifully designed with quartz countertops and all new appliances--perfectly opened to

    Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

    11 Lawton 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
    • /47

      Est $1,631,053 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

      • 2% Above List Price
      • $526/SF
      • 3 Days On Market
      • Last Sold Price $1,600,000
      • Mar 31, 2025

      Last Listing Agent Carrie Wright William Pitt

Showing Results 41 - 80, Page 2 of 18

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