Lenox, MA Homes

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  /27

  $659,800

  $14K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,100 Sq Ft

  28 Evergreen Trail Unit 28, Lenox, MA 01240

  Fantastic Offer! Custom-designed & beautifully maintained one-owner residence offering 4 bedrooms, 3.5 baths, in the most desirable location in the verdant Berkshires. Calm & Quiet with direct access to Kennedy Park - you'll enjoy the perfect balance of nature, community & the Arts. Lenox offers quality shops, farmers markets, Botanic Gardens & music. A beautiful open floor plan features a

  Heather Gallagher STONE HOUSE PROPERTIES, LLC

  28 Evergreen Trail Unit 28, Lenox, MA 01240
• 

  

  

  /29

  $302,000

  Sold Jul 03, 2026

  5 Rolling Hills Unit 4, Lenox, MA 01240

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

  Last Sold Summary

  • 1% Above List Price
  • $195/SF
  • 8 Days On Market

  Current Estimated Value $309,514

  Last Listing Agent Laiken Rapisarda Lamacchia Realty, Inc. - Dalton

  5 Rolling Hills Unit 4, Lenox, MA 01240
• 

  

  

  /75

  Est $1,867,270

  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

  Last Listing Agent Paula McLean PAULA MCLEAN REALTORS INC.
• 

  

  

  /13

  $279,900

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft

  528 Walker St, Lenox Dale, MA 01242

  Large well maintained Colonial on a half acre lot. Large open kitchen with lots of cabinet space. Sliders off kitchen leading to back deck. Bright and sunny living space with a bonus den or office. 3 full sized bedrooms. 2 full baths. Laundry hookups on 2nd floor for convenience. Seller willing to buy down the mortgage rate on this home. One year American Home Shield Warranty included. PLEASE

  Tyler Scaglione Cameron Real Estate Group

  528 Walker St, Lenox Dale, MA 01242
• 

  

  /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 $2,462,091

  Last Listing Agent Selina Lamb BIRCH PROPERTIES

  250 West St, Lenox, MA 01240
• 

  

  /28

  Est $2,157,157

  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

  Last Listing Agent Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON
• 

  

  /30

  $299,000

  Under Contract

  • 2 Beds
  • 2 Baths
  • 1,624 Sq Ft

  3 Rolling Hills Unit 2, Lenox, MA 01240

  Beautifully maintained 2 bedroom, 2 bath condo, both bedrooms/ baths on main level with covered deck & beautiful views, finished lower level w/ laundry offers whole other level of space for office, hobbies, etc. Enjoy the clubhouse (gym, pool table, hot tub, sauna, kitchen/entertainment rm, local art hangings) out door POOL, TENNIS COURTS, walking TRAILS, community GARDENS, kayak storage, fenced

  Donna DiGrigoli DIGRIGOLI REAL ESTATE

  3 Rolling Hills Unit 2, Lenox, MA 01240
• 

  

  /29

  $347,500

  Sold Aug 03, 2026

  37 Holmes Rd, Lenox, MA 01240

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1955

  Last Sold Summary

  • 3% Below List Price
  • $362/SF
  • 20 Days On Market

  Current Estimated Value $359,527

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

  37 Holmes Rd, Lenox, MA 01240
• 

  

  /23

  Est $308,933

  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

  Last Listing Agent Michael Sorrentino BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD
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  /56

  $1,149,000

  $130K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 3,691 Sq Ft

  18 Highcrest Rd, Lenox, MA 01240

  Condo at Twelve Oaks Village. End of Cul-de-sac with Mountain views. This unit offers lots of Privacy being an end unit. Come enjoy Tennis Swimming pool and Fitness center all on property. 3 Full floors of living space with Primary Suite/Walk in Closet on 1st floor. Spacious open floor plan to enjoy entertaining with plenty of outdoor space with screened in porch and private deck. Enjoy Easterly

  Suzann Ward HOUSATONIC REAL ESTATE

  18 Highcrest Rd, Lenox, MA 01240
• 

  

  /33

  $503,500

  Sold Jul 24, 2026

  11 Lawton St, Lenox, MA 01240

  • 3 Beds
  • 1.5 Baths
  • 1,376 Sq Ft
  • Built 1900

  Last Sold Summary

  • 2% Above List Price
  • $366/SF
  • 17 Days On Market

  Current Estimated Value $487,000

  Last Listing Agent Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

  11 Lawton St, Lenox, MA 01240
• 

  

  /26

  Est $553,805

  Not Listed For Sale

  170 Main St, Lenox, MA 01240

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

  170 Main St, Lenox, MA 01240

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Mary Jo Piretti PIRETTI REAL ESTATE
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  /60

  $2,498,000

  $200K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 4,581 Sq Ft

  109 Under Mountain Rd, Lenox, MA 01240

  Some homes are purchased. Others become part of a family's legacy. Welcome to 109 Under Mountain Road. There is something unmistakably special about a Berkshire summer- evening stroll to Tanglewood, morning coffee overlooking protected meadows, or relaxing on the patio as the music of the Boston Symphony Orchestra drifts softly through the evening air. Bathed in extraordinary natural light, this

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  109 Under Mountain Rd, 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 $223,902

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

  260 Pittsfield Rd Unit B11, Lenox, MA 01240
• 

  

  /33

  Est $541,114

  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

  Last Listing Agent Paula McLean PAULA MCLEAN REALTORS INC.
• 

  

  /44

  $789,900

  $57K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,680 Sq Ft

  63 Sherwood Dr, Lenox, MA 01240

  Don't miss this Lenox beauty tucked away on a quiet side street. Main level w hardwood flooring, living room with crown molding, formal dining w. large bay window, updated kitchen w extensive cabinetry. Family room w gas fireplace opens to large screened porch / patio. First floor laundry and 1/2 bath. Three bedrooms on the upper level; primary suite w adjoining dressing room/ primary bath with

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  63 Sherwood Dr, Lenox, MA 01240
• 

  

  /33

  $540,000

  Sold Jul 13, 2026

  870 East St, Lenox, MA 01240

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 1962

  Last Sold Summary

  • 2% Below List Price
  • $318/SF
  • 3 Days On Market

  Current Estimated Value $541,958

  Last Listing Agent Cristian Sanchez COHEN & WHITE ASSOCIATES

  870 East St, Lenox, MA 01240
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  /47

  Est $1,644,345

  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

  Last Listing Agent Carrie Wright WILLIAM PITT SOTHEBY'S - LENOX
• 

  

  /26

  $835,000

  $40K PRICE DROP Under Contract

  • 4 Beds
  • 2 Baths
  • 1,791 Sq Ft

  90 Hawthorne St, Lenox, MA 01240

  Beautiful historic farm house available in Lenox Massachusetts. A charming 1840s clapboard house located on the estate of ''Brookhurst'', one of the famed Berkshire ''cottages'', this formerguest house has 3 or 4 bedrooms and 2 full baths spread over three floors (primary bedroom and bath on main floor). It has a private gated driveway and an attached 2 car garage.. Luxurious traditional

  Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  90 Hawthorne St, Lenox, MA 01240
• 

  

  /55

  $465,000

  Sold Jan 09, 2026

  8 Catherine St, Lenox, MA 01240

  • 3 Beds
  • 2 Baths
  • 1,434 Sq Ft
  • Built 1921

  Last Sold Summary

  • 2% Below List Price
  • $324/SF
  • 8 Days On Market

  Current Estimated Value $485,145

  Last Listing Agent Nick Geranios WILLIAM PITT SOTHEBY'S - LENOX

  8 Catherine St, Lenox, MA 01240
• 

  

  /28

  Est $712,746

  Not Listed For Sale

  461 Under Mountain Rd, Lenox, MA 01240

  • 3 Beds
  • 2 Baths
  • 2,140 Sq Ft
  • Built 1971

  461 Under Mountain Rd, Lenox, MA 01240

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Jeffrey Loholdt Engel & Völkers Wellesley
• 

  

  /47

  $1,399,000

  $51K PRICE DROP

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

  3 A Coldbrooke Dr, Lenox, MA 01240

  Four-bedroom homes are a rarity at Coldbrooke, where most residences offer three. This one combines that hard-to-find layout and one of the community's more generous floor plans with a location beside the Miraval Berkshires resort and the historic Wyndhurst estate, putting world-class spa, dining, and golf just steps from the door. Inside, vaulted ceilings and an open layout fill the home with

  Cameron Volastro WILLIAM PITT SOTHEBY'S - LENOX

  3 A Coldbrooke Dr, Lenox, MA 01240
• 

  

  /27

  $240,000

  Sold Jan 29, 2026

  2-5 Rolling Hill Build 2 Unit 5 Ln, Lenox, MA 01240

  • 2 Beds
  • 3 Baths
  • 1,770 Sq Ft
  • Built 1976

  Last Sold Summary

  • 23% Below List Price
  • $136/SF
  • 156 Days On Market

  Last Listing Agent Toni Marie Gage SIGNATURE ASSOCIATES

  2-5 Rolling Hill Build 2 Unit 5 Ln, Lenox, MA 01240
• 

  

  /65

  Est $1,470,503

  Not Listed For Sale

  8 Melville Ct, Lenox, MA 01240

  • 5 Beds
  • 4.5 Baths
  • 3,869 Sq Ft
  • Built 2002

  8 Melville Ct, Lenox, MA 01240

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Mary Jo Piretti PIRETTI REAL ESTATE
• 

  

  /42

  $1,200,000

  Pending

  • 4 Beds
  • 5.5 Baths
  • 2,540 Sq Ft

  8 Stoneledge Rd, Lenox, MA 01240

  Beautifully maintained home set on a private one-acre lot on a quiet cul-de-sac in one of Lenox's most desirable neighborhoods. This thoughtfully designed residence offers four bedrooms and 5.5 baths, including a spacious main-level primary suite with a luxurious en-suite bath. The inviting floor plan is ideal for both everyday living and entertaining. Step outside to a beautifully landscaped

  Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  8 Stoneledge Rd, Lenox, MA 01240
• 

  

  /82

  $2,200,000

  Sold Mar 06, 2026

  13 Taconic Ave, Lenox, MA 01240

  • 6 Beds
  • 6.5 Baths
  • 7,143 Sq Ft
  • Built 1999

  Last Sold Summary

  • 14% Below List Price
  • $308/SF
  • 143 Days On Market

  Current Estimated Value $2,307,072

  Last Listing Agent Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

  13 Taconic Ave, Lenox, MA 01240
• 

  

  /39

  Est $769,037

  Not Listed For Sale

  190 Hubbard St, Lenox, MA 01240

  • 4 Beds
  • 3 Baths
  • 2,255 Sq Ft
  • Built 1967

  190 Hubbard St, Lenox, MA 01240

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Mary Jo Piretti PIRETTI REAL ESTATE
• 

  

  /37

  $685,000

  • 3 Beds
  • 2.5 Baths
  • 1,620 Sq Ft

  200 Old Stockbridge Rd Unit VA-6, Stockbridge, MA 01262

  STUNNING VIEWS for as far as you can see from this modern unit located in Winden Hills Vanna building. Open common spaces washed in natural light; Great room with scenic views, fireplace and built ins, kitchen with charm and character open to dining. Primary w/en suite full bath, two guest bedrooms and additional one and half baths. This unit comes with access to the elevator for convenience, a

  Cortney Dupont COHEN & WHITE ASSOCIATES

  200 Old Stockbridge Rd Unit VA-6, Stockbridge, MA 01262
• 

  

  /50

  $1,300,000

  Sold Nov 18, 2025

  14 A Muirfield Dr Unit 14A, Lenox, MA 01240

  • 3 Beds
  • 2.5 Baths
  • 2,266 Sq Ft
  • Built 1998

  Last Sold Summary

  • $574/SF
  • 29 Days On Market

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

  14 A Muirfield Dr Unit 14A, Lenox, MA 01240
• 

  

  /34

  Est $1,572,983

  Not Listed For Sale

  12 Housatonic St, Lenox, MA 01240

  • 4 Beds
  • 6 Baths
  • 5,664 Sq Ft
  • Built 1885

  12 Housatonic St, Lenox, MA 01240

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Suzanne Bergeron Naples Realty Group
• 

  

  /33

  $449,000

  $40K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,457 Sq Ft

  181 New Lenox Rd, Lenox, MA 01240

  Enchanting Lenox Cottage minutes to Tanglewood- 2 Bedroom / 2 Full Bath RetreatThe bright, airy living room features warm wood floors that lead into a cozy eat-in kitchen. With a heated sunporch & 1st floor full bath, the home offers multiple inviting spaces to relax or entertain. Step outside to a brand-new back deck, an ideal setting for summer evenings. 2 Bedrooms on second floor, with

  Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  181 New Lenox Rd, Lenox, MA 01240
• 

  

  /23

  $355,000

  Sold Jun 26, 2026

  792 East St, Lenox, MA 01240

  • 3 Beds
  • 1 Bath
  • 1,616 Sq Ft
  • Built 1967

  Last Sold Summary

  • 11% Below List Price
  • $220/SF
  • 24 Days On Market

  Current Estimated Value $411,117

  Last Listing Agent Mary Jo Piretti PIRETTI REAL ESTATE

  792 East St, Lenox, MA 01240
• 

  

  /25

  Est $1,010,102

  Not Listed For Sale

  108 Kemble St, Lenox, MA 01240

  • 4 Beds
  • 1.5 Baths
  • 1,758 Sq Ft
  • Built 1900

  108 Kemble St, Lenox, MA 01240

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Mary Jo Piretti PIRETTI REAL ESTATE
• 

  

  /23

  $349,000

  Pending

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

  8 Rolling Hills Unit 1, Lenox, MA 01240

  If you are seeking a home in move in condition, come see this unit.Beautifully updated townhome featuring a new Cook's kitchen, white granite countertops, gas range, stainless steel refrigerator, dishwasher & sleek range hood. Open Living Room and Dining Area. Private porch overlooking the Rolling Hills of the Berkshires. 2 bedrooms & 2 full baths. Lower level with baseboard heating offers

  Susan Baum BERKSHIRE HOMES AND CONDOS

  8 Rolling Hills Unit 1, Lenox, MA 01240
• 

  

  /51

  $1,800,000

  Sold Jan 06, 2026

  7 Hubbard St, Lenox, MA 01240

  • 12 Beds
  • 10.5 Baths
  • 7,979 Sq Ft
  • Built 1767

  Last Sold Summary

  • 10% Below List Price
  • $226/SF
  • 76 Days On Market

  Current Estimated Value $1,826,690

  Last Listing Agent Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

  7 Hubbard St, Lenox, MA 01240
• 

  

  /35

  Est $991,773

  Not Listed For Sale

  2 Dunmore Ct, Lenox, MA 01240

  • 4 Beds
  • 3.5 Baths
  • 3,048 Sq Ft
  • Built 1985

  2 Dunmore Ct, Lenox, MA 01240

  Last Sold Summary

  • 116 Days On Market

  Last Listing Agent Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON
• 

  

  /61

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 1,765 Sq Ft

  9 Bolton Dr, Lenox, MA 01240

  Located in the Heart of Downtown Lenox on a dead-end street, this move-in ready Colonial is beautifully renovated and features a comfortable open floor plan perfect for the holidays and entertaining. A new Kitchen with a farm sink and 36'' range, hardwood floors, Living Room with fireplace, a half bath on the first floor, 3 bedrooms, 2 full baths and laundry on the second floor and finished

  Wayne Ditore BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  9 Bolton Dr, Lenox, MA 01240
• 

  

  /58

  $1,050,000

  Sold Dec 18, 2025

  4 Stoneledge Rd, Lenox, MA 01240

  • 4 Beds
  • 4.5 Baths
  • 2,995 Sq Ft
  • Built 2006

  Last Sold Summary

  • 5% Below List Price
  • $351/SF
  • 29 Days On Market

  Current Estimated Value $1,132,966

  Last Listing Agent Nicole Moore KELLER WILLIAMS REALTY

  4 Stoneledge Rd, Lenox, MA 01240
• 

  

  /59

  Est $669,848

  Not Listed For Sale

  361 East St, Lenox, MA 01240

  • 3 Beds
  • 2.5 Baths
  • 2,171 Sq Ft
  • Built 1900

  361 East St, Lenox, MA 01240

  Last Sold Summary

  • 240 Days On Market

  Last Listing Agent Marc Bellora Lamacchia Realty, Inc. - Dalton
• 

  

  /42

  $845,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,964 Sq Ft

  154 Plunkett St, Lenox, MA 01240

  PERFECT IN LENOX!! This impeccably renovated Mid-Century Modern jewel has it all.....Including a BIG VIEW!! This ''down to the studs'' interior rebuild including siding, windows, heating, electrical, plumbing, A/C with 2 zones and energy efficient LED lighting offers true main level living; three bedrooms, primary with walk in closet, open living/dining with stunning kitchen, main floor

  Mary Jane White COHEN & WHITE ASSOCIATES

  154 Plunkett St, Lenox, MA 01240

Showing Results 81 - 120, Page 3 of 18