Lenox Dale, MA Homes

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  /6

  $395,000 Pending

  • Land
  • 3.3 Acres
  • $119,697 per Acre

  9 Wheatleigh Dr, Stockbridge, MA 01262

  RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

  

  Selina Lamb

  Birch Properties

  (413) 343-5283

  9 Wheatleigh Dr, Stockbridge, MA 01262
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  /20

  $1,082 plus fees

  Lenox Schoolhouse Apartments

  Studio

  109 Housatonic St, Lenox, MA 01240

  Welcome to Lenox Schoolhouse Apartments — newly renovated apartment living in the heart of the Berkshires. Offering thoughtfully updated studio and one-bedroom apartment homes, this charming community combines historic character with modern comfort in a highly walkable Lenox location. Each apartment features spacious open layouts, brand-new interiors, plush carpeting, sun-filled windows, and

  109 Housatonic St, Lenox, MA 01240
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  /47

  $660,000 Sold Aug 22, 2025

  36 Tucker St, Lenox, MA 01240

  • 4 Beds
  • 2 Baths
  • 2,242 Sq Ft
  • Built 1890

  Last Sold Summary

  • 2% Above List Price
  • $294/SF
  • 2 Days On Market

  Current Estimated Value $690,050

  Last Listing Agent Katie Soules WILLIAM RAVEIS REAL ESTATE

  36 Tucker St, Lenox, MA 01240
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  /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

  Last Listing Agent Carrie Wright William Pitt
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  /54

  $2,649,000 Under Contract

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

  250 West St, Lenox, MA 01240

  Just seconds not minutes from the main gates of Tanglewood, this stunning contemporary estate is tucked into a sunlit site surrounded by woodland, offering a rare blend of proximity and seclusion. In a region renowned for its natural beauty, it's almost unheard of to find a home this close to the cultural heart of the Berkshires that also feels so entirely removed.Perfectly positioned for

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 423-1264

  250 West St, Lenox, MA 01240
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  /26

  $12,000 per month

  • 2 Beds
  • 2 Baths
  • 1,180 Sq Ft
  • House for Rent

  45 Taconic Ave, Lenox, MA 01240

  Experience the ultimate Summer in Lenox! This fully restored carriage house is available from June 28 - July 30, offering a prime walk-to-town location just minutes from Tanglewood. Inside, enjoy a light-filled great room with cathedral ceilings, a gas fireplace, and a chef's kitchen. This 2-bed, 2-bath retreat features a first-floor primary suite, hardwood floors, and a brand-new second-floor

  John Burns WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  45 Taconic Ave, Lenox, MA 01240
• 

  

  /40

  $660,000 Sold Jul 10, 2025

  176 Old Stockbridge Rd Unit Smith 2, Stockbridge, MA 01262

  • 2 Beds
  • 2.5 Baths
  • 1,853 Sq Ft
  • Built 1988

  Last Sold Summary

  • 6% Below List Price
  • $356/SF
  • 133 Days On Market

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

  176 Old Stockbridge Rd Unit Smith 2, Stockbridge, MA 01262
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  /36

  Not Listed For Sale

  Unlisted Address

  • Built 1969

  Unlisted Address

  Last Sold Summary

  • $67/SF
  • 0 Days On Market

  Last Sold Price $1,875,000

  Last Listing Agent Elisha Poirier STONE HOUSE PROPERTIES, LLC
• 

  

  /6

  $395,000 Under Contract

  • Land
  • 3.3 Acres
  • $119,697 per Acre

  9 Wheatleigh Dr, Stockbridge, MA 01262

  RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 722-5098

  9 Wheatleigh Dr, Stockbridge, MA 01262
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  /17

  $1,305 - $3,447 plus fees

  Forge

  1 - 3 Beds

  66 Brushwood Way, Lenox, MA 01240

  Forge is a brand new mixed-income housing community in Lenox, MA. The development includes 65 apartments within 13 townhome-style buildings, and a community clubhouse. Each building at Forge contains 5-6 apartments, with a mix of one-, two-, and three-bedroom apartments available at various income tiers (30, 60, 120% AMI). Apartments have their own entrances at a new road loop, which is

  66 Brushwood Way, Lenox, MA 01240
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  /9

  $90,000 Sold Nov 10, 2025

  705 Cape St Unit 2, Lee, MA 01238

  • 5 Beds
  • 3 Baths
  • 2,316 Sq Ft
  • Built 1900

  Last Sold Summary

  • 40% Below List Price
  • $39/SF
  • 33 Days On Market

  Last Listing Agent Lisa Kelley MACCARO REAL ESTATE

  705 Cape St Unit 2, Lee, MA 01238
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  /26

  Est $407,480 Not Listed For Sale

  26 Old Stockbridge Rd Unit 4, Lenox, MA 01240

  • 3 Beds
  • 2.5 Baths
  • 1,538 Sq Ft
  • Built 1870

  26 Old Stockbridge Rd Unit 4, Lenox, MA 01240

  Last Sold Summary

  • 13% Above List Price
  • $234/SF
  • 141 Days On Market

  Last Sold Price $360,000

  Last Listing Agent Susan Calkins STONE HOUSE PROPERTIES, LLC
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  /42

  $1,650,000 Pending

  • 4 Beds
  • 3 Baths
  • 7,027 Sq Ft

  17 East St, Stockbridge, MA 01262

  Architecturally iconic and rich with history, this brick Federal home and its gracefully conceived mid-1990s expansion offer a rare opportunity for a buyer with vision. The last major renovation paired the 1830s structure with an addition that respects the original proportions while opening new possibilities for contemporary living. Set along the Stockbridge–Lenox corridor on 13+/- acres (9

  

  Selina Lamb

  Birch Properties

  (413) 300-6860

  17 East St, Stockbridge, MA 01262
• 

  

  /23

  $2,300 per month

  • Condo for Rent

  18 Morgan St Unit 1, Lenox, MA 01240

  Fully renovated, fully furnished, like new Studio Apartment with 1 full bath. Must be seen to be appreciated. Location, location, location. It does not get any better than this. Just minutes from the heart of downtown Lenox and the world class music at Tanglewood. Features include modern finishes and a rare private garage stall.

  Jim Moir WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  18 Morgan St Unit 1, Lenox, MA 01240
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  /34

  $885,000 Sold Jun 30, 2025

  3 Willard Hill Rd, Stockbridge, MA 01262

  • 4 Beds
  • 3.5 Baths
  • 2,189 Sq Ft
  • Built 1996

  Last Sold Summary

  • $404/SF
  • 17 Days On Market

  Current Estimated Value $916,062

  Last Listing Agent Tom Lynch COMPASS MASSACHUSETTS , LLC GB

  3 Willard Hill Rd, Stockbridge, MA 01262
• 

  

  /25

  Est $511,484 Not Listed For Sale

  280 Mandalay Rd, Lee, MA 01238

  • 4 Beds
  • 2 Baths
  • 1,872 Sq Ft
  • Built 1970

  280 Mandalay Rd, Lee, MA 01238

  Last Sold Summary

  • 15% Above List Price
  • $238/SF
  • 7 Days On Market

  Last Sold Price $445,000

  Last Listing Agent Ralph Harvey LISTWITHFREEDOM
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  /42

  $1,280,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 4.5 Baths
  • 2,691 Sq Ft

  18 Highcrest Rd Unit 20, Lenox, MA 01240

  

  Selina Lamb

  Birch Properties

  (413) 591-5654

  18 Highcrest Rd Unit 20, Lenox, MA 01240
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  /18

  $3,500 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • House for Rent

  165 Stockbridge Rd, Lee, MA 01238

  Modern 2bdrm guesthouse w/ private porch with sweeping views on historic property. Price does not include utilities, but we can offer an all-inclusive monthly rate. Primary bedroom and the living room have skylights (sun-filled daytime). Primary bdrm has door to porch. Bathroom has Rain-shower and tub. Top of line W/D. Kitchen used and loved by chefs. Farmhouse dining table + kitchen

  165 Stockbridge Rd, Lee, MA 01238
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  /23

  $355,000 Sold Jul 15, 2025

  9 Rolling Hills Unit 5, Lenox, MA 01240

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

  Last Sold Summary

  • $229/SF
  • 3 Days On Market

  Last Listing Agent Susan Baum BERKSHIRE HOMES AND CONDOS

  9 Rolling Hills Unit 5, Lenox, MA 01240
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  /24

  Est $401,548 Not Listed For Sale

  320 Laurel St, Lee, MA 01238

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Built 1870

  320 Laurel St, Lee, MA 01238

  Last Sold Summary

  • 4% Below List Price
  • $331/SF
  • 14 Days On Market

  Last Sold Price $417,500

  Last Listing Agent Carrie Swift Heck COMPASS MASSACHUSETTS , LLC GB
• 

  

  /43

  $445,000

  • 2 Beds
  • 3 Baths
  • 1,814 Sq Ft

  35 Chapman Rd, Pittsfield, MA 01201

  Classic New England farmhouse featuring a charming kitchen with beautiful Berkshire views and an open, inviting layout perfect for entertaining. The 1st floor offers, full bath and convenient laundry hookups, along with 2 living rooms. One ideal for relaxation and the other a perfect home office, playroom, game room. Upstairs, you'll find 2 good sized bedrooms each with their own full bathroom

  

  Laura Arseneau

  PAULA MCLEAN REALTORS INC.

  (413) 323-3512

  35 Chapman Rd, Pittsfield, MA 01201
• 

  

  /13

  $2,250 per month

  • 1 Bath
  • 750 Sq Ft
  • Property for Rent

  27 Housatonic St, Lenox, MA 01240

  Make your dreams come true! Perhaps one of the best retail locations in Historic downtown Lenox. This highly sought after space is centrally located with high foot traffic count and is located on the corner of Church St. and Housatonic. The 750 sq.ft. has two great large window wells along the sidewalk entrance and includes your own bathroom and kitchenette. Nestled amongst dozens of small shops,

  Tim Gallagher STONE HOUSE PROPERTIES, LLC

  27 Housatonic St, Lenox, MA 01240
• 

  

  /50

  $531,000 Sold Sep 30, 2025

  880 East St Unit 3A, Lee, MA 01238

  • 3 Beds
  • 3 Baths
  • 1,780 Sq Ft
  • Built 1985

  Last Sold Summary

  • 6% Above List Price
  • $298/SF
  • 14 Days On Market

  Current Estimated Value $523,250

  Last Listing Agent Jason Nocher NOCHER REALTY

  880 East St Unit 3A, Lee, MA 01238
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  /47

  Est $527,737 Not Listed For Sale

  160 Paul Dr, Lee, MA 01238

  • 3 Beds
  • 2.5 Baths
  • 2,016 Sq Ft
  • Built 1966

  160 Paul Dr, Lee, MA 01238

  Last Sold Summary

  • $263/SF
  • 5 Days On Market

  Last Sold Price $530,000

  Last Listing Agent Lisa Kelley MACCARO REAL ESTATE
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  /4

  $215,000

  • Land
  • 14.3 Acres
  • $15,035 per Acre

  L16 Reservoir Rd, Out-Of State, MA 99999

  Discover an unparalleled opportunity with this stunning 14.3-acre parcel, perfect for building your dream home or if needed, subdividing into its original three lots. Featuring a pre-installed driveway, electrical service with a transformer, and a large 36 x 50 foundation that was started for a garage/barn, this property is both convenient and versatile. Enjoy the natural beauty of streams,

  

  Gary Fuls Jr

  Gary L Fuls DBA Re/MAX Transit

  (866) 819-0148

  L16 Reservoir Rd, Out-Of State, MA 99999
• 

  

  /36

  $3,900 per month

  • 3 Beds
  • 2.5 Baths
  • 1,848 Sq Ft
  • House for Rent

  15 Martin Ave, Lee, MA 01238

  Welcome to the well maintained and updated split level home featuring three bedrooms, 2.5 bathrooms, and a finished basement. Main level includes all three bedrooms, the living room, dining room, kitchen, laundry, and one full bathroom. Second level includes a spacious family room and another full bathroom. The basement offers a large finished space for relaxing or entertaining. Being offered for

  Cory Evangelisto NOCHER REALTY

  15 Martin Ave, Lee, MA 01238
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  /2

  $750,000 Sold Aug 13, 2025

  50 Stockbridge Rd, Lee, MA 01238

  • 3 Beds
  • 2.5 Baths
  • 2,445 Sq Ft
  • Built 2005

  Last Sold Summary

  • $307/SF
  • 0 Days On Market

  Current Estimated Value $767,537

  Last Listing Agent Comparable Listing COMPARABLE LISTING ONLY

  50 Stockbridge Rd, Lee, MA 01238
• 

  

  /49

  Est $522,218 Not Listed For Sale

  85 Highfield Dr, Lee, MA 01238

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft
  • Built 1974

  85 Highfield Dr, Lee, MA 01238

  Last Sold Summary

  • 8% Above List Price
  • $359/SF
  • 5 Days On Market

  Last Sold Price $485,000

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

  

  /4

  $500,000

  • Land
  • 3.44 Acres
  • $145,349 per Acre

  117 Lime Kiln Rd, Lenox, MA 01240

  Ready to build! Build your own Berkshire Home on this beautiful 3.44 acre parcel in the heart of the Berkshires! The land is partially cleared and ready for construction, with septic design plans already with public water and power on the street. Set on a quiet road, this property offers privacy with a true Berkshire feel while being close to many cultural attractions including, Tanglewood, The

  

  Laura Arseneau

  PAULA MCLEAN REALTORS INC.

  (413) 393-2997

  117 Lime Kiln Rd, Lenox, MA 01240
• 

  

  /23

  $3,500 per month

  • 2 Beds
  • 2.5 Baths
  • 1,867 Sq Ft
  • House for Rent

  34 Galway Ct, Lenox, MA 01240

  Perfectly located within 10 minutes to Tanglewood, this all one floor Ranch home is fully furnished and nicely appointed. The Galway Court neighborhood experiences limited traffic situations while making the trip to the center of Lenox and its shops and restaurants an easy bike ride for anyone so inclined. Like to golf? The Miraval Country Club is just five minutes away. The house features a very

  George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  34 Galway Ct, Lenox, MA 01240
• 

  

  /39

  $502,500 Sold Aug 08, 2025

  80 Plunkett St, Lenox, MA 01240

  • 3 Beds
  • 1.5 Baths
  • 1,798 Sq Ft
  • Built 1953

  Last Sold Summary

  • 1% Above List Price
  • $279/SF
  • 19 Days On Market

  Current Estimated Value $535,348

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

  80 Plunkett St, Lenox, MA 01240
• 

  

  /34

  Est $659,867 Not Listed For Sale

  70 Franklin St, Lee, MA 01238

  • 5 Beds
  • 3 Baths
  • 2,978 Sq Ft
  • Built 1900

  70 Franklin St, Lee, MA 01238

  Last Sold Summary

  • 19% Above List Price
  • $186/SF
  • 48 Days On Market

  Last Sold Price $552,500

  Last Listing Agent Mary Jane White COHEN & WHITE ASSOCIATES
• 

  

  /46

  $1,280,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 4.5 Baths
  • 2,691 Sq Ft

  18 Highcrest Rd, Lenox, MA 01240

  Set within a private enclave of luxury homes just moments from downtown Lenox, this exceptional Berkshires condominium offers a rare combination of refined design, extraordinary privacy, and protected long-range views.Positioned at the far end of the development, the home benefits from owned development rights that safeguard sweeping easterly views of October Mountain and preserve the surrounding

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 319-9976

  18 Highcrest Rd, Lenox, MA 01240
• 

  

  /5

  $32 per month

  • Studio
  • 8,955 Sq Ft
  • Property for Rent

  73 W Center St, Lee, MA 01238

  Be Part of the Vibrant Lee Community. Restored Historic Mill Machine Shop Building is a Commercial Condominium available for Lease, occupancy in 2027. Tenant responsible for cost of improvements which can be amortized over the life of the lease and built into monthly lease payment. Rentable space is 8,955 sf on two levels, 5,809 sf first floor, 3,146 sf second floor plus basement. Gallery,

  Rich Aldrich WILLIAM PITT SOTHEBY'S - LENOX

  73 W Center St, Lee, MA 01238
• 

  

  /34

  $410,000 Sold Sep 30, 2025

  220 Theresa Terrace, Lee, MA 01238

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1969

  Last Sold Summary

  • 2% Below List Price
  • $293/SF
  • 9 Days On Market

  Current Estimated Value $412,532

  Last Listing Agent Andreea Duta BISHOP WEST REAL ESTATE

  220 Theresa Terrace, Lee, MA 01238
• 

  

  /41

  Est $584,707 Not Listed For Sale

  92 Hubbard St, Lenox, MA 01240

  • 3 Beds
  • 1.5 Baths
  • 1,861 Sq Ft
  • Built 1973

  92 Hubbard St, Lenox, MA 01240

  Last Sold Summary

  • 1% Above List Price
  • $311/SF
  • 7 Days On Market

  Last Sold Price $578,000

  Last Listing Agent Diane Thorson William Pitt
• 

  

  /43

  $350,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  612 E New Lenox Rd, Pittsfield, MA 01201

  Welcome to this move in ready embankment ranch in a desirable southeast neighborhood! This home has been loved by one family for the last 50 years, and is now ready to host a new family! Come see the beautiful hardwood floors in the large living room and all 3 bedrooms. Two of the bedrooms have large cedar-lined closets. The eat-in kitchen has ample cabinet space with easy access to the attached

  Juli Kowach LAMACCHIA REALTY, INC

  612 E New Lenox Rd, Pittsfield, MA 01201
• 

  

  /64

  $1,383,000 Sold Jan 15, 2026

  19 Hawthorne Rd Unit CV 7-A, Stockbridge, MA 01262

  • 3 Beds
  • 3.5 Baths
  • 3,284 Sq Ft
  • Built 1986

  Last Sold Summary

  • 20% Above List Price
  • $421/SF
  • 8 Days On Market

  Last Listing Agent Mary Jane White COHEN & WHITE ASSOCIATES

  19 Hawthorne Rd Unit CV 7-A, Stockbridge, MA 01262
• 

  

  /22

  Est $365,360 Not Listed For Sale

  395 Fairview St, Lee, MA 01238

  • 3 Beds
  • 1 Bath
  • 1,160 Sq Ft
  • Built 1910

  395 Fairview St, Lee, MA 01238

  Last Sold Summary

  • 41% Above List Price
  • $224/SF
  • 73 Days On Market

  Last Sold Price $260,000

  Last Listing Agent Matt Carlino MACCARO REAL ESTATE
• 

  

  /80

  $1,400,000

  • 4 Beds
  • 4 Baths
  • 3,379 Sq Ft

  2 Saint Andrews Ct, Lenox, MA 01240

  Welcome to elegant single-level living in one of Lenox's most coveted locations. Ideally positioned on prestigious Saint Andrews Drive, this exceptional home offers privacy, comfort, and stunning views--just minutes from the heart of the Berkshires.This expansive 3,379-square-foot residence features four bedrooms and four full baths, thoughtfully designed for both everyday living and

  Jose Larios LAMACCHIA REALTY, INC

  2 Saint Andrews Ct, Lenox, MA 01240

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