Lanesborough, MA Homes

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  $54,900

  • Land
  • 2.42 Acres
  • $22,686 per Acre

  1 Old Orebed Rd, New Ashford, MA 01237

  Price improvement, seller's are MOTIVATED!!!Stunning 2.42-Acre Lot with Breathtaking Mountain Views! Prime location just minutes from the popular Jiminy Peak Ski Resort, Mt. Greylock. The property provides an excellent opportunity to build your dream home or vacation retreat, surrounded by nature's beauty and outdoor adventure. Enjoy access to skiing, hiking, lakes and more, while being

  

  Keytoria Jenkins

  THE KINDERHOOK GROUP

  (866) 436-0912

  1 Old Orebed Rd, New Ashford, MA 01237
• Explore Lanesborough

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  /13

  $3,000 total monthly price

  • Condo for Rent

  257 S Main St, Hancock, MA 01237

  Charming and fully furnished country apartment available immediately featuring 2 beds and 1.5 baths. Warm and cozy in a well-cared for Owner occupied home, nestled in a serene rural area of Northern Berkshire. Close to Pittsfield and South Berkshire, it's just a few minutes away from Jiminy Peak skiing, with easy access to many other activities. Not only furnished, but heat, electric and internet

  Pauline Green STEEPLEVIEW REALTY - ADAMS BRANCH

  257 S Main St, Hancock, MA 01237
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  /42

  $360,000 Sold Mar 27, 2025

  61 Old Orebed Rd, Lanesborough, MA 01237

  • 2 Beds
  • 1 Bath
  • 1,066 Sq Ft
  • Built 1946

  Last Sold Summary

  • 4% Above List Price
  • $338/SF
  • 5 Days On Market

  Last Listing Agent Kimberly Kuplast LAER Realty Partners

  61 Old Orebed Rd, Lanesborough, MA 01237
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  /9

  Est $211,532 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 957 Sq Ft

  20 Irwin St, Lanesboro, MA 01237

  20 Irwin St, Lanesboro, MA 01237
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  /54

  $630,000

  • 4 Beds
  • 3 Baths
  • 4,930 Sq Ft

  342/344 New Ashford (Route 7) Rd, New Ashford, MA 01237

  A Berkshire landmark ready for its next chapter. Once home to the beloved BONDHU and Mill on the Floss restaurants, this multi-use property offers endless opportunity -- from a charming single-family residence to a live/work haven, a boutique inn, or a luxury destination dining experience reborn. The second-floor living quarters feature four bedrooms, including a primary suite, plus an open

  Stephanie Rapisarda WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  342/344 New Ashford (Route 7) Rd, New Ashford, MA 01237
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  /7

  $1,000 total monthly price

  • 700 Sq Ft
  • Property for Rent

  19 Williamstown Rd, Lanesborough, MA 01237

  This new commercial property offers 2 available spaces for lease, 700 sq ft per space, easy access, visibility to road, radiant heat, security cameras, fiber optics, 3 phase power, custom buildout options like a mezzanine, bathroom or kitchen potential, lease 1 or both spaces unlimited potential. Need more space, an additional 11 units are planned for this facility.

  Matt Jarck WILLIAM PITT SOTHEBY'S - LENOX

  19 Williamstown Rd, Lanesborough, MA 01237
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  /40

  $565,000 Sold Dec 03, 2025

  16 Iroquois St, New Ashford, MA 01237

  • 3 Beds
  • 2 Baths
  • 2,418 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Below List Price
  • $234/SF
  • 155 Days On Market

  Last Listing Agent Janet Benoit Janet L. Benoit

  16 Iroquois St, New Ashford, MA 01237
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  /65

  Est $904,372 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,567 Sq Ft

  12 Squanto Rd, Lanesborough, MA 01237

  12 Squanto Rd, Lanesborough, MA 01237
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  /75

  $765,000

  • 4 Beds
  • 2.5 Baths
  • 2,523 Sq Ft

  112 Silver St, Lanesborough, MA 01237

  Escape to an exceptional Post & Beam Berkshire Retreat nestled on the east side of Jiminy Peak Mountain Resort. Set on 25+ acres for seclusion and privacy, eat, play & live in this 4 bedroom, 2.5 bath chalet-style home with countless modern updates. Spectrum was recently added for everyday internet and tv streaming, as well as 5 new high-efficiency mini split air conditioning/heating units for

  Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

  112 Silver St, Lanesborough, MA 01237
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  /42

  $269,900 Sold Nov 03, 2025

  63 Baker St, Lanesboro, MA 01237

  • 2 Beds
  • 1 Bath
  • 1,591 Sq Ft
  • Built 1908

  Last Sold Summary

  • 7% Below List Price
  • $170/SF
  • 47 Days On Market

  Current Estimated Value $272,091

  Last Listing Agent Nadine Hiser KRG - Key Realty Group

  63 Baker St, Lanesboro, MA 01237
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  /42

  Est $503,312 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,730 Sq Ft

  162 Bailey Rd, Hancock, MA 01237

  162 Bailey Rd, Hancock, MA 01237
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  /59

  $888,800

  • 3 Beds
  • 2.5 Baths
  • 2,394 Sq Ft

  10 Aqua St, Lanesborough, MA 01237

  Berkshires Luxury & New Lakeside Living. Enjoy distant lake and mountain views from each first floor room. This elevated ranch style home creates one level living with grand open sunfilled spaces. This floorplan features open floor plan capturing lakeviews from each room on the main living level. This beauty is what you have been waiting for - a brand new never lived in newly constructed home is

  Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

  10 Aqua St, Lanesborough, MA 01237
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  /32

  $260,000 Sold Oct 03, 2025

  24 Irwin St, Lanesboro, MA 01237

  • 3 Beds
  • 2 Baths
  • 2,214 Sq Ft
  • Built 1913

  Last Sold Summary

  • 13% Below List Price
  • $117/SF
  • 28 Days On Market

  Current Estimated Value $270,241

  Last Listing Agent Jose Larios LAMACCHIA REALTY, INC

  24 Irwin St, Lanesboro, MA 01237
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  /28

  Est $557,945 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,160 Sq Ft

  52 Greylock Estates Rd, Lanesborough, MA 01237

  52 Greylock Estates Rd, Lanesborough, MA 01237
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  /19

  $159,900

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft

  37 Corey Rd Unit 212, Hancock, MA 01237

  At the base of Jiminy Peak, skiing is just steps from your door in one of these one bedroom all suites' condominiums with kitchens that offer the charm of a countryside inn and the conveniences of a slope side hotel. Whirlpools, year-round outdoor swimming pool, exercise room, in house restaurant and on-site front desk services makes this and easy decision to own. Excellent rental history and no

  Kevin Moderski JIMINY REALTY

  37 Corey Rd Unit 212, Hancock, MA 01237
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  /32

  $355,000 Sold Feb 10, 2025

  94 Summer St, Lanesboro, MA 01237

  • 4 Beds
  • 2.5 Baths
  • 2,154 Sq Ft
  • Built 1951

  Last Sold Summary

  • 19% Below List Price
  • $165/SF
  • 75 Days On Market

  Current Estimated Value $376,095

  Last Listing Agent Michele Purcell Lamacchia Realty, Inc.

  94 Summer St, Lanesboro, MA 01237
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  /36

  Est $513,174 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,467 Sq Ft

  28 National St, Pittsfield, MA 01201

  28 National St, Pittsfield, MA 01201
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  /16

  $65,000

  • Land
  • 4.38 Acres
  • $14,857 per Acre

  0 Bailey Rd, New Ashford, MA 01237

  Discover the potential of this scenic , 4.38-acre parcel located on Bailey Rd. in beautiful Lanesboro. Surrounded by nature and offering mountain views, this peaceful setting is the perfect place to build your dream home or getaway retreat. Conveniently located near trails, lakes, skiing, and all the outdoor recreation the Berkshires have to offer. Don't miss this opportunity to own a slice of

  Jessica Rizzo LAMACCHIA REALTY, INC

  0 Bailey Rd, New Ashford, MA 01237
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  /42

  $299,000 Sold Feb 18, 2025

  440 S Main St, Lanesboro, MA 01237

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft
  • Built 1948

  Last Sold Summary

  • 6% Below List Price
  • $261/SF
  • 77 Days On Market

  Current Estimated Value $313,597

  Last Listing Agent Laiken Rapisarda LAMACCHIA REALTY, INC

  440 S Main St, Lanesboro, MA 01237
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  /15

  Est $152,113 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft

  37 Corey Rd Unit 518, Hancock, MA 01237

  37 Corey Rd Unit 518, Hancock, MA 01237
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  $1,200,000

  • 3 Beds
  • 3.5 Baths
  • 4,248 Sq Ft

  221 Bailey Rd, Lanesborough, MA 01237

  Welcome to 221 Bailey Road in Lanesboro, MA., an exquisite ranch-style home offering approximately 4,200 sqft of luxurious living space. Nestled on 87 acres atop a mountain, this property provides unparalleled privacy and breathtaking views that enhance its serene atmosphere. The open-concept living area is perfect for entertaining, featuring abundant natural light and seamless flow between

  Doug Collins LAMACCHIA REALTY, INC

  221 Bailey Rd, Lanesborough, MA 01237
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  /25

  $360,000 Sold Oct 17, 2025

  9074 Mountainside Dr, Hancock, MA 01237

  • 2 Beds
  • 2 Baths
  • 1,035 Sq Ft
  • Built 2004

  Last Sold Summary

  • 8% Below List Price
  • $348/SF
  • 97 Days On Market

  Current Estimated Value $363,607

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

  9074 Mountainside Dr, Hancock, MA 01237
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  /25

  Est $259,231 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 940 Sq Ft

  23 Baker St, Lanesboro, MA 01237

  23 Baker St, Lanesboro, MA 01237
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  /40

  $1,890,000 Pending

  • 11 Beds
  • 7 Baths
  • 5,878 Sq Ft

  775 Williamstown Rd, Lanesborough, MA 01237

  HISTORIC BERKSHIRE FARM Best bargain in the Berkshires! Gather year-round with family and friends on this one-of-a kind estate, including 2 houses, 4 historic barns and maintenance building. 161 acres with stunning views, mountain paths, and Jim Kelly's stunning giant stonewalls throughout. Gorgeous New England marble stone farmhouse built in 1780, with modern addition featuring vaulted ceiling

  Andy Kelly BERKSHIRE BUSINESS PROPERTIES

  775 Williamstown Rd, Lanesborough, MA 01237
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  /41

  $685,000 Sold Nov 14, 2025

  39 N Mountain Rd, Lanesborough, MA 01237

  • 4 Beds
  • 3.5 Baths
  • 2,952 Sq Ft
  • Built 1989

  Last Sold Summary

  • 11% Below List Price
  • $232/SF
  • 33 Days On Market

  Last Listing Agent Janet Benoit Janet L. Benoit

  39 N Mountain Rd, Lanesborough, MA 01237
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  /41

  Est $390,900 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,064 Sq Ft

  159 Balance Rock Rd, Pittsfield, MA 01201

  159 Balance Rock Rd, Pittsfield, MA 01201
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  /50

  $459,900

  • 2 Beds
  • 2 Baths
  • 1,843 Sq Ft

  9063 Mountainside Dr, Hancock, MA 01237

  Discover mountain living at its finest in this spacious 2-bedroom, 2-bath condominium located mountainside at Jiminy Peak Mountain Resort. Offering 1,843 square feet of thoughtfully designed living space, this residence blends comfort, style, and the ease of resort living.The floor plan is ideal for entertaining or relaxing after a day on the slopes, featuring generous living and dining areas

  Kevin Moderski JIMINY REALTY

  9063 Mountainside Dr, Hancock, MA 01237
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  /15

  $235,000 Sold Nov 26, 2025

  8 Balance Rock Rd, Pittsfield, MA 01201

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1950

  Last Sold Summary

  • 3% Above List Price
  • $306/SF
  • 6 Days On Market

  Last Listing Agent James Gelinas GELINAS REAL ESTATE

  8 Balance Rock Rd, Pittsfield, MA 01201
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  /28

  Est $476,888 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,984 Sq Ft

  57 Old State Rd, Berkshire, MA 01224

  57 Old State Rd, Berkshire, MA 01224
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  /50

  $549,000

  • 3 Beds
  • 3 Baths
  • 3,228 Sq Ft

  16 Opeechee St, Lanesborough, MA 01237

  Welcome to this spacious and light-filled home just moments from scenic Pontoosuc Lake! Enjoy breathtaking sunrises and sunsets from your open-concept upper level, featuring soaring ceilings and expansive windows that fill the space with natural light. The beautifully updated kitchen offers ample room for dining and entertaining, complete with a breakfast bar and generous seating options--all

  Laiken Rapisarda LAMACCHIA REALTY, INC

  16 Opeechee St, Lanesborough, MA 01237
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  /47

  $308,000 Sold Jul 31, 2025

  94 Corey Rd Unit D, Hancock, MA 01237

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Below List Price
  • $220/SF
  • 50 Days On Market

  Last Listing Agent Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  94 Corey Rd Unit D, Hancock, MA 01237
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  /36

  Est $397,514 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,784 Sq Ft

  30 Balance Rock Rd, Pittsfield, MA 01201

  30 Balance Rock Rd, Pittsfield, MA 01201
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  /7

  $59,499

  • Land
  • 0.68 Acre
  • $88,015 per Acre

  4 Upper Rd, Lanesborough, MA 01237

  Views, Views, Views! This is a prime location in the sought after Greylock Estates. Close to skiing and numerous Berkshire County attractions. This lot is ready for you to let your imagination run wild and build your dream home.

  Sherry Street REALTY STREET, LLC

  4 Upper Rd, Lanesborough, MA 01237
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  /24

  $250,000 Sold Apr 07, 2025

  11 Orchard Ave, Lanesborough, MA 01237

  • 3 Beds
  • 1 Bath
  • 1,045 Sq Ft
  • Built 1953

  Last Sold Summary

  • $239/SF
  • 7 Days On Market

  Current Estimated Value $261,637

  Last Listing Agent Stacy Hebb NOCHER REALTY

  11 Orchard Ave, Lanesborough, MA 01237
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  /13

  Est $324,797 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,504 Sq Ft

  16 Alice Ave, Lanesborough, MA 01237

  16 Alice Ave, Lanesborough, MA 01237
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  /32

  $659,999

  • 3 Beds
  • 3 Baths
  • 1,968 Sq Ft

  9102 Mountainside Dr, Hancock, MA 01237

  Step into this beautifully updated 3-bedroom, 3-bathroom retreat nestled in one of Jiminy's most family-friendly neighborhoods. 2 bedrooms and 2 Full baths on the 1st floor. The open-concept living area features floor-to-ceiling windows that flood the space with natural light, highlighting the elegant hardwood flooring and cozy fireplace. The gourmet kitchen boasts quartz countertops and

  Kevin Moderski JIMINY REALTY

  9102 Mountainside Dr, Hancock, MA 01237
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  /38

  $259,900 Sold Aug 04, 2025

  19 Bridge St, Lanesboro, MA 01237

  • 2 Beds
  • 1 Bath
  • 837 Sq Ft
  • Built 1953

  Last Sold Summary

  • $311/SF
  • 3 Days On Market

  Current Estimated Value $263,636

  Last Listing Agent Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  19 Bridge St, Lanesboro, MA 01237
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  /23

  Est $223,213 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,116 Sq Ft

  10 Stormview Rd, Lanesboro, MA 01237

  10 Stormview Rd, Lanesboro, MA 01237
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  /10

  $79,900

  • Land
  • 0.41 Acre
  • $194,874 per Acre

  0 Umbagog St, New Ashford, MA 01237

  Nestled near the shores Pontoosuc Lake, this lot offers the perfect blend of natural beauty and convenience.With close proximity to a public playground, boat launch, and lake access, it's an ideal spot for outdoor enthusiasts and families alike.From boating and fishing in the summer to ice fishing in the winter, this location provides endless recreational possibilities.Located in an area with

  Barbara Osborne ASHMERE REALTY, INC.

  0 Umbagog St, New Ashford, MA 01237
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  /41

  $300,000 Sold May 22, 2025

  115 Ore Bed Rd, Lanesborough, MA 01237

  • 1 Bed
  • 2 Baths
  • 1,160 Sq Ft
  • Built 1988

  Last Sold Summary

  • 4% Above List Price
  • $259/SF
  • 3 Days On Market

  Current Estimated Value $303,128

  Last Listing Agent Janet Benoit MOCKINGBIRD REAL ESTATE

  115 Ore Bed Rd, Lanesborough, MA 01237

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