4,198

Ashley Falls, MA Homes

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  • /53

    $695,000 Pending

    • 6 Beds
    • 5 Baths
    • 4,572 Sq Ft

    604 Sheffield Plain, Sheffield, MA 01257

    A rare opportunity awaits in the heart of historic Sheffield. This exceptional multi-unit property, originally a classic 1740s farmhouse, has been thoughtfully converted into a lucrative income-producing asset while retaining its timeless New England charm. Perfectly positioned just south of Great Barrington, it offers both tenants and owners a convenient commute to local attractions, work, and

    Tony Segalla WILLIAM RAVEIS - BERKSHIRE

    604 Sheffield Plain, Sheffield, MA 01257
  • 101-7 Sand Rd, Canaan, CT 06018

    $310,000 Sold Dec 05, 2025

    101-7 Sand Rd, Canaan, CT 06018

    • 4 Beds
    • 2 Baths
    • 1,584 Sq Ft
    • Built 1987

    Last Sold Summary

    • $196/SF
    • 48 Days On Market

    Last Listing Agent Wendy Eichman Raynard & Peirce Realty,LLC

    101-7 Sand Rd, Canaan, CT 06018
    • /18

      Est $221,101 Not Listed For Sale

      139 Silver St, Sheffield, MA 01257

      • 5 Beds
      • 1,656 Sq Ft
      • Built 1910
      139 Silver St, Sheffield, MA 01257

      Last Sold Summary

      • 39% Above List Price
      • $96/SF
      • 394 Days On Market

      Last Sold Price $159,000

      Last Listing Agent Cortney Dupont COHEN & WHITE ASSOCIATES

  • /37

    $1,095,000

    • 6 Beds
    • 2.5 Baths
    • 4,753 Sq Ft

    143 E Canaan Rd, East Canaan, CT 06024

    Exceptional country estate on 16.65 pristine acres offering the ultimate in privacy and convenience without isolation. This remarkable North Canaan property features a 3 car garage-ideal for automotive enthusiasts to enjoy nearby Lime Rock Park. Inside, the chef's kitchen with commercial prep area is an entertainer's paradise, designed to accommodate everything from intimate dinners to

    Phil Fox William Pitt Sotheby's Int'l

    143 E Canaan Rd, East Canaan, CT 06024
  • 7 Lawrence Ave, Canaan, CT 06018

    $297,000 Sold Aug 20, 2025

    7 Lawrence Ave, Canaan, CT 06018

    • 3 Beds
    • 3 Baths
    • 1,456 Sq Ft
    • Built 1939

    Last Sold Summary

    • 6% Below List Price
    • $204/SF
    • 82 Days On Market

    Current Estimated Value $305,713

    Last Listing Agent Nicole Blass Raynard & Peirce Realty,LLC

    7 Lawrence Ave, Canaan, CT 06018
    • /24

      Est $492,377 Not Listed For Sale

      301 Miller Ave, Sheffield, MA 01257

      • 3 Beds
      • 2 Baths
      • 1,644 Sq Ft
      • Built 1958
      301 Miller Ave, Sheffield, MA 01257

      Last Sold Summary

      • 3% Below List Price
      • $310/SF
      • 101 Days On Market

      Last Sold Price $510,000

      Last Listing Agent Suzann Ward HOUSATONIC REAL ESTATE

  • /29

    $775,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,730 Sq Ft

    1427 Hewins St, Sheffield, MA 01257

    Beautifully Built New Construction in SheffieldMove-in ready and thoughtfully crafted by a local custom builder, this 3-bedroom, 2-bath home sits on 1.64 private acres. The open-concept living, dining, and kitchen area flows seamlessly to a lovely backyard patio--perfect for indoor-outdoor living. Nearby hiking, biking, and skiing offer endless recreation, or simply relax and enjoy the peaceful

    Claire Pollart WILLIAM RAVEIS - BERKSHIRE

    1427 Hewins St, Sheffield, MA 01257
  • /47

    $825,000 Sold Sep 15, 2025

    20 Hillside Ln, Sheffield, MA 01222

    • 3 Beds
    • 2 Baths
    • 2,057 Sq Ft
    • Built 1992

    Last Sold Summary

    • 8% Below List Price
    • $401/SF
    • 61 Days On Market

    Current Estimated Value $827,152

    Last Listing Agent Sarah Dixon WILLIAM RAVEIS - BERKSHIRE

    20 Hillside Ln, Sheffield, MA 01222
    • /19

      Est $289,256 Not Listed For Sale

      590 S Main St, Sheffield, MA 01257

      • 2 Beds
      • 1 Bath
      • 1,160 Sq Ft
      • Built 1945
      590 S Main St, Sheffield, MA 01257

      Last Sold Summary

      • 29% Above List Price
      • $194/SF
      • 195 Days On Market

      Last Sold Price $225,000

      Last Listing Agent Dan Alden ALDEN COUNTRY REAL ESTATE SERVICES

  • /33

    $775,000

    • 3 Beds
    • 2.5 Baths
    • 3,082 Sq Ft

    86 Main St, Sheffield, MA 01257

    SOUTH BERKSHIRE COUNTY, UPDATED VILLAGE CENTER HOME & OFFICEThis graciously restored vintage house has all the benefits of an ideal Sheffield setting with walkability to restaurants, Bushnell-Sage Library, Dewey Hall, post office, bank, and churches. With residential/commercial zoning, the house features an above-garage private large office/studio, a 1,000 sq. ft. outbuilding with plumbing and

    David Taylor ELYSE HARNEY REAL ESTATE

    86 Main St, Sheffield, MA 01257
  • 100 Sand Rd, Canaan, CT 06018

    $454,000 Sold Aug 15, 2025

    100 Sand Rd, Canaan, CT 06018

    • 4 Beds
    • 2 Baths
    • 1,944 Sq Ft
    • Built 1993

    Last Sold Summary

    • 21% Below List Price
    • $234/SF
    • 267 Days On Market

    Current Estimated Value $511,987

    Last Listing Agent Carol Staats Elyse Harney Real Estate

    100 Sand Rd, Canaan, CT 06018
    • /32

      Est $433,503 Not Listed For Sale

      222 Water Farm Rd, Sheffield, MA 01257

      • 2 Beds
      • 1.5 Baths
      • 1,170 Sq Ft
      • Built 1973
      222 Water Farm Rd, Sheffield, MA 01257

      Last Sold Summary

      • 13% Above List Price
      • $329/SF
      • 63 Days On Market

      Last Sold Price $385,000

      Last Listing Agent Michael Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  • /29

    $365,000

    • 3 Beds
    • 1.5 Baths
    • 1,482 Sq Ft

    153 E Main St, Ashley Falls, MA 01222

    TITLE V PASSED. Mid-1960s ranch on a quiet street with nearly 1/2 acre! A perfect family home to settle down in Southern Berkshire County. Semi-finished basement is a huge bonus, plus garage and additional detached barn/workshop. Sunny, spacious and ripe with potential. Some thoughtful updates will be needed -- or move in today and make it yours!

    John Segalla HOUSATONIC REAL ESTATE

    153 E Main St, Ashley Falls, MA 01222
  • /9

    $75,400 Sold Feb 11, 2026

    62 Hadsell St, New Marlborough, MA 01230

    • Land
    • 3.82 Acres
    • $19,738 per Acre

    Last Sold Summary

    • 15% Below List Price
    • 65 Days On Market

    Last Listing Agent Molly Thomas COMPASS MASSACHUSETTS , LLC GB

    62 Hadsell St, New Marlborough, MA 01230
    • /36

      Est $566,282 Not Listed For Sale

      78 Ashley Falls Rd, Sheffield, MA 01257

      • 3 Beds
      • 2 Baths
      • 1,400 Sq Ft
      • Built 2002
      78 Ashley Falls Rd, Sheffield, MA 01257

      Last Sold Summary

      • 1% Above List Price
      • $399/SF
      • 144 Days On Market

      Last Sold Price $559,000

      Last Listing Agent Tony Segalla WILLIAM RAVEIS - BERKSHIRE

  • /33

    $369,900 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,323 Sq Ft

    37 Greene Ave, Canaan, CT 06018

    Welcome home to this beautifully maintained 1,332 sq ft, 7-room gem nestled in the charming town of North Canaan. Set on a lightly wooded half-acre lot, this sun-filled home offers the perfect blend of comfort, style, and space. Step inside to find neutral tones and elegant decor that create a warm, inviting atmosphere throughout. In addition to three comfortable bedrooms and one full updated

    Jennifer Albanesi Berkshire Hathaway NE Prop.

    37 Greene Ave, Canaan, CT 06018
  • 27 Tobey Hill Rd, Canaan, CT 06018

    $630,000 Sold Aug 25, 2025

    27 Tobey Hill Rd, Canaan, CT 06018

    • 5 Beds
    • 3 Baths
    • 3,436 Sq Ft
    • Built 1790

    Last Sold Summary

    • 3% Below List Price
    • $183/SF
    • 73 Days On Market

    Current Estimated Value $652,226

    Last Listing Agent Tommy Connors Redfin Corporation

    27 Tobey Hill Rd, Canaan, CT 06018
    • /14

      Est $376,115 Not Listed For Sale

      689 N Main St, Sheffield, MA 01257

      • 4 Beds
      • 2 Baths
      • 2,258 Sq Ft
      • Built 1957
      689 N Main St, Sheffield, MA 01257

      Last Sold Summary

      • 79% Above List Price
      • $93/SF
      • 92 Days On Market

      Last Sold Price $210,000

      Last Listing Agent Eric Steuernagle FAIRGROUND REAL ESTATE, INC

  • /28

    $1,995,000

    • 3 Beds
    • 4 Baths
    • 4,442 Sq Ft

    552 Twin Lakes Rd, Salisbury, CT 06068

    "The Taconic School House" 1st Time on the Market in over 25 Years. Special Salisbury Location Set Amongst Large Estates & the Twin Lakes in the Coveted Taconic Section of Salisbury CT. A Gracious & Magical Paneled Room with Large Fireplace Welcomes All to this Whimsical & Eclectic c1890 Home. 3-4 Bedrooms, 4 Full Baths. Lower Level Acts as Pool Cabana & Contains Glass Enclosed Siting Room,

    Graham Klemm Klemm Real Estate Inc

    552 Twin Lakes Rd, Salisbury, CT 06068
  • 305 Ashley Falls Rd, Canaan, CT 06018

    $68,000 Sold May 23, 2025

    305 Ashley Falls Rd, Canaan, CT 06018

    • Land
    • 1.2 Acres
    • $56,667 per Acre

    Last Sold Summary

    • 9% Below List Price
    • 326 Days On Market

    Current Estimated Value $67,754

    Last Listing Agent Susan Belmonte Coldwell Banker Realty

    305 Ashley Falls Rd, Canaan, CT 06018
    • /48

      Est $1,573,160 Not Listed For Sale

      452 Shunpike Rd, Sheffield, MA 01257

      • 3 Beds
      • 3.5 Baths
      • 2,800 Sq Ft
      • Built 1986
      452 Shunpike Rd, Sheffield, MA 01257

      Last Sold Summary

      • 2% Above List Price
      • $550/SF
      • 25 Days On Market

      Last Sold Price $1,540,000

      Last Listing Agent Christian Deckert William Pitt

  • /2

    $57,900 Pending

    • Land
    • 5.1 Acres
    • $11,353 per Acre

    0 Alum Hill Unit 73415610, Sheffield, MA 01257

    OWNER FINANCING AVAILABLE! This 5.1-acre wooded parcel in peaceful Sheffield, MA offers the perfect setting for your Berkshires retreat or year-round home. Surrounded by natural beauty, you'll enjoy nearby attractions like Bartholomew’s Cobble, the Appalachian Trail, and the cultural gems of Great Barrington just minutes away. Sheffield is known for its small-town charm, farm-to-table dining, and

    Derek Greene The Greene Realty Group

    0 Alum Hill Unit 73415610, Sheffield, MA 01257
  • /38

    $258,000 Sold Oct 15, 2025

    52 Shunpike Rd, Southfield, MA 01259

    • 2 Beds
    • 2 Baths
    • 1,659 Sq Ft
    • Built 1979

    Last Sold Summary

    • 19% Below List Price
    • $156/SF
    • 200 Days On Market

    Last Listing Agent Chris LaPatin LAMACCHIA REALTY, INC

    52 Shunpike Rd, Southfield, MA 01259
    • /36

      Est $426,005 Not Listed For Sale

      1014 Salisbury Rd, Sheffield, MA 01257

      • 2 Beds
      • 1 Bath
      • 1,379 Sq Ft
      • Built 1800
      1014 Salisbury Rd, Sheffield, MA 01257

      Last Sold Summary

      • 14% Above List Price
      • $272/SF
      • 6 Days On Market

      Last Sold Price $375,000

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

  • /24

    $299,900

    • 6 Beds
    • 5.5 Baths
    • 3,683 Sq Ft

    175 Main St, Sheffield, MA 01257

    Come this charming 1820 colonial located in Downtown Sheffield! This unique property features 6 bedrooms and 5 and half bathrooms. Lovely hardwood showcasing wide plank and parquet style floors encompass 3,683 square feet of living space. Plenty of off street parking due to the oversized driveway and 2 car attached garage with loft space. Full, unfinished basement can provide additional storage

    Nicholas Decaro Property Works New England

    175 Main St, Sheffield, MA 01257
  • Unlisted Address

    $310,000 Sold Oct 22, 2025

    Unlisted Address

    • 3 Beds
    • 2 Baths
    • 1,799 Sq Ft
    • Built 1907

    Last Sold Summary

    • 10% Below List Price
    • $172/SF
    • 52 Days On Market

    Current Estimated Value $327,688

    Last Listing Agent Wendy Eichman Raynard & Peirce Realty,LLC

    Unlisted Address
    • /42

      Est $577,567 Not Listed For Sale

      575 Sheffield Plain, Sheffield, MA 01257

      • 3 Beds
      • 2.5 Baths
      • 1,960 Sq Ft
      • Built 1890
      575 Sheffield Plain, Sheffield, MA 01257

      Last Sold Summary

      • 3% Above List Price
      • $286/SF
      • 85 Days On Market

      Last Sold Price $560,000

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

  • /11

    $395,000

    • 2 Beds
    • 1 Bath
    • 1,008 Sq Ft

    1089 Canaan Southfield Rd, Southfield, MA 01259

    An enchanting parcel of land with a 2 Bedroom Ranch, in need of updates and cosmetics. The land is beautiful, 7.87 acres, with the house nicely sited up on the knoll. So much potential! There is an attached garage and full basement.The septic design is available and estimate is in hand. Being sold ''as is'', will escrow funds for the septic. A worthwhile project in a private, natural setting.

    Helen Mullany HELEN MULLANY REAL ESTATE, LLC

    1089 Canaan Southfield Rd, Southfield, MA 01259
  • /2

    $680,000 Sold Jun 30, 2025

    63 Glennanna Way, Sheffield, MA 01257

    • 4 Beds
    • 3.5 Baths
    • 2,000 Sq Ft
    • Built 1999

    Last Sold Summary

    • 2% Below List Price
    • $340/SF
    • 76 Days On Market

    Current Estimated Value $722,801

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

    63 Glennanna Way, Sheffield, MA 01257
    • /42

      Est $471,664 Not Listed For Sale

      505 Sheffield Plain, Sheffield, MA 01257

      • 3 Beds
      • 2 Baths
      • 1,900 Sq Ft
      • Built 1847
      505 Sheffield Plain, Sheffield, MA 01257

      Last Sold Summary

      • 24% Above List Price
      • $200/SF
      • 150 Days On Market

      Last Sold Price $380,000

      Last Listing Agent Eric Steuernagle FAIRGROUND REAL ESTATE, INC

  • /27

    $433,000

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    2170 Canaan Southfield Rd, Southfield, MA 01259

    Located in the desirable Clayton section of New Marlborough, this 3-bedroom, 2-bath home offers a rare opportunity to own 7.2 acres with 383 feet of frontage on the Konkapot River. The property features a natural setting with direct river access and plenty of room to make it your own.The home has a functional layout with three bedrooms and two full baths. While move-in ready, it would benefit

    Freddy Friedman BIRCH PROPERTIES

    2170 Canaan Southfield Rd, Southfield, MA 01259
  • 24 E Main St, Canaan, CT 06018

    $235,000 Sold Mar 19, 2026

    24 E Main St, Canaan, CT 06018

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Built 1955

    Last Sold Summary

    • 6% Below List Price
    • $196/SF
    • 59 Days On Market

    Current Estimated Value $241,609

    Last Listing Agent Victor Santana Santana Realty Group LLC

    24 E Main St, Canaan, CT 06018
    • /56

      Est $1,127,475 Not Listed For Sale

      49 Bow Wow Rd, Sheffield, MA 01257

      • 4 Beds
      • 2 Baths
      • 2,929 Sq Ft
      • Built 1941
      49 Bow Wow Rd, Sheffield, MA 01257

      Last Sold Summary

      • 1% Above List Price
      • $382/SF
      • 15 Days On Market

      Last Sold Price $1,120,000

      Last Listing Agent Jared Kelly William Pitt

  • /17

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 2,603 Sq Ft

    10 College Hill Rd, Canaan, CT 06018

    Privacy and Winter Views - This is a sweet Cape at the end of a private road. Features include a large Great Room with Living Room, Dining Area, and Kitchen, plus Mudroom with half Bath. The Primary Bedroom is on the Main Floor with Full Bath and walk-in closet, and 2 additional Bedrooms and a Full Bath are on the Second Floor. A large finished Family Room on the Lower Level with a Full Bath /

    Juliet Moore Elyse Harney Real Estate

    10 College Hill Rd, Canaan, CT 06018
  • 123 Lower Rd, East Canaan, CT 06024

    $385,000 Sold Dec 29, 2025

    123 Lower Rd, East Canaan, CT 06024

    • 3 Beds
    • 3 Baths
    • 1,900 Sq Ft
    • Built 1850

    Last Sold Summary

    • 8% Below List Price
    • $203/SF
    • 115 Days On Market

    Current Estimated Value $383,686

    Last Listing Agent Lauren Freedman Coldwell Banker Realty

    123 Lower Rd, East Canaan, CT 06024
    • /11

      Est $208,769 Not Listed For Sale

      704 S Main St, Sheffield, MA 01257

      • 2 Beds
      • 1 Bath
      • 875 Sq Ft
      • Built 1957
      704 S Main St, Sheffield, MA 01257

      Last Sold Summary

      • 48% Above List Price
      • $161/SF
      • 46 Days On Market

      Last Sold Price $141,000

      Last Listing Agent Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  • /39

    $330,000 Pending

    • 3 Beds
    • 1 Bath
    • 1,530 Sq Ft

    1698 Clayton Mill River Rd, Southfield, MA 01259

    charming house ready for the right person to give it the TLC it deserves to bring life back into it. This house features a large back yard, heated garage and barn that once housed horses equipped with water so no need to lug water from the house. 10 minutes from the center of Sheffield and Canaan CT but tucked away to a cozy private setting.

    John Mercer BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    1698 Clayton Mill River Rd, Southfield, MA 01259
  • /13

    $272,500 Sold Dec 05, 2025

    412 Berkshire School Rd, Sheffield, MA 01257

    • 3 Beds
    • 1 Bath
    • 900 Sq Ft
    • Built 1995

    Last Sold Summary

    • 22% Below List Price
    • $303/SF
    • 66 Days On Market

    Current Estimated Value $282,712

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

    412 Berkshire School Rd, Sheffield, MA 01257
    • /33

      Est $556,550 Not Listed For Sale

      45 Root Ln, Sheffield, MA 01257

      • 5 Beds
      • 2 Baths
      • 2,415 Sq Ft
      • Built 1950
      45 Root Ln, Sheffield, MA 01257

      Last Sold Summary

      • 20% Above List Price
      • $193/SF
      • 138 Days On Market

      Last Sold Price $465,000

      Last Listing Agent Harmony Edwards KELLER WILLIAMS REALTY

  • /13

    $150,000 Pending

    • 2 Beds
    • 1 Bath
    • 892 Sq Ft

    180 Sand Rd, Falls Village, CT 06031

    Investor Take Notice! Opportunity awaits at 180 Sand Rd, Canaan, CT. This 2-bedroom, 1-bath ranch is ready to be brought back to life and reimagined. Set on 2.95 private acres, the property also includes an adjoining 2.13-acre lot (Unique ID: 14100714 | Map Block Lot: 11-44), offering a rare chance to expand or build in a peaceful, rural setting. Make no mistake-this home needs work-but the

    Jorge Deleston Berkshire Hathaway NE Prop.

    180 Sand Rd, Falls Village, CT 06031

Showing Results 41 - 80, Page 2 of 18

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