Ashley Falls, MA Homes

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  /30

  $300,000 Sold Nov 07, 2025

  179 S Main St, Sheffield, MA 01257

  • 3 Beds
  • 2.5 Baths
  • 1,536 Sq Ft
  • Built 1826

  Last Sold Summary

  • 24% Below List Price
  • $195/SF
  • 395 Days On Market

  Current Estimated Value $354,977

  Last Listing Agent Tony Segalla WILLIAM RAVEIS - BERKSHIRE

  179 S Main St, Sheffield, MA 01257
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  /19

  Est $546,604 Not Listed For Sale

  285 Salisbury Rd, Sheffield, MA 01257

  • 3 Beds
  • 2 Baths
  • 2,220 Sq Ft
  • Built 1984

  285 Salisbury Rd, Sheffield, MA 01257

  Last Sold Summary

  • 12% Above List Price
  • $219/SF
  • 10 Days On Market

  Last Sold Price $486,000

  Last Listing Agent Helen Mullany HELEN MULLANY REAL ESTATE, LLC
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  /21

  $110,000

  • Land
  • 7.07 Acres
  • $15,559 per Acre

  730 Clayton Rd, Sheffield, MA 01222

  BOG LOVERS, come look. Officially designated to be a Bog, this property could be a great one to own for observing its nature views that change the year around. Whether you would want to build a home, and/or build a viewing platform for regular visits, it has 7.2 acres (see map with) about 3.5+acres in a bog like 'state', the remainder being usable for building and walking along the bog's

  Robin Leech Robinson Leech Real Estate

  730 Clayton Rd, Sheffield, MA 01222
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  /34

  $680,000 Sold Oct 20, 2025

  662 Foley Rd, Sheffield, MA 01257

  • 4 Beds
  • 2 Baths
  • 2,310 Sq Ft
  • Built 1992

  Last Sold Summary

  • 12% Below List Price
  • $294/SF
  • 69 Days On Market

  Current Estimated Value $735,652

  Last Listing Agent Claire Pollart WILLIAM RAVEIS - BERKSHIRE

  662 Foley Rd, Sheffield, MA 01257
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  /51

  Est $500,838 Not Listed For Sale

  259 Salisbury Rd, Sheffield, MA 01257

  • 3 Beds
  • 2.5 Baths
  • 2,866 Sq Ft
  • Built 1991

  259 Salisbury Rd, Sheffield, MA 01257

  Last Sold Summary

  • 25% Above List Price
  • $140/SF
  • 88 Days On Market

  Last Sold Price $400,000

  Last Listing Agent Lawrence Reilly THE KINDERHOOK GROUP
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  /38

  $695,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,991 Sq Ft

  483 Home Rd, Great Barrington, MA 01230

  A Berkshire dream home! Nestled in a quiet private setting to enjoy the outdoors. This 3 bedroom 3 full bath home is empty and ready to go. Great lighting nice open kitchen dining/living area. Additional room can be used as a den or 1st floor bedroom. Wood stove insert for chilly fall nights while enjoying your 3 seasoned screened porch. Oversized 2 car garage. Full basement could be completed as

  Suzann Ward HOUSATONIC REAL ESTATE

  483 Home Rd, Great Barrington, MA 01230
• 

  $430,000 Sold Nov 13, 2025

  77 Clayton Rd, Canaan, CT 06018

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Above List Price
  • $256/SF
  • 14 Days On Market

  Current Estimated Value $389,276

  Last Listing Agent Wendy Eichman Raynard & Peirce Realty,LLC

  77 Clayton Rd, Canaan, CT 06018
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  /19

  Est $494,735 Not Listed For Sale

  350 S Undermountain Rd, Sheffield, MA 01257

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1977

  350 S Undermountain Rd, Sheffield, MA 01257

  Last Sold Summary

  • 29% Above List Price
  • $241/SF
  • 122 Days On Market

  Last Sold Price $385,000

  Last Listing Agent Michael Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
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  /7

  $349,000

  • Land
  • 19.73 Acres
  • $17,689 per Acre

  0 Hayes Hill Rd Unit 247870, New Marlborough, MA 01244

  Just shy of 20 acres. Make your way to the top for views, you won't be disappointed. An abundance of wildlife, and not a building in sight. Come take a look and make this your Berkshire retreat!

  Lawrence Reilly THE KINDERHOOK GROUP

  0 Hayes Hill Rd Unit 247870, New Marlborough, MA 01244
• 

  $984,000 Sold Dec 05, 2025

  76 Washinee Heights Rd, Salisbury, CT 06068

  • 3 Beds
  • 2.5 Baths
  • 2,405 Sq Ft
  • Built 2004

  Last Sold Summary

  • 10% Above List Price
  • $409/SF
  • 19 Days On Market

  Current Estimated Value $1,000,025

  Last Listing Agent Elvia Gignoux William Pitt Sotheby's Int'l

  76 Washinee Heights Rd, Salisbury, CT 06068
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  /30

  Est $898,623 Not Listed For Sale

  815 S Undermountain Rd, Sheffield, MA 01257

  • 3 Beds
  • 2 Baths
  • 1,552 Sq Ft
  • Built 1971

  815 S Undermountain Rd, Sheffield, MA 01257

  Last Sold Summary

  • 6% Above List Price
  • $547/SF
  • 11 Days On Market

  Last Sold Price $849,000

  Last Listing Agent Tracy Macgowan ELYSE HARNEY REAL ESTATE
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  /2

  $249,000 Pending

  • 4 Beds
  • 1.5 Baths
  • 1,152 Sq Ft

  321 Salisbury Rd, Sheffield, MA 01257

  Attention investors! This property features a primary bedroom with a half bath, along with three additional bedrooms, offering plenty of living space. The combined two lots total 7.99 acres, providing ample room for expansion. Having been vacant for several years, this property presents a blank canvas, ready for someone with a vision to restore it to its former glory. Potential buyers should be

  Diane McDougald Berkshire Hathaway Home Service New England Properties

  321 Salisbury Rd, Sheffield, MA 01257
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  /37

  $644,000 Sold Aug 01, 2025

  284 Brewer Branch Rd, Great Barrington, MA 01230

  • 3 Beds
  • 2 Baths
  • 1,224 Sq Ft
  • Built 1973

  Last Sold Summary

  • 5% Below List Price
  • $526/SF
  • 21 Days On Market

  Current Estimated Value $653,611

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

  284 Brewer Branch Rd, Great Barrington, MA 01230
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  /40

  Est $726,127 Not Listed For Sale

  647 Silver St, Sheffield, MA 01257

  • 3 Beds
  • 3 Baths
  • 1,792 Sq Ft
  • Built 1991

  647 Silver St, Sheffield, MA 01257

  Last Sold Summary

  • 4% Above List Price
  • $388/SF
  • 171 Days On Market

  Last Sold Price $695,000

  Last Listing Agent Tony Segalla WILLIAM RAVEIS - BERKSHIRE
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  /39

  $3,250,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,492 Sq Ft

  247 Twin Lakes Rd, Salisbury, CT 06068

  An exceptional opportunity that merges lakefront living with privacy and stunning mountain vistas! Nestled on just over 4.5 acres, this lakeside estate features a Main Home, a Guest Cottage, two garages-one of which includes a Finished Studio Space on the upper level-a Greenhouse, and an expansive lawn that descends to a private dock on Twin Lakes. The two-story, 3-Bedroom residence has been

  Liza Reiss Elyse Harney Real Estate

  247 Twin Lakes Rd, Salisbury, CT 06068
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  /9

  $342,000 Sold Aug 01, 2025

  0 S Main St, Sheffield, MA 01257

  • Land
  • 6.25 Acres
  • $54,720 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 49 Days On Market

  Last Listing Agent Grace Golden Equine Homes Real Estate, LLC

  0 S Main St, Sheffield, MA 01257
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  /23

  Est $669,507 Not Listed For Sale

  233 Hulett Hill Rd, Sheffield, MA 01257

  • 3 Beds
  • 2.5 Baths
  • 2,016 Sq Ft
  • Built 2006

  233 Hulett Hill Rd, Sheffield, MA 01257

  Last Sold Summary

  • 31% Above List Price
  • $253/SF
  • 7 Days On Market

  Last Sold Price $510,000

  Last Listing Agent Molly DiGiovanni HOUSATONIC REAL ESTATE
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  /49

  $3,785,000 Pending

  • 7 Beds
  • 3 Baths
  • 4,386 Sq Ft

  185 Keyes Hill Rd, New Marlborough, MA 01259

  Blue Hill Farm: an 1820 Center Hall Colonial farm and farmhouse in excellent condition on 249 high acres with organic hay meadows and pastureland, an apple orchard, woodlands, gardens, tennis court, a 1970's caretaker/farmer's house and multiple barns. The main house has 6/7 bedrooms and three baths, along with a three-car attached garage. The property consists of seven parcels of contiguous land

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  185 Keyes Hill Rd, New Marlborough, MA 01259
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  /34

  $795,000 Sold Jun 09, 2025

  371 Berkshire School Rd, Sheffield, MA 01257

  • 3 Beds
  • 2.5 Baths
  • 2,633 Sq Ft
  • Built 1949

  Last Sold Summary

  • $302/SF
  • 12 Days On Market

  Current Estimated Value $812,176

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

  371 Berkshire School Rd, Sheffield, MA 01257
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  /71

  Not Listed For Sale

  2128 Canaan Southfield Rd, Southfield, MA 01259

  • 9 Beds
  • 12 Baths
  • 8,623 Sq Ft
  • Built 2014

  2128 Canaan Southfield Rd, Southfield, MA 01259

  Last Sold Summary

  • 93% Below List Price
  • $1,079/SF
  • 167 Days On Market

  Last Sold Price $9,300,000

  Last Listing Agent Elle Villetto William Pitt
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  /28

  $495,000

  • 4 Beds
  • 2 Baths
  • 1,531 Sq Ft

  95 Water Farm Rd, Sheffield, MA 01257

  New roof, siding, and house fully painted. Newer heating system. Experience the perfect blend of modern comfort and historical charm in this beautifully maintained home. Featuring 4 spacious bedrooms and 2 baths, this home offers over 1,500 sq. ft. of living space. Enjoy the character of the 1850s with updates, including new mechanics. This home is truly move-in ready. The stonework patio

  Suzann Ward HOUSATONIC REAL ESTATE

  95 Water Farm Rd, Sheffield, MA 01257
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  /20

  $350,000 Sold Oct 01, 2025

  355 Clayton Rd, Sheffield, MA 01222

  • 3 Beds
  • 3 Baths
  • 6,420 Sq Ft
  • Built 1976

  Last Sold Summary

  • 43% Below List Price
  • $55/SF
  • 234 Days On Market

  Last Listing Agent Mark Rosengren WILLIAM RAVEIS - BERKSHIRE

  355 Clayton Rd, Sheffield, MA 01222
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  /65

  Est $978,393 Not Listed For Sale

  1976 Clayton Mill River Rd, Southfield, MA 01259

  • 4 Beds
  • 4.5 Baths
  • 3,200 Sq Ft
  • Built 2024

  1976 Clayton Mill River Rd, Southfield, MA 01259

  Last Sold Summary

  • 7% Above List Price
  • $285/SF
  • 54 Days On Market

  Last Sold Price $912,000

  Last Listing Agent Vashti Poor WILLIAM RAVEIS - BERKSHIRE
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  /34

  $2,550,000

  • 3 Beds
  • 3 Baths
  • 3,894 Sq Ft

  99 Washinee Heights Rd, Salisbury, CT 06068

  Arrive at The Lake House and a profound sense of peace immediately washes over you. Situated on a quiet, exclusive street along the shores of Lake Washinee in Salisbury , this contemporary estate offers a truly private retreat. With 300 feet (+/-)of pristine water frontage, the property looks out over the quiet lake to the Taconic Range, offering spectacular, western-facing sunset views. It is a

  Elvia Gignoux William Pitt Sotheby's Int'l

  99 Washinee Heights Rd, Salisbury, CT 06068
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  /2

  $75,000 Sold Jan 20, 2026

  16 Lilac Ln, Sheffield, MA 01257

  • 2 Beds
  • 1 Bath
  • 1,230 Sq Ft
  • Built 1977

  Last Sold Summary

  • 24% Below List Price
  • $61/SF
  • 6 Days On Market

  Current Estimated Value $227,973

  Last Listing Agent Timothy Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  16 Lilac Ln, Sheffield, MA 01257
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  /46

  Est $640,821 Not Listed For Sale

  2383 Canaan Southfield Rd, Southfield, MA 01259

  • 2 Beds
  • 1.5 Baths
  • 4,232 Sq Ft
  • Built 1810

  2383 Canaan Southfield Rd, Southfield, MA 01259

  Last Sold Summary

  • 60% Above List Price
  • $95/SF
  • 190 Days On Market

  Last Sold Price $400,000

  Last Listing Agent Kenzie Fields ELYSE HARNEY REAL ESTATE
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  /86

  $3,995,000 Under Contract

  • 5 Beds
  • 6.5 Baths
  • 6,915 Sq Ft

  662 Brewer Hill Rd, New Marlborough, MA 01230

  Iconic only begins to describe this rare union of sophistication & natural splendor. Spanning 40+ secluded acres of rolling meadows, forested trails, & sweeping mountain views, this remarkable estate has welcomed world-renowned artists & hosted unforgettable gatherings, from summer soirees to intimate retreats.At its heart is the Great House--a 6,000 sq. ft. architectural masterpiece by renowned

  Claire Pollart WILLIAM RAVEIS - BERKSHIRE

  662 Brewer Hill Rd, New Marlborough, MA 01230
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  $233,300 Sold Jun 09, 2025

  18 Patty Ln, Canaan, CT 06018

  • 2 Beds
  • 1 Bath
  • 696 Sq Ft
  • Built 1940

  Last Sold Summary

  • 1% Above List Price
  • $335/SF
  • 151 Days On Market

  Current Estimated Value $230,409

  Last Listing Agent Derek Greene Derek Greene

  18 Patty Ln, Canaan, CT 06018
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  /31

  Est $866,410 Not Listed For Sale

  1289 Canaan Southfield Rd, Southfield, MA 01259

  • 4 Beds
  • 3 Baths
  • 1,875 Sq Ft
  • Built 1990

  1289 Canaan Southfield Rd, Southfield, MA 01259

  Last Sold Summary

  • 2% Above List Price
  • $453/SF
  • 64 Days On Market

  Last Sold Price $850,000

  Last Listing Agent William Melnick ELYSE HARNEY REAL ESTATE
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  /75

  $3,250,000

  • 6 Beds
  • 5.5 Baths
  • 3,416 Sq Ft

  651 Hayes Hill Rd, New Marlborough, MA 01230

  Built in 1964, this Berkshires compound comprised of three homes set on over fifty acres with panoramic southerly views to the northern Connecticut hills. The main home, a modernist design collaboration between Bauhaus designer George Giusti and architect Crane De Camp, is a two-bedroom, three-and-a-half-bath masterpiece that features a gym, sauna, and gardens designed by a local landscape

  Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

  651 Hayes Hill Rd, New Marlborough, MA 01230
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  $475,000 Sold Dec 31, 2025

  33 Granite Ave, Canaan, CT 06018

  • 5 Beds
  • 2 Baths
  • 2,494 Sq Ft
  • Built 1920

  Last Sold Summary

  • 6% Above List Price
  • $190/SF
  • 57 Days On Market

  Current Estimated Value $478,905

  Last Listing Agent Daniel Smith Raynard & Peirce Realty,LLC

  33 Granite Ave, Canaan, CT 06018
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  /78

  Est $1,264,992 Not Listed For Sale

  128 Konkapot Rd, Southfield, MA 01259

  • 6 Beds
  • 3.5 Baths
  • 4,005 Sq Ft
  • Built 1999

  128 Konkapot Rd, Southfield, MA 01259

  Last Sold Summary

  • 3% Below List Price
  • $325/SF
  • 31 Days On Market

  Last Sold Price $1,300,000

  Last Listing Agent Vashti Poor WILLIAM RAVEIS - BERKSHIRE
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  /13

  $220,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft

  41 Prospect St, Canaan, CT 06018

  Looking for small town charm, a country home, investment property or weekend retreat? This one level, three bedroom, two bath home is waiting for your creative vision. Situated on a quiet street, filled with natural light, hardwood flooring, enclosed front porch and detached garage. Just minutes to local shops, short drive to the Berkshires and a great location for outdoor enthusiasts. This home

  Dawn Sanderson Northwest CT Realty

  41 Prospect St, Canaan, CT 06018
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  /37

  $401,500 Sold Mar 24, 2026

  334 S Undermountain Rd, Sheffield, MA 01257

  • 3 Beds
  • 2 Baths
  • 1,683 Sq Ft
  • Built 1987

  Last Sold Summary

  • 3% Above List Price
  • $239/SF
  • 7 Days On Market

  Current Estimated Value $397,353

  Last Listing Agent Victoria Standring LAMACCHIA REALTY, INC

  334 S Undermountain Rd, Sheffield, MA 01257
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  /54

  Est $1,121,203 Not Listed For Sale

  227 Konkapot Rd, Southfield, MA 01259

  • 4 Beds
  • 4 Baths
  • 4,164 Sq Ft
  • Built 2002

  227 Konkapot Rd, Southfield, MA 01259

  Last Sold Summary

  • 7% Below List Price
  • $288/SF
  • 201 Days On Market

  Last Sold Price $1,200,000

  Last Listing Agent Chapin Fish William Pitt
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  /2

  $79,000

  • Land
  • 2.3 Acres
  • $34,348 per Acre

  0 Clayton Mill River Rd, New Marlborough, MA 01244

  Over 2 + acres overlooking the Konkapot River in the village of Mill River.1 mile to Umpachene Falls.

  Mary White BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  0 Clayton Mill River Rd, New Marlborough, MA 01244
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  $280,000 Sold Feb 24, 2026

  246 Ashley Falls Rd, Canaan, CT 06018

  • 4 Beds
  • 2 Baths
  • 2,214 Sq Ft
  • Built 1800

  Last Sold Summary

  • 24% Below List Price
  • $126/SF
  • 95 Days On Market

  Current Estimated Value $310,082

  Last Listing Agent Roberta Green Elyse Harney Real Estate

  246 Ashley Falls Rd, Canaan, CT 06018
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  /19

  Est $388,705 Not Listed For Sale

  358 Mill River Southfield Rd, New Marlborough, MA 01230

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft
  • Built 1970

  358 Mill River Southfield Rd, New Marlborough, MA 01230

  Last Sold Summary

  • 21% Above List Price
  • $460/SF
  • 58 Days On Market

  Last Sold Price $322,000

  Last Listing Agent Lisa Crawford BIRCH PROPERTIES
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  /52

  $1,900,000

  • 4 Beds
  • 3 Baths
  • 2,976 Sq Ft

  1269 Clayton Mill River Rd, New Marlborough, MA 01259

  Welcome to your ultimate country retreat, where the charm of history meets the ease of modern living. Here, timeless beauty and serenity reign--an escape where silence is broken only by the wind in the fields and the song of birds.The 1828 brick colonial, a masterpiece of its era, has been exquisitely restored to showcase spacious, light-filled rooms that draw the outdoors in, framing views of

  Lisa Hoe THE KINDERHOOK GROUP

  1269 Clayton Mill River Rd, New Marlborough, MA 01259
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  /63

  $720,000 Sold Oct 31, 2025

  461 Hulett Hill Rd, Sheffield, MA 01257

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • Built 1990

  Last Sold Summary

  • 1% Below List Price
  • $360/SF
  • 17 Days On Market

  Current Estimated Value $723,848

  Last Listing Agent Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  461 Hulett Hill Rd, Sheffield, MA 01257

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