Cheshire, MA Homes

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  $159,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,850 Sq Ft

  108 Church St, Cheshire, MA 01225

  Welcome to the quaint town of Cheshire, this 2-unit rental is situated in center of town convenient to coffee shop, town hall, post office, Ashuwillticook Rail Trail, local activities & more. Lower level unit is vacant - easy to show. Some charming details remain in the 2nd floor unit - tin ceiling in living room, spacious eat in kitchen. New septic system installed 2025, certificate of

  

  Nadine Hiser

  KEY REALTY

  (413) 553-1912

  108 Church St, Cheshire, MA 01225
• Explore Cheshire

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  /7

  $1,750 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft
  • Condo for Rent

  100 Church St Unit Cheshire, Cheshire, MA 01225

  Easy access in desirable Cheshire, this 2nd floor remodeled unit features 3 bedrooms, new kitchen, full bath, a living room and offers off street parking.

  100 Church St Unit Cheshire, Cheshire, MA 01225
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  $420,000 Sold May 05, 2025

  612 Notch Rd, Cheshire, MA 01225

  • 3 Beds
  • 2 Baths
  • 2,352 Sq Ft
  • Built 1987

  Last Sold Summary

  • 5% Below List Price
  • $179/SF
  • 51 Days On Market

  Current Estimated Value $437,670

  Last Listing Agent Jennifer Maxwell LAMACCHIA REALTY, INC

  612 Notch Rd, Cheshire, MA 01225
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  /89

  Est $472,650 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,068 Sq Ft

  935 Outlook Ave, Cheshire, MA 01225

  935 Outlook Ave, Cheshire, MA 01225
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  $549,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,134 Sq Ft

  132 Outlook Ave, Cheshire, MA 01225

  Classic country charm awaits you in the foothills of Cheshire Massachusetts and escape home to privacy and serenity in northern Berkshire to live and play in the great outdoors. Enjoy hiking out your door and follow the Appalachian Trail even reach Mount Greylock, bike ride north and south on the Ashuwillticook Trail exercising and exploring the beautiful farmlands and countryside as you immerse

  Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

  132 Outlook Ave, Cheshire, MA 01225
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  /7

  $400 total monthly price

  • 2 Baths
  • 320 Sq Ft
  • Property for Rent

  80 Church St, Cheshire, MA 01225

  The town of Cheshire is offering this third floor double connecting room for rent. Offering approximately 320 square feet of space, making it suitable for a variety of office spaces or operations. The rental agreement is inclusive, covering the costs of heat, hot water, electricity, trash removal, and grounds maintenance. This simplifies budgeting and ensures predictable monthly expenses for

  Jason Nocher NOCHER REALTY

  80 Church St, Cheshire, MA 01225
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  /14

  $82,000 Sold May 29, 2025

  10 3rd Ave, Cheshire, MA 01225

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

  Last Sold Summary

  • 3% Below List Price
  • $89/SF
  • 5 Days On Market

  Last Listing Agent Jesse Dimitropolis RE/MAX COMPASS

  10 3rd Ave, Cheshire, MA 01225
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  /28

  Est $322,866 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 570 Sq Ft

  205 Lake Shore Dr, Cheshire, MA 01225

  205 Lake Shore Dr, Cheshire, MA 01225
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  /5

  $114,900

  • Land
  • 1.38 Acres
  • $83,417 per Acre

  Lot 9E Stewart White Rd, Cheshire, MA 01225

  Discover the perfect setting for your dream home on this gently sloping, 1.4-acre lot located in the rural countryside of Cheshire. With breathtaking views and a cleared, ready-to-build landscape, this property offers the ideal blend of privacy and natural beauty. Situated on a town-maintained road and includes drilled well and perc test. Additional 1.4 acre adjacent lot available.

  Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

  Lot 9E Stewart White Rd, Cheshire, MA 01225
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  $1,500 total monthly price

  • Studio
  • 0.5 Baths
  • 3,500 Sq Ft
  • Property for Rent

  106 Church St, Cheshire, MA 01225

  Large commercial space for lease. Versatile layout, suitable for retail, restaurant, office/meeting space. Endless possibilities to customize for your business needs.3 phase electric in place.Bring your business to Cheshire or start your dream business!

  Pauline Green STEEPLEVIEW REALTY - ADAMS BRANCH

  106 Church St, Cheshire, MA 01225
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  $260,000 Sold Jun 02, 2025

  27 Church St, Cheshire, MA 01225

  • 4 Beds
  • 2 Baths
  • 1,531 Sq Ft
  • Built 1850

  Last Sold Summary

  • 15% Below List Price
  • $170/SF
  • 73 Days On Market

  Current Estimated Value $278,646

  Last Listing Agent Colleen Zajac MONARCH REALTY, INC.

  27 Church St, Cheshire, MA 01225
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  /30

  Est $283,642 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,004 Sq Ft

  116 Wells Rd, Cheshire, MA 01225

  116 Wells Rd, Cheshire, MA 01225
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  $599,000

  • Land
  • 1.7 Acres
  • $352,353 per Acre

  12 South St, Cheshire, MA 01225

  Property on corner of busy 4 way stoplight in the heart of town with 256 ft of frontage. High visibility and high traffic count: 11,777 on average. Multi-zoned for multiple different uses & possibilities. The source of all representations are from the seller or a public source; broker has not verified same. It is recommended that buyer independently verify all information.

  Pat Roberts STEEPLEVIEW REALTY - N. ADAMS

  12 South St, Cheshire, MA 01225
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  /20

  $61,525 Sold Jan 06, 2026

  16 2nd Ave, Cheshire, MA 01225

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft

  Last Sold Summary

  • 23% Below List Price
  • $79/SF
  • 75 Days On Market

  Last Listing Agent THE KAHN TEAM BISHOP WEST REAL ESTATE

  16 2nd Ave, Cheshire, MA 01225
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  /23

  Est $308,202 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,674 Sq Ft

  83 Richardson St, Cheshire, MA 01225

  83 Richardson St, Cheshire, MA 01225
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  $539,900

  • 5 Beds
  • 3.5 Baths
  • 3,307 Sq Ft

  867 Notch Rd, Cheshire, MA 01225

  Home on a dream lot--over 7 secluded acres framed by mountains and backing to the Chalet Wildlife Management Area (7,000+ acres of protected state land). Enjoy total privacy, wide-open views, and dark-night skies away from city lights. Step inside to a grand entrance with a glistening chandelier. The main level features a flowing layout: a spacious kitchen with sufficient storage and generous

  Mariah Worth LAMACCHIA REALTY, INC

  867 Notch Rd, Cheshire, MA 01225
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  /14

  $30,000 Sold Mar 31, 2025

  Unlisted Address

  • Land
  • 3.1 Acres
  • $9,677 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 27 Days On Market

  Last Listing Agent Nathan Girard ROYAL PROPERTY GROUP

  Unlisted Address
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  /30

  Est $265,519 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft

  6 Arnold Ct, Cheshire, MA 01225

  6 Arnold Ct, Cheshire, MA 01225
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  /22

  $384,900

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft

  53 Depot St, Cheshire, MA 01225

  Nestled in the heart of downtown Cheshire, this beautifully updated New England farmhouse blends classic charm with modern comforts. Featuring a convenient first-floor bedroom and full bath, plus two additional bedrooms and a second full bath upstairs. The recently renovated kitchen boasts granite countertops, abundant cabinet space, stainless steel appliances, and an abundance of natural light.

  Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

  53 Depot St, Cheshire, MA 01225
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  $328,000 Sold Jan 29, 2025

  236 Devonshire Dr, Cheshire, MA 01225

  • 2 Beds
  • 2 Baths
  • 1,431 Sq Ft
  • Built 1976

  Last Sold Summary

  • 1% Above List Price
  • $229/SF
  • 3 Days On Market

  Current Estimated Value $356,262

  Last Listing Agent Jason Nocher NOCHER REALTY

  236 Devonshire Dr, Cheshire, MA 01225
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  /13

  Est $319,367 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,557 Sq Ft

  517 N State Rd, Cheshire, MA 01225

  517 N State Rd, Cheshire, MA 01225
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  $119,900 Pending

  • Land
  • 1.38 Acres
  • $87,047 per Acre

  Lot 10E Stewart White Rd, Cheshire, MA 01225

  Discover the perfect setting for your dream home on this gently sloping, 1.4-acre lot located in the rural countryside of Cheshire. With breathtaking views and a cleared, ready-to-build landscape, this property offers the ideal blend of privacy and natural beauty. Situated on a town-maintained road and includes drilled well and perc test. Additional 1.4 acre adjacent lot available.

  Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

  Lot 10E Stewart White Rd, Cheshire, MA 01225
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  /18

  $230,000 Sold Aug 11, 2025

  901 S State Rd, Cheshire, MA 01225

  • 4 Beds
  • 1 Bath
  • 1,690 Sq Ft
  • Built 1920

  Last Sold Summary

  • $136/SF
  • 7 Days On Market

  Current Estimated Value $242,364

  Last Listing Agent Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

  901 S State Rd, Cheshire, MA 01225
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  /29

  Est $438,266 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,581 Sq Ft

  77 Willow Ln, Cheshire, MA 01225

  77 Willow Ln, Cheshire, MA 01225
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  /16

  $599,000

  • Land
  • 1.7 Acres
  • $352,353 per Acre

  12 South St, Cheshire, MA 01225

  Property on corner of busy 4 way stoplight in the heart of town with 256 ft of frontage. High visibility and high traffic count: 11,777 on average. Multi-zoned for multiple different uses & possibilities. The source of all representations are from the seller or a public source; broker has not verified same. It is recommended that buyer independently verify all information.

  Deb Trzcinski Steepleview Realty - Mass

  12 South St, Cheshire, MA 01225
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  /23

  $45,900 Sold Feb 12, 2025

  Unlisted Address

  • 2 Beds
  • 1 Bath
  • 980 Sq Ft
  • Built 1976

  Last Sold Summary

  • $47/SF
  • 3 Days On Market

  Last Listing Agent THE KAHN TEAM BISHOP WEST REAL ESTATE

  Unlisted Address
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  /16

  Est $329,566 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,048 Sq Ft

  511 Stafford Hill Rd, Cheshire, MA 01225

  511 Stafford Hill Rd, Cheshire, MA 01225
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  $539,000

  • 4 Beds
  • 2.5 Baths
  • 2,892 Sq Ft

  268 Devonshire Dr, Cheshire, MA 01225

  Super spacious Colonial with amazing mountain views! This 4 bedroom / 3 bath home will check all of your boxes. Located towards the top of the Hutchinson Development this home boasts, an enormous primary bedroom, a wood burning fireplace, a completely finished lower level which contains the family room along with a full bath, Granite kitchen countertops, 2892 sq ft of living space, a large 2 bay

  Timothy Johnson NOCHER REALTY

  268 Devonshire Dr, Cheshire, MA 01225
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  $810,000 Sold Oct 08, 2025

  611 N State Rd, Cheshire, MA 01225

  • 3 Beds
  • 3.5 Baths
  • 4,500 Sq Ft
  • Built 1989

  Last Sold Summary

  • 4% Above List Price
  • $180/SF
  • 5 Days On Market

  Current Estimated Value $801,985

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

  611 N State Rd, Cheshire, MA 01225
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  /64

  Est $538,878 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,992 Sq Ft

  459 Stafford Hill Rd, Cheshire, MA 01225

  459 Stafford Hill Rd, Cheshire, MA 01225
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  $539,900 Pending

  • 4 Beds
  • 1.5 Baths
  • 1,865 Sq Ft

  573 Stafford Hill Rd, Cheshire, MA 01225

  Welcome to this spacious 4-bedroom, 2-bathroom home offering 1,865 sq ft. of comfortable living space on a generous 1.42 acre lot in the beautiful town of Cheshire. This property features a bright and inviting layout, well-sized bedrooms, and ample room for everyday living or entertaining. New vinyl siding, gutters & awnings added in the most recent years. Enjoy the privacy and outdoor

  Sara Bresett NOCHER REALTY

  573 Stafford Hill Rd, Cheshire, MA 01225
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  $385,963 Sold May 05, 2025

  187 Wells Rd, Cheshire, MA 01225

  • 3 Beds
  • 1.5 Baths
  • 1,624 Sq Ft
  • Built 1947

  Last Sold Summary

  • 3% Above List Price
  • $238/SF
  • 36 Days On Market

  Current Estimated Value $386,684

  Last Listing Agent Claire Shomphe BIRCH PROPERTIES

  187 Wells Rd, Cheshire, MA 01225
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  /25

  Est $275,836 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,373 Sq Ft

  28 Prospect St, Cheshire, MA 01225

  28 Prospect St, Cheshire, MA 01225
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  $489,999

  • 3 Beds
  • 2 Baths
  • 2,670 Sq Ft

  40 Curran Rd, Cheshire, MA 01225

  Welcome to 40 Curran Rd. This beautifully updated modern home sits on over an acre of private land. This turnkey home offers 3 bedrooms, 2 full baths, an open-flow layout filled with natural light. The inviting living room features a cozy wood-burning fireplace, perfect for gathering on cool fall evenings with pumpkin spice everything! Primary bedroom includes private en-suite bath. Updated

  Laura Arseneau PAULA MCLEAN REALTORS INC.

  40 Curran Rd, Cheshire, MA 01225
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  /9

  $80,000 Sold Jul 22, 2025

  #16 Jenks Rd, Cheshire, MA 01225

  • Land
  • 10.01 Acres
  • $7,992 per Acre

  Last Sold Summary

  • 27% Below List Price
  • 29 Days On Market

  Last Listing Agent Tracy Munger KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  #16 Jenks Rd, Cheshire, MA 01225
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  /34

  Est $180,951 Not Listed For Sale

  • 7 Beds
  • 5.5 Baths
  • 4,403 Sq Ft

  24 South St Unit 34, Cheshire, MA 01225

  24 South St Unit 34, Cheshire, MA 01225
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  /58

  $849,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,438 Sq Ft

  20 Pleasant View Dr, Cheshire, MA 01225

  Unique home overlooking Mount Greylock range. Early morning, afternoon and evening sun fill this 4 bedroom 2.5 bathroom, open floor plan home with light all year round.The entire first floor has been renovated and now has an open floor plan with a new doublesided propane fireplace. Opportunity for single floor living exists since primary bedroom and laundry are on first floor in addition to a

  Sean Taylor MORESI REAL ESTATE PARTNERS

  20 Pleasant View Dr, Cheshire, MA 01225
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  /30

  $397,000 Sold Mar 28, 2025

  147 E Harbor Rd, Cheshire, MA 01225

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft
  • Built 1963

  Last Sold Summary

  • $249/SF
  • 6 Days On Market

  Current Estimated Value $416,417

  Last Listing Agent Mary Blair SIGNATURE ASSOCIATES

  147 E Harbor Rd, Cheshire, MA 01225
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  /36

  Est $623,020 Not Listed For Sale

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

  278 E Harbor Rd, Cheshire, MA 01225

  278 E Harbor Rd, Cheshire, MA 01225
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  $304,000 Sold Oct 24, 2025

  53 Wells Rd, Cheshire, MA 01225

  • 2 Beds
  • 1 Bath
  • 1,237 Sq Ft
  • Built 1950

  Last Sold Summary

  • 2% Above List Price
  • $246/SF
  • 5 Days On Market

  Last Listing Agent Laiken Rapisarda LAMACCHIA REALTY, INC

  53 Wells Rd, Cheshire, MA 01225

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