Cheshire, MA Homes

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  /27

  $232,000 Sold Aug 07, 2025

  • 1,040 Sq Ft
  • $223/SF
  • 3 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1955

  65 Daniels Terrace, Cheshire, MA 01225

  Charming One-Story Home in the Heart of the BerkshiresJust half a mile from the scenic Cheshire Lake and the Ashwillticook Trail, this delightful one-story home offers easy living in a serene and private setting. Located at the end of a peaceful dead-end street. This property provides both tranquility and convenience--imagine enjoying lovely walks or bike rides to Adams or Pittsfield. If you

  Pam Tworig BISHOP WEST REAL ESTATE

  65 Daniels Terrace, Cheshire, MA 01225
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• 

  

  

  /44

  Est $590,668 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,776 Sq Ft

  222 Brough Rd, Cheshire, MA 01225

  222 Brough Rd, Cheshire, MA 01225
• 

  

  

  /5

  $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
• 

  

  

  /66

  $675,000 Sold Jul 25, 2025

  • 3,240 Sq Ft
  • $208/SF
  • 19 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1968

  147 Brough Rd, Cheshire, MA 01225

  This sprawling home is set back from the main rd offering the perfect blend of privacy and convenience. Step out onto the large front porch and enjoy the peaceful setting with a small pond. There is a large kitchen with plenty of granite counter space, ideal for preparing your favorite meal. The floor to ceiling fireplace is the focal point of the great room. The primary en-suite bedroom is

  Janet Benoit MOCKINGBIRD REAL ESTATE

  147 Brough Rd, Cheshire, MA 01225
• 

  

  

  /33

  Est $418,209 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,032 Sq Ft

  192 Willow Cove Rd, Cheshire, MA 01225

  192 Willow Cove Rd, Cheshire, MA 01225
• 

  

  /46

  $439,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 2,254 Sq Ft

  136 Ingalls Rd, Cheshire, MA 01225

  Experience refined living in this beautifully renovated and thoughtfully designed home in the heart of Cheshire! This turnkey property offers the perfect blend of comfort, style, and functionality. Step outside to your private backyard oasis, complete with a recently upgraded in-ground pool, ideal for summer entertaining or relaxing evenings while watching the sunset. Inside, you'll find gleaming

  Laiken Rapisarda LAMACCHIA REALTY, INC

  136 Ingalls Rd, Cheshire, MA 01225
• 

  

  /35

  $272,500 Sold Jul 24, 2025

  • 1,984 Sq Ft
  • $137/SF
  • 277 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1920

  44 Richmond St, Cheshire, MA 01225

  NEW UPDATES IN LAST MONTH! Experience the charm of this dreamy home located just around the corner from Cheshire Lake and the Bike Trail. With an abundance of natural light pouring in through skylights, large windows, and triple wide doors leading to the front porch, this home feels inviting and spacious. The primary room measures 22x18 ft and features a stunning vaulted cherry pine ceiling, a

  Mariah Worth LAMACCHIA REALTY, INC

  44 Richmond St, Cheshire, MA 01225
• 

  

  /67

  Est $534,379 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,890 Sq Ft

  145 Maple Dr, Cheshire, MA 01225

  145 Maple Dr, Cheshire, MA 01225
• 

  

  /9

  $80,000 Sold Jul 22, 2025

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

  • 29 Days On Market

  #16 Jenks Rd, Cheshire, MA 01225

  Affordable, private and picturesque 10+ acres in Cheshire, with potential views galore is the perfect place to build your new home! Although tucked away in the hills, this location is in close proximity to shopping and dining and nearby to the Ashuwillticook Rail Trail and Cheshire Lake. Some light clearing has already been done!

  Tracy Munger KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  #16 Jenks Rd, Cheshire, MA 01225
• 

  

  /45

  Est $445,274 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,380 Sq Ft

  10 Hutchinson Ln, Cheshire, MA 01225

  10 Hutchinson Ln, Cheshire, MA 01225
• 

  

  /18

  $420,000 Sold Jul 22, 2025

  • 2,100 Sq Ft
  • $200/SF
  • 13 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1978

  632 N State Rd, Cheshire, MA 01225

  Welcome to your dream home in the heart of Cheshire! This stunning 4 bedroom 2 bath raised ranch has been completely renovated with modern touches and high quality finishes throughout. Step inside to discover brand-new-life proof vinyl and porcelain vinyl flooring that combines style and durability in every room. The kitchen is a chefs delight, featuring all-new cabinets, gleaming quartz

  James Gelinas GELINAS REAL ESTATE

  632 N State Rd, Cheshire, MA 01225
• 

  

  /25

  Est $252,468 Not Listed For Sale

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

  54 Pleasant View Dr, Cheshire, MA 01225

  54 Pleasant View Dr, Cheshire, MA 01225
• 

  

  /10

  $80,000 Sold Jul 21, 2025

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

  • 35 Days On Market

  16 Jenks Rd, Cheshire, MA 01225

  Affordable, private and picturesque 10+ acres in Cheshire, with potential views galore is the perfect place to build your new home! Although tucked away in the hills, this location is in close proximity to shopping and dining and nearby to the Ashuwillticook Rail Trail and Cheshire Lake. Some light clearing has already been done!

  Tracy Munger Kempf-Vanderburgh Realty Consultants, Inc.

  16 Jenks Rd, Cheshire, MA 01225
• 

  

  /49

  Est $446,822 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,685 Sq Ft

  213 Devonshire Dr, Cheshire, MA 01225

  213 Devonshire Dr, Cheshire, MA 01225
• 

  

  /44

  $274,450 Sold Jul 18, 2025

  • 1,098 Sq Ft
  • $250/SF
  • 21 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1788

  1400 Wells Rd, Cheshire, MA 01225

  Charming Old-Style Home on Expansive 3,7 acre lot!Step back in time with this cozy 2-bedroom, 1-bathroom home full of character and potential. Nestled on a beautiful, flat 3.7 acre lot, this property offers endless possibilities--whether you're looking to renovate, build your dream home, or enjoy peaceful country living as-is. The spacious lot provides room for gardens, recreation or future

  Sara Bresett NOCHER REALTY

  1400 Wells Rd, Cheshire, MA 01225
• 

  

  /48

  Est $523,501 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,340 Sq Ft

  4 Devonshire Dr, Cheshire, MA 01225

  4 Devonshire Dr, Cheshire, MA 01225
• 

  

  /21

  $64,000 Sold Jul 14, 2025

  • 768 Sq Ft
  • $83/SF
  • 8 Days On Market

  • 2 Beds
  • 1 Bath

  22 2nd Ave, Cheshire, MA 01225

  Easy Living in Cheshire! This well-maintained two-bedroom, one-bathroom mobile home in Berkshire Villages is a great starter home or those seeking to downsize. This mobile home has newer carpet, doors, and a spacious living room and dining area. Take in the views while relaxing on the outdoor deck

  Jim Thurston LAMACCHIA REALTY, INC

  22 2nd Ave, Cheshire, MA 01225
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  /35

  Est $296,224 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,872 Sq Ft

  105 Depot St, Cheshire, MA 01225

  105 Depot St, Cheshire, MA 01225
• 

  

  /22

  $190,000 Sold Jun 16, 2025

  • 858 Sq Ft
  • $221/SF
  • 78 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1928

  114 E Main St, Cheshire, MA 01225

  Cheshire, cute as a button! enclosed front porch, wood floors, updated kitchen and bath, stainless appliances, furnace about 10 years, hot water tank 1 year old, and owned. Shed with electric, plenty of off-street parking.Close proximity to the Ashuwillticook Rail Trail

  Marnie Garzone THE KINDERHOOK GROUP

  114 E Main St, Cheshire, MA 01225
• 

  

  /39

  Est $295,425 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,674 Sq Ft

  894 W Mountain Rd, Cheshire, MA 01225

  894 W Mountain Rd, Cheshire, MA 01225
• 

  

  /47

  $260,000 Sold Jun 02, 2025

  • 1,531 Sq Ft
  • $170/SF
  • 73 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1850

  27 Church St, Cheshire, MA 01225

  This delightful 1850s Colonial home, nestled in the scenic Berkshires, seamlessly combines timeless character with modern upgrades. Offering 1,750 sq. ft. of living space, this home features a newly renovated (Sept. 2022) eat-in kitchen with Hickory cabinets, granite countertops, and high-quality Maytag appliances--perfect for culinary creations and family gatherings. The inviting living room

  Colleen Zajac MONARCH REALTY, INC.

  27 Church St, Cheshire, MA 01225
• 

  

  /30

  Est $376,108 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,547 Sq Ft

  480 Savoy Rd Unit 494, Cheshire, MA 01225

  480 Savoy Rd Unit 494, Cheshire, MA 01225
• 

  

  /14

  $82,000 Sold May 29, 2025

  • 924 Sq Ft
  • $89/SF
  • 5 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1995

  10 3rd Ave, Cheshire, MA 01225

  Step into this well-maintained 1995 mobile home offering 3 bedrooms and 1 full bathroom--perfect for anyone seeking affordable and comfortable living. This home features a bright and inviting living area, a functional kitchen with plenty of storage, and a cozy dining space ideal for everyday meals or casual gatherings.Enjoy the ease of single-level living with generous natural light throughout

  Jesse Dimitropolis RE/MAX COMPASS

  10 3rd Ave, Cheshire, MA 01225
• 

  

  /20

  Est $295,168 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,366 Sq Ft

  321 Fred Mason Rd, Cheshire, MA 01225

  321 Fred Mason Rd, Cheshire, MA 01225
• 

  

  /78

  $522,000 Sold May 21, 2025

  • 1,940 Sq Ft
  • $269/SF
  • 45 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1985

  520 Stafford Hill Rd, Cheshire, MA 01225

  This property not only offers 7.73 acres of land but an immaculate maintained house w/3 bedrooms, 2 full baths, partially finished basement, huge deck overlooking the most breathtaking views of Mt. Greylock Range along with a 2-car garage & a detached 24 x 24 2-car+ garage! Large kitchen with brand new appliances opens to dining area that looks out new sliders over back yard. Spacious living

  Dennis D'Arcangelo MONARCH REALTY, INC.

  520 Stafford Hill Rd, Cheshire, MA 01225
• 

  

  /24

  Est $211,348 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft

  104 Fred Mason Rd, Cheshire, MA 01225

  104 Fred Mason Rd, Cheshire, MA 01225
• 

  

  /45

  $294,000 Sold May 16, 2025

  • 2,400 Sq Ft
  • $122/SF
  • 56 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1830

  121 Depot St, Cheshire, MA 01225

  Welcome to your dream home! This charming property boasts an impressive 2,400 SF of versatile, living space, featuring five spacious bedrooms and two bathrooms. With a thoughtfully designed layout, this home can easily accommodate various living styles and configurations, making it perfect for remote work or even a home daycare, with its lead compliance certificate. The recent updates enhance the

  Jessica Rizzo LAMACCHIA REALTY, INC

  121 Depot St, Cheshire, MA 01225
• 

  

  /20

  Est $348,929 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 1,151 Sq Ft

  574 Outlook Ave, Cheshire, MA 01225

  574 Outlook Ave, Cheshire, MA 01225
• 

  

  /23

  $257,000 Sold May 12, 2025

  • 1,513 Sq Ft
  • $170/SF
  • 135 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1950

  527 N State Rd, Cheshire, MA 01225

  Discover this charming 3-bedroom, 1-bathroom detached home with 1,513 sq ft of living space. This lovely property offers a beautifully remodeled interior, updated in 2012, complete with a finished basement that provides extra versatility for your lifestyle needs. Ideally situated midway between the City of Pittsfield and the Town of Adams, you'll enjoy the best of both worlds with convenient

  Amanda Alexander 360BERKSHIRE REALTY GROUP

  527 N State Rd, Cheshire, MA 01225
• 

  

  /28

  Est $256,217 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,176 Sq Ft

  100 Yorkshire Dr, Cheshire, MA 01225

  100 Yorkshire Dr, Cheshire, MA 01225
• 

  

  /45

  $420,000 Sold May 05, 2025

  • 2,352 Sq Ft
  • $179/SF
  • 51 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  612 Notch Rd, Cheshire, MA 01225

  This Ranch-style home has undergone some fantastic upgrades, making it a comfortable and inviting space for you to call home. Enjoy the feeling of new with recently installed windows on the main floor, along with brand-new carpeting and a fresh coat of paint throughout the interior. The basement family room has been revamped with new carpeting, fresh paint, a modern drop ceiling with recessed

  Jennifer Maxwell LAMACCHIA REALTY, INC

  612 Notch Rd, Cheshire, MA 01225
• 

  

  /29

  Est $295,434 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,371 Sq Ft

  119 Yorkshire Dr, Cheshire, MA 01225

  119 Yorkshire Dr, Cheshire, MA 01225
• 

  

  /28

  $385,963 Sold May 05, 2025

  • 1,624 Sq Ft
  • $238/SF
  • 36 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1947

  187 Wells Rd, Cheshire, MA 01225

  Nestled in the heart of the Berkshires, this thoughtfully updated 3-bedroom home offers the perfect blend of modern comfort and classic charm with stunning views.Set on 2 acres of picturesque land, this home provides ample outdoor space to relax, play, and explore. Step inside to find a beautifully remodeled kitchen and bathroom, featuring quality finishes that modernize the space while retaining

  Claire Shomphe BIRCH PROPERTIES

  187 Wells Rd, Cheshire, MA 01225
• 

  

  /33

  Est $555,500 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,698 Sq Ft

  68 Mallard Cove, Cheshire, MA 01225

  68 Mallard Cove, Cheshire, MA 01225
• 

  

  /14

  $30,000 Sold Mar 31, 2025

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

  • 27 Days On Market

  Unlisted Address

  Prime 3.1-Acre Commercial Lot - Ready for Redevelopment!Seize the opportunity to own this versatile 3.1-acre commercial-zoned property, ideally located near the north entrance of the former Berkshire Mall. This flat, partially cleared parcel is primed for redevelopment and offers endless potential for business owners and investors alike.Zoned for Business: Perfect for commercial development,

  Nathan Girard ROYAL PROPERTY GROUP

  Unlisted Address
• 

  

  /20

  Est $550,188 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,289 Sq Ft

  400 Ingalls Rd, Cheshire, MA 01225

  400 Ingalls Rd, Cheshire, MA 01225
• 

  

  /30

  $397,000 Sold Mar 28, 2025

  • 1,596 Sq Ft
  • $249/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1963

  147 E Harbor Rd, Cheshire, MA 01225

  Very desirable Ranch Home, for one level living in a country setting with beautiful views. Three bedrooms 2 full baths, primary has en suite bath. Updated kitchen & baths. Large open basement . 15 min to Allendale 18 min to General Dynamic, 13 min to Berkshire Crossing. Be prepared to remove shoes upon entering.. Updates include Appliances 2016, HW Heater 2021, Water Softener 2021, Furnace 2020,

  Mary Blair SIGNATURE ASSOCIATES

  147 E Harbor Rd, Cheshire, MA 01225
• 

  

  /12

  Not Listed For Sale

  Unlisted Address

  Unlisted Address
• 

  

  /22

  $290,000 Sold Mar 13, 2025

  • 1,297 Sq Ft
  • $224/SF
  • 90 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1860

  1008 N State Rd, Cheshire, MA 01225

  This totally renovated home is ready for the Holidays. Enjoy the easy maintenance of a freshly painted stucco exterior, flat yard, new driveway, new windows and new septic system. The interior boasts a new Kitchen top to bottom with granite countertops, new laminate flooring in the foyer and kitchen, refinished hardwoods, ceramic tile bathroom, fresh carpet on the second floor, custom built in

  Michele Purcell Lamacchia Realty, Inc.

  1008 N State Rd, Cheshire, MA 01225
• 

  

  /34

  Est $332,362 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,826 Sq Ft

  659 N State Rd, Cheshire, MA 01225

  659 N State Rd, Cheshire, MA 01225

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