Cheshire, MA Homes

• 

  

  

  /9

  $115,000

  • 3 Beds
  • 1 Bath
  • 1,681 Sq Ft

  57 Church St, Cheshire, MA 01225

  An exceptional investment property nestled in the heart of Cheshire MA. The Property has 7 rooms total . 3 bedrooms and 1 full bath. Whether you're looking to expand your rental portfolio or embark on a fix-and-flip project, this property caters to a variety of investment strategies. With its flexible layout and potential for customization there is possibility to add 4th bed and 2nd bath if town

  Letizia Dutra Cameron Real Estate Group

  57 Church St, Cheshire, MA 01225
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  

  /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
• 

  

  

  /67

  Est $499,627 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
• 

  

  

  /16

  $799,000

  • Land
  • 1.7 Acres
  • $470,000 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
• 

  

  

  /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
• 

  

  /45

  Est $428,601 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
• 

  

  /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
• 

  

  /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 - PITTSFIELD

  114 E Main St, Cheshire, MA 01225
• 

  

  /49

  Est $425,345 Not Listed For Sale

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

  213 Devonshire Dr, Cheshire, MA 01225

  213 Devonshire Dr, Cheshire, MA 01225
• 

  

  /40

  $315,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,010 Sq Ft

  74 South St, Cheshire, MA 01225

  This spacious home has a nice size kitchen with quartz counters, lots of cabinets, dining room, fireplace living room and 3 large bedrooms. The addition on the first floor is being used as 4th bedroom with an ensuite bathroom, it can also be used for a large family room or in-law suite/guest room since it has private door entrance. Enjoy all the natural bright light coming through the many

  Toni Marie Gage SIGNATURE ASSOCIATES

  74 South St, 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
• 

  

  /48

  Est $506,095 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
• 

  

  /79

  $779,900 Pending

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

  611 N State Rd, Cheshire, MA 01225

  Awash with natural light and surrounded by breathtaking mountain vistas, including the beacon light atop Mt. Greylock, this stunning Cheshire contemporary offers the best of Berkshire living. Spacious and thoughtfully designed, the home features 3+ bedrooms, 3.5 tiled baths, and an open layout ideal for both everyday living and entertaining.With 4,500 square feet of living space plus additional

  Nick Geranios WILLIAM PITT SOTHEBY'S - LENOX

  611 N State Rd, 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
• 

  

  /35

  Est $299,630 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,872 Sq Ft

  105 Depot St, Cheshire, MA 01225

  105 Depot St, Cheshire, MA 01225
• 

  

  /31

  $299,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,237 Sq Ft

  53 Wells Rd, Cheshire, MA 01225

  This beautifully updated home blends modern comfort with classic charm. Featuring an open-concept layout, a stunning remodeled kitchen with a spacious island, tasteful finishes, and updated lighting throughouta"it's perfect for everyday living and entertaining. Step outside to a large covered deck overlooking a private, fenced backyarda"ideal for relaxing or hosting family and friends. The

  Laiken Rapisarda LAMACCHIA REALTY, INC

  53 Wells 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
• 

  

  /30

  Est $384,752 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
• 

  

  /36

  $319,900 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft

  83 Devonshire Dr, Cheshire, MA 01225

  This inviting 3-bedroom, 2-bath ranch offers comfortable living in a desirable neighborhood. Inside, you'll find a bright and open layout with a mix of oak, tile, and vinyl flooring for both warmth and easy care. The home features a 2-car attached garage for convenience and plenty of storage. Recent updates include a new septic system installed in 2017, giving peace of mind for years to come.

  Jim Thurston LAMACCHIA REALTY, INC

  83 Devonshire Dr, 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 $304,048 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
• 

  

  /39

  $549,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 2,184 Sq Ft

  230 Curran Rd, Cheshire, MA 01225

  Welcome to this beautifully crafted, move-in ready chalet-style home, set on over 4 private acres with a spacious cleared backyard, wooded surroundings, and stunning mountain views. Inside, you're greeted by a welcoming mudroom and convenient first-floor laundry. The open-concept living area features vaulted ceilings, hardwood floors, and large windows that fill the space with natural light and

  Laiken Rapisarda LAMACCHIA REALTY, INC

  230 Curran Rd, 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
• 

  

  /24

  Est $204,978 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
• 

  

  /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
• 

  

  /20

  Est $313,019 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
• 

  

  /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
• 

  

  /28

  Est $237,827 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,176 Sq Ft

  100 Yorkshire Dr, Cheshire, MA 01225

  100 Yorkshire Dr, 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
• 

  

  /29

  Est $278,561 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,371 Sq Ft

  119 Yorkshire Dr, Cheshire, MA 01225

  119 Yorkshire Dr, 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
• 

  

  /33

  Est $535,917 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,698 Sq Ft

  68 Mallard Cove, Cheshire, MA 01225

  68 Mallard Cove, Cheshire, MA 01225
• 

  

  /36

  $446,500 Sold Feb 28, 2025

  • 2,546 Sq Ft
  • $175/SF
  • 117 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1988

  41 Curran Rd, Cheshire, MA 01225

  Ranch-style home on 4.4 acres of serene land abutting the majestic Mt. Greylock. Built in 1988, this well-maintained home offers 3 spacious bedrooms, 2 full baths, and a convenient half-bath. The low-maintenance vinyl siding adds to its appeal, ensuring easy upkeep, while the expansive yard provides ample space for outdoor activities, gardening, or simply enjoying the peaceful surroundings.

  Kellie Perrault NOCHER REALTY

  41 Curran Rd, Cheshire, MA 01225
• 

  

  /20

  Est $509,673 Not Listed For Sale

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

  400 Ingalls Rd, Cheshire, MA 01225

  400 Ingalls Rd, Cheshire, MA 01225
• 

  

  /23

  $45,900 Sold Feb 12, 2025

  • 980 Sq Ft
  • $47/SF
  • 3 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1976

  Unlisted Address

  Affordable manufactured home in Berkshire Village, located in scenic Cheshire. This 1976 home offers two bedrooms and one bathroom with a large, oversized bathtub, accessible from both the hallway and the primary bedroom. Enjoy the convenience of an included washer, dryer, stove, and refrigerator. The home features natural gas heating and two dedicated parking spaces. Additional highlights

  THE KAHN TEAM BISHOP WEST REAL ESTATE

  Unlisted Address
• 

  

  /12

  Not Listed For Sale

  Unlisted Address

  Unlisted Address
• 

  

  /22

  $367,050 Sold Jan 31, 2025

  • 988 Sq Ft
  • $372/SF
  • 51 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1950

  153 Shadowland Cove Rd, Cheshire, MA 01225

  Nestled at the end of a quiet road, this enchanting 2-bedroom cottage offers 96 feet of pristine lake frontage on beautiful Cheshire Lake. Sitting on a generous .82-acre lot, this property promises serenity and stunning lake views in every season. The cozy living room features a wood-burning fireplace, for added ambiance on chilling evenings. The second floor offers two spacious bedrooms,

  Erin Scott BURNHAM GOLD REAL ESTATE, LLC

  153 Shadowland Cove Rd, Cheshire, MA 01225
• 

  

  /34

  Est $313,712 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
• 

  

  /59

  $450,000 Sold Jan 31, 2025

  • 3,906 Sq Ft
  • $115/SF
  • 63 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1850

  64 North St, Cheshire, MA 01225

  Nestled in the heart of town lies a hidden gem-A Victorian home exuding old-world charm on nearly 4 acres of serene privacy. This enchanting homey offers an inground pool, a picturesque circular driveway leading to a timeless carriage house and a sprawling wrap around porch that beckons relaxation and outdoor enjoyment. Although renovations are needed, there are many modern comforts that include

  Cindy Carrigan LAMACCHIA REALTY, INC

  64 North St, Cheshire, MA 01225
• 

  

  /29

  Est $353,921 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,447 Sq Ft

  185 School St, Cheshire, MA 01225

  185 School St, Cheshire, MA 01225

Showing Results 41 - 80, Page 2 of 18