Cheshire, MA Homes

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  /32

  $169,000

  • 5 Beds
  • 3 Baths
  • 2,250 Sq Ft

  136 Church St Unit 142, Cheshire, MA 01225

  Situated in the heart of the quaint town of Cheshire, this 3 family offers potential for the new owner as an investment or owner occupied. First floor has 2 bedrooms, primary is large, living room and kitchen are also spacious and kitchen offers pantry w/ potential laundry hook ups. Upstairs back unit is 2 bedroom, Upstairs front unit is 1 bedrooms & currently vacant. Long term tenants &

  

  Nadine Hiser

  KRG - Key Realty Group

  (413) 475-9494

  136 Church St Unit 142, Cheshire, MA 01225
• 

  

  

  /16

  $1,800 per month

  • 3 Beds
  • 1.5 Baths
  • 1,100 Sq Ft
  • Condo for Rent

  100 Church St, Cheshire, MA 01225

  Easy access in desirable Cheshire, this 2nd floor remodeled unit features 3 bedrooms, brand new kitchen, full bath, living room and offers off street parking. NO laundry.

  100 Church 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 - PITTSFIELD

  114 E Main St, Cheshire, MA 01225
• 

  

  

  /89

  Est $424,461 Not Listed For Sale

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

  935 Outlook Ave, Cheshire, MA 01225

  935 Outlook Ave, Cheshire, MA 01225
• 

  

  

  /26

  $159,000

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

  108 Church St, Cheshire, MA 01225

  Available. Welcome to the quaint town of Cheshire, this 2-unit rental is situatated in center of town convenient to coffee shop, town hall, post office, Ashuwillticook Rail Trail, local activites & more. Some charming details remain in the 2nd floor unit - tin ceiling in living room, spacious eat in kitchen. 1st floor unit also offers spacious eat in kitchen, spacious primary bedroom. New

  

  Nadine Hiser

  KRG - Key Realty Group

  (413) 481-1596

  108 Church St, Cheshire, MA 01225
• 

  

  /7

  $400 per month

  • 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
• 

  

  /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
• 

  

  /28

  Est $312,283 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
• 

  

  /35

  $299,900

  • 3 Beds
  • 2 Baths
  • 1,984 Sq Ft

  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
• 

  

  /16

  $1,750 per month

  • 3 Beds
  • 1.5 Baths
  • 1,100 Sq Ft
  • Condo for Rent

  100 Church St, Cheshire, MA 01225

  Easy access in desirable Cheshire, this 2nd floor remodeled unit features 3 bedrooms, brand new kitchen, full bath, living room and offers off street parking. NO laundry.

  100 Church St, 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 BISHOP WEST REAL ESTATE

  10 3rd Ave, Cheshire, MA 01225
• 

  

  /39

  Est $266,401 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,359 Sq Ft

  19 Fisk St, Cheshire, MA 01225

  19 Fisk St, Cheshire, MA 01225
• 

  

  /66

  $699,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 3,240 Sq Ft

  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
• 

  

  /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
• 

  

  /41

  Est $519,237 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,945 Sq Ft

  1008 W Mountain Rd, Cheshire, MA 01225

  1008 W Mountain Rd, Cheshire, MA 01225
• 

  

  /51

  $499,900

  • 3 Beds
  • 2.5 Baths
  • 2,269 Sq Ft

  329 Lanesboro Rd, Cheshire, MA 01225

  Discover your perfect water views retreat! This charming ranch style home home offers stunning water views that will take your breath away. Boasting three spacious bedrooms and two and a half bathrooms, it provides plenty of space for family and guests. Enjoy two inviting living rooms--ideal for relaxing or entertaining--and the comfort a two car garage for parking and storage. Bright, airy, and

  Jason Nocher NOCHER REALTY

  329 Lanesboro 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
• 

  

  /23

  Est $264,567 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
• 

  

  /59

  $514,900

  • 4 Beds
  • 3 Baths
  • 4,302 Sq Ft

  149 Wilshire Dr, Cheshire, MA 01225

  Set on a quiet, elevated lot, this home enjoys a peaceful hilltop location with a sense of privacy while still being conveniently located. Outside you will find a two car garage, storage shed, a front porch, and expansive deck in the back yard. Inside you will enter through an open foyer with access to all levels. A stunning, recently renovated kitchen with modern cabinets, custom backsplash,

  Cory Evangelisto NOCHER REALTY

  149 Wilshire Dr, 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
• 

  

  /22

  Est $414,652 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,191 Sq Ft

  37 Main St, Cheshire, MA 01225

  37 Main St, Cheshire, MA 01225
• 

  

  /18

  $419,900 Pending

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

  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
• 

  

  /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 $336,141 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,917 Sq Ft

  709 Savoy Rd, Cheshire, MA 01225

  709 Savoy Rd, Cheshire, MA 01225
• 

  

  /62

  $550,000 Pending

  • 4 Beds
  • 4 Baths
  • 3,814 Sq Ft

  131 Wilshire Dr, Cheshire, MA 01225

  Tucked away on a private and generously sized lot, this expansive Cheshire home is the perfect blend of comfort, flexibility, and entertainment. Boasting 4-5 spacious bedrooms, 4 full bathrooms, an attached two-car garage, and multiple living areas, it offers room for every need and lifestyle. Whether you're looking for a home office, fitness space, or in-law accommodations, the versatile layout

  Jessie Downer LAMACCHIA REALTY, INC

  131 Wilshire 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
• 

  

  /13

  Est $300,018 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
• 

  

  /27

  $249,900

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft

  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
• 

  

  /14

  $30,000 Sold Mar 31, 2025

  • Land
  • 3.10 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
• 

  

  /16

  Est $269,964 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
• 

  

  /40

  $299,999

  • 3 Beds
  • 1.5 Baths
  • 1,560 Sq Ft

  192 Curran Rd, Cheshire, MA 01225

  Tucked away on a quiet country road in central Cheshire, this charming 3-bedroom, 1.5-bath home offers peace, privacy, and a connection to nature--yet it's just a short drive to both North and South County amenities. Set on nearly 2 acres bordered by woods and state land, enjoy walking trails, wildflowers, and young pear and apple trees right outside your door. The home is neat and well-kept,

  Dennis D'Arcangelo MONARCH REALTY, INC.

  192 Curran 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
• 

  

  /64

  Est $468,428 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
• 

  

  /9

  $125,000

  • 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
• 

  

  /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
• 

  

  /47

  Est $491,149 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,468 Sq Ft

  425 Wells Rd, Cheshire, MA 01225

  425 Wells Rd, Cheshire, MA 01225
• 

  

  /23

  $569,000

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

  867 Notch Rd, Cheshire, MA 01225

  A charming, spacious Colonial with privacy, and lovely grounds. Breathtaking mountain views. Built in 2005 and set on 7.25 acres, this 5-bedroom, 4.5-bathroom residence offers 3,307 square feet of living space. Two primary suites, one up and one down. The open-concept kitchen flows seamlessly into a great room, perfect for entertaining. Your dream property awaits!

  Marnie Garzone THE KINDERHOOK GROUP - PITTSFIELD

  867 Notch Rd, 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
• 

  

  /25

  Est $248,176 Not Listed For Sale

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

  28 Prospect St, Cheshire, MA 01225

  28 Prospect St, Cheshire, MA 01225
• 

  

  /10

  $679,000

  • Land
  • 1.70 Acres
  • $399,412 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

Showing Results 1 - 40, Page 1 of 18