Cheshire, MA Homes

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  /32

  $149,900

  • 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
• Explore Cheshire

• 

  

  

  /7

  $400 per month plus fees

  • 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
• 

  

  

  /35

  $515,000 Sold Sep 19, 2025

  • 1,822 Sq Ft
  • $283/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  86 Sandmill Hill, Cheshire, MA 01225

  Looking to get away from it all-without really leaving it all behind? Just minutes from town, this beautifully remodeled ranch on 1.5 private acres feels secluded yet keeps you close to everything. Completely updated in 2019-20, this 3- bedrm, 2 ba home offers the modern features you've been looking for:- A bright & comfortable year-round sunroom. - Open living & dining spaces flowing into a

  Pauline Green STEEPLEVIEW REALTY - ADAMS BRANCH

  86 Sandmill Hill, Cheshire, MA 01225
• 

  

  

  /89

  Est $433,902 Not Listed For Sale

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

  935 Outlook Ave, Cheshire, MA 01225

  935 Outlook Ave, Cheshire, MA 01225
• 

  

  

  /15

  $397,000

  • 2 Beds
  • 1 Bath
  • 699 Sq Ft

  115 Lake Shore Dr, Cheshire, MA 01225

  Cozy four season home with incredible views. 2 bedroom, one bath, on the water with new dock on beautiful Hoosac Lake. Large two-level deck. Near popular lake-side bike trail. Town water, natural gas heat. Perfect for all-season living or summer weekend getaway.

  John Garber

  115 Lake Shore Dr, Cheshire, MA 01225
• 

  

  /28

  $235,000 Sold Sep 17, 2025

  • 1,503 Sq Ft
  • $156/SF
  • 13 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1850

  139-141 Main St, Cheshire, MA 01225

  This two family is perfect for investors or those looking for a multi-generational living arrangement. Lower apartment offers two bedrooms; one full bath and the upstairs apartment offers one bedroom and one full bath all on almost an acre of land, walking distance to the Ashuwillticook Rail Trail. Don't miss out on this rare opportunity to own in the town of Cheshire where taxes are low.

  Michelle Picard NOCHER REALTY

  139-141 Main St, Cheshire, MA 01225
• 

  

  /28

  Est $320,466 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
• 

  

  /39

  $499,900

  • 3 Beds
  • 1.5 Baths
  • 1,799 Sq Ft

  642 Notch Rd, Cheshire, MA 01225

  Fully renovated cape situated on a picturesque clear lot. Including three acres with an oversized two car garage. New vinyl siding, roof, windows, and drilled well. Bright and open interior featuring an enclosed porch on the front which enters into a custom kitchen with new cabinets, granite countertops, tile backsplash, and stainless steel appliances. Hardwood flooring throughout the kitchen,

  Cory Evangelisto NOCHER REALTY

  642 Notch Rd, Cheshire, MA 01225
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  /62

  $500,000 Sold Aug 29, 2025

  • 3,814 Sq Ft
  • $131/SF
  • 49 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1976

  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
• 

  

  /23

  Est $288,769 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
• 

  

  /33

  $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
• 

  

  /33

  $540,000 Sold Aug 28, 2025

  • 2,200 Sq Ft
  • $245/SF
  • 6 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1987

  805 Savoy Rd, Cheshire, MA 01225

  Your Dream Ranch Awaits - Privacy, Space, and Stunning Views! Escape to this serene and private 4 bedroom, 2 bath ranch, perfectly positioned on 9.66 Acres in a highly sought-after Cheshire location! This spacious home features a grand great room, ideal for entertaining, along with many updates. Enjoy the breathtaking sunsets and views from your own slice of paradise! The land offers endless

  Erik Pizani GREYLOCK REALTY, LLC.

  805 Savoy Rd, Cheshire, MA 01225
• 

  

  /33

  Est $381,824 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
• 

  

  /46

  $439,000

  • 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

  Laiken Rapisarda LAMACCHIA REALTY, INC

  136 Ingalls Rd, Cheshire, MA 01225
• 

  

  /51

  $518,000 Sold Aug 13, 2025

  • 2,269 Sq Ft
  • $228/SF
  • 51 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1970

  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
• 

  

  /13

  Est $313,748 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
• 

  

  /20

  $79,900

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft

  16 2nd Ave, Cheshire, MA 01225

  Cozy and move-in ready! This well maintained 2 bedroom, 1 bath mobile home features a bright kitchen with stainless steel appliances, a freshly renovated bath, and flexible 3-season room that could be extra living space or even a 3rd bedroom with some work. Enjoy a covered porch for relaxing outdoors, updated roof, and well-kept exterior. The renovated bathroom features subway tile, built-in

  THE KAHN TEAM BISHOP WEST REAL ESTATE

  16 2nd Ave, Cheshire, MA 01225
• 

  

  /59

  $515,000 Sold Aug 13, 2025

  • 4,302 Sq Ft
  • $120/SF
  • 53 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1984

  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
• 

  

  /16

  Est $285,844 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
• 

  

  /23

  $295,000

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

  19 Fisk St, Cheshire, MA 01225

  Located in the heart of desirable Cheshire, this cozy Colonial is just a short walk from the Ashuwillticook Trail. The outside offers a newly installed shed 20'x12' with plenty of storage surrounded by a fenced in yard. The foyer to the home is spacious to accommodate a small home office or for additional storage. Entertain guests in an open dining room / living room with a good flow to the

  Diane Dandurand-Burdick STEEPLEVIEW REALTY - ADAMS BRANCH

  19 Fisk St, Cheshire, MA 01225
• 

  

  /18

  $230,000 Sold Aug 11, 2025

  • 1,690 Sq Ft
  • $136/SF
  • 7 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1920

  901 S State Rd, Cheshire, MA 01225

  Spacious 4-Bedroom Colonial close to Cheshire Lake! Don't miss this opportunity to own this charming colonial offering nearly 1,700 square feet of living space with vinyl windows and flooring throughout. The home features a generous living room with sliding doors that lead out to a spacious deck--perfect for entertaining or relaxing. The eat-in kitchen includes a cozy coffee bar nook, along with

  Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

  901 S State Rd, Cheshire, MA 01225
• 

  

  /64

  Est $494,541 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
• 

  

  /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
• 

  

  /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
• 

  

  /47

  Est $511,409 Not Listed For Sale

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

  425 Wells Rd, Cheshire, MA 01225

  425 Wells Rd, Cheshire, MA 01225
• 

  

  /51

  $309,000

  • 3 Beds
  • 1 Bath
  • 1,297 Sq Ft

  1008 N State Rd, Cheshire, MA 01225

  Welcome to 1008 North State Road, a beautifully updated home offering the perfect blend of modern convenience and rustic charm. This recently renovated property boasts a spacious layout, updated finishes, and ample outdoor space for relaxation and recreation.Inside, you'll find a tastefully renovated kitchen featuring stainless steel appliances, granite countertops, and shaker-style cabinetry.

  Marci Levesque BISHOP WEST REAL ESTATE

  1008 N State 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
• 

  

  /25

  Est $270,549 Not Listed For Sale

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

  28 Prospect St, Cheshire, MA 01225

  28 Prospect St, Cheshire, MA 01225
• 

  

  /58

  $849,000 Open Sat 10:30AM - 12:30PM

  • 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
• 

  

  /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
• 

  

  /34

  Est $180,123 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
• 

  

  /24

  $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. This home does need work but is priced accordingly. Make

  Marnie Garzone THE KINDERHOOK GROUP - PITTSFIELD

  867 Notch Rd, 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
• 

  

  /24

  Est $429,040 Not Listed For Sale

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

  205 Wells Rd, Cheshire, MA 01225

  205 Wells 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
• 

  

  /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
• 

  

  /36

  Est $553,073 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
• 

  

  /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
• 

  

  /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
• 

  

  /33

  Est $376,305 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

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