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 multi- 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

• 

  

  

  /6

  $1,800 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,100 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, brand new kitchen, full bath, living room and offers off street parking. No laundry.

  100 Church St Unit Cheshire, Cheshire, MA 01225
• 

  

  

  /39

  $430,000 Sold Nov 19, 2025

  • 1,799 Sq Ft
  • $239/SF
  • 23 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1830

  642 Notch Rd, Cheshire, MA 01225

  Fully renovated cape situated on a picturesque clear lot. Including 2.5 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
• 

  

  

  /89

  Est $450,324 Not Listed For Sale

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

  935 Outlook Ave, Cheshire, MA 01225

  935 Outlook Ave, Cheshire, MA 01225
• 

  

  

  /49

  $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
• 

  

  /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
• 

  

  /39

  $532,000 Sold Nov 14, 2025

  • 2,184 Sq Ft
  • $244/SF
  • 52 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2015

  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
• 

  

  /28

  Est $318,848 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
• 

  

  /44

  $539,900

  • 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
• 

  /2

  $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
• 

  

  /31

  $304,000 Sold Oct 24, 2025

  • 1,237 Sq Ft
  • $246/SF
  • 5 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1950

  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
• 

  

  /30

  Est $269,627 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
• 

  

  /16

  $389,900

  • 3 Beds
  • 1.5 Baths
  • 2,747 Sq Ft

  18 W Mountain Rd, Cheshire, MA 01225

  Center of town 1820s colonial home with natural sunlight throughout. Oversized garage with attic storage/access. Seasonal Cabin with own septic, water, gas and electric (needs updates/repair). Irregular lot with privacy, fencing and wooded boundaries to neighbors.

  Chris Warner CHRISTOPHER A WARNER REALTY

  18 W Mountain Rd, Cheshire, MA 01225
• 

  

  /40

  $295,000 Sold Oct 24, 2025

  • 2,010 Sq Ft
  • $147/SF
  • 21 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1947

  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
• 

  

  /23

  Est $299,381 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
• 

  

  /22

  $399,900

  • 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
• 

  

  /79

  $810,000 Sold Oct 08, 2025

  • 4,500 Sq Ft
  • $180/SF
  • 5 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1989

  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
• 

  

  /13

  Est $328,178 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
• 

  

  /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
• 

  

  /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
• 

  

  /29

  Est $450,157 Not Listed For Sale

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

  77 Willow Ln, Cheshire, MA 01225

  77 Willow Ln, 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
• 

  

  /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
• 

  

  /16

  Est $313,561 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
• 

  

  /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
• 

  

  /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
• 

  

  /64

  Est $519,201 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
• 

  

  /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
• 

  

  /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
• 

  

  /47

  Est $514,375 Not Listed For Sale

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

  425 Wells Rd, Cheshire, MA 01225

  425 Wells Rd, Cheshire, MA 01225
• 

  

  /20

  $69,900 Pending

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft

  16 2nd Ave, Cheshire, MA 01225

  Clean, bright, & move-in ready. This remodeled 2-bedroom, 1-bath mobile home offers simple Berkshire living with a comfortable layout & plenty of updates. The kitchen shines with stainless steel appliances & fresh paint. The bathroom was fully renovated with subway tile, built-in shower seat, & modern finishes. There's a 3-season room that could easily be extra living space or a 3rd bedroom with

  THE KAHN TEAM BISHOP WEST REAL ESTATE

  16 2nd Ave, 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
• 

  

  /25

  Est $278,899 Not Listed For Sale

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

  28 Prospect St, Cheshire, MA 01225

  28 Prospect St, Cheshire, MA 01225
• 

  

  /13

  $148,500 Pending

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft

  29 4th Ave, Cheshire, MA 01225

  Built in 2022, this move-in ready 3 bedroom, 2 bath mobile home offers modern convenience and scenic mountain views. The open living-room floor plan creates a bright, airy feeling and flows easily to the kitchen area. ideal for everyday living or entertaining. Located in Berkshire Village and only minutes from Route 7, you'll enjoy quick drives to Williamstown, Jiminy Peak, and Mount Greylock for

  Tiffany Roberts ROBERTS & ASSOC. REALTY, INC

  29 4th 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
• 

  

  /34

  Est $179,842 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
• 

  

  /9

  $115,000 Pending

  • 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
• 

  

  /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
• 

  

  /36

  Est $605,226 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
• 

  

  /36

  $319,900 Pending

  • 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

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