Cheshire, MA Homes

/33
$485,000 Under Contract
- 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.

(413) 216-4239

40 Curran Rd, Cheshire, MA 01225
Explore Cheshire
/3
$1,650 per month
- 3 Beds
- 1 Bath
- 1,100 Sq Ft
- Condo for Rent
104 Church St, Cheshire, MA 01225

Bright, modern second floor apartment in a sought-after Cheshire location. Enjoy a new kitchen, refinished floors and updated windows for comfort and efficiency.

Pauline Green STEEPLEVIEW REALTY - ADAMS BRANCH

104 Church St, Cheshire, MA 01225
/13
$150,350 Sold Mar 27, 2026

115 Main St, Cheshire, MA 01225
- 3 Beds
- 1 Bath
- 1,335 Sq Ft
- Built 1850
Last Sold Summary
- 1% Below List Price
- $113/SF
- 19 Days On Market
Current Estimated Value $190,029

Last Listing Agent john oliveri Property Works New England

115 Main St, Cheshire, MA 01225

/30
Est $416,052 Not Listed For Sale

147 E Harbor Rd, Cheshire, MA 01225
- 3 Beds
- 2 Baths
- 1,596 Sq Ft
- Built 1963
147 E Harbor Rd, Cheshire, MA 01225

Last Sold Summary
- 5% Above List Price
- $249/SF
- 6 Days On Market
Last Sold Price $397,000

Last Listing Agent Mary Blair SIGNATURE ASSOCIATES

/30
$399,900 Pending
- 6 Beds
- 2.5 Baths
- 3,619 Sq Ft
Unlisted Address

You'll find classical charm around every corner in this beautiful Victorian farmhouse nestled in the town of Cheshire. The main residence showcases timeless details including hardwood floors, granite countertops, original millwork, and beautifully preserved staircases and trim. The living space features three bedrooms, a full bath, formal dining room, living room and den. An attached two-bedroom

Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

Unlisted Address
/2
$1,500 per month
- 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
/45
$420,000 Sold May 05, 2025

612 Notch Rd, Cheshire, MA 01225
- 3 Beds
- 2 Baths
- 2,352 Sq Ft
- Built 1987
Last Sold Summary
- 5% Below List Price
- $179/SF
- 51 Days On Market
Current Estimated Value $438,841

Last Listing Agent Jennifer Maxwell LAMACCHIA REALTY, INC

612 Notch Rd, Cheshire, MA 01225

/14
Not Listed For Sale

Unlisted Address
Unlisted Address

Last Sold Summary
- 27 Days On Market
Last Sold Price $30,000

Last Listing Agent Nathan Girard ROYAL PROPERTY GROUP

/29
$389,900
- 3 Beds
- 2 Baths
- 2,747 Sq Ft
18 W Mountain Rd, Cheshire, MA 01225

Discover the warmth and character of this inviting post and beam home, showcasing wood floors and cozy fireplaces that create the perfect setting for comfortable living. A walk-up attic offers exciting potential for additional space, while the oversized garage provides ample storage for vehicles, hobbies, and equipment. Set on just over an acre, the property also features a seasonal cabin with

Robin Moore 413 REAL ESTATE

18 W Mountain Rd, Cheshire, MA 01225
/14
$82,000 Sold May 29, 2025

10 3rd Ave, Cheshire, MA 01225
- 3 Beds
- 1 Bath
- 924 Sq Ft
- Built 1995
Last Sold Summary
- 3% Below List Price
- $89/SF
- 5 Days On Market
Last Listing Agent Jesse Dimitropolis RE/MAX COMPASS

10 3rd Ave, Cheshire, MA 01225

/89
Est $453,534 Not Listed For Sale

935 Outlook Ave, Cheshire, MA 01225
- 3 Beds
- 2 Baths
- 2,068 Sq Ft
- Built 1978
935 Outlook Ave, Cheshire, MA 01225

Last Sold Summary
- 13% Above List Price
- $193/SF
- 33 Days On Market
Last Sold Price $400,000

Last Listing Agent Dennis D'Arcangelo MONARCH REALTY, INC.

/2
$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.

Pat Roberts STEEPLEVIEW REALTY - N. ADAMS

12 South St, Cheshire, MA 01225
/47
$260,000 Sold Jun 02, 2025

27 Church St, Cheshire, MA 01225
- 4 Beds
- 2 Baths
- 1,531 Sq Ft
- Built 1850
Last Sold Summary
- 15% Below List Price
- $170/SF
- 73 Days On Market
Current Estimated Value $275,701

Last Listing Agent Colleen Zajac MONARCH REALTY, INC.

27 Church St, Cheshire, MA 01225

/28
Est $331,389 Not Listed For Sale

205 Lake Shore Dr, Cheshire, MA 01225
- 2 Beds
- 1 Bath
- 570 Sq Ft
- Built 1950
205 Lake Shore Dr, Cheshire, MA 01225

Last Sold Summary
- 9% Above List Price
- $532/SF
- 4 Days On Market
Last Sold Price $303,000

Last Listing Agent Doug Collins LAMACCHIA REALTY, INC

/37
$539,900
- 5 Beds
- 3.5 Baths
- 3,307 Sq Ft
867 Notch Rd, Cheshire, MA 01225

Home on a dream lot--over 7 secluded acres framed by mountains and backing to the Chalet Wildlife Management Area (7,000+ acres of protected state land). Enjoy total privacy, wide-open views, and dark-night skies away from city lights. Step inside to a grand entrance with a glistening chandelier. The main level features a flowing layout: a spacious kitchen with sufficient storage and generous

Mariah Worth LAMACCHIA REALTY, INC

867 Notch Rd, Cheshire, MA 01225
/20
$61,525 Sold Jan 06, 2026

16 2nd Ave, Cheshire, MA 01225
- 2 Beds
- 1 Bath
- 780 Sq Ft
Last Sold Summary
- 23% Below List Price
- $79/SF
- 75 Days On Market
Last Listing Agent THE KAHN TEAM BISHOP WEST REAL ESTATE

16 2nd Ave, Cheshire, MA 01225

/30
Est $300,451 Not Listed For Sale

116 Wells Rd, Cheshire, MA 01225
- 3 Beds
- 1.5 Baths
- 2,004 Sq Ft
- Built 1850
116 Wells Rd, Cheshire, MA 01225

Last Sold Summary
- 26% Above List Price
- $119/SF
- 126 Days On Market
Last Sold Price $239,000

Last Listing Agent Carrie Wright William Pitt

/43
$335,900
- 3 Beds
- 2 Baths
- 1,567 Sq Ft
1020 Sandmill Rd, Adams, MA 01220

Welcome to this expansive ranch style home set on a peaceful acre with scenic views of a babbling brook and beautiful woodlands. Designed for easy one-level living, this home features two bedrooms and full bath in addition to a spacious primary en-suite with sliders that open to the outdoors-perfect for enjoying morning coffee or wine under the stars. The living and dinning room combination

Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

1020 Sandmill Rd, Adams, MA 01220
/49
$149,900 Sold Mar 16, 2026

108 Church St, Cheshire, MA 01225
- 4 Beds
- 2 Baths
- 1,850 Sq Ft
- Built 1850
Last Sold Summary
- 6% Below List Price
- $81/SF
- 35 Days On Market
Current Estimated Value $183,351

Last Listing Agent Nadine Hiser KEY REALTY

108 Church St, Cheshire, MA 01225

/23
Est $310,453 Not Listed For Sale

83 Richardson St, Cheshire, MA 01225
- 4 Beds
- 1.5 Baths
- 1,674 Sq Ft
- Built 1860
83 Richardson St, Cheshire, MA 01225

Last Sold Summary
- 27% Above List Price
- $146/SF
- 8 Days On Market
Last Sold Price $245,000

Last Listing Agent Erin Scott BURNHAM GOLD REAL ESTATE, LLC

/6
$119,900
- Land
- 1.38 Acres
- $87,047 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.

Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

Lot 9E Stewart White Rd, Cheshire, MA 01225
/50
$535,000 Sold Feb 24, 2026

132 Outlook Ave, Cheshire, MA 01225
- 3 Beds
- 2.5 Baths
- 2,134 Sq Ft
- Built 1987
Last Sold Summary
- 3% Below List Price
- $251/SF
- 71 Days On Market
Current Estimated Value $533,884

Last Listing Agent Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

132 Outlook Ave, Cheshire, MA 01225

/30
Est $274,172 Not Listed For Sale

6 Arnold Ct, Cheshire, MA 01225
- 2 Beds
- 2 Baths
- 1,600 Sq Ft
- Built 1955
6 Arnold Ct, Cheshire, MA 01225

Last Sold Summary
- 19% Above List Price
- $144/SF
- 69 Days On Market
Last Sold Price $230,500

Last Listing Agent Tammy Christen BISHOP WEST REAL ESTATE

/46
$519,000
- 4 Beds
- 2.5 Baths
- 2,892 Sq Ft
268 Devonshire Dr, Cheshire, MA 01225

Escape to this stunning 4-bedroom, 3-bathroom Colonial where classic charm meets modern efficiency. Boasting breathtaking mountain views, this home offers expansive living spaces including oversized bedrooms and a finished walk-out basement with a full bath. The updated kitchen shines with granite countertops, while the wood-burning fireplace adds a touch of warmth to the main living area.

Timothy Johnson NOCHER REALTY

268 Devonshire Dr, Cheshire, MA 01225
/18
$230,000 Sold Aug 11, 2025

901 S State Rd, Cheshire, MA 01225
- 4 Beds
- 1 Bath
- 1,690 Sq Ft
- Built 1920
Last Sold Summary
- $136/SF
- 7 Days On Market
Current Estimated Value $255,602

Last Listing Agent Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

901 S State Rd, Cheshire, MA 01225

/13
Est $324,146 Not Listed For Sale

517 N State Rd, Cheshire, MA 01225
- 3 Beds
- 1 Bath
- 1,557 Sq Ft
- Built 1955
517 N State Rd, Cheshire, MA 01225

Last Sold Summary
- 5% Above List Price
- $199/SF
- 3 Days On Market
Last Sold Price $310,000

Last Listing Agent Jesse Dimitropolis RE/MAX

/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
/79
$810,000 Sold Oct 08, 2025

611 N State Rd, Cheshire, MA 01225
- 3 Beds
- 3.5 Baths
- 4,500 Sq Ft
- Built 1989
Last Sold Summary
- 4% Above List Price
- $180/SF
- 5 Days On Market
Current Estimated Value $813,233

Last Listing Agent Nick Geranios WILLIAM PITT SOTHEBY'S - LENOX

611 N State Rd, Cheshire, MA 01225

/29
Est $450,397 Not Listed For Sale

77 Willow Ln, Cheshire, MA 01225
- 3 Beds
- 2 Baths
- 1,581 Sq Ft
- Built 1989
77 Willow Ln, Cheshire, MA 01225

Last Sold Summary
- 10% Above List Price
- $258/SF
- 28 Days On Market
Last Sold Price $408,000

Last Listing Agent Christine Girard STEEPLEVIEW REALTY - N. ADAMS

/45
$284,000 Under Contract
- 3 Beds
- 2 Baths
- 1,359 Sq Ft
19 Fisk St, Cheshire, MA 01225

Charming New England home with space, character, and a great yard! This 3-bedroom, 2 full bath home features hardwood floors, first floor laundry and a functional, easy-flow layout. Built in 1890 this move in ready home blends classic style with modern comfort with vinyl siding, a slate roof, and an updated high-efficiency gas combi boiler/on-demand hot water system installed in 2025. Set on a

Ed Rich BISHOP WEST REAL ESTATE

19 Fisk St, Cheshire, MA 01225
/28
$385,963 Sold May 05, 2025

187 Wells Rd, Cheshire, MA 01225
- 3 Beds
- 1.5 Baths
- 1,624 Sq Ft
- Built 1947
Last Sold Summary
- 3% Above List Price
- $238/SF
- 36 Days On Market
Current Estimated Value $385,121

Last Listing Agent Claire Shomphe BIRCH PROPERTIES

187 Wells Rd, Cheshire, MA 01225

/16
Est $324,350 Not Listed For Sale

511 Stafford Hill Rd, Cheshire, MA 01225
- 3 Beds
- 1 Bath
- 1,048 Sq Ft
- Built 1977
511 Stafford Hill Rd, Cheshire, MA 01225

Last Sold Summary
- 38% Above List Price
- $224/SF
- 5 Days On Market
Last Sold Price $235,000

Last Listing Agent Erik Pizani GREYLOCK REALTY, LLC.

/37
$209,900 Under Contract
- 3 Beds
- 2 Baths
- 2,326 Sq Ft
971 N State Rd, Cheshire, MA 01225

Bring your vision and restore this spacious home to its full potential. Offering 7+ rooms set on almost 1 acre of land with a wraparound front porch in the heart of Berkshire County. The generous layout offers flexibility for 3-4 bedrooms, home office space or expanded living areas. Plus, a large, detached garage. Original features and ample square footage create the perfect canvas for

Cindy Carrigan LAMACCHIA REALTY, INC

971 N State Rd, Cheshire, MA 01225
/9
$80,000 Sold Jul 22, 2025

#16 Jenks Rd, Cheshire, MA 01225
- Land
- 10.01 Acres
- $7,992 per Acre
Last Sold Summary
- 27% Below List Price
- 29 Days On Market
Last Listing Agent Tracy Munger KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

#16 Jenks Rd, Cheshire, MA 01225

/64
Est $524,332 Not Listed For Sale

459 Stafford Hill Rd, Cheshire, MA 01225
- 4 Beds
- 2.5 Baths
- 2,992 Sq Ft
- Built 1976
459 Stafford Hill Rd, Cheshire, MA 01225

Last Sold Summary
- 18% Above List Price
- $149/SF
- 160 Days On Market
Last Sold Price $445,000

Last Listing Agent Jennifer Maxwell LAMACCHIA REALTY, INC

/31
$304,000 Sold Oct 24, 2025

53 Wells Rd, Cheshire, MA 01225
- 2 Beds
- 1 Bath
- 1,237 Sq Ft
- Built 1950
Last Sold Summary
- 2% Above List Price
- $246/SF
- 5 Days On Market
Current Estimated Value $299,819

Last Listing Agent Laiken Rapisarda LAMACCHIA REALTY, INC

53 Wells Rd, Cheshire, MA 01225

/34
Est $180,302 Not Listed For Sale

24 South St Unit 34, Cheshire, MA 01225
- 7 Beds
- 5.5 Baths
- 4,403 Sq Ft
- Built 1880
24 South St Unit 34, Cheshire, MA 01225

Last Sold Summary
- 3% Above List Price
- $40/SF
- 23 Days On Market
Last Sold Price $175,000

Last Listing Agent Sandra Sorel Coldwell Banker Realty - Western MA

/35
$515,000 Sold Sep 19, 2025

86 Sandmill Hill, Cheshire, MA 01225
- 3 Beds
- 2 Baths
- 1,822 Sq Ft
- Built 1973
Last Sold Summary
- 5% Above List Price
- $283/SF
- 3 Days On Market
Last Listing Agent Pauline Green STEEPLEVIEW REALTY - ADAMS BRANCH

86 Sandmill Hill, Cheshire, MA 01225

/36
Est $582,298 Not Listed For Sale

278 E Harbor Rd, Cheshire, MA 01225
- 4 Beds
- 2.5 Baths
- 2,100 Sq Ft
- Built 2006
278 E Harbor Rd, Cheshire, MA 01225

Last Sold Summary
- 13% Above List Price
- $245/SF
- 6 Days On Market
Last Sold Price $515,000

Last Listing Agent Maggie Gavin William Pitt

/51
$518,000 Sold Aug 13, 2025

329 Lanesboro Rd, Cheshire, MA 01225
- 3 Beds
- 2.5 Baths
- 2,269 Sq Ft
- Built 1970
Last Sold Summary
- 4% Above List Price
- $228/SF
- 51 Days On Market
Current Estimated Value $516,809

Last Listing Agent Jason Nocher NOCHER REALTY

329 Lanesboro Rd, Cheshire, MA 01225

Showing Results 1 - 40, Page 1 of 18

Massachusetts Berkshire County Cheshire

Home Trends in Cheshire, MA

On average, homes in Cheshire, MA sell after 46 days on the market compared to the national average of 55 days. The median sale price for homes in Cheshire, MA over the last 12 months is $416,500, up 10% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$416,500

Median Single Family Sale Price

$397,000

Average Price Per Sq Ft

$209

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

1.30

Median List Price

$425,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

10%

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Cheshire, MA Homes

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Home Trends in Cheshire, MA

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