Section Image Section Image

Explore Similar Townhomes Within 10 Miles of Cheshire, MA

  • 1 River Run Unit 1, Williamstown, MA 01267
    1 River Run Unit 1, Williamstown, MA 01267
    1 River Run Unit 1, Williamstown, MA 01267
    /25

    $949,000

    • 3 Beds
    • 2 Baths
    • 1,811 Sq Ft

    1 River Run Unit 1, Williamstown, MA 01267

    Loft-Inspired Townhouse | Williamstown, MA – Gateway to the BerkshiresExperience modern loft-style living in this 3-bed, 2-bath townhouse just steps from the heart of Williamstown. Set along the scenic Green River, this elegant home features soaring ceilings, sunlit open-concept living, and a chef’s kitchen with sleek finishes and energy-efficient appliances. A fireplace warms the expansive

    Agent Photo

    Selina Lamb

    Birch Properties

    (413) 613-4813

    1 River Run Unit 1, Williamstown, MA 01267
  • 25 Taft St, North Adams, MA 01247
    25 Taft St, North Adams, MA 01247
    25 Taft St, North Adams, MA 01247
    /18

    $275,000

    • 3 Beds
    • 1.5 Baths
    • 1,568 Sq Ft

    25 Taft St, North Adams, MA 01247

    Experience maintenance-free living in this stunning 3-bedroom, 1.5-bath townhouse, meticulously renovated to blend contemporary design with practicality. The open floor plan showcases exposed brick and stunning wood laminate flooring, complemented by energy-efficient stainless-steel appliances that enhance everyday living. Enjoy the convenience of flat, easy parking with a covered carport and

    Agent Photo

    Gary Fuls Jr

    RE/MAX Transitions

    (413) 937-7308

    25 Taft St, North Adams, MA 01247
  • 160 Water St Unit 112, Williamstown, MA 01267
    160 Water St Unit 112, Williamstown, MA 01267
    160 Water St Unit 112, Williamstown, MA 01267
    /8

    $475,000

    • 1 Bed
    • 1.5 Baths
    • 850 Sq Ft

    160 Water St Unit 112, Williamstown, MA 01267

    Unit 112, a beautiful appointed 1-bedroom in town condominium, a perfect blend of industrial and contemporary design. Upon entering, you'll immediately appreciate the spacious open-concept layout flooded with natural light from oversized windows that highlight the gleaming bamboo floors throughout. The living area provides ample space for both relaxation and entertaining, with a seamless flow

    Kim Burnham

    160 Water St Unit 112, Williamstown, MA 01267
  • 2 Amy Ct Unit 2, Pittsfield, MA 01201
    2 Amy Ct Unit 2, Pittsfield, MA 01201
    2 Amy Ct Unit 2, Pittsfield, MA 01201
    /54

    $629,900

    • 4 Beds
    • 3.5 Baths
    • 3,561 Sq Ft

    2 Amy Ct Unit 2, Pittsfield, MA 01201

    Stunning and beautifully designed three-level end unit condominium with luxury finishes throughout. Enter into an open-concept main level, highlighted by gleaming hardwood floors, recessed lighting, and expansive windows that flood the space with natural light. The kitchen offers stainless steel appliances, granite countertops, and custom cabinetry. The spacious living and dining areas are

    Cory Evangelisto NOCHER REALTY

    2 Amy Ct Unit 2, Pittsfield, MA 01201
  • 5 Windflower Way, Williamstown, MA 01267
    5 Windflower Way, Williamstown, MA 01267
    5 Windflower Way, Williamstown, MA 01267
    /39

    $440,000

    • 2 Beds
    • 2 Baths
    • 1,683 Sq Ft

    5 Windflower Way, Williamstown, MA 01267

    Welcome to your dream condo located at 5 Windflower Way. This beautifully updated residence offers a blend of comfort & convenience, making it a perfect place for those seeking low maintenance. The well-equipped kitchen features modern appliances, quartz countertops, a beautiful, tiled floor, & ample cabinets. This condo includes 2 generously sized bedrooms, and two bathrooms. The attached

    Jessica Rizzo LAMACCHIA REALTY, INC

    5 Windflower Way, Williamstown, MA 01267
  • 9201 Mountainside Dr, Hancock, MA 01237
    9201 Mountainside Dr, Hancock, MA 01237
    9201 Mountainside Dr, Hancock, MA 01237
    /25

    $659,000

    • 4 Beds
    • 3 Baths
    • 2,122 Sq Ft

    9201 Mountainside Dr, Hancock, MA 01237

    Turnkey ski home at Jiminy Peak—New England’s premier mountain resort under 2.5hrs to NYC & Boston. Steps from the slopes, it offers 2 living rooms, a fireplace for cozy winter evenings, master bedroom with ensuite jacuzzi, deck overlooking forest and mountain, and ample parking. Enjoy heated pools, hot tubs, tennis courts, onsite dining from the Mezze Hospitality Group, the convenience of an

    Derek Greene The Greene Realty Group

    9201 Mountainside Dr, Hancock, MA 01237
  • 160 Water St Unit 23, Williamstown, MA 01267
    160 Water St Unit 23, Williamstown, MA 01267
    160 Water St Unit 23, Williamstown, MA 01267
    /57

    $650,000

    • 2 Beds
    • 1.5 Baths
    • 1,388 Sq Ft

    160 Water St Unit 23, Williamstown, MA 01267

    Cable Mills consists of three former industrial mill buildings restored into beautiful homes featuring 12ft to 16ft tall ceilings, massive windows, and exposed brick and beam, steel and timber throughout, stainless steel appliances, granite countertops, gas-fired ranges, generous closets and in home laundry. Cable Mills offers stunning views of the famed 'Purple Mountains' and the rolling Green

    StreamLine Communities STREAMLINE COMMUNITIES

    160 Water St Unit 23, Williamstown, MA 01267
  • 2 River Run, Williamstown, MA 01267
    2 River Run, Williamstown, MA 01267
    2 River Run, Williamstown, MA 01267
    /38

    $1,490,000

    • 3 Beds
    • 2.5 Baths
    • 2,499 Sq Ft

    2 River Run, Williamstown, MA 01267

    Coveted corner River House on the bend of the Green River. This is the first three-bedroom River House to be listed for resale, meticulously maintained and move in ready. Model home with all original upgrade options, including paperbark maple tree well in living room, Ortal fireplace, brick surround at front entry, built-in bookshelves in den, whole house water filter. Oversized windows, double

    Sarah Haskins Streamline Communities - Williamstown

    2 River Run, Williamstown, MA 01267
  • 55 Pomeroy Ave Unit 6, Pittsfield, MA 01201
    55 Pomeroy Ave Unit 6, Pittsfield, MA 01201
    55 Pomeroy Ave Unit 6, Pittsfield, MA 01201
    /20

    $229,000

    • 2 Beds
    • 1 Bath
    • 867 Sq Ft

    55 Pomeroy Ave Unit 6, Pittsfield, MA 01201

    Charming Historic Carriage House Condo Enjoy carefree living in this beautifully converted historic carriage house, now a cozy and tastefully renovated condo. Tucked within a peaceful community, this unique home features a private rear deck and a charming stone patio—perfect for relaxing or entertaining. Inside, modern updates blend seamlessly with original character. Just a short stroll brings

    Michele Purcell Lamacchia Realty, Inc.

    55 Pomeroy Ave Unit 6, Pittsfield, MA 01201
  • 2 Rolling Hills Unit bldg2-4, Lenox, MA 01240
    2 Rolling Hills Unit bldg2-4, Lenox, MA 01240
    2 Rolling Hills Unit bldg2-4, Lenox, MA 01240
    /39

    $244,900

    • 2 Beds
    • 2 Baths
    • 1,552 Sq Ft

    2 Rolling Hills Unit bldg2-4, Lenox, MA 01240

    As summer winds down... if you are looking for your fall/winter project - take a look at this value-priced Rolling Hills condo! Priced below assessed value to offer immediate equity, this two-bedroom/two bath unit has much to offer. Original parquet flooring now revealed under the former wall-to-wall carpet. Private rear deck looks toward Yokun Brook. Partially finished lower level with

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    2 Rolling Hills Unit bldg2-4, Lenox, MA 01240
  • 11 Corey Rd, Hancock, MA 01237
    11 Corey Rd, Hancock, MA 01237
    11 Corey Rd, Hancock, MA 01237
    /39

    $308,000

    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    11 Corey Rd, Hancock, MA 01237

    Country Village furnished end unit condo with 3 bedrooms, 2.5 baths walkable to pool, slopes, main lodge and country store.Living room has wood burning fireplace with upstairs open seating area/loft overlooking lower level. nice rear deck with distant west views over back meadow. Good storage for skis and outdoor equipment.

    Carolyn Umlauf HARSCH ASSOCIATES

    11 Corey Rd, Hancock, MA 01237
  • 2-5 Rolling Hill Build 2 Unit 5 Ln, Lenox, MA 01240
    2-5 Rolling Hill Build 2 Unit 5 Ln, Lenox, MA 01240
    2-5 Rolling Hill Build 2 Unit 5 Ln, Lenox, MA 01240
    /18

    $313,000

    • 2 Beds
    • 3 Baths
    • 1,770 Sq Ft

    2-5 Rolling Hill Build 2 Unit 5 Ln, Lenox, MA 01240

    If you are looking for location, Rolling Hills is the place to be. Just minutes from Tanglewood, Shakespeare & Company, skiing, arts, and all of the Culture the Berkshires has to offer. This unit is right across from the Clubhouse/Pool/fitness room. This unit has 2 bedrooms, 3 baths, additional family room on the lower level and newer appliances. Enjoy the Tennis/pickle ball courts or take swim

    Toni Marie Gage SIGNATURE ASSOCIATES

    2-5 Rolling Hill Build 2 Unit 5 Ln, Lenox, MA 01240
Massachusetts Berkshire County Cheshire

Townhomes for Sale in Cheshire, MA

Why Live in Cheshire

Cheshire, Massachusetts, nestled in the scenic Berkshires, offers a quaint small-town experience with a rich history dating back to its 18th-century dairy farming roots. Known for its outdoor recreation, Cheshire is a haven for nature enthusiasts, featuring the nearly 13-mile Ashuwillticook Rail Trail and sections of the Appalachian Trail. Mount Greylock, the state's highest peak, is an 8-mile hike away, while The Cobbles offers views of the Taconic Mountains. The town hosts community events like the Appalachian Trail Community Celebration Day, enhancing its close-knit atmosphere. Housing in Cheshire includes classic New England styles such as farmhouses, Colonial Revivals, and midcentury ranches, with competitive prices lower than the state median. The Hoosac Valley Regional School District serves the area, though schools receive average ratings. Shopping and dining options are limited, with a few local businesses like Cheshire Glassworks and Common Table, a popular eatery. For more variety, residents often travel to nearby Pittsfield. Massachusetts Route 8 connects Cheshire to Pittsfield and Adams, with Albany International Airport about 50 miles away. While cell phone service can be spotty, the town's charm lies in its natural beauty and community spirit.

Learn more about living in Cheshire

Home Trends in Cheshire, MA

On average, homes in Cheshire, MA sell after 43 days on the market compared to the national average of 52 days. The median sale price for homes in Cheshire, MA over the last 12 months is $373,525, up 20% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$373,525
Median Single Family Sale Price
$348,475
Median Townhouse Sale Price
$312,500
Average Price Per Sq Ft
$195
Number of Homes for Sale
11
Last 12 months Home Sales
48
Months of Supply
2.80
Median List Price
$397,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
20%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group