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Cheshire Property Search

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Our website features the best Cheshire real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

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Hot Cheshire Properties

44 Richmond St, Cheshire image
44 Richmond St, Cheshire $269,900

There are many notable features of this DREAMY home located in Cheshire, MA. This house is walking distance to Cheshire Lake, the Ashuwillticook Bike Trail and the center...

  • 3 Beds
  • 2 Baths
  • 237661 MLS
28 Furnace Hill, Cheshire image
28 Furnace Hill, Cheshire $349,000

Immaculate four bedroom, two full bathroom home in Cheshire. Upon entering this move-in ready home you can hang your coat in the custom-built cabinets, enter the updated...

  • 4 Beds
  • 2 Baths
  • 237609 MLS
Cheshire image
Cheshire $299,900

Currently the home of Harry's Auto, this commercial garage building is well maintained offering low maintenance exterior with vinyl signing and metal roof. The office bui...

  • 237583 MLS
221-227 North St, Cheshire image
221-227 North St, Cheshire $324,900

Handsome 4 Family in the Heart of Cheshire. This multi-family is fully rented and has had updates over the years including vinyl siding, vinyl windows, asphalt architectu...

  • 6 Beds
  • 4 Baths
  • 237582 MLS
213 Devonshire Dr, Cheshire image
213 Devonshire Dr, Cheshire $275,000

Enjoy this charming & move in ready Cheshire Home with views of Mount Greylock! This property features 4 bedroom & 2 bathrooms, the upstairs bedrooms are very spacious. ...

  • 4 Beds
  • 2 Baths
  • 237527 MLS
40 Curran Rd, Cheshire image
40 Curran Rd, Cheshire $200,000

Raised Ranch in Cheshire!This 3 bedroom 2 bath home needs some finishing touches! Bring your tool belt and build your own sweat equity! Great lot over an acre with a deta...

  • 3 Beds
  • 2 Baths
  • 237496 MLS
415-417 State Rd North, Cheshire image
415-417 State Rd North, Cheshire $249,900

Colonial Style 3-Family located in Cheshire on Route 8. This multi-family investment offers a flat style setting on the main house and an addition to the left with a 2 be...

  • 5 Beds
  • 4 Baths
  • 237472 MLS
192 Willow Cove Rd, Cheshire image
192 Willow Cove Rd, Cheshire $299,900

Move right in to this recently renovated (2021) lakefront cottage on Cheshire lake featuring new flooring throughout and updated bath. The deck has full southern exposu...

  • 1 Beds
  • 1 Baths
  • 237445 MLS
108 Depot St, Cheshire image
108 Depot St, Cheshire $324,900 ▼

Totally renovated home. Some of the updates includes; All new electric, plumbing, roof and septic system. This home offers 4 bedrooms and two full bath, (1 bed is on the ...

  • 4 Beds
  • 2 Baths
  • 237233 MLS
53 Depot St, Cheshire image
53 Depot St, Cheshire $324,900

Gorgeous farmhouse In the heart of ''The Berkshires,'' in the quaint little town of Cheshire just down the street from direct access to the Ashuwillticook Rail Trail - a ...

  • 3 Beds
  • 2 Baths
  • 237109 MLS
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402 Park Street | PO Box 547 | Housatonic, MA 01236
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