MLS Search Results - Better Homes and Gardens | The Shanahan Group

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Browse Real Estate For Sale in the Winchester Area of MA

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Recently Updated
New Listing
160 Woodland Way Chatham MA 02650

$5,800,000

Chatham, MA

160 Woodland Way

  • 3 Beds
  • 6 Baths
  • 0.49 Acres
  • 4,902 SqFt
  • 1 Day on Market
MLS#: 73593924
New Listing

$299,000

North Chatham, MA

216 Orleans Road, Unit C

  • 1986 Year Built
  • 420 SqFt
  • 2 Days on Market
MLS#: 22605364
New Listing

$5,800,000

North Chatham, MA

160 Woodland Way

  • 3 Beds
  • 6 Baths
  • 0.49 Acres
  • 4,902 SqFt
  • 3 Days on Market
MLS#: 22605344
New Listing

$6,495,000

Chatham, MA

200 Crows Pond Road

  • 5 Beds
  • 6 Baths
  • 0.92 Acres
  • 4,588 SqFt
  • 7 Days on Market
MLS#: 73592001
New Listing

$6,495,000

North Chatham, MA

200 Crows Pond Road

  • 5 Beds
  • 6 Baths
  • 0.92 Acres
  • 4,588 SqFt
  • 7 Days on Market
MLS#: 22605305

$4,950,000

North Chatham, MA

5 Hillcrest Lane

  • 4 Beds
  • 5 Baths
  • 0.39 Acres
  • 3,811 SqFt
  • 37 Days on Market
MLS#: 22604664
Open House

$1,795,000

North Chatham, MA

71 Rowland Drive

NEXT OPEN HOUSE:

Sat 10/24 12:00 PM to 1:30 PM

  • 3 Beds
  • 3 Baths
  • 0.65 Acres
  • 1,398 SqFt
  • 78 Days on Market
MLS#: 22603834

$1,750,000

North Chatham, MA

303 Orleans Road

  • 1963 Year Built
  • 0.92 Acres
  • 5,101 SqFt
  • 130 Days on Market
MLS#: 22602912

$2,295,000

North Chatham, MA

41 Court Street

  • 3 Beds
  • 3 Baths
  • 0.69 Acres
  • 3,504 SqFt
  • 249 Days on Market
MLS#: 22600472

$485,000

North Chatham, MA

212 Orleans Road, Unit A

  • 1986 Year Built
  • 1,123 SqFt
  • 499 Days on Market
MLS#: 22502876

$2,295,000

Chatham, MA

North Chatham

41 Court Street

  • 3 Beds
  • 3 Baths
  • 0.69 Acres
  • 3,504 SqFt
  • 249 Days on Market
MLS#: 73477537

$619,000

Chatham, MA

216 Orleans Road, Unit D

  • 2 Beds
  • 2 Baths
  • 1,000 SqFt
  • Nickerson Corners Unit Name
  • 44 Days on Market
MLS#: 73571094

Real estate in the Winchester area offers a mix of charming traditional homes, modern properties, and everything in between. View available listings in Winchester, Arlington, Medford, Woburn, Reading, and surrounding towns.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLSPIN and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

broker reciprocity The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate | The Shanahan Group are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor Better Homes and Gardens Real Estate | The Shanahan Group shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless.

This site was last updated October 23, 2026 5:51 AM EDT. All properties are subject to prior sale, changes, or withdrawal.

Better Homes and Gardens Real Estate | The Shanahan Group has chosen to display only certain towns and/or types or styles of properties. This site may not show all listings that are available through the Cape Cod & Islands Multiple Listing Service, Inc.