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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New Listing
65 Harbor View Road Chatham MA 02633

$4,995,000

Chatham, MA

65 Harbor View Road

  • 5 Beds
  • 6 Baths
  • 0.47 Acres
  • 4,763 SqFt
  • 1 Day on Market
MLS#: 22604593
New Listing

$1,495,000

Chatham, MA

87 Cranberry Lane

  • 3 Beds
  • 2 Baths
  • 0.32 Acres
  • 1,415 SqFt
  • 16 Days on Market
MLS#: 22604234
Open House

$2,499,000

Chatham, MA

72 Ridgevale Road

NEXT OPEN HOUSE:

Sun 9/13 10:00 AM to 12:00 PM

  • 2 Beds
  • 2 Baths
  • 0.22 Acres
  • 1,547 SqFt
  • 13 Days on Market
MLS#: 22604319
Open House

$1,200,000

Chatham, MA

122 Forest Beach Road

NEXT OPEN HOUSE:

Sun 9/13 11:00 AM to 12:30 PM

  • 4 Beds
  • 2 Baths
  • 0.28 Acres
  • 2,050 SqFt
  • 4 Days on Market
MLS#: 22604514

$975,000

Chatham, MA

65 Captain Kendrick Drive

  • 3 Beds
  • 3 Baths
  • 0.67 Acres
  • 3,384 SqFt
  • 87 Days on Market
MLS#: 22602982
New Listing

$5,250,000

Chatham, MA

106 Barcliff Avenue

  • 4 Beds
  • 5 Baths
  • 0.95 Acres
  • 4,000 SqFt
  • 10 Days on Market
MLS#: 22604428
Open House

$4,250,000

Chatham, MA

222 Barcliff Avenue

NEXT OPEN HOUSE:

Sun 9/13 11:00 AM to 1:00 PM

  • 4 Beds
  • 6 Baths
  • 0.47 Acres
  • 3,980 SqFt
  • 173 Days on Market
MLS#: 22600932
Open House

$2,850,000

Chatham, MA

336 Stage Island Road

NEXT OPEN HOUSE:

Sun 9/13 2:00 PM to 4:00 PM

  • 3 Beds
  • 3 Baths
  • 1.07 Acre
  • 2,205 SqFt
  • 131 Days on Market
MLS#: 22601983

$2,295,000

Chatham, MA

55 Winterset Drive

  • 4 Beds
  • 4 Baths
  • 1.94 Acre
  • 4,066 SqFt
  • 63 Days on Market
MLS#: 22603375
Open House

$875,000

Chatham, MA

31 Old Village Road

NEXT OPEN HOUSE:

Sun 9/13 12:30 PM to 2:00 PM

  • 3 Beds
  • 2 Baths
  • 0.51 Acres
  • 2,167 SqFt
  • 2 Days on Market
MLS#: 73574852
Open House

$2,499,000

Chatham, MA

72 Ridgevale Road So

NEXT OPEN HOUSE:

Sun 9/13 10:00 AM to 12:00 PM

  • 2 Beds
  • 2 Baths
  • 0.22 Acres
  • 1,547 SqFt
  • 2 Days on Market
MLS#: 73574801

$829,000

Chatham, MA

33 Duck Marsh Lane

  • 3 Beds
  • 2 Baths
  • 0.56 Acres
  • 1,192 SqFt
  • 282 Days on Market
MLS#: 22505803

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.

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 September 12, 2026 11:51 PM 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.

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.