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
68 Chippingstone Road Chatham MA 02633

$1,299,000

Chatham, MA

68 Chippingstone Road

  • 4 Beds
  • 3 Baths
  • 0.73 Acres
  • 2,391 SqFt
  • 28 Days on Market
MLS#: 22602848
Open House

$4,750,000

Chatham, MA

48 Sylvan Way

NEXT OPEN HOUSE:

Sat 7/11 11:30 AM to 1:30 PM

  • 6 Beds
  • 7 Baths
  • 1.63 Acre
  • 5,721 SqFt
  • 135 Days on Market
MLS#: 22600543
Open House

$2,995,000

Chatham, MA

336 Stage Island Road

NEXT OPEN HOUSE:

Sat 7/11 12:30 PM to 2:30 PM

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

$2,795,000

Chatham, MA

44 Baileys Path

NEXT OPEN HOUSE:

Sat 7/11 11:00 AM to 1:00 PM

  • 3 Beds
  • 4 Baths
  • 0.46 Acres
  • 3,514 SqFt
  • 6 Days on Market
MLS#: 22603263
Open House

$2,795,000

Chatham, MA

44 Baileys Path

NEXT OPEN HOUSE:

Sat 7/11 11:00 AM to 1:00 PM

  • 3 Beds
  • 4 Baths
  • 0.46 Acres
  • 3,514 SqFt
  • 0 Days on Market
MLS#: 73544509
Open House

$3,695,000

Chatham, MA

83 Old Mail Road

NEXT OPEN HOUSE:

Sat 7/11 1:00 PM to 2:30 PM

  • 3 Beds
  • 5 Baths
  • 0.5 Acres
  • 5,154 SqFt
  • 74 Days on Market
MLS#: 22601738
New Listing

$2,199,000

Chatham, MA

Chatham (village)

330 Champlain Road

  • 4 Beds
  • 3 Baths
  • 0.98 Acres
  • 2,520 SqFt
  • 1 Day on Market
MLS#: 73543021

$1,499,000

Chatham, MA

856 Main Street

  • 1970 Year Built
  • 0.51 Acres
  • 2,015 SqFt
  • 157 Days on Market
MLS#: 22600313

$1,499,000

Chatham, MA

856 Main Street

  • 1970 Year Built
  • 0.51 Acres
  • 122 Days on Market
MLS#: 73484112
New Listing

$1,800

Chatham, MA

1589 Main Street, Unit E

  • 1959 Year Built
  • 1.81 Acre
  • 10,669 SqFt
  • 1 Day on Market
MLS#: 22603315

$829,000

Chatham, MA

33 Duck Marsh Lane

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

$2,199,000

Chatham, MA

330 Champlain Road

  • 4 Beds
  • 3 Baths
  • 0.98 Acres
  • 2,520 SqFt
  • 10 Days on Market
MLS#: 22603168

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 July 9, 2026 5:51 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.