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Browse Real Estate For Sale in the Winchester Area of MA

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Recently Updated
New Listing
44 Trotters Lane West Dennis MA 02670

$550,000

West Dennis, MA

44 Trotters Lane

  • 2 Beds
  • 1 Bath
  • 0.16 Acres
  • 696 SqFt
  • 4 Days on Market
MLS#: 22603609

$2,495,000

Provincetown, MA

134 Commercial Street

  • 2 Beds
  • 4 Baths
  • 0.04 Acres
  • 1,770 SqFt
  • 68 Days on Market
MLS#: 22602431
New Listing

$695,000

Mashpee, MA

29 Sheffield Place

  • 3 Beds
  • 3 Baths
  • 0.4 Acres
  • 1,736 SqFt
  • 14 Days on Market
MLS#: 22603446

$1,099,000

Dennis, MA

9 Chase Avenue, Unit 7

  • 2 Beds
  • 4 Baths
  • 1,986 SqFt
  • 50 Days on Market
MLS#: 73533069
New Listing

$2,495,000

Provincetown, MA

134 Commercial Street

  • 1880 Year Built
  • 0.04 Acres
  • 1,770 SqFt
  • 17 Days on Market
MLS#: 22603382
New Listing

$665,000

Osterville, MA

17 Galleon Way

  • 3 Beds
  • 3 Baths
  • 0.47 Acres
  • 1,297 SqFt
  • 17 Days on Market
MLS#: 22603408
Open House

$1,295,000

Barnstable, MA

Barnstable (village)

2839 Main Street

NEXT OPEN HOUSE:

Sat 8/1 12:00 PM to 2:00 PM

  • 8 Beds
  • 9 Baths
  • 1.09 Acre
  • 3,800 SqFt
  • 1 Day on Market
MLS#: 73556749

$2,750,000

Falmouth, MA

38 Nemasket Road

  • 4 Beds
  • 5 Baths
  • 0.55 Acres
  • 4,484 SqFt
  • 80 Days on Market
MLS#: 22602146
New Listing

$2,395,000

Dennis, MA

11 Perseverance Path

  • 4 Beds
  • 4 Baths
  • 1.01 Acre
  • 3,300 SqFt
  • 1 Day on Market
MLS#: 73556738

$725,000

Harwich, MA

6 Carefree Way

  • 3 Beds
  • 2 Baths
  • 0.23 Acres
  • 1,502 SqFt
  • 57 Days on Market
MLS#: 22602045
New Listing

$2,475,000

Provincetown, MA

24 Cottage Street

  • 2 Beds
  • 3 Baths
  • 0.04 Acres
  • 1,422 SqFt
  • 28 Days on Market
MLS#: 22603244
Open House

$595,900

Brewster, MA

52 Court Way, Unit 52

NEXT OPEN HOUSE:

Sat 8/1 10:00 AM to 1:00 PM

  • 2 Beds
  • 2 Baths
  • 1,380 SqFt
  • The Colony Unit Name
  • 1 Day on Market
MLS#: 73556735

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 29, 2026 7:51 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.