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

76Results

Browse Real Estate For Sale in the Winchester Area of MA

Contact Better Homes and Gardens Real Estate The Shanahan Group with questions or schedule a showing. Sign up to save your favorite Winchester area properties and be notified when similar listings become available. 

Recently Updated
46 Great Bay Road Osterville MA 02655

$6,500,000

Osterville, MA

46 Great Bay Road

  • 3 Beds
  • 6 Baths
  • 0.78 Acres
  • 4,831 SqFt
  • 144 Days on Market
MLS#: 22602282
Open House

$799,000

Osterville, MA

329 Swift Avenue

NEXT OPEN HOUSE:

Sun 10/11 1:30 PM to 3:00 PM

  • 3 Beds
  • 2 Baths
  • 0.31 Acres
  • 1,856 SqFt
  • 41 Days on Market
MLS#: 22604277
Open House

$3,225,000

Osterville, MA

32 Starboard Lane

NEXT OPEN HOUSE:

Sat 10/10 10:00 AM to 12:00 PM

  • 3 Beds
  • 3 Baths
  • 1.21 Acre
  • 1,506 SqFt
  • 2 Days on Market
MLS#: 22605105
Open House

$975,000

Barnstable, MA

227 Bumps River Road

NEXT OPEN HOUSE:

Sat 10/10 12:00 PM to 2:00 PM

  • 3 Beds
  • 2 Baths
  • 0.98 Acres
  • 1,706 SqFt
  • 2 Days on Market
MLS#: 73587619
Open House

$990,000

Osterville, MA

82 Falling Leaf Lane

NEXT OPEN HOUSE:

Sat 10/10 10:30 AM to 12:30 PM

  • 3 Beds
  • 3 Baths
  • 0.34 Acres
  • 2,116 SqFt
  • 31 Days on Market
MLS#: 22604478
Open House

$2,825,000

Osterville, MA

55 Seapuit Road

NEXT OPEN HOUSE:

Sun 10/11 12:15 PM to 1:30 PM

  • 4 Beds
  • 4 Baths
  • 1.52 Acre
  • 3,523 SqFt
  • 24 Days on Market
MLS#: 22604641
Open House

$1,895,000

Osterville, MA

420 Starboard Lane

NEXT OPEN HOUSE:

Sun 10/11 10:30 AM to 12:30 PM

  • 4 Beds
  • 3 Baths
  • 1.68 Acre
  • 2,636 SqFt
  • 123 Days on Market
MLS#: 22602737

$1,895,000

Barnstable, MA

Osterville

420 Starboard Lane

  • 4 Beds
  • 3 Baths
  • 1.68 Acre
  • 2,636 SqFt
  • 123 Days on Market
MLS#: 73531658
New Listing

$5,695,000

Barnstable, MA

Oyster Harbors

108 Seapuit River Road

  • 4 Beds
  • 4 Baths
  • 1 Acre
  • 3,012 SqFt
  • 6 Days on Market
MLS#: 73586285
New Listing

$16,500,000

Barnstable, MA

Osterville

143 Bayberry Way

  • 8 Beds
  • 11 Baths
  • 3.02 Acres
  • 8,763 SqFt
  • 6 Days on Market
MLS#: 73586293
Open House

$4,695,000

Osterville, MA

22 Scudder Road

NEXT OPEN HOUSE:

Sat 10/10 9:00 AM to 12:00 PM

  • 5 Beds
  • 7 Baths
  • 0.52 Acres
  • 4,100 SqFt
  • 102 Days on Market
MLS#: 22603117
Open House

$1,425,000

Osterville, MA

955 Main Street

NEXT OPEN HOUSE:

Sun 10/11 12:00 PM to 2:00 PM

  • 3 Beds
  • 2 Baths
  • 0.46 Acres
  • 1,765 SqFt
  • 171 Days on Market
MLS#: 22601611

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 October 8, 2026 11:22 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.