Luxury Homes For Sale, Winchester MA

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Browse listings for luxury homes in Winchester, MA. Contact Better Homes and Gardens Real Estate The Shanahan Group with any questions or to schedule a showing. Sign up to save your favorite luxury properties in Winchester and be notified when similar listings become available. 

Newest
New Listing
10 Bonad Road Winchester MA 01890

$1,499,000

Winchester, MA

10 Bonad Road

  • 4 Beds
  • 3 Baths
  • 0.15 Acres
  • 2,233 SqFt
  • 5 Days on Market
MLS#: 73530345
New Listing

$1,350,000

Winchester, MA

15 Thornberry Road

  • 4 Beds
  • 3 Baths
  • 0.36 Acres
  • 4,062 SqFt
  • 5 Days on Market
MLS#: 73529811
New Listing

$1,799,000

Winchester, MA

24 Hinds Road

  • 4 Beds
  • 3 Baths
  • 0.3 Acres
  • 2,814 SqFt
  • 6 Days on Market
MLS#: 73529658
New Listing

$1,999,000

Winchester, MA

Winchester Highlands

22 Hollywood Road

  • 5 Beds
  • 4 Baths
  • 0.34 Acres
  • 3,136 SqFt
  • 8 Days on Market
MLS#: 73527768
New Listing

$1,110,000

Winchester, MA

41 Cross Street

  • 4 Beds
  • 2 Baths
  • 0.14 Acres
  • 2,085 SqFt
  • 8 Days on Market
MLS#: 73527486
New Listing

$2,599,000

Winchester, MA

78 Bacon Street

  • 5 Beds
  • 4 Baths
  • 0.31 Acres
  • 5,230 SqFt
  • 11 Days on Market
MLS#: 73526460
New Listing

$1,799,000

Winchester, MA

94 Johnson Road

  • 4 Beds
  • 3 Baths
  • 0.82 Acres
  • 3,366 SqFt
  • 12 Days on Market
MLS#: 73525571
New Listing

$2,599,000

Winchester, MA

Wedgemere

53 Winford Way

  • 5 Beds
  • 4 Baths
  • 0.49 Acres
  • 5,083 SqFt
  • 13 Days on Market
MLS#: 73525195
New Listing

$1,925,000

Winchester, MA

8 Hawthorne

  • 5 Beds
  • 4 Baths
  • 0.45 Acres
  • 3,315 SqFt
  • 18 Days on Market
MLS#: 73522773
New Listing

$3,600,000

Winchester, MA

2 Atherton Road

  • 6 Beds
  • 7 Baths
  • 0.3 Acres
  • 7,400 SqFt
  • 26 Days on Market
MLS#: 73519229
New Listing

$1,225,000

Winchester, MA

53 Lake Street

  • 3 Beds
  • 3 Baths
  • 0.15 Acres
  • 2,235 SqFt
  • 26 Days on Market
MLS#: 73519082
New Listing

$2,795,000

Winchester, MA

18 Middlesex Street

  • 4 Beds
  • 5 Baths
  • 0.25 Acres
  • 5,233 SqFt
  • 26 Days on Market
MLS#: 73518621

Explore Luxury Homes for Sale in Winchester, MA

Luxury homes in Winchester offer timeless architecture, high-end finishes, and expansive living spaces. Many properties feature custom millwork, gourmet kitchens, and professionally landscaped grounds. Located just eight miles from Boston, Winchester blends small-town charm with convenient commuter access. With top-tier amenities and proximity to the town center, these homes reflect elevated living in a prime Greater Boston location.

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.