Luxury Homes for Sale in Winchester, MA

28Results

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Winchester Luxury Homes for Sale in Massachusetts

Newest
Open House
18 Middlesex Street Winchester MA 01890

$2,650,000

Winchester, MA

18 Middlesex Street

NEXT OPEN HOUSE:

Sat 10/24 11:30 AM to 1:00 PM

  • 4 Beds
  • 5 Baths
  • 0.25 Acres
  • 5,233 SqFt
  • 1 Day on Market
MLS#: 73593868
New Listing

$3,799,000

Winchester, MA

15 Foxcroft Road

  • 8 Beds
  • 6 Baths
  • 0.32 Acres
  • 7,081 SqFt
  • 2 Days on Market
MLS#: 73593484
New Listing

$2,950,000

Winchester, MA

18 Surrey Road

  • 6 Beds
  • 4 Baths
  • 0.48 Acres
  • 4,752 SqFt
  • 4 Days on Market
MLS#: 73592433
Open House

$1,985,000

Winchester, MA

30 Surrey Road

NEXT OPEN HOUSE:

Sun 10/25 1:00 PM to 2:30 PM

  • 4 Beds
  • 4 Baths
  • 1.02 Acre
  • 4,241 SqFt
  • 9 Days on Market
MLS#: 73589478
Open House

$2,049,000

Winchester, MA

21 Amberwood Drive

NEXT OPEN HOUSE:

Sat 10/24 11:30 AM to 1:00 PM

  • 5 Beds
  • 4 Baths
  • 0.46 Acres
  • 4,063 SqFt
  • 16 Days on Market
MLS#: 73588059
New Listing

$18,000,000

Winchester, MA

15 Vinson Circle

  • 6 Beds
  • 7 Baths
  • 0.98 Acres
  • 10,000 SqFt
  • 22 Days on Market
MLS#: 73585235
New Listing

$3,299,000

Winchester, MA

1 Plymouth Road

  • 7 Beds
  • 8 Baths
  • 0.43 Acres
  • 7,226 SqFt
  • 22 Days on Market
MLS#: 73585058
New Listing

$1,529,000

Winchester, MA

25 Arlington Street

  • 4 Beds
  • 4 Baths
  • 0.39 Acres
  • 2,709 SqFt
  • 23 Days on Market
MLS#: 73584817
New Listing

$1,750,000

Winchester, MA

Wedgemere

1 Overlook Way

  • 4 Beds
  • 3 Baths
  • 0.36 Acres
  • 3,604 SqFt
  • 30 Days on Market
MLS#: 73581571
Open House

$3,200,000

Winchester, MA

30 Willowdale Road

NEXT OPEN HOUSE:

Sat 10/24 2:30 PM to 4:00 PM

  • 8 Beds
  • 7 Baths
  • 0.23 Acres
  • 5,750 SqFt
  • 38 Days on Market
MLS#: 73577116

$4,299,000

Winchester, MA

4 Dartmouth

  • 5 Beds
  • 6 Baths
  • 0.67 Acres
  • 6,526 SqFt
  • 43 Days on Market
MLS#: 73574948

$1,650,000

Winchester, MA

117 Highland

  • 5 Beds
  • 4 Baths
  • 0.17 Acres
  • 3,722 SqFt
  • 44 Days on Market
MLS#: 73573887

The high end in Winchester concentrates around the Mystic Lakes, on Myopia Hill, and in the Rangeley and Wedgemere neighbourhoods near the commuter rail. Above one and a half million dollars the inventory is largely turn of the century architecture, shingle style and Colonial Revival houses on substantial lots, many of them carefully restored. New construction appears but is constrained by lot availability, so most transactions at this level involve an established property. Browse Winchester waterfront homes or explore Winchester homes with a pool.

Frequently Asked Questions

Which neighbourhoods are strongest?
The areas around the Mystic Lakes, Myopia Hill, and the Rangeley and Wedgemere neighbourhoods near the commuter rail station.
Is there much new construction?
Some, but lot availability limits it. Most high end sales here involve established houses, frequently restored.

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.