Luxury Homes for Sale in Winchester MA

24Results

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Luxury Homes in Winchester, Massachusetts

Winchester offers a picturesque town center, strong schools, and a quick commute to Boston, anchoring a solid luxury market. This page gathers listings priced above $1.5M. Explore luxury homes in a nearby town or browse Boston-suburb luxury homes.

Newest
Open House
143 Arlington Street Winchester MA 01890

$1,599,000

Winchester, MA

143 Arlington Street

NEXT OPEN HOUSE:

Sat 9/12 1:00 PM to 2:00 PM

  • 5 Beds
  • 3 Baths
  • 0.28 Acres
  • 2,944 SqFt
  • 2 Days on Market
Listed by Kim Covino & Co. Team of Compass
MLS#: 73575069
Open House

$4,299,000

Winchester, MA

4 Dartmouth

NEXT OPEN HOUSE:

Sat 9/12 1:00 PM to 2:30 PM

  • 5 Beds
  • 6 Baths
  • 0.67 Acres
  • 6,526 SqFt
  • 2 Days on Market
Listed by The Pallotta Group of Gibson Sotheby's International Realty
MLS#: 73574948
Open House

$2,995,000

Winchester, MA

8 Priscilla Lane

NEXT OPEN HOUSE:

Sat 9/12 1:30 PM to 3:30 PM

  • 5 Beds
  • 6 Baths
  • 0.23 Acres
  • 6,500 SqFt
  • 3 Days on Market
Listed by The Pezzano Group of Rise Signature Homes
MLS#: 73574330
Open House

$2,249,000

Winchester, MA

11 Locke Street

NEXT OPEN HOUSE:

Sat 9/12 1:00 PM to 2:30 PM

  • 5 Beds
  • 4 Baths
  • 0.22 Acres
  • 4,368 SqFt
  • 3 Days on Market
Listed by Lesley Smith of Barrett Sotheby's International Realty
MLS#: 73574117
Open House

$1,650,000

Winchester, MA

117 Highland

NEXT OPEN HOUSE:

Sun 9/13 12:00 PM to 1:30 PM

  • 5 Beds
  • 4 Baths
  • 0.17 Acres
  • 3,722 SqFt
  • 3 Days on Market
Listed by Dara Singleton of Better Homes and Gardens Real Estate - The Shanahan Group
MLS#: 73573887
Open House

$3,149,000

Winchester, MA

37 Mayflower Road

NEXT OPEN HOUSE:

Sat 9/12 1:30 PM to 3:00 PM

  • 7 Beds
  • 8 Baths
  • 0.46 Acres
  • 8,540 SqFt
  • 3 Days on Market
Listed by Kim Covino & Co. Team of Compass
MLS#: 73573670
Open House

$2,199,000

Winchester, MA

19 Hancock Street

NEXT OPEN HOUSE:

Sat 9/12 1:30 PM to 3:00 PM

  • 4 Beds
  • 4 Baths
  • 0.17 Acres
  • 3,570 SqFt
  • 4 Days on Market
Listed by Vita Realty Group of Compass
MLS#: 73572955
Open House

$1,749,000

Winchester, MA

17 Churchill Road

NEXT OPEN HOUSE:

Sat 9/12 11:30 AM to 1:30 PM

  • 5 Beds
  • 4 Baths
  • 0.24 Acres
  • 3,508 SqFt
  • 4 Days on Market
Listed by Domingo Medina of Coldwell Banker Realty - Lexington
MLS#: 73572890
New Listing

$1,679,900

Winchester, MA

5 Willowdale Road

  • 3 Beds
  • 2 Baths
  • 0.33 Acres
  • 2,483 SqFt
  • 4 Days on Market
Listed by Erica Carson of Coldwell Banker Realty - Lexington
MLS#: 73572791
Open House

$2,049,000

Winchester, MA

26 N Gateway

NEXT OPEN HOUSE:

Sat 9/12 10:30 AM to 11:30 AM

  • 4 Beds
  • 4 Baths
  • 0.23 Acres
  • 3,210 SqFt
  • 4 Days on Market
Listed by Pirani & Wile Group of Gibson Sotheby's International Realty
MLS#: 73572687
Open House

$1,699,000

Winchester, MA

4 Churchill Road

NEXT OPEN HOUSE:

Sat 9/12 11:00 AM to 12:30 PM

  • 3 Beds
  • 2 Baths
  • 0.23 Acres
  • 2,421 SqFt
  • 5 Days on Market
Listed by Kim Covino & Co. Team of Compass
MLS#: 73572661
Open House

$1,999,000

Winchester, MA

85 High Street

NEXT OPEN HOUSE:

Sun 9/13 12:00 PM to 1:30 PM

  • 4 Beds
  • 3 Baths
  • 0.29 Acres
  • 3,757 SqFt
  • 24 Days on Market
Listed by Catherine Albiani of Better Homes and Gardens Real Estate - The Shanahan Group
MLS#: 73565817
What defines a luxury home in Winchester?
This page uses a $1.5M and above price point, which in Winchester typically includes larger custom homes, premium finishes, and prime locations.
Why is Winchester popular with luxury buyers?
Winchester pairs commuter-rail access with top schools and gracious homes near its lakes and center, supporting high-end demand.

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