Colonial Homes for Sale in Winchester, MA

27Results

Colonials are one of the most common house styles in Winchester, from early 20th century homes near the center to newer builds on the west side. Browse all single-family homes in Winchester, create a free account to save this search and receive alerts, or call Better Homes and Gardens Real Estate The Shanahan Group at 781-729-9030 to speak with an agent.

Newest
New Listing
15 Foxcroft Road Winchester MA 01890

$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

$890,000

Winchester, MA

80 Nelson Street

NEXT OPEN HOUSE:

Sun 10/25 11:30 AM to 1:00 PM

  • 2 Beds
  • 1 Bath
  • 0.1 Acres
  • 1,489 SqFt
  • 8 Days on Market
MLS#: 73591108
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
Open House

$974,900

Winchester, MA

Winchester Highlands

258 Cross Street

NEXT OPEN HOUSE:

Sat 10/24 3:00 PM to 4:30 PM

  • 3 Beds
  • 3 Baths
  • 0.18 Acres
  • 1,719 SqFt
  • 42 Days on Market
MLS#: 73575764

$1,650,000

Winchester, MA

117 Highland

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

$3,149,000

Winchester, MA

37 Mayflower Road

NEXT OPEN HOUSE:

Sat 10/24 11:30 AM to 12:30 PM

  • 7 Beds
  • 8 Baths
  • 0.46 Acres
  • 8,540 SqFt
  • 44 Days on Market
MLS#: 73573670

Classic Center-Entrance Homes Near the Mystic Lakes

Winchester sits about eight miles north of Boston, between the Mystic Lakes and the Middlesex Fells Reservation, with commuter rail service from Winchester Center and Wedgemere stations. Its neighborhoods have a deep stock of colonial houses, including Colonial Revival homes from the early 1900s and larger colonials built in later decades on quieter streets. Many have been updated with expanded kitchens, family rooms and finished lower levels. Our team is based on Main Street in Winchester and knows how style, lot and location vary from street to street. Learn more in our Winchester real estate guide or browse colonial homes north of Boston.

Frequently Asked Questions

What styles of colonial homes are found in Winchester, MA?
Winchester has Colonial Revival homes from the early 20th century, Garrison and center-entrance colonials from the mid-1900s, and newer colonial-style construction.
How do you get to Boston from Winchester?
The Lowell commuter rail line stops at Winchester Center and Wedgemere, and Interstate 93 and Route 3 are close by for driving.

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