Homes with 4+ Bedrooms for Sale in Winchester, MA

32Results

Explore Winchester, MA homes for sale with four or more bedrooms, from classic colonials to updated family homes, updated as new listings reach the market. Call Better Homes and Gardens Real Estate The Shanahan Group at 781-729-9030 or contact us for local guidance, or create an account to save this search and receive new-listing alerts.

Newest
New Listing
85 High Street Winchester MA 01890

$1,899,000

Winchester, MA

85 High Street

  • 4 Beds
  • 3 Baths
  • 0.29 Acres
  • 3,757 SqFt
  • 3 Days on Market
MLS#: 73596915
New Listing

$1,699,000

Winchester, MA

3 Sunset Road

  • 4 Beds
  • 3 Baths
  • 0.55 Acres
  • 2,736 SqFt
  • 4 Days on Market
MLS#: 73596720
New Listing

$2,999,000

Winchester, MA

5 Forest Circle

  • 5 Beds
  • 5 Baths
  • 0.52 Acres
  • 4,900 SqFt
  • 10 Days on Market
MLS#: 73594545
New Listing

$2,650,000

Winchester, MA

18 Middlesex Street

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

$3,799,000

Winchester, MA

15 Foxcroft Road

  • 8 Beds
  • 6 Baths
  • 0.32 Acres
  • 7,081 SqFt
  • 12 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
  • 14 Days on Market
MLS#: 73592433
New Listing

$1,999,000

Winchester, MA

21 Amberwood Drive

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

$18,000,000

Winchester, MA

15 Vinson Circle

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

$3,299,000

Winchester, MA

1 Plymouth Road

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

$1,750,000

Winchester, MA

Wedgemere

1 Overlook Way

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

$1,325,000

Winchester, MA

Symmes Corner

9 Priscilla Lane

  • 4 Beds
  • 2 Baths
  • 0.23 Acres
  • 1,922 SqFt
  • 45 Days on Market
MLS#: 73579538

$2,400,000

Winchester, MA

7 Lakeview Terrace

  • 6 Beds
  • 4 Baths
  • 0.23 Acres
  • 3,534 SqFt
  • 47 Days on Market
MLS#: 73578443

Four-Bedroom and Larger Homes in Winchester

Winchester pairs a commuter-friendly downtown and strong schools with gracious larger homes near the Mystic Lakes and Fells. Explore all Winchester real estate or compare 4+ bedroom homes in Concord.

How many 4-bedroom homes are for sale in Winchester?
The count changes as listings are added or sell. This page updates automatically to show current four-bedroom and larger homes in Winchester.
Why is Winchester popular?
Winchester offers top schools, a walkable center with commuter rail to Boston, and access to the Middlesex Fells and Mystic Lakes.

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