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Historic Homes for Sale in Winchester, MA

53 Homes for Sale

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HotHot
Photo 1 of Single family home for sale at 1 Overlook Way, Winchester, MA 01890 | MLS# 73581571 | Listing updated on 2026-10-30

$1,750,000

Views: 19

Bedrooms: 4Bds

Bathrooms: 3Ba

Area: 3,604sqft

Single family home for sale

1 Overlook Way, Winchester, MA 01890

Better Homes And Gardens Real Estate - The Shanahan Group

New
Photo 1 of Single family home for sale at 85 High St, Winchester, MA 01890 | MLS# 73596915 | Listing updated on 2026-11-03

$1,899,000

Bedrooms: 4Bds

Bathrooms: 3Ba

Area: 3,757sqft

Single family home for sale

85 High St, Winchester, MA 01890

Better Homes And Gardens Real Estate - The Shanahan Group

HotHot
Price CutPrice Drop: $49K
Photo 1 of Single family home for sale at 39 Henry St, Winchester, MA 01890 | MLS# 73585414 | Listing updated on 2026-10-26

$850,000

Views: 23

Bedrooms: 3Bds

Bathrooms: 1Ba

Area: 1,313sqft

Single family home for sale

39 Henry St, Winchester, MA 01890

Coldwell Banker Realty - Belmont

HotHot
Photo 1 of Single family home for sale at 117 Highland, Winchester, MA 01890 | MLS# 73573887 | Listing updated on 2026-11-03

$1,650,000

Views: 23

Bedrooms: 5Bds

Bathrooms: 4Ba

Area: 3,722sqft

Single family home for sale

117 Highland, Winchester, MA 01890

Better Homes And Gardens Real Estate - The Shanahan Group

Price CutPrice Drop: $200K
Photo 1 of Single family home for sale at 7 Lakeview Ter, Winchester, MA 01890 | MLS# 73578443 | Listing updated on 2026-11-03

$2,400,000

Views: 18

Bedrooms: 6Bds

Bathrooms: 4Ba

Area: 3,534sqft

Single family home for sale

7 Lakeview Ter, Winchester, MA 01890

Berkshire Hathaway Homeservices Commonwealth Real Estate

Showing 1 - 42 of 53 homes for sale in Winchester, MA

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  • mls-img
    Based on information provided to and compiled by MLS Property Information Network, Inc. covering through Nov 4, 2026, 5:45 AM. The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third-party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. 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. MLS Property Information Network, Inc. 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. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified. © 2026 MLS Property Information Network, Inc. All Rights Reserved.
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