$1,699,000
Views: 5
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,736sqft
Single family home for sale
Compass
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3 Sunset Rd, Winchester, MA 01890 
28 Olive St, Winchester, MA 01890
Price Drop: $205K
9 Albamont Rd, Winchester, MA 01890
85 High St, Winchester, MA 01890
HotPrice Drop: $50K
21 Amberwood Dr, Winchester, MA 01890
18 Middlesex St, Winchester, MA 01890
5 Forest Cir, Winchester, MA 01890Hot
15 Foxcroft Rd, Winchester, MA 01890 
419 421 Washington St, Winchester, MA 01890Hot
18 Surrey Rd, Winchester, MA 01890 
15 Lloyd St, Winchester, MA 01890Price Drop: $100K
4 Churchill Rd, Winchester, MA 01890 Price Drop: $49K
14 Nassau Dr, Winchester, MA 01890 
30 Surrey Rd, Winchester, MA 01890
4 Harrington Rd, Winchester, MA 01890
6 Aricia Ln, Winchester, MA 01890Hot
276 High St, Winchester, MA 01890 
63 Wedgemere Ave, Winchester, MA 01890Hot
117 Highland, Winchester, MA 01890 Price Drop: $200K
7 Lakeview Ter, Winchester, MA 01890 HotPrice Drop: $21K
Hot
Hot
15 Vinson Cir, Winchester, MA 01890 
1 Plymouth Rd, Winchester, MA 01890
53 Lake St, Winchester, MA 01890Hot
8 N Gateway, Winchester, MA 01890 
26 Mayflower Rd, Winchester, MA 01890HotPrice Drop: $20K
24 Richardson St, Winchester, MA 01890 
11 Viking Rd, Winchester, MA 01890Hot
47 Water St, Winchester, MA 01890 Hot
258 Cross St, Winchester, MA 01890 Hot
30 Willowdale Rd, Winchester, MA 01890 Price Drop: $101K
Hot
37 Mayflower Rd, Winchester, MA 01890 
10 Dartmouth St, Winchester, MA 01890
4 Dartmouth, Winchester, MA 01890Price Drop: $50K
465 Washington St, Winchester, MA 01890 Price Drop: $50K
8 Priscilla Ln, Winchester, MA 01890
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Homes for Sale with AC in Winchester, MA
64 Homes for Sale
Sort by:
$1,049,900
Views: 9
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,783sqft
Single family home for sale
The Aland Realty Group Llc
Price Drop: $205K$2,995,000
Views: 16
Bedrooms: 6Bds
Bathrooms: 6Ba
Area: 6,100sqft
Mansion for sale
Compass
$1,899,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 3,757sqft
Single family home for sale
Better Homes And Gardens Real Estate - The Shanahan Group
HotPrice Drop: $50K$1,999,000
Views: 16
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 4,063sqft
Single family home for sale
Compass
$2,650,000
Views: 3
Bedrooms: 4Bds
Bathrooms: 5Ba
Area: 5,233sqft
Single family home for sale
Coldwell Banker Realty - Boston
$2,999,000
Views: 3
Bedrooms: 5Bds
Bathrooms: 5Ba
Area: 4,900sqft
Single family home for sale
Leading Edge Real Estate
Hot$3,799,000
Views: 12
Bedrooms: 8Bds
Bathrooms: 6Ba
Area: 7,081sqft
Mansion for sale
Better Homes And Gardens Real Estate - The Shanahan Group
$1,299,000
Views: 4
Bedrooms: 6Bds
Bathrooms: 2Ba
Area: 2,946sqft
Multi family home for sale
Coldwell Banker Realty - Lexington
Hot$2,950,000
Views: 15
Bedrooms: 6Bds
Bathrooms: 4Ba
Area: 4,752sqft
Single family home for sale
Century 21 Property Central Inc.
$1,399,000
Views: 7
Bedrooms: 5Bds
Bathrooms: 2Ba
Area: 2,071sqft
Sale Pending
Compass
Price Drop: $100K$1,499,000
Views: 19
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 2,421sqft
Single family home for sale
Compass
Price Drop: $49K$2,750,000
Views: 9
Bedrooms: 6Bds
Bathrooms: 7Ba
Area: 6,968sqft
Mansion for sale
Winn Real Estate & Consulting
$1,985,000
Views: 8
Bedrooms: 4Bds
Bathrooms: 4Ba
Area: 4,241sqft
Single family home for sale
Barrett Sotheby'S International Realty
$1,599,000
Views: 10
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 2,966sqft
Sale Pending
Compass
$1,399,000
Views: 8
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,975sqft
Single family home for sale
Leading Edge Real Estate
Hot$2,195,000
Views: 23
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 5,006sqft
Mansion for sale
Compass
20 Arthur St #20, Winchester, MA 01890
Laer Realty Partners
Building 1 Unit Available
Unit #20
$2,399,000
Views: 11
Bedrooms: 4Bds
Bathrooms: 4Ba
Area: 3,550sqft
Sale Pending
Better Homes And Gardens Real Estate - The Shanahan Group
Hot$1,650,000
Views: 23
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 3,722sqft
Single family home for sale
Better Homes And Gardens Real Estate - The Shanahan Group
Price Drop: $200K$2,400,000
Views: 18
Bedrooms: 6Bds
Bathrooms: 4Ba
Area: 3,534sqft
Single family home for sale
Berkshire Hathaway Homeservices Commonwealth Real Estate
HotPrice Drop: $21K666 Main St #211, Winchester, MA 01890
Berkshire Hathaway Homeservices Commonwealth Real Estate
Building 2 Units Available
Unit #211
Hot666 Main St #217, Winchester, MA 01890
Berkshire Hathaway Homeservices Commonwealth Real Estate
Hot$18,000,000
Views: 14
Bedrooms: 6Bds
Bathrooms: 7Ba
Area: 10,000sqft
Mansion for sale
The Marino Group Collection
$3,299,000
Views: 6
Bedrooms: 7Bds
Bathrooms: 8Ba
Area: 7,226sqft
Mansion for sale
Gibson Sotheby'S International Realty
$1,025,000
Views: 11
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,235sqft
Single family home for sale
Compass
Hot$1,299,000
Views: 12
Bedrooms: 6Bds
Bathrooms: 3Ba
Area: 3,910sqft
Sale Pending
Compass
$1,950,000
Views: 11
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 3,371sqft
Sale Pending
The Simply Sold Realty Co.
HotPrice Drop: $20K$1,049,000
Views: 19
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,411sqft
Single family home for sale
Keller Williams Realty Boston Northwest
7 Wainwright Rd #47, Winchester, MA 01890
Better Homes And Gardens Real Estate - The Shanahan Group
Building 2 Units Available
Unit #47
200 Swanton St #727, Winchester, MA 01890
Shore Real Estate Llc
Building 4 Units Available
Unit #727
$3,600,000
Views: 15
Bedrooms: 7Bds
Bathrooms: 8Ba
Area: 7,429sqft
Mansion for sale
Engel & Volkers Boston
Hot$899,000
Views: 20
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,356sqft
Single family home for sale
Leading Edge Real Estate
Hot$974,900
Views: 21
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,719sqft
Single family home for sale
Fiv Realty Co.
Hot$3,200,000
Views: 22
Bedrooms: 8Bds
Bathrooms: 7Ba
Area: 5,750sqft
Mansion for sale
Gibson Sotheby'S International Realty
Price Drop: $101KHot$3,149,000
Views: 24
Bedrooms: 7Bds
Bathrooms: 8Ba
Area: 8,540sqft
Mansion for sale
Compass
$2,999,000
Views: 20
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 4,028sqft
Sale Pending
Compass
$4,299,000
Views: 18
Bedrooms: 5Bds
Bathrooms: 6Ba
Area: 6,526sqft
Mansion for sale
Gibson Sotheby'S International Realty
Price Drop: $50K$1,250,000
Views: 12
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,666sqft
Single family home for sale
Gibson Sotheby'S International Realty
Price Drop: $50K465 Washington St #465, Winchester, MA 01890
Gibson Sotheby'S International Realty
Building 1 Unit Available
Unit #465
$2,995,000
Views: 4
Bedrooms: 5Bds
Bathrooms: 6Ba
Area: 6,500sqft
Sale Pending
Laer Realty Partners
Showing 1 - 42 of 64 homes for sale in Winchester, MA
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Based on information provided to and compiled by MLS Property Information Network, Inc. covering through Nov 4, 2026, 12:30 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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