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4 Bedroom Homes in Winchester, MA

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4 Bedroom Homes in Winchester, MA

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12 Listings

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12 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

36Active
$1,899,000
4 bd · 3 ba · 3,757 sqft
85 High Street, Winchester, MA
Catherine Albiani · Better Homes and Gardens Real Estate - The Shanahan Group
42Active
$1,699,000
4 bd · 3 ba · 2,736 sqft
3 Sunset Road, Winchester, MA
Kim Covino & Co. Team · Compass
32Active
$2,650,000
4 bd · 5 ba · 5,233 sqft
18 Middlesex St, Winchester, MA
Jennifer Taves · Coldwell Banker Realty - Boston

Price Reduced40Active
$1,750,000
4 bd · 3 ba · 3,604 sqft
1 Overlook Way, Winchester, MA
Lynne Russo · Better Homes and Gardens Real Estate - The Shanahan Group
31Active
$1,325,000
4 bd · 2 ba · 1,922 sqft
9 Priscilla Ln, Winchester, MA
Robert Del Greco · Compass
Price Reduced28Active
$1,250,000
4 bd · 3 ba · 2,666 sqft
465 Washington Street, Winchester, MA
The Pallotta Group · Gibson Sotheby's International Realty
Price Reduced28Active
$1,250,000
4 bd · 3 ba · 2,666 sqft
465 Washington Street #465, Winchester, MA
The Pallotta Group · Gibson Sotheby's International Realty
Price Reduced40Active
$2,149,000
4 bd · 4 ba · 3,570 sqft
19 Hancock Street, Winchester, MA
Vita Realty Group · Compass
Price Reduced42Active
$1,499,000
4 bd · 2 ba · 2,421 sqft
4 Churchill Road, Winchester, MA
Kim Covino & Co. Team · Compass
Price Reduced40Active
$1,049,000
4 bd · 3 ba · 2,411 sqft
24 Richardson St, Winchester, MA
Andersen Group Realty · Keller Williams Realty Boston Northwest
Price Reduced29Active
$919,999
4 bd · 2 ba · 2,326 sqft
96 Loring Ave, Winchester, MA
Jeremy Smith · StartPoint Realty
Price Reduced42Active
$2,299,000
4 bd · 5 ba · 4,450 sqft
54 Squire Road, Winchester, MA
Anthony Marino · The Marino Group Collection

Listing data & MLS disclosures

MLS Property Information Network (MLS PIN): The property listing data and information 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 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 set forth herein.
Listing information ©2026 MLS Property Information Network, Inc®. All Rights Reserved. Last Updated: 2026-11-03 08:05:00 UTC

About 4 Bedroom Homes in Winchester, MA

4 Bedroom Homes in Winchester, MA: 12 active listings as of November 3, 2026, 23:54 UTC.

Winchester housing market

October 2026 · This period is still settling

Selling at 99.7% of asking price

Sales here are closing essentially at asking. MLS · 16 sales · as of Oct 30, 2026

Homes on the market · MLS, as of Oct 25, 2026

Median list price: $1,549,000
Homes for sale: 57

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

Median home size: 2,706 sq. ft.

Winchester, MA community profile

Area: 6.5 sq. mi.

Source: HJN community data

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Listing data & MLS disclosures

MLS Property Information Network (MLS PIN): The property listing data and information 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 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 set forth herein.
Listing information ©2026 MLS Property Information Network, Inc®. All Rights Reserved. Last Updated: 2026-11-03 08:05:00 UTC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

Winchester, MA community profile

Area: 6.5 sq. mi.

Source: HJN community data

Winchester housing market

October 2026 · This period is still settling

Selling at 99.7% of asking price

Sales here are closing essentially at asking. MLS · 16 sales · as of Oct 30, 2026

Homes on the market · MLS, as of Oct 25, 2026

Median list price: $1,549,000
Homes for sale: 57

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

Median home size: 2,706 sq. ft.