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4 Bedroom Homes in Winchester, MA
15 listings

4 Bedroom Homes in Winchester, MA

4 Bedroom Homes in Winchester, MA

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15 Listings
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4 Bedroom Homes in Winchester, MA

15 Listings

  1. 63 Wedgemere Avenue — photoOpen house Sat, Oct 10 · 11:00 AM39

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas
Active

$2,399,000

4 bd · 4 ba · 3,550 sqft

63 Wedgemere Avenue, Winchester, MA

Paula R. Sughrue · Better Homes and Gardens Real Estate - The Shanahan Group

  • 25 Arlington St — photoOpen house Sat, Oct 10 · 12:00 PM32Active

    $1,529,000

    4 bd · 4 ba · 2,709 sqft

    25 Arlington St, Winchester, MA

    Domingo Medina · Coldwell Banker Realty - Lexington

  • 1 Overlook Way — photoOpen house Sat, Oct 10 · 11:00 AM41Active

    $1,850,000

    4 bd · 3 ba · 3,604 sqft

    1 Overlook Way, Winchester, MA

    Lynne Russo · Better Homes and Gardens Real Estate - The Shanahan Group

  • 9 Priscilla Ln — photoOpen house Sat, Oct 10 · 11:30 AM31Active

    $1,325,000

    4 bd · 2 ba · 1,922 sqft

    9 Priscilla Ln, Winchester, MA

    Robert Del Greco · Compass

  • 7 Sherman Place #7 — photo42Active

    $1,495,000

    4 bd · 3 ba · 2,973 sqft

    7 Sherman Place #7, Winchester, MA

    John Dean · Engel & Volkers Boston

  • 465 Washington Street — photoOpen house Sun, Oct 11 · 1:00 PM28Active

    $1,300,000

    4 bd · 3 ba · 2,666 sqft

    465 Washington Street, Winchester, MA

    The Pallotta Group · Gibson Sotheby's International Realty

  • 465 Washington Street #465 — photoOpen house Sun, Oct 11 · 1:00 PM28Active

    $1,300,000

    4 bd · 3 ba · 2,666 sqft

    465 Washington Street #465, Winchester, MA

    The Pallotta Group · Gibson Sotheby's International Realty

  • 19 Hancock Street — photo40Active

    $2,199,000

    4 bd · 4 ba · 3,570 sqft

    19 Hancock Street, Winchester, MA

    Vita Realty Group · Compass

  • 24 Richardson St — photoPrice ReducedOpen house Sat, Oct 10 · 1:00 PM40Active

    $1,069,000

    4 bd · 3 ba · 2,411 sqft

    24 Richardson St, Winchester, MA

    Andersen Group Realty · Keller Williams Realty Boston Northwest

  • 85 High St — photoPrice ReducedOpen house Sat, Oct 10 · 12:00 PM38Active

    $1,899,000

    4 bd · 3 ba · 3,757 sqft

    85 High St, Winchester, MA

    Catherine Albiani · Better Homes and Gardens Real Estate - The Shanahan Group

  • 96 Loring Ave — photoPrice Reduced29Active

    $919,999

    4 bd · 2 ba · 2,326 sqft

    96 Loring Ave, Winchester, MA

    Jeremy Smith · StartPoint Realty

  • 54 Squire Road — photoPrice ReducedOpen house Sat, Oct 10 · 1:00 PM42Active

    $2,399,000

    4 bd · 5 ba · 4,450 sqft

    54 Squire Road, Winchester, MA

    Anthony Marino · The Marino Group Collection

  • 7 Wainwright Road #113 — photoPrice ReducedOpen house Sun, Oct 11 · 12:00 PM42Active

    $1,999,000

    4 bd · 4 ba · 3,640 sqft

    7 Wainwright Road #113, Winchester, MA

    Kim Covino & Co. Team · Compass

  • 423 Washington St — photo42Active

    $1,350,000

    4 bd · 3 ba · 2,690 sqft

    423 Washington St, Winchester, MA

    Danielle Fleming · MA Properties

  • 18 Middlesex St — photoPrice ReducedOpen house Sat, Oct 10 · 12:30 PM32Active

    $2,695,000

    4 bd · 5 ba · 5,233 sqft

    18 Middlesex St, Winchester, MA

    Tina Natale · Luxury Living Real Estate

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    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

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    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.

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #1000018

    Call Thomas

    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: 2026-10-08 16:56:00 UTC

    Winchester, MA community profile

    Area
    6.5 sq. mi.

    Source: HJN community data

    Winchester housing market

    September 2026 · This period is still settling

    Selling at 98.4% of asking price

    Buyers here are paying below asking. MLS · 12 sales · as of Sep 28, 2026

    Homes on the market · MLS, as of Sep 27, 2026

    Median list price
    $1,300,000
    Homes for sale
    61

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 10, 2026

    Median home size
    2,706 sq. ft.