27 Shepard Ct #27, Winchester, MA 01890
OFF MARKET

27 Shepard Ct #27
Winchester, MA 01890

    Local Information

    • Map ViewExplore the area around 27 Shepard Ct #27.
    • Schools1 Preschool School1 Elementary School1 Middle School1 High School
    • Shop & Eat
    -- mins to
    Commute Destination

    About this House

    27 Shepard Ct #27 is in Winchester, MA and in ZIP code 01890.
    27 Shepard Ct #27, Winchester, MA 01890 is a unknown. It is currently off market. The Trulia Estimate rent is $2,992/month.

    Home Details for 27 Shepard Ct #27

    Property Information

    Property Type / Style
    Property Type: Unknown

    Price History for 27 Shepard Ct #27

    DatePriceEventSource
    06/03/2022ListingRemovedMLS PIN #72851511
    07/08/2021$989,000PendingMLS PIN #72848085
    06/20/2021$989,000PendingToActiveMLS PIN #72851511
    06/20/2021$989,000ContingentMLS PIN #72851511
    06/10/2021$989,000Listed For SaleMLS PIN #72848085

    Market trends in Winchester

    Last updated June 2026
    Buyer'sMarketSeller'sMarket
    Avg. sale price
    $1.41M
    Sale-to-List Price
    101.7%
    Price per sq ft
    $571
    Available listings
    77
    2    MoM
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    Comparable Sales for 27 Shepard Ct #27

    Address
    Distance
    Property Type
    Sold Price
    Sold Date
    Bed
    Bath
    Sqft
    29 Shepard Ct, Winchester, MA
    0.02
    Single-Family Home
    $2,450,000
    01/09/26
    6
    5
    4,594
    237 Swanton St, Winchester, MA
    0.11
    Single-Family Home
    $1,850,000
    05/29/26
    5
    4
    4,334
    87 Wendell St, Winchester, MA
    0.17
    Single-Family Home
    $1,250,000
    05/29/26
    4
    2
    2,046
    104 Wendell St, Winchester, MA
    0.18
    Single-Family Home
    $1,100,000
    05/28/26
    3
    1.5
    1,675
    307 Cross St, Winchester, MA
    0.20
    Single-Family Home
    $1,730,000
    07/24/26
    5
    5
    3,500
    112 Wendell St, Winchester, MA
    0.20
    Single-Family Home
    $1,335,000
    02/04/26
    4
    3
    2,854
    10 Farrow St, Winchester, MA
    0.29
    Single-Family Home
    $1,660,000
    08/07/26
    4
    3.5
    2,768
    9 Sylvester Ct, Winchester, MA
    0.33
    Single-Family Home
    $1,015,000
    12/01/25
    4
    1.5
    2,001
    235 Cross St, Winchester, MA
    0.34
    Single-Family Home
    $868,000
    09/04/25
    3
    1.5
    1,931
    40 Pickering St, Winchester, MA
    0.35
    Single-Family Home
    $1,330,000
    04/14/26
    4
    2.5
    2,454

    Nearby homes

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    Assigned Schools

    These are the assigned schools for 27 Shepard Ct #27.
    View nearby schools on GreatSchools
    The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

    What Locals Say about Winchester

    At least 93 Trulia users voted on each feature.

    • 92 % Say it's dog friendly

    • 88 % Say yards are well-kept

    • 87 % Say people would walk alone at night

    • 85 % Say parking is easy

    • 79 % Say there are sidewalks

    • 79 % Say car is needed

    • 77 % Say it's walkable to restaurants

    • 77 % Say kids play outside

    • 75 % Say streets are well-lit

    • 74 % Say there's holiday spirit

    • 67 % Say they plan to stay for at least 5 years

    • 67 % Say there's wildlife

    • 66 % Say neighbors are friendly

    • 65 % Say it's walkable to grocery stores

    • 64 % Say it's quiet

    • 54 % Say there are community events

    Sourced by Trulia users. Learn more about our methodology.
    • Diana P.
      "Winchester is the cutest town, perfect for families. There is Town Say, and Enka, and everything is very family oriented. We even have great pubs/restaurants as well as sub shops, Greek food, nail salons, anything you could want in a home town!"
      7
      Flag
    • Dominic
      "Phenomenal public school system beginning from Kindergarten and extremely welcoming to new residents transferring in."
      0
      Flag
    • Stacie
      "Very family oriented. Not a great neighborhood if you don’t have children. Great, easy commute into the city. Not enough good restaurants that aren’t overpriced though. "
      0
      Flag
    • Yjchoi7
      "Very safe neighborhood.there are often summer events on the common. Teenagers can take train into Boston area fairly easily as there are two stops within Winchester. Fells is a great place for summer walks. "
      2
      Flag
    • Luis B.
      "perfect for my family It is livable stores Closer to me Barbershop computer store Restaurants I will love to buy a house in this area "
      2
      Flag
    • Yjchoiyjchoi
      "It’s very quiet and safe generally. Yet it’s close to Boston and Cambridge city life within a few stops of the commuter from Winchester. "
      0
      Flag
    • Tara
      "I have lived in this neighborhood for 25 years. I love it. Everybody is friendly and kind. The crime is minimal and it’s very quiet. "
      2
      Flag
    • Katie41287
      "I’m not afraid to walk home at 11pm, the town is clean and has plenty of events around town, the people are friendly and it is near public transportation. "
      1
      Flag
    • Anna S.
      "Excellent school Easy commute to Boston Downtown Great parks and pond nearby"
      0
      Flag
    • tod g.
      "Lovely town with easy access to Boston and easy getaway to northern New England."
      0
      Flag
    • jfrancis6
      "Family community built around three streets that form a circle that only has traffic of residents. The area borders the Town of Winchester forest that is great for walks and snow shoeing in winter. All homes are large and attract families were children can safely play and bike in the neighborhood. Many homes have residents who grow up in the neighborhood as children and returned to raise their families. A short walk 4/10 of a mile to train station for those who work in Boston a trip that takes 12 minutes with only one stop. Schools in Winchester are among the best in Massachusetts, a primary attraction to the Town. The Town center is only one mile away and has an addition train station there as well. The Mystic lakes are just beyond the train station with a Town beach and boating opportunities. The Town also borders a 2500 acre forest known as the Fells consisting of the Town water supply and miles of hiking or mountain biking."
      0
      Flag
    • marta3467
      "Can see kids playing ball in street; people walking their dog and Horn Pond and several nice restaurants all within walking distance"
      1
      Flag

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    Homes for sale near 27 Shepard Ct #27

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    Off Market Homes Near 27 Shepard Ct #27

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    Frequently asked questions about 27 Shepard Ct #27

    • Is Winchester a buyer's or seller's market?
      Winchester is currently a seller's market, based on recent for-sale activity.
    • What's the median sale price in Winchester?
      The median sale price in Winchester is $1.41M.
    • What do residents say about Winchester?
      Residents describe Winchester, MA as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Winchester, MA.
    • What are the closest schools to 27 Shepard Ct #27?
      The closest schools to 27 Shepard Ct #27 in Winchester, MA are Lynch Elementary School (Pre-K, rated 9/10), McCall Middle School (rated 9/10), Winchester High School (rated 10/10).