Windward Ln, Shepherdstown, WV 25443
OFF MARKET

Windward Ln
Shepherdstown, WV 25443

    (on 2.78 acres)

    Home Value

    Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

    Comparable sales

    These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
    Address
    Distance
    Property Type
    Sold Price
    Sold Date
    Bed
    Bath
    Sqft
    306 Tinsley Cir, Shepherdstown, WV
    0.24
    Single-Family Home
    $605,000
    10/10/25
    3
    3
    2,540
    63 Hackberry Cir, Shepherdstown, WV
    0.40
    Single-Family Home
    $590,000
    08/10/26
    3
    2.5
    2,745
    21 Steamboat Run Rd, Shepherdstown, WV
    0.72
    Single-Family Home
    $649,999
    10/14/25
    3
    2.5
    2,231
    44 N Tamarac Dr, Shepherdstown, WV
    0.51
    Single-Family Home
    $535,000
    02/24/26
    3
    2.5
    2,975
    200 Meadow Ridge Dr, Shepherdstown, WV
    0.47
    Single-Family Home
    $485,000
    03/30/26
    3
    3
    2,446
    22 Reachcliff Cir, Shepherdstown, WV
    0.65
    Single-Family Home
    $725,000
    10/15/25
    4
    4.5
    4,910
    278 Chandler Dr, Shepherdstown, WV
    1.06
    Single-Family Home
    $560,000
    10/17/25
    4
    3
    2,144
    64 Wildflower Ln, Shepherdstown, WV
    0.88
    Single-Family Home
    $475,000
    12/02/25
    3
    2
    3,300
    79 Chandler Dr, Shepherdstown, WV
    1.07
    Single-Family Home
    $525,000
    06/08/26
    4
    3
    2,460
    325 Chandler Dr, Shepherdstown, WV
    1.11
    Single-Family Home
    $460,000
    09/18/25
    3
    2.5
    2,279

    Nearby home prices

    Get a sense of expected prices in the area by checking the value of nearby homes.
    Address
    Distance
    Price
    Bed
    Bath
    Sqft
    Status
    115 Windward Ln, Shepherdstown, WV 25443
    0.09
    $983,300
    5
    5
    5,778
    Off Market
    Shepherd Grade Rd, Shepherdstown, WV 25443
    0.19
    $200,000
    -
    -
    -
    Recently Sold
    6 Andover Ct, Bunker Hill, WV 25413
    0.28
    $279,600
    3
    2.5
    1,600
    Off Market
    26 Andover Ct, Bunker Hill, WV 25413
    0.28
    $279,200
    3
    2.5
    1,620
    Off Market
    306 Tinsley Cir, Shepherdstown, WV 25443
    0.24
    $608,300
    3
    3
    2,540
    Off Market
    1075 Willowdale Dr, Shepherdstown, WV 25443
    0.30
    $579,300
    3
    3.5
    2,916
    Off Market
    92 Fidlers Way, Shepherdstown, WV 25443
    0.35
    $749,000
    3
    3
    3,500
    For Sale
    63 Hackberry Cir, Shepherdstown, WV 25443
    0.40
    $590,000
    3
    2.5
    2,745
    Recently Sold
    250 Meadow Ridge Dr, Shepherdstown, WV 25443
    0.41
    $747,400
    3
    2.5
    2,869
    Off Market
    890 Willowdale Dr, Shepherdstown, WV 25443
    0.40
    $569,200
    3
    3
    2,604
    Off Market
    447 Howard Farm Rd, Shepherdstown, WV 25443
    0.48
    $750,700
    3
    2.5
    2,525
    Off Market
    200 Meadow Ridge Dr, Shepherdstown, WV 25443
    0.47
    $485,000
    3
    3
    2,446
    Recently Sold

    Local Information

    • Map ViewExplore the area around Windward Ln.
    • Schools1 Preschool School1 Elementary School1 Middle School1 High School
    • Shop & Eat
    -- mins to
    Commute Destination

    Home Highlights

    Lot Size
    2.78 acres

    About this House

    Windward Ln is in Shepherdstown, WV and in ZIP code 25443. This property has a lot size of 2.78 acres.
    Windward Ln, Shepherdstown, WV 25443 is a unknown. It is currently off market. The Trulia Estimate rent is $1,923/month.

    Home Details for Windward Ln

    Property Information

    Property Type / Style
    Property Type: Unknown

    Community

    Units in Building: 1

    Lot Information

    Lot Area: 2.78 acres

    Price and Tax history

    YearProperty taxTax assessment
    2025
    $1,225
    $87,900
    Home facts updated by county records

    Market trends in Shepherdstown

    Last updated July 2026
    Buyer'sMarketSeller'sMarket
    Avg. sale price
    —
    Sale-to-List Price
    —
    Price per sq ft
    —
    Available listings
    30
    7    MoM

    Around this home

    What Locals Say about Shepherdstown

    At least 21 Trulia users voted on each feature.

    • 97 % Say it's dog friendly

    • 87 % Say there's holiday spirit

    • 79 % Say kids play outside

    • 77 % Say there's wildlife

    • 77 % Say people would walk alone at night

    • 75 % Say yards are well-kept

    • 72 % Say car is needed

    • 72 % Say parking is easy

    • 68 % Say it's walkable to restaurants

    • 64 % Say it's quiet

    • 63 % Say streets are well-lit

    • 57 % Say neighbors are friendly

    • 56 % Say there are sidewalks

    • 52 % Say it's walkable to grocery stores

    • 44 % Say they plan to stay for at least 5 years

    • 41 % Say there are community events

    Sourced by Trulia users. Learn more about our methodology.
    • Shana Reed
      "Super family friendly, but quite an expensive area for new families. Lots of local programming for kids, access to nature and well maintained parks. Easy to find community and make friends."
      0
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    • Rasha Saleem
      "Beautiful … scenic…. Charming… great for nature lovers………………………………. Small college town with liberal art college "
      0
      Flag
    • Oliviaf0ster
      "The downtown area is very dog friendly, there are side walks and clean up stations throughout. Also outside and inside of town there’s public parks where you can take your dogs on walks."
      0
      Flag
    • Jguedel
      "Parades, outdoor activities, quiet, fresh air. Small businesses. Farmers markets . Craft beer. Local coffee shops. "
      0
      Flag
    • Skyraallen
      "The whole community is unique in their own way. Shepherdstown is a very pleasant and safe place to raise a family. "
      3
      Flag
    • Melissa N. S.
      "Christmas in Shepherdstown is fun for the whole family including bon fires, pictures with the grinch and Santa, etc "
      1
      Flag
    • Kaylee9
      "Most of the town is dog-friendly! Many of the shops and restaurants downtown will allow dogs inside. "
      0
      Flag
    • Alex K.
      "Very close knit community. Everyone is very friendly. Fun fact, Shepherdstown was considered as one of the possible locations for our nation's capital and it is arguably the birthplace of the United States Army as the first Colonial troops began training in what is now Morgans Grove Park."
      1
      Flag
    • Dichotomouz
      "Dog friendly, but if neighbors feel no one is looking; they allow their pets to urinate and poo in other people’s lawns without picking it up. This is what backyards and parks are for... :-]"
      3
      Flag
    • Markgatz
      "I know people who live here. It’s nice quiet small town with a lot of history all around. You can walk your dog at night with very little traffic issues. "
      1
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    • w e. l.
      "Shepherdstown, West Virginia is the perfect place to live if you enjoy all seasons, with neither summer or winter too extreme."
      0
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    • Clara C.
      "Walk to Shep U library, bank, P.O., bike to Food Lion for groceries. Safe, friendly, private. Park across the street, near C & O Canal.Easy train commute to DC. Wildlife habitat, zoning allows some domestic animals such as chickens. Think sustainability, quiet."
      1
      Flag

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