John Benjamin Dr, New Windsor, MD 21776
OFF MARKET

    John Benjamin Dr, New Windsor, MD 21776

    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
    1414 Old New Windsor Rd, New Windsor, MD
    1.11
    Single-Family Home
    $550,000
    12/23/25
    5
    4
    3,216
    1326 Old New Windsor Rd, New Windsor, MD
    1.19
    Single-Family Home
    $252,000
    12/09/25
    4
    2
    1,772
    1912 Old New Windsor Rd, New Windsor, MD
    1.19
    Single-Family Home
    $370,000
    11/10/25
    3
    2.5
    1,618
    1324 Old New Windsor Rd, New Windsor, MD
    1.21
    Single-Family Home
    $125,000
    01/09/26
    1
    1,296
    3263 Hawks Hill Rd, New Windsor, MD
    1.30
    Single-Family Home
    $190,000
    12/15/25
    3
    2
    1,184
    414 High St, New Windsor, MD
    1.36
    Single-Family Home
    $464,000
    06/15/26
    3
    2.5
    2,668
    3300 Hawks Hill Rd, New Windsor, MD
    1.37
    Single-Family Home
    $535,000
    08/03/26
    2
    3
    2,714
    2802 Town View Cir, New Windsor, MD
    1.38
    Single-Family Home
    $599,900
    11/19/25
    6
    3
    2,604
    2822 Town View Cir, New Windsor, MD
    1.38
    Single-Family Home
    $600,000
    10/30/25
    5
    3.5
    4,024
    3180 Vista Ct, New Windsor, MD
    1.39
    Single-Family Home
    $272,500
    06/25/26
    1
    1,188

    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
    Dennings Rd, New Windsor, MD 21776
    0.00
    -
    -
    -
    -
    Off Market
    Strawbridge Ln, New Windsor, MD 21776
    0.32
    -
    -
    -
    -
    Off Market
    Wakefield Valley Rd, New Windsor, MD 21776
    0.34
    -
    -
    -
    -
    Off Market
    2116 Marston Rd, New Windsor, MD 21776
    0.59
    $462,700
    5
    2
    2,364
    Off Market
    2932 Union Square Rd #41, New Windsor, MD 21776
    0.62
    $524,300
    3
    2.5
    2,224
    Off Market
    2888 Union Square Rd #26, New Windsor, MD 21776
    0.65
    $516,700
    3
    3.5
    2,224
    Off Market
    2200 Wilt Rd, New Windsor, MD 21776
    0.70
    $799,100
    4
    2
    2,592
    Off Market
    2426 Marston Rd, New Windsor, MD 21776
    0.94
    $258,800
    2
    1
    1,173
    Off Market
    1604 Old New Windsor Rd, New Windsor, MD 21776
    0.97
    $550,000
    5
    2.5
    2,074
    For Sale
    2538 Marston Rd N, New Windsor, MD 21776
    1.05
    $388,000
    2
    1.5
    1,257
    Off Market
    1414 Old New Windsor Rd, New Windsor, MD 21776
    1.11
    $550,000
    5
    4
    3,216
    Recently Sold

    Local Information

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

    About this House

    John Benjamin Dr is in New Windsor, MD and in ZIP code 21776.
    John Benjamin Dr, New Windsor, MD 21776 is a unknown. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate rent is $2,474/month.

    Home Details for John Benjamin Dr

    Property Information

    Property Type / Style
    Property Type: Unknown

    Market trends in New Windsor

    Last updated July 2026
    Buyer'sMarketSeller'sMarket
    Avg. sale price
    —
    Sale-to-List Price
    —
    Price per sq ft
    —
    Available listings
    23

    Around this home

    What Locals Say about New Windsor

    At least 17 Trulia users voted on each feature.

    • 100 % Say yards are well-kept

    • 95 % Say it's dog friendly

    • 95 % Say car is needed

    • 86 % Say parking is easy

    • 79 % Say there are sidewalks

    • 73 % Say it's quiet

    • 71 % Say people would walk alone at night

    • 71 % Say there's holiday spirit

    • 71 % Say kids play outside

    • 70 % Say streets are well-lit

    • 59 % Say there's wildlife

    • 58 % Say neighbors are friendly

    • 44 % Say it's walkable to restaurants

    • 41 % Say they plan to stay for at least 5 years

    • 26 % Say there are community events

    Sourced by Trulia users. Learn more about our methodology.
    • Charlene C.
      "New Windsor is a wonderful small town however the water prices are ridiculous and drives many people away "
      0
      Flag
    • Jgmeerdter
      "Lots of dogs and friendly people around. Dogs are always on leash and people pick up after their dogs."
      0
      Flag
    • Jgmeerdter
      "It’s a nice and quiet area. Very safe and friendly. It’s tucked away and located in a close proximity to a bigger city."
      0
      Flag
    • Margaret C.
      "No public transportation. Bedroom community. Rural. Town was founded in the 1790’s. There are a few family-owned restaurants and a 7-Eleven w/ gas station."
      0
      Flag
    • Aokigahara169
      "New windsor has a great heritage and a quiet feel. Miss it everyday. Really hope to move back soon. "
      0
      Flag
    • Harriet725
      "You see plenty of dogs in this neighborhood. There is plenty of space for walking dogs. Most people are dog friendly."
      1
      Flag

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