2 John Benjamin Dr, New Windsor, MD 21776
OFF MARKET

2 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
    4215 Buffalo Rd, Mount Airy, MD
    0.44
    Single-Family Home
    $400,000
    06/22/26
    5
    3
    2,957
    3870 Roop Rd, New Windsor, MD
    0.46
    Single-Family Home
    $500,000
    01/15/26
    -
    1,851
    15539 Liberty Rd, Mount Airy, MD
    0.53
    Single-Family Home
    $655,000
    04/10/26
    4
    2.5
    2,592
    15535 Liberty Rd, Mount Airy, MD
    0.56
    Single-Family Home
    $680,000
    10/29/25
    3
    2
    2,887
    3788 Roop Rd, New Windsor, MD
    0.65
    Single-Family Home
    $625,000
    08/06/26
    3
    2.5
    2,343
    3895 Buffalo Rd, New Windsor, MD
    0.65
    Single-Family Home
    $635,000
    06/05/26
    4
    2.5
    2,568
    3870 Roop Rd, New Windsor, MD
    0.69
    Single-Family Home
    $500,000
    01/02/26
    3
    2
    1,851
    3720 Buffalo Rd, New Windsor, MD
    0.83
    Single-Family Home
    $715,000
    12/01/25
    4
    3.5
    3,540
    3330 Oakwood Dr, New Windsor, MD
    0.90
    Single-Family Home
    $600,000
    06/24/26
    4
    3.5
    2,332
    4417 Buffalo Rd, Mount Airy, MD
    1.03
    Single-Family Home
    $360,000
    01/26/26
    2
    1
    912

    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
    3207 Liberty Rd, New Windsor, MD 21776
    0.12
    -
    4
    2.5
    3,263
    Off Market
    4177 John Benjamin Dr, New Windsor, MD 21776
    0.11
    $1,060,800
    5
    4.5
    4,699
    Off Market
    3235 W Old Liberty Rd, New Windsor, MD 21776
    0.24
    $529,900
    3
    2
    2,688
    For Sale
    4075 Roop Rd, New Windsor, MD 21776
    0.26
    -
    -
    -
    -
    Off Market
    3065 Windsor Place Dr, New Windsor, MD 21776
    0.28
    $1,235,200
    5
    5.5
    7,244
    Off Market
    4036 Roop Rd, New Windsor, MD 21776
    0.29
    $675,000
    4
    2.5
    2,688
    For Sale
    4024 Roop Rd, New Windsor, MD 21776
    0.30
    $640,900
    4
    3.5
    3,320
    Off Market
    4181 Buffalo Rd, Mount Airy, MD 21771
    0.35
    $527,500
    3
    2.5
    2,038
    Off Market
    4000 Roop Rd, New Windsor, MD 21776
    0.40
    $530,600
    5
    3
    2,034
    Off Market
    4215 Buffalo Rd, Mount Airy, MD 21771
    0.44
    $400,000
    5
    3
    2,957
    Recently Sold
    3922 Buffalo Rd, New Windsor, MD 21776
    0.48
    $942,900
    5
    5
    3,192
    Off Market
    15539 Liberty Rd, Mount Airy, MD 21771
    0.53
    $655,000
    4
    2.5
    2,592
    Recently Sold

    Local Information

    • Map ViewExplore the area around 2 John Benjamin Dr.
    • Schools1 Preschool School1 Elementary School1 Middle School1 High School
    • Shop & Eat
    -- mins to
    Commute Destination

    About this House

    2 John Benjamin Dr is in New Windsor, MD and in ZIP code 21776.
    2 John Benjamin Dr, New Windsor, MD 21776 is a unknown. It is currently off market. The Trulia Estimate rent is $2,681/month.

    Home Details for 2 John Benjamin Dr

    Property Information

    Property Type / Style
    Property Type: Unknown

    Market trends in Mount Airy

    Last updated July 2026
    Buyer'sMarketSeller'sMarket
    Avg. sale price
    $679K
    $19.17K    MoM
    Sale-to-List Price
    100.3%
    0.3%    MoM
    Price per sq ft
    $252
    $3    MoM
    Available listings
    67
    12    MoM

    Around this home

    What Locals Say about Mount Airy

    At least 85 Trulia users voted on each feature.

    • 91 % Say parking is easy

    • 91 % Say yards are well-kept

    • 90 % Say car is needed

    • 86 % Say it's dog friendly

    • 85 % Say people would walk alone at night

    • 81 % Say there's holiday spirit

    • 74 % Say kids play outside

    • 74 % Say it's quiet

    • 67 % Say neighbors are friendly

    • 65 % Say there's wildlife

    • 55 % Say streets are well-lit

    • 52 % Say they plan to stay for at least 5 years

    • 49 % Say there are sidewalks

    • 36 % Say there are community events

    • 34 % Say it's walkable to grocery stores

    • 26 % Say it's walkable to restaurants

    Sourced by Trulia users. Learn more about our methodology.
    • Brenda Calvillo
      "Holiday parades "
      0
      Flag
    • Calidara56
      "Nice people, beautiful natural areas, history, and convenience of shopping and close to many larger towns and cities. Love it here!"
      1
      Flag
    • Trulia User
      "Good school system. Downtown is cute. Good local restaurants. Neighborhood is quite but everyone is super nice"
      0
      Flag
    • Shaun W.
      "The peace and quiet with wonderful nice warming people all around. I’m from San Diego, California and brings me back to a western feel of hospitality! "
      0
      Flag
    • Anne C. -. B.
      "Great community environment, good schools, lots of kiDs clubs & sports, restaurants close by, pet friendly."
      3
      Flag
    • Anne C. -. B.
      "Plenty of sidewalks for walking your dog, Watkins park is nearby with a mile long sidewalk to walk your dog."
      0
      Flag
    • Dorrie H.
      "Very dog friendly neighborhood. Many people own dogs here & most of the dogs are friendly. I walk my dog 4x a day and always clean up after her as do most of my neighbors. There’s also a dog park very close by with two sections for the dogs to run and play. "
      1
      Flag
    • Baclauser
      "Local golf course has family dinner night every Friday Great place for daily neighborhood walks quiet neighborhood with a wonderful setting and country road maintenance "
      1
      Flag
    • Baclauser
      "My neighborhood is quite, safe and welcoming to all owners, guests and neighborhoods. We have a lovely golf course, the Links of Challedon, which we surround where all walkers, joggers and bikers are welcomed "
      0
      Flag
    • Sparks
      "Mt. Airy is a nice town, it is growing too quickly but that’s a normal thing in Maryland. I have been in this area 30 years, coming to this area for 45 years. "
      0
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    • lrivizzig
      "I've lived in Mt. Airy over 15 years. It's a small town feel, but yet close to major cities and larger shopping areas. Great place to live!"
      0
      Flag
    • Susan-cf
      "It a nice place to live it is a little far for commuting into Washington, not quite as far for Baltimore."
      1
      Flag
    • Alison M. E.
      "no sidewalks to walk dog. Neighbors stay to themselves. It is close to shopping and doctors. There is a a medical facility nearby, you can walk to it."
      0
      Flag
    • Alison M. E.
      "Restaurant, Medical Complex & businesses nearby. A lawyer, chiropracter, hair salon and gas station are within walking distance. You can even walk to Walmart and many other businesses"
      0
      Flag
    • Laura S.
      "Dogs are welcome in our neighborhood. all shapes and sizes. Our neighbors are really courteous, they all pick up after their dogs. I love our neighborhood abd we have 2 little dogs ourselves. "
      0
      Flag
    • Anne B.
      "We have lived in this area for 12 years and love it. The location to DC & Baltimore, the public school, kids sports programs, etc. Plenty of parks, dog friendly, neighbors look out for each other including a neighborhood watch Facebook page. Close to route 70 & 270 for easy commuting."
      0
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    • Jane E. C.
      "Mount Airy is a beautiful place to live. Lots of community engagement. Restaurants are fantastic lots of services!"
      0
      Flag
    • Jane E. C.
      "Horses and sheep are in each house. We have chickens. Old fashioned values are the rule. People look out for each other!"
      1
      Flag
    • Sindrirune
      "Close to shopping tree lined dead end street with safe areas for kids to ride bikes also borders a farm on both sides ..... off of a two lane road that leads to the interstate yet quiet country feel"
      0
      Flag
    • Prenupt
      "Great school system for elementary and middle school. Lots of great family activities and shopping. Nice restaurants and good health care providers in the area."
      0
      Flag
    • Sindrirune
      "Dog owners would love this neighborhood It consist of two dead end streets but lined with trees as is most of the yards:.... each house is custom built so it’s not a cookie cutter area and the yards are large enough to fence for dogs safety, though most neighbors still walk their dogs..... we also have a park with dog park 5 mins away"
      0
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    • Sindrirune
      "Best of both worlds ..... stores 10mins Drive..... art restaurants and entertainment within 20-60mins..... country drives yet near inner states for easy access to work.... great schools perfect family environment or retirement "
      0
      Flag
    • Bradburdette
      "The carnivals are always a good time and so are the other events that are held at the carnival grounds. Also, it's always a good time to meet up with friends and family and go to the local bars and restaurants. A lot of people know each other and there's always familiar and friendly faces."
      0
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    • Karen p.
      "No sidewalks. I don’t have a dog but I would imagine that it would be easier to walk the dog somewhere where there is sidewalks."
      0
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    • Karen p.
      "Easy access to downtown. Love the shops and restaurants on Main Street. A short 5 minute drive to route 70."
      0
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    LGBTQ Local Legal Protections

    Frequently asked questions about 2 John Benjamin Dr

    • Is New Windsor a buyer's or seller's market?
      New Windsor is currently a seller's market, based on recent for-sale activity.
    • What's the median sale price in New Windsor?
      The median sale price in New Windsor is $679K. That is up $19.17K from the prior month.
    • What do residents say about New Windsor?
      Residents describe New Windsor, MD as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in New Windsor, MD.
    • What are the closest schools to 2 John Benjamin Dr?
      The closest schools to 2 John Benjamin Dr in New Windsor, MD are Mount Airy Middle School (rated 8/10), South Carroll High School (rated 9/10), Winfield Elementary School (Pre-K, rated 6/10).

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