4165 John Benjamin Dr, New Windsor, MD 21776
OFF MARKET

4165 John Benjamin Dr
New Windsor, MD 21776

  • 5 Beds
  • 3.5 Baths
  • 4,014 sqft (on 2.66 acres)

$839,500

Trulia Estimate
as of Jun 19, 2026
Est. Refi. Payment $4,890/mo*
Refinance Your Home

$839,500

Trulia Estimate
as of Jun 19, 2026
Est. Refi. Payment $4,890/mo*
Refinance Your Home
5 Beds
3.5 Baths
4,014 sqft
(on 2.66 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

$20,000 PRICE REDUCTION-Won't Last at New Price! Conveniently located near Rt 26 for easy commute yet still offers a Large, Level Private Backyard w/ Picturesque Sunrise View, Deck, Hardscape Patio & Firepit! Inside features-Wood Floors, Granite & Stainless Kitchen, Island w/ seating & 2nd Wall Oven! Master Bedroom w/ Gas Fireplace..Large Rec Room in Basement, 5th Bdrm, Full Bath & Exercise Room!!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 4165 John Benjamin Dr

Interior Features

Interior Details
BasementNumber of Rooms: 12Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Office, Pantry, Recreation RoomCeiling Fan
Heating & Cooling
Heating: Forced Air, Electric, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Carpet, Hardwood
Appliances & Utilities
Cable ReadyDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceJetted Bath Tub
Security
Security System

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: Stone, VinylPatioPorch
Parking & Garage
GarageParking Spaces: 4Parking: Garage Attached, Garage Detached

Property Information

Year Built
Year Built: 2005
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 2.66 acres

Price History for 4165 John Benjamin Dr

DatePriceEventSource
05/16/2016$524,900Sold
N/A
04/16/2016$519,900PendingAgent Provided
04/09/2016$519,900PriceChange
Agent Provided
03/04/2016$540,000Listed For SaleAgent Provided
08/09/2013$539,900Sold
N/A
03/01/2006$652,200Sold
N/A
11/08/2005$652,200Sold
N/A
03/17/2005$240,000Sold
N/A
03/16/2004$169,900Sold
N/A

Market trends in Mount Airy

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$641K
$81.67KMoM
Sale-to-List Price
100.0%
Price per sq ft
$253
$10MoM
Available listings
79
11MoM
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Property Tax and Assessment

Year2025
Tax$7,340
Assessment$658,000
Home facts updated by county records

Homeowner tools

Estimated monthly rent$4,034/mo
List your home for rent

Comparable Sales for 4165 John Benjamin Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
4024 Roop Rd, New Windsor, MD
0.30
Single-Family Home
$629,000
08/15/25
4
3.5
3,320
15539 Liberty Rd, Mount Airy, MD
0.53
Single-Family Home
$655,000
04/10/26
4
2.5
2,592
3895 Buffalo Rd, New Windsor, MD
0.65
Single-Family Home
$635,000
06/05/26
4
2.5
2,568
15535 Liberty Rd, Mount Airy, MD
0.56
Single-Family Home
$680,000
10/29/25
3
2
2,887
3720 Buffalo Rd, New Windsor, MD
0.83
Single-Family Home
$715,000
12/01/25
4
3.5
3,540
3870 Roop Rd, New Windsor, MD
0.69
Single-Family Home
$500,000
01/02/26
3
2
1,851
2990 Honeywood Dr, Mount Airy, MD
1.08
Single-Family Home
$710,000
12/02/25
4
2.5
3,178
4367 Ridge Rd, Mount Airy, MD
1.24
Single-Family Home
$560,000
10/03/25
4
2.5
2,164
2659 Leslie Rd, Mount Airy, MD
1.39
Single-Family Home
$725,000
10/16/25
4
2.5
3,098
5140 Perry Rd, Mount Airy, MD
1.57
Single-Family Home
$590,000
06/03/26
4
3
2,082

Nearby homes

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Assigned Schools

These are the assigned schools for 4165 John Benjamin Dr.
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 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

  • 73 % 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.
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Karen p.
    "Easy access to downtown. Love the shops and restaurants on Main Street. A short 5 minute drive to route 70."
    0
    Flag

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Off Market Homes Near 4165 John Benjamin Dr

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4165 John Benjamin Dr, New Windsor, MD 21776 is a 5 bedroom, 4 bathroom, 4,014 sqft single-family home built in 2005. This property is not currently available for sale. 4165 John Benjamin Dr was last sold on May 16, 2016 for $524,900. The current Trulia Estimate for 4165 John Benjamin Dr is $839,500.