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

$818,900

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

4165 John Benjamin Dr, New Windsor, MD 21776

Est. Refi. Payment $4,870/mo*
Refinance Your Home
Currently Off Market - Sold May 16, 2016 for $524,900

Home Value

Trulia Estimate
$819K
Since last month
Decreased$4K (-0.5%)
Since last year
Increased$4K (+0.4%)
Since last sale
Increased$294K (+56.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +57% in the last 10 years
MonthEstimated value
2026
August 2026$819K
August 2026$818K
July 2026$823K
June 2026$836K
May 2026$836K
April 2026$830K
March 2026$829K
February 2026$814K
January 2026$810K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
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
3788 Roop Rd, New Windsor, MD
0.65
Single-Family Home
$625,000
08/06/26
3
2.5
2,343
3330 Oakwood Dr, New Windsor, MD
0.90
Single-Family Home
$600,000
06/24/26
4
3.5
2,332
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
3625 Hooper Rd, New Windsor, MD
1.00
Single-Family Home
$670,000
09/01/26
4
3
3,440
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

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
0.10
$1,061,600
5
4.5
4,699
Off Market
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
$645,200
4
3.5
3,320
Off Market
4181 Buffalo Rd, Mount Airy, MD 21771
0.35
$530,600
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
$943,400
5
5
3,192
Off Market
15539 Liberty Rd, Mount Airy, MD 21771
0.53
$655,000
4
2.5
2,592
Recently Sold
15535 Liberty Rd, Mount Airy, MD 21771
0.56
$676,500
3
2
2,887
Off Market

Local Information

  • Map ViewExplore the area around 4165 John Benjamin Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2005
Lot Size
2.66 acres
Living Area
4,014 sqft
Price/Sqft
$204
Parking
Garage

About this House

$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!!
4165 John Benjamin Dr, New Windsor, MD 21776 is a 5 bedroom, 4 bathroom, 4,014 sqft single-family home built in 2005. It last sold for $524,900 on May 16, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $818,900, with a rent estimate of $4,004/month.

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 and Tax history

DateEventPrice
May 16, 2016
Source: N/A
Sold
$524,900
Apr 16, 2016
Source: Agent Provided
Pending
$519,900
Apr 9, 2016
Source: Agent Provided
PriceChange
$519,900
Price decreased by 4%
Mar 4, 2016
Source: Agent Provided
Listed For Sale
$540,000
Aug 9, 2013
Source: N/A
Sold
$539,900

Market trends in Mount Airy

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

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
    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

LGBTQ Local Legal Protections

Frequently asked questions about 4165 John Benjamin Dr

  • What is 4165 John Benjamin Dr estimated to be worth?
    Trulia's estimated value for 4165 John Benjamin Dr in New Windsor, MD is $818,900.
  • What is the price history for 4165 John Benjamin Dr?
    4165 John Benjamin Dr in New Windsor, MD last sold for $524,900 in May 2016.
  • 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.
  • Does 4165 John Benjamin Dr have air conditioning?
    Yes, 4165 John Benjamin Dr in New Windsor, MD has air conditioning.
  • Does 4165 John Benjamin Dr have laundry facilities?
    Yes, 4165 John Benjamin Dr in New Windsor, MD has in-unit laundry.

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