4180 John Benjamin Dr, New Windsor, MD 21776
SOLD
SEP 4, 2026

$1,298,800

Trulia Estimate
  • 5 Beds
  • 5.5 Baths
  • 7,120 sqft (on 7.09 acres)

4180 John Benjamin Dr, New Windsor, MD 21776

Est. Refi. Payment $7,680/mo*
Refinance Your Home
Currently Off Market - Sold Sep 4, 2026 for $1,400,000 (8% above list price)

Home Value

Trulia Estimate
$1.3M
Since last month
Decreased$1K (-0.1%)
Since last year
Increased$45K (+3.6%)
Since last sale
Decreased$103K (-7.3%)
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 +73% in the last 10 years
MonthEstimated value
2026
August 2026$1.3M
July 2026$1.3M
June 2026$1.3M
May 2026$1.29M
April 2026$1.28M
March 2026$1.28M
February 2026$1.25M
January 2026$1.25M
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
0.32
Single-Family Home
$400,000
06/22/26
5
3
2,957
15539 Liberty Rd, Mount Airy, MD
0.50
Single-Family Home
$655,000
04/10/26
4
2.5
2,592
15535 Liberty Rd, Mount Airy, MD
0.51
Single-Family Home
$680,000
10/29/25
3
2
2,887
3895 Buffalo Rd, New Windsor, MD
0.68
Single-Family Home
$635,000
06/05/26
4
2.5
2,568
2990 Honeywood Dr, Mount Airy, MD
1.00
Single-Family Home
$710,000
12/02/25
4
2.5
3,178
3720 Buffalo Rd, New Windsor, MD
0.91
Single-Family Home
$715,000
12/01/25
4
3.5
3,540
3625 Hooper Rd, New Windsor, MD
1.14
Single-Family Home
$670,000
09/01/26
4
3
3,440
3330 Oakwood Dr, New Windsor, MD
0.99
Single-Family Home
$600,000
06/24/26
4
3.5
2,332
3788 Roop Rd, New Windsor, MD
0.76
Single-Family Home
$625,000
08/06/26
3
2.5
2,343

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
4177 John Benjamin Dr, New Windsor, MD 21776
0.05
$1,061,600
5
4.5
4,699
Off Market
3207 Liberty Rd, New Windsor, MD 21776
0.10
-
4
2.5
3,263
Off Market
4075 Roop Rd, New Windsor, MD 21776
0.24
-
-
-
-
Off Market
4181 Buffalo Rd, Mount Airy, MD 21771
0.25
$530,600
3
2.5
2,038
Off Market
4036 Roop Rd, New Windsor, MD 21776
0.32
$675,000
4
2.5
2,688
For Sale
4215 Buffalo Rd, Mount Airy, MD 21771
0.32
$400,000
5
3
2,957
Recently Sold
4024 Roop Rd, New Windsor, MD 21776
0.35
$645,200
4
3.5
3,320
Off Market
3065 Windsor Place Dr, New Windsor, MD 21776
0.43
$1,235,200
5
5.5
7,244
Off Market
4241 Buffalo Rd, Mount Airy, MD 21771
0.42
$453,800
4
2
2,304
Off Market
4000 Roop Rd, New Windsor, MD 21776
0.48
$530,600
5
3
2,034
Off Market
4249 Buffalo Rd, Mount Airy, MD 21771
0.46
$545,200
4
3
1,936
Off Market

Local Information

  • Map ViewExplore the area around 4180 John Benjamin Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2012
7.09 acre lot
7,120 sqft
$197/sqft
3 Car Garage

About this House

Welcome to 4180 John Benjamin Drive, a custom-built natural light-filled estate with dual geothermal HVAC systems, an elevator for all 3 levels and fabulous potential In-Law/ADU space nestled on 7.09 picturesque acres in Caroline’s Crossing. With entertaining and family fun in mind, this exceptional property features lots of open yard, multiple acres of woods and a lovely (33’ x 16’ ) heated in-ground pool surrounded by a concrete pool deck and natural stone coping. Pool is approximately 3' to 6' deep, includes a safety barrier cover, new pump (2024/2025) and robotic cleaner. A charming front porch and pretty stone and vinyl exterior create exceptional curb appeal, complemented by 8' tall garage doors and beautifully landscaped grounds. Leaded glass front door framed by 2 sidelights and a transom window lead to the entrance Foyer featuring shadow box molding and a classic hardwood cascading staircase. 9' ceilings (excl. BR and BA's over garage) and hardwood flooring throughout the Main Level enhance the home’s spacious feel, while wide windowsills and beautiful millwork details add timeless elegance. High quality Milgard windows throughout. Off the Foyer, a charming Library offers built-in shelving and cabinets as well as an expansive Living Room and Dining Room. At the heart of the home is a gourmet chef-inspired Kitchen with expansive granite countertops, tumbled-stone tile backsplash, 2 islands (including a dine-at island with seating for 8), 3 sinks, abundant 42-inch cabinetry with custom storage features, stainless steel appliances, propane cooktop framed by a custom wood range hood, wall oven, warming drawer, built-in microwave, dishwasher, French door refrigerator and a walk-in Pantry closet. Just beyond the Kitchen, enjoy the Breakfast/Sun Room with 6 windows and transoms and a slider leading to the composite deck with a SunSetter awning (2023/2024). Adjoining Butler’s Pantry with cabinets, mini fridge, prep sink and room for a coffee station. The Family Room offers a stunning coffered ceiling, recessed lighting, a propane gas fireplace, and access to the composite screened porch (25'3" x 13'7") with new screening (2026) and cathedral ceiling. Upstairs, hardwood flooring extends through the landing and hallway featuring a large linen closet (7'x3'). The Primary Suite features a tray ceiling, Sitting Room (or a great nursery), walk-in closet (13'6"x11'5") and spa bath with BainUltra hydro thermo massage air jet tub, double bowl vanity, and custom tile shower with multiple shower heads. Bedrooms 2 and 3 each include a private bath and large walk-in closets. Potential Bedroom 4 is currently configured as a home office with awesome built-in work-from-home space, a sink, mini refrigerator and cabinetry. Convenient 2nd floor Laundry Rm includes LG front-load washer and dryer, utility sink, and cabinetry. The fully finished walkout Lower Level is ideal for multi-generational living, featuring full size above grade windows and a walkout slider with integral blinds, spacious Great Room, a private bedroom suite with full bath including a separate shower with ceramic tile surround and soaking tub, 1 additional bedroom, a bonus/exercise room, new carpet (2026), a full bath, and a separate Laundry Room with a laundry sink . Utility Room (17'x13') offers a pair Water Furnace Envision GeoThermal heating/cooling system (2012), Bradford White water heater (2022). Additional highlights include 36" wide interior doors, lever door handles, a 3-car garage, Tesla EV charger, dual 200-amp electrical panels equipped with generator plugs and mechanical interlock kits to support backup power options, 325 gal propane tank and abundant storage. Exterior accents-NEW roof, roof gables, tin roofing and shake siding (2021). Opportunities like this are rare - 7+ acres, luxury amenities, elevator access, and a resort-style backyard create a truly unforgettable place to call home!
4180 John Benjamin Dr, New Windsor, MD 21776 is a 5 bedroom, 6 bathroom, 7,120 sqft single-family home built in 2012. It last sold for $1,400,000 on Sep 4, 2026 (8% above the $1,300,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,298,800, with a rent estimate of $6,471/month.
Last check for updates: about 6 hours ago
Listed by Shari Hodges, (410) 456-1311
Cummings & Co. Realtors
Bought with: Rich Fox, (301) 788-4141, RE/MAX Realty Centre, Inc.
Co-Buyer's Agent: Molly Love, (240) 397-4109, RE/MAX Realty Centre, Inc.
Source: Bright MLS, MLS#MDCR2035864

Home Details for 4180 John Benjamin Dr

Interior Features

Interior Details
Basement: Full,Finished,Heated,Improved,Interior Entry,Exterior Entry,Rear Entrance,Shelving,Sump Pump,Walk-Out Access,WindowsNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 7120 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Natural Gas Available, CableAppliances: Microwave, Cooktop, Dishwasher, Disposal, Exhaust Fan, Ice Maker, Oven, Range Hood, Refrigerator, Stainless Steel Appliance(s), Water Heater, Self Cleaning Oven, Oven/Range - Electric, Washer, Dryer, Electric Water HeaterDishwasherDisposalDryerLaundry: Upper Level,In BasementMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Heat Pump,GeothermalHas CoolingAir Conditioning: Ceiling Fan(s),Central Air,GeothermalHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Mantel(s), Gas/PropaneSpa: BathHas a FireplaceHas a Spa
Gas & Electric
Electric: 200+ Amp Service, Generator
Windows, Doors, Floors & Walls
Window: Transom, Screens, Double Pane Windows, Energy Efficient, Insulated Windows, Bay/Bow, Double Hung, Vinyl Clad, Window Treatments, Stain/Lead GlassDoor: Sliding Glass, Double Entry, French Doors, Insulated, Six PanelFlooring: Hardwood, Carpet, Ceramic Tile, Wood
Levels, Entrance, & Accessibility
Stories: 3Levels: ThreeAccessibility: Accessible Elevator Installed, Accessible Hallway(s), Accessible Doors, Doors - Lever Handle(s), Doors - Swing InElevatorFloors: Hardwood, Carpet, Ceramic Tile, Wood
View
Has a ViewView: Garden, Trees/Woods
Security
Security: Security System, Smoke Detector(s), Fire Sprinkler System

Exterior Features

Exterior Home Features
Roof: Architectural ShinglePatio / Porch: Deck, Patio, Enclosed, Roof, ScreenedOther Structures: Above Grade, Below GradeExterior: Lighting, Awning(s), Flood Lights, SidewalksFoundation: Active Radon MitigationHas a Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3Open Parking Spaces: 10No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 13Parking: Garage Faces Side,Garage Door Opener,Inside Entrance,Asphalt,Driveway,Circular Driveway,Attached
Pool
Pool: In Ground, Heated, Concrete, PrivatePool
Frontage
Responsible for Road Maintenance: Private Maintained Road, Road Maintenance AgreementRoad Surface Type: Black TopNot on Waterfront
Water & Sewer
Sewer: Septic Exists
Finished Area
Finished Area (above surface): 4909 Square FeetFinished Area (below surface): 2211 Square Feet

Property Information

Year Built
Year Built: 2012
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Colonial
Building
Construction Materials: Vinyl Siding, StoneNot a New Construction
Property Information
Condition: ExcellentNot Included in Sale: Garage RefrigeratorIncluded in Sale: All Appliances, Ceiling Fans, Window Treatments And (8) Kitchen Stools. Electric Car Charger, (2) Generator Outlets, Pet Invisible FenceParcel Number: 0709034498

Price & Status

Price
List Price: $1,300,000Price Per Sqft: $197/sqft
Status Change & Dates
Off Market Date: Fri Sep 04 2026Possession Timing: 0-30 Days CD, Negotiable

Active Status

MLS Status: CLOSED

Media

Location

Direction & Address
City: NEW WINDSORCommunity: Carolines Crossing
School Information
Elementary School: WinfieldElementary School District: Carroll County Public SchoolsJr High / Middle School: Mt AiryJr High / Middle School District: Carroll County Public SchoolsHigh School: South CarrollHigh School District: Carroll County Public Schools

Building

Building Area
Building Area: 7341 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 7.09 Acres

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: MDCR2035864Above Grade Unfinished Area: 4909

Additional Information

Source Internet Automated Valuation Display: YSource Internet Consumer Comment: YSource Internet Entire Listing Display: YSource Internet Address Display: Y

Price and Tax history

DateEventPrice
Sep 4, 2026
Source: Bright MLS #MDCR2035864
Sold
$1,400,000
Jul 3, 2026
Source: Bright MLS #MDCR2035864
Pending
$1,300,000
Jun 25, 2026
Source: Bright MLS #MDCR2035864
Listed For Sale
$1,300,000
Jul 21, 2020
Source: N/A
Sold
$940,000
May 23, 2020
Source: Agent Provided
Pending
$995,000

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

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

Frequently asked questions about 4180 John Benjamin Dr

  • What is 4180 John Benjamin Dr estimated to be worth?
    Trulia's estimated value for 4180 John Benjamin Dr in New Windsor, MD is $1,298,800.
  • What is the price history for 4180 John Benjamin Dr?
    4180 John Benjamin Dr in New Windsor, MD last sold for $1,400,000 in September 2026.
  • 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 4180 John Benjamin Dr have air conditioning?
    Yes, 4180 John Benjamin Dr in New Windsor, MD has air conditioning.
  • Does 4180 John Benjamin Dr have a pool?
    Yes, 4180 John Benjamin Dr in New Windsor, MD has a pool.

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