216 E Main St, Middletown, MD 21769
Property image
Property image
SOLD
JUN 29, 2026

216 E Main St
Middletown, MD 21769

  • 5 Beds
  • 5 Baths
  • 3,296 sqft (on 0.54 acres)

$810,000

Last Sold: Jun 29, 2026
5% over list $775K
$246/sqft
Est. Refi. Payment $4,866/mo*
Refinance Your Home

$810,000

Last Sold: Jun 29, 2026
5% over list $775K
$246/sqft
Est. Refi. Payment $4,866/mo*
Refinance Your Home
5 Beds
5 Baths
3,296 sqft
(on 0.54 acres)

Local Information

  • Map ViewExplore the area around 216 E Main St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1900
Lot Size
0.54 acres
Living Area
3,296 sqft
Price/Sqft
$246/sqft
Parking
Garage

About this House

***Highest & Best offers due Saturday, May 16 8PM***Featured in WASHINGTONIAN, this iconic Victorian “Painted Lady” in the heart of Middletown’s historic district, offering timeless architecture paired with modern comfort. This one-of-a-kind residence showcases striking curb appeal with its signature twin turrets, intricate woodwork, and charming front porch that sets the tone for what awaits inside. Boasting 5 bedrooms, 4 full baths, and 2 half baths, this home offers exceptional space and flexibility for everyday living and entertaining. Interior features include soaring ceilings, original hardwood floors with detailed inlay, pocket doors, and elegant millwork that highlight the home’s historic craftsmanship. Multiple living and dining areas are anchored by beautiful fireplaces, creating warm, inviting spaces throughout. A bright sunroom adds additional living space, perfect for relaxing year-round. The home has been thoughtfully updated to meet today’s lifestyle while preserving its character, including a modernized kitchen, a butler’s pantry with a wine fridge, and key system improvements. Large windows fill the home with natural light, enhancing its bright and airy feel. Step outside to a private backyard oasis featuring a pool, a 6-person hot tub, and outdoor living space, perfect for relaxing or hosting gatherings. A fenced garden space on the south side of the property offers excellent sunlight—ideal for gardening enthusiasts or those seeking a peaceful outdoor retreat. A rare 3-car garage provides ample parking and storage—an exceptional find for a property of this era. Situated on a generous lot just moments from downtown Middletown, enjoy convenient access to local shops, dining, parks, and commuter routes. A true statement property combining historic charm, functional space, and lifestyle amenities—opportunities like this are rare. Located just across the street from Middletown’s 3rd–12th grade school campus and town park—offering exceptional convenience for school drop-offs, sports, events, and activities.
216 E Main St, Middletown, MD 21769 is a 5 bedroom, 6 bathroom, 3,296 sqft single-family home built in 1900. It last sold for $810,000 on Jun 29, 2026 (5% above the $775,000 asking price). It is currently off market. The Trulia Estimate is $809,500, with a rent estimate of $5,301/month.

Home Details for 216 E Main St

Interior Features

Interior Details
Basement: Partially FinishedNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 6Number of Bathrooms (full): 4Number of Bathrooms (half): 2Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 3296 Square Feet
Appliances & Utilities
Appliances: Refrigerator, Cooktop, Ice Maker, Dishwasher, Electric Water HeaterDishwasherRefrigerator
Heating & Cooling
Heating: Radiator,OilHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Radiator
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Flooring: Wood
Levels, Entrance, & Accessibility
Stories: 4Levels: FourAccessibility: NoneFloors: Wood
View
No View

Exterior Features

Exterior Home Features
Patio / Porch: PorchOther Structures: Above Grade, Below GradeFoundation: OtherHas a Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 3Parking: Garage Faces Rear,Driveway,Detached
Pool
Pool: In Ground, PrivatePool
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2896 Square FeetFinished Area (below surface): 400 Square Feet

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Victorian
Building
Construction Materials: FrameNot a New Construction
Property Information
Parcel Number: 1103139530

Price & Status

Price
List Price: $775,000Price Per Sqft: $246/sqft
Status Change & Dates
Off Market Date: Thu Jul 02 2026Possession Timing: Negotiable, Close Of Escrow

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: MIDDLETOWNCommunity: Middletown
School Information
Elementary School District: Frederick County Public SchoolsJr High / Middle School District: Frederick County Public SchoolsHigh School District: Frederick County Public Schools

Building

Building Area
Building Area: 4344 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.54 acres

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: MDFR2080572Municipality: MiddletownAbove Grade Unfinished Area: 2896

Additional Information

Source Internet Entire Listing Display: Y
Last check for updates: about 8 hours ago
Listed by Denise Briggs, (240) 304-0366
Redfin Corp
Bought with: Dana Angleberger, (410) 371-3421, Charis Realty Group
Source: Bright MLS, MLS#MDFR2080572

Price History for 216 E Main St

DatePriceEventSource
06/29/2026$810,000Sold
Bright MLS #MDFR2080572
05/19/2026$775,000ContingentBright MLS #MDFR2080572
04/29/2026$775,000Listed For SaleBright MLS #MDFR2080572
11/04/2020$550,000Sold
N/A
08/28/2020$550,000Sold
N/A
08/02/2020$550,000PriceChange
Agent Provided
05/21/2020$575,000PriceChange
Agent Provided
02/11/2020$599,000PriceChange
Agent Provided
11/18/2019$617,000PriceChange
Agent Provided
10/04/2019$637,000Listed For SaleAgent Provided
02/26/2014$612,000Sold
N/A
12/17/2013$639,000PendingAgent Provided
09/06/2013$639,000Listed For SaleAgent Provided

Market trends in Middletown

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
28
7MoM
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Property Tax and Assessment

Year2025
Tax$10,646
Assessment$726,167
Home facts updated by county records

Comparable Sales for 216 E Main St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
114 E Main St, Middletown, MD
0.13
Single-Family Home
$950,000
03/20/26
5
5.5
4,785
7217 Dogwood Ln, Middletown, MD
0.16
Single-Family Home
$675,000
08/15/25
4
3
3,190
3 Woodmere Cir, Middletown, MD
0.26
Single-Family Home
$905,000
09/15/25
5
4.5
6,144
326 Ingalls Dr, Middletown, MD
0.44
Single-Family Home
$725,000
08/11/25
6
5
3,747
7 Dean Ln, Middletown, MD
0.24
Single-Family Home
$810,000
08/25/25
5
4.5
4,630
95 E Green St, Middletown, MD
0.18
Single-Family Home
$669,000
12/12/25
4
3.5
2,748
215 Broad St, Middletown, MD
0.29
Single-Family Home
$560,000
04/09/26
4
3
2,580
6 Gaver Way, Middletown, MD
0.24
Single-Family Home
$815,000
06/01/26
5
5.5
5,510
124 E Main St, Middletown, MD
0.10
Single-Family Home
$585,000
07/24/26
3
2
2,474

Nearby homes

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Assigned Schools

These are the assigned schools for 216 E Main St.
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 Middletown

At least 39 Trulia users voted on each feature.

  • 96 % Say yards are well-kept

  • 93 % Say car is needed

  • 89 % Say people would walk alone at night

  • 85 % Say it's dog friendly

  • 83 % Say parking is easy

  • 82 % Say it's quiet

  • 82 % Say there's holiday spirit

  • 73 % Say kids play outside

  • 71 % Say streets are well-lit

  • 70 % Say neighbors are friendly

  • 64 % Say it's walkable to restaurants

  • 58 % Say there are sidewalks

  • 51 % Say they plan to stay for at least 5 years

  • 51 % Say there are community events

  • 47 % Say there's wildlife

  • 44 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Chloe Bishop
    "It’s a nice small-town feel with friendly neighborhoods. Great schools. People are friendly. Close to major highways with minimal traffic compared to Frederick. "
    0
    Flag
  • Trulia User
    "Very quiet, nice neighbors, many of whom grew up in the neighborhood. Siuth Mountain Creamery is a great destination for families, and even delivers. Schools are terrific--the main reason families move and stay here."
    1
    Flag
  • Trulia User
    "Owners are responsible for making sure their dogs are leashed up and under control. Also they pick up after their pets. "
    0
    Flag
  • Trulia User
    "we've lived here for 17 years. neighbors are pleasant and respectful of each otbers privacy. many of them are related, grew up in this neighborhood,(Bolivar). No complaints, except for the cars that speed on the road during rush hour. "
    1
    Flag
  • Trulia User
    "Movie night, Fourth of July celebration, golf course, ice cream parlor, mostly single-family homes, pretty rural,farmers market, good roads, great schools "
    0
    Flag
  • Haileyrockwell
    "Quiet, well kept. everyone is neighborly, small town vibe. Local farmers, schools are close together. "
    0
    Flag
  • Ctauscher10@gmail.com
    "Yes you see dog owners walking their dogs all the time. People are friendly and enjoy being in a rural area. There is also a lot of wildlife here you see deer skunks possums and foxes and I saw a bear once Ion Braddock Heights. You have quick access to interstate 70 east and west."
    0
    Flag
  • Michele M.
    "I often see plenty of dog owners walking their dogs throughout the neighborhood. Many times, you will even find families taking a walk with their pooch. It's a nice little scene. The only problem I think a dog owner might have is if his/her dog has socialization issues. Because they will run into other dogs constantly."
    0
    Flag
  • Graysonramsburg
    "20 minute drive to Frederick... about 12 miles distance. Traffic usually moving but can be heavy during school year."
    0
    Flag
  • Michele M.
    "well kept yards, safe to walk day and night, kid's community sports, award winning schools, quiet community"
    0
    Flag
  • Regis g.
    "amazing schools, great place to raise kids. great family free events all the time, such as movies at the park"
    0
    Flag
  • Gogenevago
    "I just moved here and the neighbors look out for one another. super nice area and I'm glad I own a home in this area. "
    0
    Flag
  • Robynrmason
    "Great school system and safe area. Beautiful views and great community. Very convenient to interstate and to stores. Have lived here 10 years and love it. "
    1
    Flag
  • Dotty D.
    "House is located in Brookridge neighborhood, surrounded by beautiful Wiles Branch Park. Middletown is a wonderful small town community with best schools in the area. "
    1
    Flag
  • mcbee
    "My friends live there on Tobias Run and it's a great street with a hidden open/park like area the size of 2 football fields with a spotless play area, sitting benches, and walking paths all with in 1-2 blocks of the Hollow Creek golf course, club house and Valley Grill restaurant & Sports Bar. There are beautiful views of the golf course and surrounding mountains. Plus, it is serviced by FCPS school buses that bring children to all of Middletown's schools (elementary, middle, high school) ... all of this for a fantastic home and a mere $50 HOA fee!"
    0
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  • Guillermo A. J.
    "WHY IS ANYWHERE IN MIDDLETOWN MD A POOR NEIGHBORHOOD IS BECAUSE THERE NOT ENOUGH PLACES TO WORK @ IN MIDDLETOWN MD BECAUSE YOU DON'T SEE THAT MUCH BUILDING'S IN MIDDLETOWN MD TO WORK @ AS A JOB AND BECAUSE NOBODY IN MIDDLETOWN MD MAKE'S TOO MUCH MONEY AND THERE'S NOT ENOUGH PLACE'S TO EAT @ AND WHOEVER YOU ARE NEVER EVER EVER EVER MOVE TO MIDDLETOWN MD"
    0
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Apartments for Rent

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Explore by feature - Pet Friendly

6 pet-friendly rentals in Middletown, MD

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Homes for sale near 216 E Main St

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Off Market Homes Near 216 E Main St

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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