Are yards well-kept in Middletown, MD?

As of early 2026, 96% of users say yards are well-kept

Is a car needed in Middletown, MD?

As of early 2026, 93% of users say car is needed

Would people walk alone at night in Middletown, MD?

As of early 2026, 89% of users say people would walk alone at night

Is Middletown, MD dog-friendly?

As of early 2026, 85% of users say it's dog friendly

Is parking easy in Middletown, MD?

As of early 2026, 83% of users say parking is easy

Is Middletown, MD quiet?

As of early 2026, 82% of users say it's quiet

Does Middletown, MD show holiday spirit?

As of early 2026, 82% of users say there's holiday spirit

Do kids play outside in Middletown, MD?

As of early 2026, 73% of users say kids play outside

Are the streets well-lit in Middletown, MD?

As of early 2026, 71% of users say streets are well-lit

Are neighbors friendly in Middletown, MD?

As of early 2026, 70% of users say neighbors are friendly

Is Middletown, MD walkable to restaurants?

As of early 2026, 64% of users say it's walkable to restaurants

Does Middletown, MD have sidewalks?

As of early 2026, 58% of users say there are sidewalks

Do residents of Middletown, MD plan to stay at least 5 years?

As of early 2026, 51% of users say they plan to stay for at least 5 years

Are there community events in Middletown, MD?

As of early 2026, 51% of users say there are community events

Is there wildlife in Middletown, MD?

As of early 2026, 47% of users say there's wildlife

Is Middletown, MD walkable to grocery stores?

As of early 2026, 44% of users say it's walkable to grocery stores

FOR SALE

0.54 ACRES

216 E Main St
Middletown, MD 21769

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

$775,000

Est. Mortgage $4,004/mo*

Get Pre-Qualified

$775,000

Est. Mortgage $4,004/mo*

Get Pre-Qualified

5 Beds

5 Baths

3,296 sqft

(on 0.54 acres)

We estimate this home will sell faster than 89% nearby.

Local Information

-- mins to

Commute Destination

Description

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.

We estimate this home will sell faster than 89% nearby.

Home Highlights

Parking

Garage

Outdoor

Porch, Pool

A/C

Heating & Cooling

HOA

None

Price/Sqft

$235

Listed

9 days ago

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

Days on Market
Days on Market: 9

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: $235
Status Change & Dates Possession Timing: Negotiable, Close Of Escrow

Active Status
MLS Status: ACTIVE

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

Agent Information
Listing Agent Listing ID: MDFR2080572

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 11 hours ago

Listing courtesy of Denise Briggs, (240) 304-0366

Redfin Corp, (301) 658-6186

Source: Bright MLS, MLS#MDFR2080572

Also Listed on Bright MLS.

Price History for 216 E Main St

Date	Price	Event	Source
04/29/2026	$775,000	Listed For Sale	Bright MLS #MDFR2080572

11/04/2020	$550,000	Sold	N/A
Recording Date 11/04/2020 Contract Date 08/26/2020 County Transfer Tax N/A Total Transfer Tax $28
08/28/2020	$550,000	Sold	N/A
Recording Date 08/28/2020 County Transfer Tax N/A Total Transfer Tax N/A
08/02/2020	$550,000	PriceChange	Agent Provided
Price Change $25,000 (-4%)
05/21/2020	$575,000	PriceChange	Agent Provided
Price Change $24,000 (-4%)
02/11/2020	$599,000	PriceChange	Agent Provided
Price Change $18,000 (-3%)
11/18/2019	$617,000	PriceChange	Agent Provided
Price Change $20,000 (-3%)
10/04/2019	$637,000	Listed For Sale	Agent Provided

02/26/2014	$612,000	Sold	N/A
Recording Date 02/26/2014 Contract Date 02/21/2014 County Transfer Tax N/A Total Transfer Tax N/A
12/17/2013	$639,000	Pending	Agent Provided

09/06/2013	$639,000	Listed For Sale	Agent Provided

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Property Tax and Assessment

Year	2025
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
7217 Dogwood Ln, Middletown, MD	0.16	Single-Family Home	$675,000	08/15/25	4	3	3,190
114 E Main St, Middletown, MD	0.13	Single-Family Home	$950,000	03/20/26	5	5.5	4,785
326 Ingalls Dr, Middletown, MD	0.44	Single-Family Home	$725,000	08/11/25	6	5	3,747
3 Woodmere Cir, Middletown, MD	0.26	Single-Family Home	$905,000	09/15/25	5	4.5	6,144
215 Broad St, Middletown, MD	0.29	Single-Family Home	$560,000	04/09/26	4	3	2,580
95 E Green St, Middletown, MD	0.18	Single-Family Home	$669,000	12/12/25	4	3.5	2,748
210 Lombardy Ct, Middletown, MD	0.43	Single-Family Home	$700,000	05/21/25	5	3	3,464
107 Broad St, Middletown, MD	0.12	Single-Family Home	$350,000	09/05/25	3	2.5	2,484
7 Dean Ln, Middletown, MD	0.24	Single-Family Home	$810,000	08/25/25	5	4.5	4,630
207 Broad St, Middletown, MD	0.21	Single-Family Home	$500,000	03/13/26	4	2	2,210

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

Learn more about our methodology.

Chloe Bishop
Resident
9mo ago
"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
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Trulia User
Resident
4y ago
"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
Resident
4y ago
"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
Resident
4y ago
"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
Resident
6y ago
"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
Visitor
6y ago
"Quiet, well kept. everyone is neighborly, small town vibe. Local farmers, schools are close together. "
0
Flag
Ctauscher10@gmail.com
Resident
6y ago
"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.
Resident
7y ago
"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
Resident
7y ago
"20 minute drive to Frederick... about 12 miles distance. Traffic usually moving but can be heavy during school year."
0
Flag
Michele M.
Resident
7y ago
"well kept yards, safe to walk day and night, kid's community sports, award winning schools, quiet community"
0
Flag
Regis g.
Resident
7y ago
"amazing schools, great place to raise kids. great family free events all the time, such as movies at the park"
0
Flag
Gogenevago
Resident
7y ago
"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
Resident
8y ago
"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.
11y ago
"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
11y ago
"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.
13y ago
"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
Flag

LGBTQ Local Legal Protections

Additional Cost

Denise Briggs, Redfin Corp, (301) 658-6186

Agent Phone: (240) 304-0366

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

216 E Main St, Middletown, MD 21769 is a 5 bedroom, 6 bathroom, 3,296 sqft single-family home built in 1900. This property is currently available for sale and was listed by Bright MLS on Apr 20, 2026. The MLS # for this home is MLS# MDFR2080572.

216 E Main St Middletown, MD 21769

$775,000

$775,000

Local Information

Description

Home Highlights

Home Details for 216 E Main St

Interior Features

Exterior Features

Days on Market

Property Information

Price & Status

Active Status

Location

Agent Information

Building

Community

HOA

Lot Information

Listing Info

Offer

Business

Miscellaneous

Additional Information

Price History for 216 E Main St

Similar Homes You May Like

New Listings near 216 E Main St

Property Tax and Assessment

Comparable Sales for 216 E Main St

Assigned Schools

What Locals Say about Middletown

LGBTQ Local Legal Protections

Housing

Employment

Public accommodations

Additional Cost

216 E Main St
Middletown, MD 21769