Are yards well-kept in Middletown, MD?

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

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

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

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

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

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

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

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

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

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

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FOR SALE

3D VIEW

0.31 ACRES

19 E Main St
Middletown, MD 21769

4 Beds
3.5 Baths
3,130 sqft (on 0.31 acres)

$1,150,000

Est. Mortgage $6,617/mo*

Get Pre-Qualified

$1,150,000

Est. Mortgage $6,617/mo*

Get Pre-Qualified

4 Beds

3.5 Baths

3,130 sqft

(on 0.31 acres)

Local Information

Map ViewExplore the area around 19 E Main St.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

Carefully reimagined between 2018 and 2021, this historic Main Street home now lives like a luxury boutique retreat hidden in the heart of Middletown — complete with a secret speakeasy concealed behind a swinging bookshelf, a breathtaking custom kitchen addition, and a covered courtyard entertaining area anchored by a stunning stone fireplace. Rich in history yet thoughtfully transformed for modern luxury living, this extraordinary four-bedroom residence with dedicated office space blends timeless craftsmanship with sophisticated design rarely found in historic homes. Perched above historic Main Street with sunset views toward South Mountain, the home showcases soaring ceilings, original architectural details, custom Mennonite-crafted millwork, designer Circa lighting, and extensive infrastructure updates throughout. At the heart of the home is the stunning kitchen addition featuring exposed historic brick, dramatic steel scissor-beam trusses, handcrafted cabinetry, quartz perimeter counters, granite center island, GE Monogram appliances, farmhouse sink, induction cooktop, and a dramatic picture window overlooking the beautifully landscaped courtyard and covered side porch. The original kitchen was transformed into a spacious dining room, creating exceptional flow for entertaining while preserving the home’s historic character. Outdoor living spaces feel like an extension of the home itself with stamped concrete, custom stone fireplace, a covered entertaining area, integrated storage, and beautifully landscaped gathering spaces designed for both intimate evenings and large-scale entertaining. The front parlor was transformed into a stunning library with built-in shelving, restored historic shutters, statement lighting, and the hidden swinging bookshelf leading to the speakeasy featuring a solid wood bar, wet bar, beverage refrigerator, custom ceiling paneling, and dramatic finishes. The family room was created by opening two original parlors and is crowned by a dramatic bay window that floods the space with natural light. Upstairs, the home offers two primary suites along with spacious secondary bedrooms featuring exceptional flexibility, including a custom Murphy bed/work table system and built-in bay window seating. A dedicated office conceals a hidden opening into an untouched portion of the original home, creating a fascinating preserved time capsule rarely found in homes of this era. A covered upper porch overlooks the courtyard below, while the redesigned laundry room introduces marble countertops, statement lighting, and additional storage. The finished attic was transformed into a truly unique owner’s retreat featuring reclaimed oak flooring, exposed brick chimneys, preserved historic wall surfaces, dressing room, laundry chute, separate staircase access, and a spa-inspired bath with a hidden Japanese-inspired Ofuro soaking tub room. Infrastructure improvements include dedicated high-end Carrier HVAC systems with hospital-grade filtration and smart thermostats, radiant heated floors, replaced electrical systems in 2020, updated copper plumbing, Japanese toilets, hand-tooled standing seam metal roof, replacement gutters, energy-efficient wooden sash windows, composite porch decking, central vacuum, Sonos integration, and extensive custom woodworking throughout. Stretching from Main Street to West Green Street, the property also includes a subdivided, buildable rear lot. The purchaser of 19 E Main Street will have first right of refusal on the lot, which is also available separately, creating a rare opportunity for future expansion or investment in the heart of Middletown. Located on one of Maryland’s historic designated Main Streets, just steps from Middletown’s restaurants, library, shops, parks, & sought-after schools, this extraordinary residence offers a lifestyle as rare as the home itself. Owned by only three families in 100+ years, this one-of-a-kind home blends history, luxury, & craftsmanship.

Home Highlights

Parking

4 Open Spaces

Outdoor

Porch, Patio

A/C

Heating & Cooling

HOA

None

Price/Sqft

$367

Listed

33 days ago

Home Details for 19 E Main St

Interior Features
Interior Details Basement: UnfinishedNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout Living Area: 3130 Square Feet
Appliances & Utilities Appliances: Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Microwave, Oven, Range Hood, Refrigerator, Stainless Steel Appliance(s), Washer, Water HeaterDishwasherDisposalDryerLaundry: Upper Level,Laundry ChuteMicrowaveRefrigeratorWasher
Heating & Cooling Heating: Heat Pump,Radiant,Zoned,Electric,PropaneHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa Number of Fireplaces: 1Fireplace: Wood BurningHas a Fireplace
Windows, Doors, Floors & Walls Window: Vinyl CladFlooring: Wood, Tile/Brick
Levels, Entrance, & Accessibility Stories: 4Levels: FourAccessibility: NoneFloors: Wood, Tile Brick
View Has a ViewView: City, Scenic Vista

Exterior Features
Exterior Home Features Roof: MetalPatio / Porch: Patio, Porch, RoofOther Structures: Above Grade, Below GradeExterior: Chimney Cap(s), Extensive Hardscape, Lighting, BalconyFoundation: SlabNo Private Pool
Parking & Garage Open Parking Spaces: 4No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 4Parking: Asphalt,Driveway
Pool Pool: None
Frontage Not on Waterfront
Water & Sewer Sewer: Public Sewer
Finished Area Finished Area (above surface): 3130 Square Feet

Days on Market
Days on Market: 33

Property Information
Year Built Year Built: 1910
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Colonial
Building Construction Materials: BrickNot a New Construction
Property Information Condition: ExcellentParcel Number: 1103150526

Price & Status
Price List Price: $1,150,000Price Per Sqft: $367
Status Change & Dates Possession Timing: Close Of Escrow

Active Status
MLS Status: ACTIVE

Media
See Virtual Tour

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

Agent Information
Listing Agent Listing ID: MDFR2082574

Building
Building Area Building Area: 4209 Square Feet

Community
Not Senior Community

HOA
No HOA

Lot Information
Lot Area: 0.31 acres

Listing Info
Special Conditions: Standard

Offer
Listing Agreement Type: Exclusive Right To Sell

Business
Business Information Ownership: Fee Simple

Miscellaneous
BasementMls Number: MDFR2082574Municipality: MiddletownAbove Grade Unfinished Area: 3130

Additional Information
Source Internet Entire Listing Display: Y

Last check for updates: about 1 hour ago

Listing courtesy of Bobbi Prescott, (301) 514-6163

RE/MAX Results, (301) 698-5005

Listing Team: Bobbi Prescott & Associates

Source: Bright MLS, MLS#MDFR2082574

Also Listed on Bright MLS.

Market trends in Middletown

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

5MoM

Price History for 19 E Main St

Date	Price	Event	Source
05/28/2026	$1,150,000	Listed For Sale	Bright MLS #MDFR2082574

04/13/2018	$399,900	Sold	N/A
Recording Date 04/13/2018 Contract Date 04/10/2018 County Transfer Tax N/A Total Transfer Tax $2,000
03/27/2018	$359,900	Pending	Agent Provided

03/27/2018	$359,900	PendingToActive	Agent Provided

03/27/2018	$359,900	Pending	Agent Provided

03/07/2018	$359,900	Listed For Sale	Agent Provided

09/02/2017	$399,999	ListingRemoved	Agent Provided

06/09/2017	$399,999	PendingToActive	Agent Provided

06/09/2017	$399,999	Pending	Agent Provided

05/26/2017	$399,999	PendingToActive	Agent Provided

05/26/2017	$399,999	Pending	Agent Provided

05/26/2017	$399,999	Pending	Agent Provided

05/05/2017	$399,999	Listed For Sale	Agent Provided

05/02/2017	$300	Sold	N/A
Recording Date 05/02/2017 Contract Date 04/19/2017 County Transfer Tax N/A Total Transfer Tax $6
03/25/2017	$414,900	PriceChange	Agent Provided
Price Change $10,000 (-2%)
03/18/2017	$424,900	PendingToActive	Agent Provided

02/27/2017	$424,900	Pending	Agent Provided

02/22/2017	$424,900	PriceChange	Agent Provided
Price Change $35,000 (-8%)
12/05/2016	$459,900	PriceChange	Agent Provided
Price Change $15,100 (-3%)
11/08/2016	$475,000	PriceChange	Agent Provided
Price Change $24,900 (-5%)
10/28/2016	$499,900	PriceChange	Agent Provided
Price Change $15,000 (-3%)
09/22/2016	$514,900	PriceChange	Agent Provided
Price Change $20,000 (-4%)
08/09/2016	$534,900	Listed For Sale	Agent Provided

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Property Tax and Assessment

Year	2025
Tax	$8,925
Assessment	$607,800

Home facts updated by county records

Comparable Sales for 19 E Main St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
107 Broad St, Middletown, MD	0.25	Single-Family Home	$350,000	09/05/25	3	2.5	2,484
206 Prospect St, Middletown, MD	0.23	Single-Family Home	$425,000	10/07/25	4	2	1,954
95 E Green St, Middletown, MD	0.20	Single-Family Home	$669,000	12/12/25	4	3.5	2,748
7217 Dogwood Ln, Middletown, MD	0.19	Single-Family Home	$675,000	08/15/25	4	3	3,190
207 Broad St, Middletown, MD	0.28	Single-Family Home	$500,000	03/13/26	4	2	2,210
107 S Jefferson St, Middletown, MD	0.20	Single-Family Home	$435,000	04/21/26	3	2	1,584
215 Broad St, Middletown, MD	0.30	Single-Family Home	$560,000	04/09/26	4	3	2,580
209 Ingalls Dr, Middletown, MD	0.23	Single-Family Home	$679,900	08/01/25	3	3	2,774
26 Walnut St, Middletown, MD	0.44	Single-Family Home	$685,000	04/28/26	4	2.5	2,712
200 E Main St, Middletown, MD	0.22	Single-Family Home	$700,000	04/30/26	6	2	3,441

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Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 19 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
Resident
10mo 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
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Haileyrockwell
Visitor
7y ago
"Quiet, well kept. everyone is neighborly, small town vibe. Local farmers, schools are close together. "
0
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Ctauscher10@gmail.com
Resident
7y 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
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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
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Graysonramsburg
Resident
7y ago
"20 minute drive to Frederick... about 12 miles distance. Traffic usually moving but can be heavy during school year."
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Michele M.
Resident
7y ago
"well kept yards, safe to walk day and night, kid's community sports, award winning schools, quiet community"
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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"
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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. "
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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. "
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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
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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!"
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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"
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LGBTQ Local Legal Protections

Bobbi Prescott, RE/MAX Results, (301) 698-5005

Agent Phone: (301) 514-6163

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

19 E Main St, Middletown, MD 21769 is a 4 bedroom, 4 bathroom, 3,130 sqft single-family home built in 1910. This property is currently available for sale and was listed by Bright MLS on May 21, 2026. The MLS # for this home is MLS# MDFR2082574.

19 E Main St Middletown, MD 21769

$1,150,000

$1,150,000

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19 E Main St
Middletown, MD 21769