19 E Main Street

Middletown, MD
$ 1,050,000 Beds 4 Baths 3.5 Sq 3,130
Monthly Estimate* How much can I afford?

Carefully reimagined between 2018 and 2021 with over $1.5M in updates, 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 homes historic character. Outdoor living spaces feel like an extension of the home itself with stamped concrete, custom stone fireplace, a covered entertaining area, 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 statement lighting and additional storage. The finished attic was transformed into a truly unique owners 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 has 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 Marylands historic designated Main Streets, just steps from Middletowns restaurants, library, shops, parks, & sought-after schools, this extraordinary residence offers a lifestyle as rare as the home itself. Sellers are sad to leave, as they finished it as their forever home.

ACTIVE

  • Price
  • $ 1,050,000
  • City
  • Middletown
  • Bedrooms
  • 4
  • Full Bathrooms
  • 3
  • County
  • FREDERICK
  • Half Bathrooms
  • 1
  • Area
  • Lot Size
  • 0.31 Acres
  • Zip
  • 21769
  • Sqr Footage
  • 3,130
  • Year Built
  • 1910
  • Taxes
  • $ 9842
  • Style
  • Colonial
  • MLS#
  • MDFR2088452
Listed By: Bobbi Prescott with RE/MAX Results - 3016985005;
Data Source: Bright MLS

Features

General

Living Area 3130
Sewer Public Sewer
Heating Heat Pump - Gas BackUp,Radiant,Zoned
Cooling Central A/C
Possession Settlement
Roof Metal
Appliances Cooktop,Dishwasher,Disposal,Dryer,Exhaust Fan,Microwave,Oven - Wall,Range Hood,Refrigerator,Stainless Steel Appliances,Washer,Water Heater
Zoning R
Patio/Porch Features Balcony,Patio(s),Porch(es),Roof
Architectural Style Colonial
Construction Materials Brick
School District FREDERICK COUNTY PUBLIC SCHOOLS
Year Built 1910
View City,Scenic Vista
Levels 4
Tax Year 2027
Ownership Fee Simple
Cool Fuel Electric
Accessibility None
County FREDERICK
New Construction No
Property Type Residential
HOA No
Subdivision Name MIDDLETOWN VALLEY
Garage Y/N No
Water Access Y/N No
Other Structures Above Grade,Below Grade
Full Baths 3
Status ACTIVE
Directions Traveling West on Main Street into Middletown,Home is on the Right,just before you arrive at 17.
City MIDDLETOWN
Disclosures Prop Disclosure
Senior Community Y/N No
Lot Size Units Square Feet
Lot Size Square Feet 13296.00
Tax Assessed Value 670900.0
Tax Annual Amount 9842.89
Property Condition Excellent
Structure Type Detached
Condo/Coop Association fee Y/N No
Bathrooms Count Main Level 1.00
Price Per Sq Ft Total AG 335.46
Avg. Electric Per Month 341.0
Avg. Gas Per Month 181.58
Vacation Rental Y/N No
Avg. Water Per Month 60.0
Total SQFT 4209
Standard Status Active
Year Built Source Assessor

Interior Features

Interior Amenities Bar,Bathroom - Soaking Tub,Built-Ins,Floor Plan - Open,Formal/Separate Dining Room,Kitchen - Island,Laundry Chute,Primary Bath(s),Recessed Lighting,Sound System,Upgraded Countertops,Walk-in Closet(s)
Heating Fuel Electric,Propane - Owned
Basement Unfinished
Flooring Wood,Tile/Brick
Total Fireplaces 1
Fireplace Features Wood
Hot Water Propane
Basement (Y/N) Yes
Heating Y/N Yes
Window Features Vinyl Clad
Fireplace Y/N Yes
Above Grade Finished Area 3130
Half Baths 1
Central Air Y/N Yes
Total Bedrooms 4
Below Grade Finished Area Unit Type Square Feet
LivingAreaSource Assessor
Laundry Type Upper Floor
Below Grade Unfin Area Units Square Feet
Below Grade Unfin SQFT 1079
Below Grade Unfin SQFT Source Assessor
Below Grade Finished Area Source Assessor
Bedrooms Count All Upper Levels 4
Bedrooms Count Upper Level 1 3
Bedrooms Count Upper Level 2 1
Bathrooms Half Main Level 1
Bathrooms Full Upper Level 2 1
Bathrooms Full Upper Level 1 2
Bathrooms Full All Upper Levels 3
Bathrooms Count Upper Level 2 1.00
Bathrooms Count Upper Level 1 2.00
Bathrooms Count All Upper Levels 3
Above Grade Finished Area Source Assessor
Above Grade Finished Area Unit Type Square Feet
Total Baths 4

Exterior Features

Exterior Amenities Chimney Cap(s),Extensive Hardscape,Exterior Lighting
Pool No Pool
Parking Features Asphalt Driveway,Paved Driveway
Lot Features Additional Lot(s)
Water Source Public
Total Parking Spaces 4
Type of Parking Driveway
Foundation Details Slab
Water View Y/N No
Lot Size Acres 0.31
Lot Size Source Assessor
Waterfront Y/N No
Navigable Water Y/N No
Water Oriented Y/N No

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Martinsburg, WV office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
Adjust Payment Options
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Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Middletown Elementary School
Middle School Middletown Middle School
High School Middletown High School

Price History

8/28/2026 Listed $1,050,000

Property vs Zip Code Average in 21769

Price
AVG $860K
$1.05M
Taxes
AVG $6,144
$9,842
Year Built
AVG 1969
1910
Visits
AVG 127
73
Data Provided by Inside Real Estate®

Areas That We Cover

19 E Main Street Middletown, MD is a Single Family Home for sale at $1050000 with 3130 sqft and a lot size of 0.31 Acres Acre(s). 19 E Main Street Middletown has 4 bedrooms, 3 baths and was built in 1910. The property's zip code is 21769 which is in Middletown, MD

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.