# 19 E MAIN Street, Middletown, MD 21769 > **TL;DR:** 4bd/4ba single family, $1,050,000 ($335/sqft), built 1910, 3,130 sqft. > Fireplace, A/C. Est. $5,615/mo. Listed 22 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $1,050,000 | | Price/sqft | $335 | | Bedrooms | 4 | | Bathrooms | 3 full, 1 half | | Square Feet | 3,130 | | Year Built | 1910 | | Lot Size | 13,295 sqft (0.31 acres) | | Stories | 4 | | Property Type | Single Family (Other) | | Status | Active | | Days on Market | 22 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $5,309 | | Estimated Insurance | $306 | | **Total** | **$5,615** | ## Nearby Schools - **Elementary:** MIDDLETOWN - **Middle:** MIDDLETOWN - **High:** MIDDLETOWN ## Key Amenities - Fireplace - A/C ## Property Highlights - Built in 1910 - 0.31 acre lot - 4 stories - 4 parking spaces - Fireplace ## Description ### Agent Description 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 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, 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 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 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 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. Sellers are sad to leave, as they finished it as their forever home. ## Location - **Address:** 19 E MAIN Street, Middletown, MD 21769 - **County:** FREDERICK - **Neighborhood:** MIDDLETOWN VALLEY - **Coordinates:** 39.44396429, -77.54368974 - **Google Maps:** https://www.google.com/maps?q=39.44396429,-77.54368974 ## Listing Agent - **Name:** Bobbi Prescott · **License:** 603372 - **Brokerage:** RE/MAX Results - **Phone:** (301) 698-5005 - **Broker Phone:** (301) 698-5005 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/19-E-Main-St_Middletown_MD_21769_M68667-44979?f=listhub&s=TRENDPA&m=MDFR2088452&c=propsimple) ## Photos ![19 E MAIN Street - Photo 1](http://lh.rdcpix.com/6bca9f4d93f475685c193c85cd1076cbl-f745424363r.jpg) ![19 E MAIN Street - Photo 2](http://lh.rdcpix.com/6bca9f4d93f475685c193c85cd1076cbl-f2823368550r.jpg) ![19 E MAIN Street - Photo 3](http://lh.rdcpix.com/6bca9f4d93f475685c193c85cd1076cbl-f3048257803r.jpg) ![19 E MAIN Street - 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Photo 124](http://lh.rdcpix.com/6bca9f4d93f475685c193c85cd1076cbl-f459385884r.jpg) ![19 E MAIN Street - Photo 125](http://lh.rdcpix.com/6bca9f4d93f475685c193c85cd1076cbl-f4201239352r.jpg) ![19 E MAIN Street - Photo 126](http://lh.rdcpix.com/6bca9f4d93f475685c193c85cd1076cbl-f2452173225r.jpg) ![19 E MAIN Street - Photo 127](http://lh.rdcpix.com/6bca9f4d93f475685c193c85cd1076cbl-f2403468134r.jpg) ![19 E MAIN Street - Photo 128](http://lh.rdcpix.com/6bca9f4d93f475685c193c85cd1076cbl-f3234065772r.jpg) ![19 E MAIN Street - Photo 129](http://lh.rdcpix.com/6bca9f4d93f475685c193c85cd1076cbl-f313419625r.jpg) ![19 E MAIN Street - Photo 130](http://lh.rdcpix.com/6bca9f4d93f475685c193c85cd1076cbl-f3605744243r.jpg) ![19 E MAIN Street - Photo 131](http://lh.rdcpix.com/6bca9f4d93f475685c193c85cd1076cbl-f2095902817r.jpg) ![19 E MAIN Street - Photo 132](http://lh.rdcpix.com/6bca9f4d93f475685c193c85cd1076cbl-f1925015646r.jpg) --- **MLS#:** MDFR2088452 | **Updated:** 2026-08-28 **Source:** listhub *Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/19-e-main-street-middletown-md-21769-r2088452) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/19-e-main-street-middletown-md-21769-r2088452#listing", "url": "https://www.propertysimple.ai/listing/19-e-main-street-middletown-md-21769-r2088452", "name": "19 E MAIN Street, Middletown, MD 21769", "description": "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 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, 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 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 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 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. 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