Change Real Estate Presents:

19 E Main Street
Middletown MD 21769

For Sale: $1,150,000.00 Active

List Date: 2026-05-28

Middletown
4 bedrooms
4 bathrooms
3,130 build ft2
13,296 land ft2

About This Property

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.

Listing Agent: Bobbi Prescott. RE/MAX Results 301-514-6163 bobbiprescott@gmail.com

Virtual Tours / Videos

https://keycitymedia.hd.pics/19-E-Main-St/idx

Property Features

Location Information
County:
Subdivision: MIDDLETOWN VALLEY
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Interior Features
Appliances: Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Microwave, Oven - Wall, Range Hood, Refrigerator, Stainless Steel Appliances, Washer, WaterHeater
Interior: 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), Wood Floors
Laundry:
Furnished: None
Flooring: Wood, Tile/Brick
Water: Public
Cooling: Central A/C
Heating: Heat Pump - Gas BackUp, Radiant, Zoned
Fireplaces: 1
Windows: Vinyl Clad
Utilities:
Sewer: Public Sewer
Exterior Features
Year Built: 1910
Subdivision Name: Middletown Valley
Exterior Features: Chimney Cap(s), Extensive Hardscape, Exterior Lighting
Parking: Asphalt Driveway, Paved Driveway
Schools
Elementary School: Middletown
Junior High School: Middletown
High School: Middletown

IDXListing Courtesy of Bobbi Prescott. RE/MAX Results 301-514-6163 bobbiprescott@gmail.com

Property Photos [Click to enlarge]

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