19 E MAIN STREET, MIDDLETOWN, MD 21769 - Breathe Easy Properties Collaborative

$1,150,000

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… Read More 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. Read Less

Courtesy of Bobbi Prescott, RE/MAX Results 301-698-5005

Listing Snapshot

Days Online

Last Updated

May 24, 2026

Property Type

Single Family Residential

Beds

Full Baths

Partial Baths

Square Ft.

3,130

Lot Size

0.31 Acres

Year Built

1910

MLS Number

MDFR2082574

Additional Details

Appliances & Equipment

Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Microwave, Oven - Wall, Range Hood, Refrigerator, Stainless Steel Appliances, Washer, Water Heater

Basement

Unfinished

Building

Built in 1910, Living area: 3130, Levels: 4, Construction Materials: Brick

Cooling

Central A/C

Accessibility Features

None

Exterior Features

Patio/Porch Features: Balcony, Patio(s), Porch(es), Roof, Chimney Cap(s), Extensive Hardscape, Exterior Lighting

Fireplaces

1 fireplace, Wood

Floors

Wood, Tile/Brick

Foundation

Slab

Heating

Heat Pump - Gas BackUp, Radiant, Zoned

Interior Features

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

Lot

0.31 acres, Additional Lot(s)

Parking

Asphalt Driveway, Paved Driveway

Property

Excellent, Other structures: Above Grade, Below Grade, City, Scenic Vista

Roof

Metal

Sewer

Public Sewer

Taxes

Annual Amount: $8,777, Year: 2025, Zoning: R

Utilities

Water Source: Public

Windows

Vinyl Clad

Find The Perfect Home

'VIP' Listing Search

Whenever a listing hits the market that matches your criteria you will be immediately notified.

Join The List

Mortgage Calculator

Selling price

Down payment

Term (years)

Interest rate (%)

Monthly Payment

19 E MAIN STREET

'VIP' Listing Search

Schools In The Area

Similar Listings

Find My Dream Home

1. Neighborhoods

2. Home Type

3. Send

Sitemap