Back 216 E Main St
Active

216 E Main St

Middletown MD 21769

5
6
3
4344 sq. ft.
23490 sq. ft.
Single-Family
Currently for sale - view listing

Overview

***Highest & Best offers due Saturday, May 16 8PM***Featured in WASHINGTONIAN, this iconic Victorian “Painted Lady” in the heart of Middletown’s historic district, offering timeless architecture paired with modern comfort. This one-of-a-kind residence showcases striking curb appeal with its signature twin turrets, intricate woodwork, and charming front porch that sets the tone for what awaits inside. Boasting 5 bedrooms, 4 full baths, and 2 half baths, this home offers exceptional space and flexibility for everyday living and entertaining. Interior features include soaring ceilings, original hardwood floors with detailed inlay, pocket doors, and elegant millwork that highlight the home’s historic craftsmanship. Multiple living and dining areas are anchored by beautiful fireplaces, creating warm, inviting spaces throughout. A bright sunroom adds additional living space, perfect for relaxing year-round. The home has been thoughtfully updated to meet today’s lifestyle while preserving its character, including a modernized kitchen, a butler’s pantry with a wine fridge, and key system improvements. Large windows fill the home with natural light, enhancing its bright and airy feel. Step outside to a private backyard oasis featuring a pool, a 6-person hot tub, and outdoor living space, perfect for relaxing or hosting gatherings. A fenced garden space on the south side of the property offers excellent sunlight—ideal for gardening enthusiasts or those seeking a peaceful outdoor retreat. A rare 3-car garage provides ample parking and storage—an exceptional find for a property of this era. Situated on a generous lot just moments from downtown Middletown, enjoy convenient access to local shops, dining, parks, and commuter routes. A true statement property combining historic charm, functional space, and lifestyle amenities—opportunities like this are rare. Located just across the street from Middletown’s 3rd–12th grade school campus and town park—offering exceptional convenience for school drop-offs, sports, events, and activities.

Features

5 bedrooms
6 bathrooms
3 carspaces
3 garage spaces
4344 sq. ft. floor area
23490 sq. ft. lot size
Single-Family

Property history for 216 E Main St

2020
Sold
$550,000
28 Aug 2020 by Terry LaScola, of Welcome Home Realty Group

Happy sellers in Middletown

~%

We have insufficient information to provide an overview of customer satisfaction for Middletown. Viewing the agent profiles, reviews and sales for Middletown can provide insights for this location.

Local market activity for 5 bedroom single-family properties in Middletown

In the last 12 months, 23 five-bedroom single-family properties similar to 216 E Main St, have been sold.

This represents a 5% increase in five-bedroom single-family properties sales when compared to the previous 12 months.

© 2026 RateMyAgent