216 E Main St

Middletown MD 21769

4344 sq. ft.

23490 sq. ft.

Single-Family

Last sold for $810,000

Denise Briggs, last sold this property on 29 June 2026 after 61 days on market.

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

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in Middletown over the last 12 months, the estimated median property value of 216 E Main St is $810k.

Median value

$810k

Estimated value range

$1 - $1.23m

Median days on market

Estimated value trend

increase over the last 12 months

Average days on market is based on recent, comparable sales in Middletown. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 216 E Main St

2026

Sold

$810,000

29 Jun 2026 by Denise Briggs, of Redfin Corp

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.