216 E Main St, Middletown, MD 21769 | Pending

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Off-Market Call for Pricing

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  • (0)
  • 5 Bedrooms
  • 6 Bathrooms
  • 3,296 Sq Ft
  • 23,490 Sq Ft

Description

***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.

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Amenities

Garage
Pool
Garden
Security System
Internet
Telephone
Heating
Fireplace
Balcony & Patio
TV / Cable
Laundry
Hardwood Floors
Spa
Air Conditioning
Solar Power
Floor Plan
Great Views
Natural Light
Quiet
Water View
Elevator
Guest Unit(s)
Furnished
220 Volt

Income

Rental Units


The income description goes here to explain

Expenses

Property Details

List Price $775,000
Property Type Single Family Homes
Usable Sqft 3,296
Number of Stories 0 stories
Parking Spots 3 spots
Year Built 1900
Last Sold Unknown
Sold Price Unknown
APN # 1103139530
MLS # MDFR2080572
Property ID 294419230
Lot Sqft 23,490
Zoning RESIDENTIAL
Days on Market 30
Original List Price Unknown
Applicances Refrigerator,Stove,Icemaker,Dishwasher%
Date Updated May 19, 2026
Date Created April 28, 2026

Listing Provided By

Denise M Briggs an agent of . Lic #582475


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Data last updated: May 28, 2026.
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