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33 E Main St, 
Middletown, MD 21769

$375,000


6

Beds


4

Baths


3,034

Sq Ft


Single Family

Pending

Listed by

Patrick Skees

Pearson Smith Realty, LLC., listinginquires@pearsonsmithrealty.com

Last updated:

July 12, 2026, 10:09 AM

MLS#

MDFR2082944

Source:

BRIGHTMLS

About This Home

33 E Main St

Rare Opportunity: Own 2 Units for the Price of 1 in Historic Middletown! Discover this exceptional multi-unit property in the heart of charming, historic Middletown—perfectly positioned for a lifestyle of convenience, character, and potential. Stroll to your favorite restaurants, boutique shopping on vibrant Main Street, and scenic local parks featuring jogging trails, streams, and lush green spaces. Immerse yourself in the rich history and timeless beauty this community has to offer! The main residence is a classic Historic Victorian boasting 3 bedrooms and 1.5 baths, rich with the architectural elegance and original details you’d expect: ornate moldings, grand proportions, and old-world charm. This diamond in the rough offers incredible potential for the visionary buyer or investor—Investor Alert! The primary residence requires renovation and will not qualify for standard financing options (such as FHA 203(b), Conventional, VA, or USDA) due to the lack of operational heat and other needed repairs. Bring your creativity and contractor to restore this beauty to its former glory. Complementing the main home is a spacious detached 3-bedroom, 1-bath apartment with its own entrance, located at the rear of the property. This unit is in excellent, move-in ready condition and includes a 3-car garage—an incredible bonus for parking, storage, or hobbies. Versatile Living Options: Occupy the apartment while renovating the main Victorian at your own pace or possible rental /Airbnb for strong income potential. Ideal for extended family, guests, or generating passive revenue in a highly desirable historic district. This rare package combines historic appeal, modern practicality, and strong investment upside in one of Middletown’s most walkable locations. Don’t miss your chance to own a piece of history with immediate income or living flexibility! Schedule your private showing today—properties like this don’t last long.

Home Facts

Single Family

4 Baths

6 Bedrooms

Built in 1910

Price Summary

375,000

$123 per Sq. Ft.

MLS #:

MDFR2082944

Last Updated:

July 12, 2026, 10:09 AM

Added:

12 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

6

Bathrooms

Total Bathrooms:

4

Full Bathrooms:

2

Interior

Living Area:

3,034 Sq. Ft.


Structure

Structure

Architectural Style:

Colonial

Building Area:

3,034 Sq. Ft.

Year Built:

1910


Lot

Lot Size (Sq. Ft):

13,503


Finances & Disclosures

Finances

Price:

$375,000

Price per Sq. Ft:

$123 per Sq. Ft.

Source:BRIGHTMLS
The information being provided by Bright Mls is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Bright Mls All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.