Under Contract

MLS: #MDFR2088606, Listed By: Bobbi Prescott, RE/MAX Results, Source:Bright MLS

305 E Main Street

MIDDLETOWN, MD 21769
Mark as Favorite
Bed 3

Bed

Bath 3

Bath

SqFt3,000

Sqft

Acres0.60

Acre(Lot)

Step into timeless charm without leaving behind today's comforts. This distinctive Painted Lady captures the character, craftsmanship, and gracious proportions that make a home truly memorable, right in the heart of Middletown. Set well back from historic Main Street behind an expansive front lawn, the home has an impressive presence, with a wide wraparound porch inviting you to sit awhile and enjoy the rhythm of small-town living. Located within the sought-after Middletown school district, this is a home that feels a part of the town’s story. Offering over 3,000 finished square feet above grade, the home has been lovingly cared for by the same owners since 1997. Natural light and tall ceilings on every level create a remarkably open and airy feel, while fresh paint complements the beauti ful architectural details throughout. An impressive entry foyer sets the tone with original millwork and wood floors, fireplace mantels, pocket doors, a built-in bookcase, and a distinctive split staircase. Stacked bay windows on separate levels feature diamond-pattern divided-light upper sashes and clear glass below—one of the many details that makes this home so special. The spacious front living room features custom built-ins, a fireplace, and pocket doors connecting both the foyer and dining room. The large dining room is ready for holidays, celebrations, and everyday dinners, with a side door opening directly onto the wraparound porch. The updated kitchen blends classic character with modern function, featuring a large center island, wall oven, cooktop, built-in cabinetry, and a charming original pass-through cupboard. A mudroom provides a practical everyday entrance and access to the covered rear porch, while a main-level half bath adds convenience. Upstairs are three generously sized bedrooms, including a spacious primary suite with a private full bath, plus an additional hall bath. An open loft area provides flexible space for an office, study, reading nook, or sitting area. The completely remodeled finished third floor adds another exceptional level of living space, with tall ceilings, abundant natural light, a large recreation room, separate den, and laundry area. Use it as an office, studio, exercise space, media room, hobby room, or private retreat. A unique glass-floor feature allows light to pass through and adds an unexpected architectural element. Outside, there is room to breathe—something increasingly difficult to find right in the heart of town. The large, level property stretches from Main Street to Green Street with access from both streets, offering an expansive front lawn and spacious backyard. A detached one-car garage adds convenience, while eligibility for future subdivision through the Town of Middletown adds another unique dimension. Additional features include air conditioning, radiator heat, updated electrical, a clean unfinished basement for utility and storage, and eligibility for a one-year home warranty. Perhaps what makes this home most memorable is simply the feeling of it—the sunlight, tall ceilings, warmth of the wood floors, beautiful architectural details, and the ability to step onto that wonderful wraparound porch and watch Main Street go by. Filled with charm and personality, yet offering the light, space, and functionality for the way we live today, this gracious Painted Lady is ready for its next chapter.

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Detail Ic Property Details

Property Type : Residential

Price : $650,000

AD Id : 90913978

MLS Id : MDFR2088606

Beds : 3

Lot Size : 0.60 Acre

Living Area Size : 3,000

Tax Amount : 7550.52

Year Built : 1913

Garage : 1

County : FREDERICK

Subdivision: Middletown

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Map

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Feature Features

  • Bedroom Information

    Total beds: 3

    Bathroom Information

    Total Baths: 3 Full Baths: 2 Half Baths: 1

    Room Information

    Has Basement: Yes Basement: Daylight, Partial
  • Flooring Information

    Wood, Hardwood
  • Roofing Information

    Slate
  • Interior Features

    Kitchen Island, Built-in Features Roof: Slate Appliances: Oven, Electric Water Heater, Stainless Steel Appliance(s), Refrigerator, Cooktop, Dishwasher, Disposal, Washer, Dryer Laundry Features: Upper Level Window Features: Bay Window(s)
  • Heating & Cooling

    Has Heating: Yes Heating: Oil, Radiant Has Cooling: Yes Cooling: Central Air, Electric

  • Building Information

    Year Built: 1913 Building Area Total: 3000 Construction Materials: Wood Siding Patio And Porch Features: Porch Pool Features: None Private Pool: No

  • Lot Information

    Lot Size Acres: 0.6 Lot Size Source: Estimated Lot Size Square Feet: 26100

    Property Information

    Subdivision: MIDDLETOWN Source Property Type: Residential Postal Code Plus 4: 7928 Property SubType: Single Family Residence Levels: Three Or More Property Age: 113

  • Listing Price Information

    Listing Price: $650000

  • Tax Information

    Parcel Number: 1103130002 Tax Year: 2027 Annual Tax: $7550.52

  • Parking Information

    Parking Total: 7 Garage, Driveway, Detached

    Garage Information

    Has Garage: Yes Garage Space: 1

  • School Information

    Elementary School: MIDDLETOWN
    Junior High School: MIDDLETOWN
    Senior High School: MIDDLETOWN
  • Location Information

    Direction: Main Street, center of town by Schoolhouse Drive WaterSource: Public
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
Mountain Church Road, Middletown, MD, 21769 $924,500 3 3 3,000 2.25 Acres
8939 Hawbottom Road, Middletown, MD, 21769 $989,000 3 3 3,236 32.39 Acres
4492 Jade Court, Middletown, MD, 21769 $539,900 4 3 2,200 0.55 Acre
7 Derr Lane, Middletown, MD, 21769 $625,000 3 3 2,208 0.09 Acre
411 Glenbrook Drive, Middletown, MD, 21769 $799,900 4 4 4,603 0.24 Acre
718 E Main Street, Middletown, MD, 21769 $499,900 4 2 1,862 0.57 Acre
9001 Hollow Road, Middletown, MD, 21769 $499,900 4 3 1,432 2 Acres
708 E Main Street, Middletown, MD, 21769 $475,000 4 2 2,036 0.26 Acre
5901 Cloudberry Court, Middletown, MD, 21769 $1,185,000 4 4 3,600 1.70 Acres
5 Dean Lane, Middletown, MD, 21769 $849,000 4 5 4,497 0.16 Acre

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which ByOwner participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have closed or are no longer being offered for sale. Information Deemed Reliable But Not Guaranteed. Copyright © 2026 Bright MLS. All rights reserved.

ByOwner last updated this listing 09/08/2026 @ 08:17

MLS: MDFR2088606 LISTED BY: Bobbi Prescott, RE/MAX Results 301-698-5005 SOURCE: Bright MLS

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