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7 Beds
10 Baths
6,048 sqft

$1,299,000

4 S MAIN STREET, WOODSBORO MD, 21798

Price per sqft$214.78
Built in1919
Property size6,048 sqft
Property typeResidential

Overview

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Listed Oct 20, 2026

Updated 10h ago

Step into a remarkable piece of history at The George F. Smith House, a magnificent all-brick mansion with a fascinating connection to the Rosebud Perfume Company, which remains in business today under the ownership of his heirs. Beautifully renovated and thoughtfully updated, this extraordinary property blends historic character, timeless architectural details, and modern conveniences, offering a truly unique opportunity for its next owner. The main residence features 6 bedrooms and 5½ bathrooms, complemented by a separate guest house with 1 bedroom and 1 full bathroom. From the inviting wraparound porch with three entrances to the main level to the original stained-glass front door, this home makes a memorable first impression. Step inside the grand foyer, where a marble fireplace, built-in glass shelving, and an elegant curved staircase set the tone for the historic charm found throughout. The original portion of the home showcases hardwood flooring with decorative inlay borders and an impressive hardwood medallion in the hallway. The spacious dining room features another marble fireplace, while the family room offers beautiful wood trim and a distinctive wood coffered ceiling. The redesigned, modern kitchen seamlessly combines style and functionality with crisp white cabinetry, a center island, stainless steel appliances, and a generous butler’s pantry and serving area. Just beyond, the bright and spacious sunroom overlooks the backyard, creating a wonderful place to relax and enjoy the view. A full bathroom and a half bathroom complete the main level. The home's thoughtful design continues upstairs, where dual staircases provide convenient access to the second level. A charming sitting bench beneath overhead windows creates a lovely transition between floors. The bedroom level offers four bedrooms, including a private bedroom suite with its own bathroom and an additional primary suite with an ensuite bath. A full hall bathroom, spacious laundry room, and enclosed porch overlooking the backyard add to the home's functionality. The laundry room also offers the potential for conversion to an additional bedroom, if desired. Historic transom windows above the bedroom doors provide character and architectural interest throughout. The upper level features three additional bedrooms and a full bathroom, providing even more room for family, guests, or flexible living arrangements. The bathrooms on the upper levels retain their original octagon-and-dot patterned tile flooring, preserving another distinctive detail of the home's historic character. The unfinished lower level features a concrete floor and offers abundant space for dry storage. Significant improvements provide modern comfort and peace of mind, including a brand-new barrel tile roof, two new zoned heat pumps, and new windows throughout, along with numerous additional updates. Outside, enjoy peaceful evenings on the concrete patio surrounded by a weeping cherry tree and a charming water fountain. The fully fenced backyard also features a separate guest house with one bedroom, one full bathroom, heating and air conditioning, and the option to add a kitchen and laundry area. Whether used for extended family, guests, a private office, or other potential uses, this additional living space offers exceptional flexibility. Two storage sheds provide extra utility, while a brand-new asphalt driveway behind the fence offers ample off-street parking. The possibilities are as impressive as the property itself. With its generous living spaces, separate guest accommodations, historic significance, and extensive renovations, this remarkable mansion offers opportunities for multigenerational living, working from home, or exploring a potential bed-and-breakfast or health-related facility, subject to applicable zoning, licensing, and other requirements. A rare opportunity to own a beautifully renovated piece of Woodsboro history, where timeless elegance meets modern living.

$8,642/mo

Est. mortgage payment based on a $1,299,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
MDFR2090856

Interior Features

Bedrooms
7
Bathrooms
10
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
0.38 Acres

Other Property Details

Taxes
$9,571
Tax Frequency
Annually
View
Yes
55+/Senior Community
No
MLS provider logo

Listed by Charis Realty Group
Listing Contact: 3017480434 

The IDX display contains information sourced from the Bright MLS, Inc. as of 10/27/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

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Data last updated on 10/27/2026 at 3:35 AM UTC

 

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