UPDATED PROFESSIONAL PHOTOS POSTED 3/19. Welcome to 400 S Main St, a versatile and well-located 4 bedroom, 2 full bath detached home in the heart of historic Woodsboro. The current layout and use offer the unique ability to function as a single-family residence or convert back to be utilized/rented as a 2 unit multi-family, providing excellent flexibility for owner-occupants or investors alike. Inside, the home offers light-filled living areas with a practical floor plan that easily accommodates multi-generational living or separate living spaces. Each level features comfortable bedrooms and renovated full bath access, allowing for privacy and functional separation if needed. Outside, enjoy a manageable yard, off-street driveway with a 6+car parking lot, and a convenient Main Street location just steps from local shops, dining, parks, and community amenities. With close proximity to major commuter routes while maintaining a small-town feel, this property presents a rare opportunity for flexible living, rental income potential, or long-term investment in a sought-after Woodsboro location. 2026 UPGRADES: structural repairs to foundation, side porch concrete being redone, painted metal roof, new LVP flooring throughout upper and lower level, fresh paint throughout, bathrooms renovated, turn key move in ready!
HUGE PRICE IMPROVEMENT BY THESE MOTIVATED SELLERS!! If you’re looking for easy, one level living, look no further! This well cared for, one owner home will give you everything you want and more. With gorgeous Oak flooring throughout, you will appreciate the openness of the living spaces. Maple, soft close cabinets frame the kitchen, giving you tons of storage along with beautiful Corian countertops. The kitchen island is the cherry on top of the sundae, providing seating and extra counter space. For convenience you have a separate laundry room space with Maple cabinets that carry over from the kitchen for consistency. A large, full bath is located in the hall, as you walk back towards the bedrooms. Both bedrooms are spacious with large walk in closets that have charming pocket doors and the main bedroom has a spacious en-suite bath with walk-in shower and grab bars. But wait! There’s still more! A larger oversized garage will provide you lots of room for storage or maybe a small workshop….but that’s not even the best part….how about a 1200 sq foot basement? Ready for you to use your creativity on and create that ideal space. Sky is the limit down here, and there’s room for making it multiple rooms. This home is truly a must see! Professional photos coming soon!
This well-maintained duplex is located directly on Main Street and offers a strong investment opportunity with reliable, long-term tenants in place. Both units are separately metered, and tenants pay their own utilities in addition to rent. Unit A (Main Level) • 1 Bedroom 1 Full Bath • Rented for $960 per month • Spacious living room with large front-facing window overlooking the porch and Main Street • Generously sized bedroom (king-sized) • Full bath and functional kitchen with appliances • Access to basement for private laundry and storage (washer and dryer are tenant-owned) The current tenant in Unit A also serves as the property caretaker and has maintained the home responsibly. Unit B (Upper Level – Two Floors) • 2 Bedrooms 1 Full Bath • Rented for $1,070 per month • Private entrance • Remodeled kitchen with updated cabinetry and flooring • Balcony off kitchen overlooking fenced backyard • Hardwood flooring throughout most of the main level • Large second-floor bedroom plus substantial storage space Additional features include off-street parking for two vehicles and a fenced yard. Recent Capital Improvements: • Roof replaced (2021), Chimney repairs (2021), New sump pump (2021), Unit A: New water heater, and furnace burner replacement (2022), Replacement windows, • Plaster repairs and gutter replacement (2024) Both tenants have a strong payment history and have expressed interest in remaining with a new owner, offering continuity of income from day one. With Main Street positioned for continued revitalization, this property presents both immediate cash flow and long-term appreciation potential.
Bright and well-maintained, this 2-bedroom, 2-bath garden-style condo offers low-maintenance living in the heart of Woodsboro. Located on the third floor with elevator access, this home provides both comfort and convenience at an excellent value. The spacious eat-in kitchen flows into a comfortable living area with access to a private balcony—ideal for everyday living or entertaining. A detached one-car garage adds valuable storage and parking convenience. The hot water heater was replaced just two years ago, offering efficiency and peace of mind for the next owner. Motivated sellers are offering $3,000 toward buyer closing costs, creating a great opportunity to reduce out-of-pocket expenses. Set in a quiet, friendly community with easy access to parks, dining, and major commuter routes, this condo checks the boxes for affordability, location, and lifestyle.
Welcome to this charming and updated farmhouse-style home in the heart of Woodsboro. Originally built in 1900 and fully renovated in 2016, this property beautifully blends classic character with modern updates. Throughout the home, you'll find updated flooring, fresh paint, recessed lighting, and energy-efficient systems including a newer HVAC heat pump, washer and dryer and a brand new water heater. The insulation, siding, windows, roof, electrical, and plumbing have all been updated, giving peace of mind and move-in ready confidence. Offering 3 bedrooms and 2 full bathrooms, this sun filled home features an open main level with a spacious living and dining area, a well-appointed kitchen, and a convenient main-level laundry and mudroom. Outside, enjoy the welcoming front porch, rear deck, and fenced rear yard with a storage shed—perfect for relaxing or entertaining. The property also has a well established garden including multiple berry bushes, perennials, native species, and wildflowers, and a ready to go chicken coop /run approved through the town for up to 5 chickens. Sitting on a 0.12-acre lot with both residential and commercial zoning, this home offers added flexibility for work-from-home needs or future business potential. Located just minutes from local parks, commuter routes, and highly rated Frederick County schools, this home is a rare find in a quaint small-town setting—no HOA and full of charm!
Spanning 83 acres of scenic countryside, this farm property features a thoughtfully renovated log home, a spacious barn, and a functional shed, providing a comfortable and practical living space. Strategically placed across the property are 10 custom hunting blinds, offering privacy and an exceptional hunting experience for deer, doves, and ducks. Embrace the tranquility of the expansive landscape, where nature's beauty meets modern functionality. The property also boasts up to 5 ag cluster development rights, offering potential for further development. Whether you're seeking a serene retreat or a hunter's paradise, this property offers endless possibilities for relaxation, outdoor activities, and the enjoyment of nature's bounty.
Woodsboro is located in Maryland. Woodsboro, Maryland has a population of 1,242. Woodsboro is less family-centric than the surrounding county with 31.68% of the households containing married families with children. The county average for households married with children is 35.88%.
The median household income in Woodsboro, Maryland is $123,333. The median household income for the surrounding county is $106,129 compared to the national median of $69,021. The median age of people living in Woodsboro is 45.7 years.
The average high temperature in July is 87.5 degrees, with an average low temperature in January of 23.1 degrees. The average rainfall is approximately 42.4 inches per year, with 22.7 inches of snow per year.
