Woodsboro MD Real Estate

Woodsboro is located in the North East of Frederick County, just outside of Carroll County. This town has a population of 1,200 residents and is ideal small-town living! It is a close-knit community found at the foothills of the Appalachian Mountains. With lots of parks and natural space, you have plenty options from single family homes or historic row houses.  

Browse current Woodsboro MD real estate listings below.
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2 Thru 6 Main Street Woodsboro MD 21798

Woodsboro, MD2 Thru 6 Main Street

Price$850,000

Est. Mortgage: $/month

MLS Number MDFR2060224

  • Single Family
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 1,950
  • Acreage 0.37

Live in #2 and the other 2 units #4 and #6 are rented so are the storage units. This property includes 2 Main Street, which is a single family colonial, along with 4 & 6 Main Street which is a duplex, and at the rear of the property is 12 storage garages which are all currently rented. The main house 2 Main Street has 4 bedrooms and 2 full baths, new roof, remodeled from top to bottom, fresh paint, all new vinyl windows, upstairs has plumbing for up stairs laundry, primary bedroom has a decorative fireplace. This home has a new water line, new HVAC, new concrete floors in the basement, new PVC plumbing and all new electric. The duplex 4 and 6 Main Street has been remodeled, new water line, new PVC plumbing and all new electric, new concrete floors in the basement. Egress windows installed to meet code, metal roof recently coated, remodeled kitchen and baths, fresh paint, new carpet, new HVAC, new electric, new hot water heater, new flooring and the list goes on! #2 is currently not rented. #4 is currently rented for $1650 and #6 is rented for $1700. THIS PROPERTY ALSO INCLUDES 12 STORAGE UNITS THAT ARE CURRENTLY RENTED.

Listed by Hubert R Brown III of Real Estate Teams,LLC

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$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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14 James Street Woodsboro MD 21798

Woodsboro, MD14 James Street

Price$499,000

Est. Mortgage: $/month

Open House

MLS Number MDFR2059860

  • Single Family
  • Next Open House: Sun 03/23 1:00 pm. to 3:00 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,362

Looking for small-town charm just minutes from city conveniences? Look no further! This stunning four-level split home on the edge of historic Woodsboro is the perfect match! This property offers peace of mind with major updates already taken care of and NO HOA! Nestled on a peaceful half-acre lot (approx.) at the end of a quiet, non-through street, this updated home provides a serene taste of country living. The spacious backyard offers picturesque views, and you're just a short walk from Woodsboro Park. Step onto the charming front porch and into the entry foyer, the perfect place to hang your coat. Inside, the main level features a cozy living room with beautiful hardwood floors and an upgraded kitchen boasting granite countertops and newer appliances. The upper level offers a relaxing retreat, complete with a primary suite, freshly painted and featuring a private bath. Two additional bedrooms and another full bath complete this level. The lower level is an entertainer's dream, featuring a spacious family room with a wood-burning stove and a wet bar- ideal for hosting gatherings or family game nights. A third full bath with a jetted tub adds extra convenience. But that's not all! The fourth level offers two versatile rooms, giving you plenty of space to make it your own-whether it's a home office, gym, or hobby room. Don't miss your chance to call 14 James St. home! Schedule your tour today and experience the perfect blend of small-town charm and modern convenience.

Listed by Cara Via of Charis Realty Group

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$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2 Woodsboro Creagerstown Road Woodsboro MD 21798
Pending

MLS Number MDFR2059714

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,256
  • Acreage 0.63

This charming, refurbished Colonial home in the historic town of Woodsboro offers the perfect blend of classic elegance and modern comfort. Restored with love and care, the home preserves its timeless architectural details while featuring updated amenities throughout. Inside, you'll find spacious living areas, a bright and inviting kitchen, and tasteful finishes that combine the old-world charm of hardwood floors and decorative attributes with the convenience of modern appliances and fixtures. The beautiful yard provides a serene outdoor space for relaxation and entertainment, with lush landscaping and plenty of room to enjoy the outdoors with amazing views. A unique opportunity to live in a historic setting without sacrificing contemporary comfort! This home has completely updated plumbing, electrical, windows, HVAC and appliances. Nothing to do but move in and enjoy!!

Listed by Kathy S Bromwell of RE/MAX Plus

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$
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$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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12-14 N 2nd Street Woodsboro MD 21798

Woodsboro, MD12-14 N 2nd Street

Price$225,000

Est. Mortgage: $/month

MLS Number MDFR2058998

  • MultiFamily
  • Square Feet 1,244
  • Acreage 0.18
  • Property SubType Duplex

"Exciting opportunity! An investment home is now available for future appreciation. An opportunity to own both sides. Each unit has separate electrical meters and one water meter. Lock box is on the back door, both keys in lockbox. Property Sold As Is. Don't miss out on this fantastic addition to your portfolio. Contact me for more details!"

Listed by Humberto Benitez and Crystal N Smith of Keller Williams Realty Centre

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$
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$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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125 Second Street N Woodsboro MD 21798

Woodsboro, MD125 Second Street N

Price$416,655

Est. Mortgage: $/month

Pending

MLS Number MDFR2058974

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 1,632
  • Acreage 0.06

MOVE-IN READY - LAST UNIT AVAILABLE! Welcome to Arnold Place by PDR Homes! This beautiful new construction townhome features three finished levels, oak stairs and a modern, open layout. The main living area and upper hallway showcase luxury vinyl plank flooring. The stunning kitchen is equipped with a large center island, quartz countertops, subway tile backsplash, and stainless steel appliances. The spacious owner's suite includes a walk-in closet and is complemented by a beautifully designed owner's bathroom, featuring floor-to-ceiling ceramic tile. Enjoy a low-maintenance exterior with a large rear yard. An extensive builder warranty is included for your peace of mind, and there is NO HOA. The community is conveniently located within walking distance of restaurants, shopping, and the charming downtown area of Woodsboro. Additionally, zero money down USDA financing is available, along with assistance for closing costs!! Photos are representative. Other homesites are available. Photos are representative.

Listed by Christina M Poss of Verdant Realty Group LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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11715 Clyde Young Road Woodsboro MD 21798

Woodsboro, MD11715 Clyde Young Road

Price$675,000

Est. Mortgage: $/month

MLS Number MDFR2058362

  • Single Family
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,634
  • Acreage 3

Nestled on 3 beautifully landscaped acres in the heart of Woodsboro, MD, 11715 Clyde Young Rd is a homesteader's dream come true. This historic stone home, built in the 1800s, blends timeless charm with modern upgrades. The property boasts vibrant gardens and an array of colorful flowers that come alive in the warmer months, creating a stunning outdoor oasis that's not fully visible in the winter. Offering over 1,600 square feet of living space, this property features 2 bedrooms, 1 1/2 baths, and ample room for expansion, providing the perfect combination of historic appeal and country living. The main home features updated bathrooms and a spacious second floor with plenty of headspace, ideal for a variety of uses. The newly renovated kitchen is a showstopper with top-of-the-line Craft-Made cabinets, granite countertops, a custom backsplash, and new appliances-modernizing the heart of the home while preserving its historic charm. Additional updates throughout the house include new HVAC, a 500-gallon propane tank, new chimneys, fresh interior paint, and newly reinsulated walls. Original oak floors are preserved beneath new updated 100 year floors, and new water lines have been installed to both the house and barn from the well. The detached 300+ square foot summer kitchen is a true bonus, offering a beautifully finished space with new doors, electric and a upgraded woodstove-perfect for a home office, hosting, or simply enjoying the peaceful surroundings in any season with the indoor outdoor appeal. For those seeking homesteading opportunities, this property is a dream come true. The 2400 sqft, 30x40x14 detached garage with 3 bays (including one larger bay with electric) provides abundant space for storage or workshop needs. A small barn with 2 stalls, a run-in, feed room, and chicken coop-fully equipped with electric and water-ensures that animal care is both easy and efficient. The property is fully fenced with over 1.5 acres of pasture, coated electric wire, no-climb fencing, and a PVC board fence for your dogs. The property also features extensive garden areas with raised beds, a garden shed, a koi pond, and a large fishable creek for tranquil outdoor enjoyment. With Xfinity internet and a whole-home Generac generator, modern conveniences are never out of reach and everyone can be happy! This property offers the ideal blend of old-world charm and contemporary comforts. The home comes with a transferable American Home Shield warranty for peace of mind. This one-of-a-kind historic property must be seen to truly appreciate all it has to offer. Schedule your private showing today. The pictures do not do it justice.

Listed by Kathryn E Klenk of Keller Williams Realty Partners

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$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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9575 Woodland Drive Woodsboro MD 21798

Woodsboro, MD9575 Woodland Drive

Price$449,900

Est. Mortgage: $/month

MLS Number MDFR2056442

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,456
  • Acreage 0.92

Homes in this desirable community rarely come on the market, making this 3-bedroom, 2-bath rancher a special find. Enjoy the ease of one-level living with a bright kitchen, separate dining room, and a bonus space that would be perfect for an office or playroom. There is a spacious deck overlooking a large, level lot with amazing views. The primary bedroom features an ensuite bathroom with a shower, adding comfort and convenience. With a roof that's approximately a year old, some updated windows, and a new HVAC system from 2018, this home is move-in ready. The full, walk-out basement offers excellent potential for additional space. Embrace peaceful country living with convenient access to nearby amenities!

Listed by Eleanore Louise Smith of J&B Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2 Thru 6 Main Street Woodsboro MD 21798

Woodsboro, MD2 Thru 6 Main Street

Price$850,000

Est. Mortgage: $/month

MLS Number MDFR2053444

  • MultiFamily
  • Square Feet 3,824
  • Acreage 0.37
  • Property SubType Triplex

This property includes 2 Main Street, which is a single family colonial, along with 4 & 6 Main Street which is a duplex, and at the rear of the property is 12 storage garages which are all currently rented. The main house 2 Main Street has 4 bedrooms and 2 full baths, new roof, remodeled from top to bottom, fresh paint, all new vinyl windows, upstairs has plumbing for up stairs laundry, primary bedroom has a decorative fireplace. This home has a new water line, new HVAC, new concrete floors in the basement, new PVC plumbing and all new electric. The duplex 4 and 6 Main Street has been remodeled, new water line, new PVC plumbing and all new electric, new concrete floors in the basement. Egress windows installed to meet code, metal roof recently coated, remodeled kitchen and baths, fresh paint, new carpet, new HVAC, new electric, new hot water heater, new flooring and the list goes on! Live in one unit and rent the others or rent all three. #4 is currently rented for $1650 and #6 is rented for $1700. THIS PROPERTY ALSO INCLUDES 12 STORAGE UNITS THAT ARE CURRENTLY RENTED. Also, listed in Commercial MDFR2053070.

Listed by Hubert R Brown III of Real Estate Teams,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Copyright 2025 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. 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 Premier Group | Long & Foster Real Estate, Inc. 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.Data last updated March 21, 2025. 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.