21 Woodlawn Avenue • Annapolis, MD 21401

$899,000 Beds: 3 • Baths: 2 full • Sq. Feet: 1442 • MLS ID: MDAA2144864 • Subdivision: HOMEWOOD • School Dist: ANNE ARUNDEL COUNTY PUBLIC SCHOOLS
Step into the charm and character of Annapolis living at 21 Woodlawn Ave — a beautifully updated 1905 home in the Germantown-Homewood community, blending timeless architecture with thoughtful modern improvements, all in one of the city’s most walkable locations. This 3-bedroom, 2-bath home is filled with warmth and original character, featuring high ceilings, hardwood floors, natural light, and a stunning wrap-around three-seasons porch that acts like an extension of the living space. The renovated kitchen offers brand-new cabinetry, appliances, and finishes while maintaining the home’s historic charm. Additional recent updates include all new interior and exterior paint, newly refinished hardwood floors on the second level, bathroom upgrades, and the addition of a functional mudroom at the rear entrance. Beyond the home itself, the property offers something truly rare in downtown Annapolis — an exceptionally spacious backyard with incredible flexibility and future potential. Whether you envision expanding outdoor living space, creating gardens, building an in-law suite or private office above/within the existing garage footprint, or exploring the possibility of subdivision (buyer to verify), the opportunities here add meaningful long-term value. Bonus features include a walk-up unfinished attic with potential to create additional finished living space, an unfinished basement with laundry area and exterior access, and off-street parking that is increasingly hard to find this close to town. Enjoy the lifestyle that comes with this location — just moments from downtown Annapolis, City Dock, Navy-Marine Corps Memorial Stadium, Naval Academy events, Maryland Hall, restaurants, coffee shops, the library, and the Poplar Trail bike path. A rare opportunity to own a piece of Annapolis history with space, flexibility, and future potential close to the heart of the city. View this listing at: http://ryanbrennerrealtor.com/mls=MDAA2144864

Property Features

  • Garage: 1
  • Taxes: $6,831
  • Basement: Yes
  • Exterior: Aluminum Siding
  • Parking Notes: 1 Total Parking Spaces
  • Lot Size: 0.26 Acres
  • Lot Dimensions: 0.26 Acre(S)
  • Heating: Heat Pump(s)
  • Fuel Type: Natural Gas
  • Cooling: Central A/C
  • Year Built: 1905
  • Water: Public
  • Sewer: Public Sewer
  • Stories: 3.0
  • Municipality: Annapolis
  • Additional Structures: Above Grade,Below Grade
  • Structure Type: Detached
  • Total Garage/Parking Spaces: 1
  • Appliances: Microwave,Dishwasher,Disposal,Dryer,Refrigerator,Stainless Steel Appliances,Range Hood,Washer,Water Heater,Oven/Range - Gas
  • Basement: Unfinished,Connecting Stairway,Outside Entrance
  • SQFT Total Finished: 1442
  • SQFT Above Finished: 1442
  • Interior: Attic,Bathroom - Stall Shower,Crown Moldings,Dining Area,Floor Plan - Traditional,Formal/Separate Dining Room,Kitchen - Island,Wood Floors
  • Flooring: Ceramic Tile,Hardwood

School Information

  • High School: ANNAPOLIS
  • Middle School: BATES
  • Elementary School: GERMANTOWN
  • School District: ANNE ARUNDEL COUNTY PUBLIC SCHOOLS
Printed May 09, 2026


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Ryan Brenner 

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