21 Woodlawn Avenue • Annapolis, MD 21401

$819,000 Beds: 3 • Baths: 2 full • Sq. Feet: 1549 • MLS ID: MDAA2144864 • Subdivision: HOMEWOOD • School Dist: ANNE ARUNDEL COUNTY PUBLIC SCHOOLS
**NEW PRICE, UPDATED SQUARE FOOTAGE + NEW PHOTOS ADDED — INCREDIBLE OPPORTUNITY!** Boasting 1,549 sq. ft. of finished historic charm, this 1905 Homewood treasure sits on a rare, oversized 0.26-acre lot—offering space and flexibility nearly impossible to find this close to City Dock. While the main house charms with high ceilings, refinished hardwoods, and a light-filled 3-seasons wrap-around porch, the true crown jewel is the backyard oasis. Surrounded by stunning, mature trees, the sprawling lawn features an existing 1-car garage ripe for transformation. Bring your vision to easily rebuild this structure into a premier Accessory Dwelling Unit (ADU), income-producing apartment, or a private home office oasis. Walk to the Navy Stadium, local cafes, and the Poplar Trail. With room to grow, update, and build equity, this is a rare Annapolis footprint waiting for your personal touch! Note on Square Footage: Finished square footage has been updated to 1,549 sq. ft. based on recent agent measurements. Public tax records currently reflect inaccurate historical data (1,442 sq. ft.) and do not fully capture the complete finished living area. View this listing at: http://yermangainesteam.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: 1549
  • SQFT Above Finished: 1549
  • 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 July 01, 2026


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The Gaines Group
Brandon Gaines, Jeffrey Gaines, Colin Gaines 

1425 Clarkview Road, Suite 700, Baltimore, MD 21209
410-583-0400