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For sale
Price cut: $50K (5/21)
$849,000

21 Woodlawn Ave, Annapolis, MD 21401

3beds
1,442sqft
: Get pre-qualified
Single Family Residence
Built in 1905
0.26 Acres Lot
$827,400 Zestimate®
$589/sqft
$-- HOA

What's special

Renovated kitchenThoughtful modern improvementsBathroom upgradesExceptionally spacious backyardTimeless architectureHigh ceilingsHardwood floors
NEW PRICE — INCREDIBLE VALUE - 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.
25 days
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1,658
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76
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Zillow last checked:

Listing updated:

Listed by:

Elizabeth Leighty 410-212-3273,

Real Broker, LLC - Annapolis 8554500442

Source: Bright MLS,MLS#: MDAA2144864MLS Logo

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    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 3
    • Bathrooms: 2
    • Full bathrooms: 2
    • Main level bathrooms: 1
    Basement
    • Area: 672
    Heating
    • Heat Pump, Natural Gas
    Cooling
    • Central Air, Electric
    Appliances
    • Included: Microwave, Dishwasher, Disposal, Dryer, Refrigerator, Stainless Steel Appliance(s), Range Hood, Washer, Water Heater, Oven/Range - Gas, Gas Water Heater
    Features
    • Attic, Bathroom - Stall Shower, Crown Molding, Dining Area, Floor Plan - Traditional, Formal/Separate Dining Room, Kitchen Island
    • Flooring: Ceramic Tile, Hardwood, Wood
    • Basement: Unfinished,Connecting Stairway,Exterior Entry
    • Has fireplace: No
    Interior area
    • Total structure area: 2,114
    • Total interior livable area: 1,442 sqft
    • Finished area above ground: 1,442
    • Finished area below ground: 0
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    Property

    Parking
    • Total spaces: 1
    • Parking features: Garage Faces Front, Detached, Driveway
    • Garage spaces: 1
    • Has uncovered spaces: Yes
    Accessibility
    • Accessibility features: None
    Features
    • Levels: Three
    • Stories: 3
    • Pool features: None
    Lot
    • Size: 0.26 Acres
    Details
    • Additional structures: Above Grade, Below Grade
    • Parcel number: 020600000751750
    • Zoning: R
    • Special conditions: Standard

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Colonial
    • Property subtype: Single Family Residence
    Materials
    • Aluminum Siding
    • Foundation: Block, Slab
    Condition
    • New construction: No
    • Year built: 1905

    Utilities & green energy

    • Sewer: Public Sewer
    • Water: Public

    Community & HOA

    Community
    • Subdivision: Homewood
    HOA
    • Has HOA: No
    Location
    • Region: Annapolis
    • Municipality: Annapolis

    Financial & listing details

    • Price per square foot: $589/sqft
    • Tax assessed value: $503,367
    • Annual tax amount: $6,831
    • Date on market: 5/8/2026
    • Listing agreement: Exclusive Right To Sell
    • Ownership: Fee Simple
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      Estimated market value

      $827,400

      $786,000 - $869,000

      $3,076/mo

      Price history

      DateEventPrice
      5/21/2026Price change$849,000-5.6%$589/sqft
      Source: Bright MLS #MDAA2144864 Report a problem
      5/8/2026Listed for sale$899,000+49.8%$623/sqft
      Source: Bright MLS #MDAA2144864 Report a problem
      9/5/2025Sold$600,000-8.4%$416/sqft
      Source: Bright MLS #MDAA2121600 Report a problem
      8/23/2025Contingent$654,900$454/sqft
      Source: Bright MLS #MDAA2121600 Report a problem
      7/23/2025Listed for sale$654,900$454/sqft
      Source: Bright MLS #MDAA2121600 Report a problem

      Public tax history

      YearProperty taxesTax assessment
      2025$5,390 -21.1%$503,367 +5.9%
      2024$6,832 +6.3%$475,433 +6.2%
      2023$6,426 +4.4%$447,500 +2.4%
      2022$6,157 +2.5%$437,000 +2.5%
      2021$6,009 +2.5%$426,500 +2.5%
      2020$5,866 +0.3%$416,000
      2019$5,847 +1.8%$416,000 +0.8%
      2018$5,741 +7%$412,733 +0.4%
      2017$5,365 $411,100 +5.1%
      2016-- $391,200 +5.4%
      2015-- $371,300 +5.7%
      2014-- $351,400
      2013-- $351,400
      2012-- $351,400 -4.7%
      2011-- $368,710
      2010-- $368,710
      2009-- $368,710 -10.6%
      2008-- $412,310 +17%
      2007-- $352,270 +20.5%
      2006-- $292,230 +25.9%
      2005-- $232,190 +19%
      2004-- $195,080 +23.5%
      2003-- $157,970 +30.7%
      2002-- $120,860
      2001-- $120,860

      Find assessor info on the county website

      Monthly payment

      Est. payment

        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 21401

        Getting around

        77 / 100
        Very Walkable
        41 / 100
        Some Transit
        80 / 100
        Very Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Germantown
        • Middle: Bates
        • High: Annapolis
        • District: Anne Arundel County Public Schools

        Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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