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.
For sale
Price cut: $50K (5/21)
$849,000
21 Woodlawn Ave, Annapolis, MD 21401
3beds
1,442sqft
Est.: 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
- 25 days |
- 1,658 |
- 76 |
Zillow last checked:
Listing updated:
Listed by:
Elizabeth Leighty 410-212-3273,
Real Broker, LLC - Annapolis 8554500442
Source: Bright MLS,MLS#: MDAA2144864
Tour with a local agent
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
Video & virtual tour
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
Estimated market value
$827,400
$786,000 - $869,000
$3,076/mo
Price history
| Date | Event | Price |
|---|---|---|
| 5/21/2026 | Price change | $849,000-5.6%$589/sqft |
Source: | ||
| 5/8/2026 | Listed for sale | $899,000+49.8%$623/sqft |
Source: | ||
| 9/5/2025 | Sold | $600,000-8.4%$416/sqft |
Source: | ||
| 8/23/2025 | Contingent | $654,900$454/sqft |
Source: | ||
| 7/23/2025 | Listed for sale | $654,900$454/sqft |
Source: | ||
Public tax history
| Year | Property taxes | Tax 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 | -- | $120,860 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.
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.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 21401
Nearby schools
GreatSchools rating
- 7/10Germantown Elementary SchoolGrades: PK-5Distance: 0.5 mi
- 5/10Wiley H. Bates Middle SchoolGrades: 6-8Distance: 0.4 mi
- 5/10Annapolis High SchoolGrades: 9-12Distance: 3 mi
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.
A local agent can set up tours, give advice and negotiate with sellers.
- Maryland
- Anne Arundel County
- Annapolis
- 21401
- 21 Woodlawn Ave





