Nestled in the highly sought-after Hillsmere community—one of Annapolis' premier waterfront neighborhoods—this charming home offers access to an exceptional array of amenities, including a private beach, boat ramp, community pool, playground, and more. This 3-bedroom, 1.5-bath residence features a full, partially finished basement, a spacious screened porch perfect for relaxing or entertaining, ample off-street parking, and a beautifully landscaped, fenced yard with mature trees and plantings. Enjoy the best of coastal living in one of the area's most desirable communities.
Under contract
Price cut: $34K (7/11)
$430,000
406 Holly Dr, Annapolis, MD 21403
3beds
1,368sqft
:
Get pre-qualified$2,935/mo
Single Family Residence
Built in 1962
0.27 Acres Lot
$426,600 Zestimate®
$314/sqft
$-- HOA
What's special
Full partially finished basementAmple off-street parking
- 26 days |
- 1,321 |
- 50 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Darlene Winegardner 410-991-1456,
RE/MAX Executive 4432741900
Source: Bright MLS,MLS#: MDAA2147188
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 1
- 1/2 bathrooms: 1
- Main level bathrooms: 2
- Main level bedrooms: 3
Basement
- Area: 912
Heating
- Baseboard, Oil
Cooling
- Ceiling Fan(s), Window Unit(s), Electric
Appliances
- Included: Electric Water Heater
Features
- Flooring: Wood
- Basement: Connecting Stairway,Full,Improved,Exterior Entry,Sump Pump,Windows
- Number of fireplaces: 1
Interior area
- Total structure area: 1,824
- Total interior livable area: 1,368 sqft
- Finished area above ground: 912
- Finished area below ground: 456
Property
Parking
- Total spaces: 3
- Parking features: Driveway
- Uncovered spaces: 3
Accessibility
- Accessibility features: None
Features
- Levels: Two
- Stories: 2
- Patio & porch: Porch
- Pool features: Community
- Fencing: Back Yard
Lot
- Size: 0.27 Acres
- Features: Landscaped, Level
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 020241211265200
- Zoning: R2
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Ranch/Rambler
- Property subtype: Single Family Residence
Materials
- Metal Siding
- Foundation: Block
- Roof: Asphalt
Condition
- Average
- New construction: No
- Year built: 1962
Utilities & green energy
- Sewer: Public Sewer
- Water: Well
Community & HOA
Community
- Features: Pool
- Subdivision: Hillsmere Shores
HOA
- Has HOA: No
- Amenities included: Beach Access, Baseball Field, Boat Ramp, Picnic Area, Pier/Dock, Pool, Tot Lots/Playground, Water/Lake Privileges
Location
- Region: Annapolis
Financial & listing details
- Price per square foot: $314/sqft
- Tax assessed value: $396,200
- Annual tax amount: $4,550
- Date on market: 6/28/2026
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Estimated market value
$426,600
$405,000 - $448,000
$3,323/mo
Price history
| Date | Event | Price |
|---|---|---|
| 7/14/2026 | Contingent | $430,000$314/sqft |
Source:  Bright MLS #MDAA2147188 Report a problem | ||
| 7/11/2026 | Price change | $430,000-7.3%$314/sqft |
Source: Bright MLS #MDAA2147188 Report a problem | ||
| 6/28/2026 | Listed for sale | $464,000$339/sqft |
Source: Bright MLS #MDAA2147188 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $3,315 -16.2% | $378,667 +4.9% |
| 2024 | $3,954 +5.4% | $361,133 +5.1% |
| 2023 | $3,752 +5% | $343,600 +0.5% |
| 2022 | $3,572 +0.5% | $341,833 +0.5% |
| 2021 | $3,554 +0.4% | $340,067 +0.5% |
| 2020 | $3,539 +2.1% | $338,300 |
| 2019 | $3,466 +5.6% | $338,300 +4.5% |
| 2018 | $3,283 +1.8% | $323,767 +2.3% |
| 2017 | $3,226 | $316,500 +5.7% |
| 2016 | -- | $299,367 +6.1% |
| 2015 | -- | $282,233 +6.5% |
| 2014 | -- | $265,100 |
| 2013 | -- | $265,100 |
| 2012 | -- | $265,100 -11.8% |
| 2011 | -- | $300,710 |
| 2010 | -- | $300,710 |
| 2009 | -- | $300,710 -9% |
| 2008 | -- | $330,560 +15.9% |
| 2007 | -- | $285,166 +18.9% |
| 2006 | -- | $239,773 +23.4% |
| 2005 | -- | $194,380 +11.3% |
| 2004 | -- | $174,622 +12.8% |
| 2003 | -- | $154,866 +14.6% |
| 2002 | -- | $135,110 +3.5% |
| 2001 | -- | $130,502 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 21403
Nearby schools
GreatSchools rating
- 9/10Hillsmere Elementary SchoolGrades: PK-5Distance: 0.4 mi
- 4/10Annapolis Middle SchoolGrades: 6-8Distance: 1.7 mi
- 5/10Annapolis High SchoolGrades: 9-12Distance: 4.6 mi
Schools provided by the listing agent
- Elementary: Hillsmere
- Middle: Annapolis
- 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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A local agent can set up tours, give advice and negotiate with sellers.
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