Price Improvement! Experience the best of Annapolis living in this beautifully updated 4-bedroom, 3-bath home located in a waterfront community. This move-in-ready home offers the perfect blend of modern updates, comfortable living, and an exceptional Chesapeake Bay lifestyle. The heart of the home has also been refreshed with updated kitchen countertops and appliances (2024/2025), making it ideal for everyday living and entertaining. Additional major improvements include a new HVAC system (2025), hot water heater (2025), water conditioning system (2025), and garage door (2025), providing peace of mind for years to come. Outside, the partially fenced backyard offers the perfect space to relax, entertain, or enjoy outdoor activities. All three full bathrooms have been completely renovated with designer tile, new flooring, and modern vanities. The thoughtfully updated interior showcases updated flooring throughout, featuring newly refinished hardwood floors on upper level, new fixtures, and along with a new staircase railing. The inviting fireplace has been refaced on the lower level, creating a stylish focal point in the living space. The home also offers a versatile den/office and a one-car garage. Enjoy Hillsmere’s community amenities including private sandy beaches on the South River, a private marina with boat slips and direct access to the South River, boat ramps, waterfront pavilions, a community swimming pool, playgrounds, volleyball courts, and picnic areas. Whether you're boating, kayaking, fishing, or simply taking in the waterfront scenery, this community offers an unmatched coastal lifestyle. Conveniently located just minutes from historic downtown Annapolis, Quiet Waters Park, shopping, and dining, this exceptional home combines extensive recent updates with one of the area's most desirable waterfront communities. Don't miss the opportunity to make this beautifully renovated home your own.
For sale
Price cut: $16K (8/31)
$799,000
100 Oak Dr, Annapolis, MD 21403
4beds
2,229sqft
Single Family Residence
Built in 1975
0.29 Acres Lot
$787,700 Zestimate®
$358/sqft
$2/mo HOA
What's special
New staircase railingOne-car garagePartially fenced backyardUpdated flooring throughoutNew fixtures
- 57 days
- 403
- 15
Zillow last checked:
Listing updated:
Listed by:
Lauren Dorsey 443-775-7237,
Innovative Properties, Inc. 410-268-8400
Source: Bright MLS,MLS#: MDAA2149498
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
- Main level bathrooms: 2
- Main level bedrooms: 3
Basement
- Area: 1094
Heating
- Heat Pump, Electric
Cooling
- Central Air, Electric
Appliances
- Included: Electric Water Heater
Features
- Flooring: Ceramic Tile, Hardwood, Luxury Vinyl
- Basement: Finished
- Number of fireplaces: 1
Interior area
- Total structure area: 2,408
- Total interior livable area: 2,229 sqft
- Finished area above ground: 1,314
- Finished area below ground: 915
Property
Parking
- Total spaces: 1
- Parking features: Garage Faces Front, Attached, Driveway
- Attached garage spaces: 1
- Has uncovered spaces: Yes
- Details: Garage Sqft: 352
Accessibility
- Accessibility features: None
Features
- Levels: Multi/Split,Two
- Stories: 2
- Exterior features: Private Beach
- Pool features: Community
- Waterfront features: River
- Body of water: South River
Lot
- Size: 0.29 Acres
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 020241208020602
- Zoning: R2
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Brick, Vinyl Siding
- Foundation: Slab
Condition
- Excellent
- New construction: No
- Year built: 1975
Utilities & green energy
- Sewer: Public Sewer
- Water: Well
Community & HOA
Community
- Subdivision: Hillsmere Estates
HOA
- Has HOA: Yes
- HOA fee: $25 annually
- HOA name: HILLSMERE SHORES IMPROVEMENT ASSOCIATION
Location
- Region: Annapolis
Financial & listing details
- Price per square foot: $358/sqft
- Tax assessed value: $444,600
- Annual tax amount: $5,654
- Date on market: 7/6/2026
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Estimated market value
$787,700
$748,000 - $827,000
$4,090/mo
Price history
| Date | Event | Price |
|---|---|---|
| 8/31/2026 | Price change | $799,000-2%$358/sqft |
Source: | ||
| 8/24/2026 | Listed for rent | $4,250+13.3%$2/sqft |
Source: Zillow Rentals Report a problem | ||
| 8/19/2026 | Price change | $815,000-3.6%$366/sqft |
Source: | ||
| 7/21/2026 | Listed for sale | $845,000+48.2%$379/sqft |
Source: | ||
| 4/22/2025 | Listing removed | $3,750$2/sqft |
Source: Zillow Rentals Report a problem | ||
| 2/18/2025 | Price change | $3,750-5.1%$2/sqft |
Source: Zillow Rentals Report a problem | ||
| 1/9/2025 | Listed for rent | $3,950$2/sqft |
Source: Zillow Rentals Report a problem | ||
| 12/10/2024 | Sold | $570,000-2.6%$256/sqft |
Source: | ||
| 12/3/2024 | Pending sale | $585,000$262/sqft |
Source: | ||
| 11/16/2024 | Contingent | $585,000$262/sqft |
Source: | ||
| 10/27/2024 | Price change | $585,000-1.7%$262/sqft |
Source: | ||
| 9/30/2024 | Price change | $595,000-1.7%$267/sqft |
Source: | ||
| 9/25/2024 | Listed for sale | $605,000+112.3%$271/sqft |
Source: | ||
| 4/1/2003 | Sold | $285,000+99.3%$128/sqft |
Source: Public Record Report a problem | ||
| 3/24/1998 | Sold | $143,000$64/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $5,500 +20.5% | $430,767 +3.3% |
| 2024 | $4,565 +3.7% | $416,933 +3.4% |
| 2023 | $4,402 +6.4% | $403,100 +1.8% |
| 2022 | $4,136 +1.9% | $395,833 +1.9% |
| 2021 | $4,061 +1.8% | $388,567 +1.9% |
| 2020 | $3,988 +2.7% | $381,300 |
| 2019 | $3,882 +6.3% | $381,300 +5.8% |
| 2018 | $3,653 +2.5% | $360,300 +3% |
| 2017 | $3,566 | $349,800 +4.2% |
| 2016 | -- | $335,700 +4.4% |
| 2015 | -- | $321,600 +4.6% |
| 2014 | -- | $307,500 |
| 2013 | -- | $307,500 |
| 2012 | -- | $307,500 -6.8% |
| 2011 | -- | $329,790 |
| 2010 | -- | $329,790 |
| 2009 | -- | $329,790 -10.9% |
| 2008 | -- | $370,060 +14.5% |
| 2007 | -- | $323,150 +17% |
| 2006 | -- | $276,240 +20.5% |
| 2005 | -- | $229,330 +12.3% |
| 2004 | -- | $204,252 +14% |
| 2003 | -- | $179,176 +16.3% |
| 2002 | -- | $154,100 |
| 2001 | -- | $154,100 |
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
Schools provided by the listing agent
- 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.





