Located in the highly desirable Hillsmere Shores community, 102 Oak Drive offers a comfortable lifestyle in one of Annapolis’ most well-established neighborhoods. Conveniently located just minutes from downtown Annapolis, the U.S. Naval Academy, and major commuter routes, this home provides easy access to shopping, dining, and everyday essentials. Residents of Hillsmere Shores also enjoy easy access to Quiet Waters Park, with miles of scenic walking and biking trails, dog parks, playgrounds, and year-round outdoor recreation. Inside, the home is filled with natural light, creating bright and inviting living spaces. Designed for both everyday living and entertaining, the layout offers flexibility to suit a variety of needs. The finished family room provides direct access to the backyard, where thoughtfully designed hardscaping with extensive brickwork creates multiple areas for outdoor dining, grilling, and gathering. A hot tub adds to the appeal, offering a perfect spot to relax and unwind. With its great neighborhood setting and convenient location, 102 Oak Drive presents an excellent opportunity to enjoy all that Annapolis has to offer.
Sold for $498,000
$498,000
102 Oak Dr, Annapolis, MD 21403
2beds
0baths
1,433sqft
Single Family Residence
Built in 1956
0.28 Acres Lot
$498,100 Zestimate®
$348/sqft
$3,711 Estimated rent
Home value
$498,100
$468,000 - $528,000
$3,711/mo
Zestimate® history
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$3,040/mo
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Zillow last checked:
Listing updated:
Listed by:
Amy Presley 301-526-7435,
Samson Properties,
Co-Listing Agent: Andrew Spagnolo 240-601-4431,
Samson Properties
Bought with:
Vicki Van Horne, 0225246467
Long & Foster Real Estate, Inc.
Source: Bright MLS,MLS#: MDAA2141166
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 0
Rooms
- Room types: Living Room, Dining Room, Primary Bedroom, Kitchen, Family Room, Bedroom 1, Laundry, Other, Utility Room, Attic
Primary bedroom
- Features: Flooring - HardWood
- Level: Upper
Bedroom 1
- Features: Flooring - HardWood
- Level: Upper
Other
- Level: Unspecified
Dining room
- Features: Flooring - HardWood
- Level: Main
Family room
- Level: Unspecified
Kitchen
- Features: Flooring - Vinyl
- Level: Main
Laundry
- Level: Unspecified
Living room
- Features: Flooring - HardWood, Fireplace - Wood Burning
- Level: Upper
Other
- Level: Unspecified
Utility room
- Level: Unspecified
Heating
- Other, Radiator, Oil
Cooling
- Ceiling Fan(s), Other, Electric
Appliances
- Included: Dishwasher, Dryer, Cooktop, Washer, Water Heater
- Laundry: Washer/Dryer Hookups Only, Laundry Room
Features
- Kitchen - Table Space, Dining Area, Open Floorplan, Cathedral Ceiling(s)
- Flooring: Wood
- Doors: Storm Door(s)
- Windows: Screens, Window Treatments
- Has basement: No
- Number of fireplaces: 2
- Fireplace features: Screen
Interior area
- Total structure area: 1,433
- Total interior livable area: 1,433 sqft
- Finished area above ground: 1,433
Property
Parking
- Total spaces: 1
- Parking features: Off Street, Attached Carport
- Carport spaces: 1
Accessibility
- Accessibility features: None
Features
- Levels: Multi/Split,Two
- Stories: 2
- Pool features: Community
- Fencing: Back Yard
- Has view: Yes
- View description: Trees/Woods
Lot
- Size: 0.28 Acres
- Features: Backs to Trees, Wooded
Details
- Additional structures: Above Grade
- Parcel number: 020241209593700
- Zoning: R2
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Other
- Foundation: Block
Condition
- New construction: No
- Year built: 1956
Utilities & green energy
- Sewer: Public Sewer
- Water: Other, Well
Community & HOA
Community
- Subdivision: Hillsmere Estates
HOA
- Has HOA: Yes
- Amenities included: Beach Access, Common Grounds, Pool, Tot Lots/Playground
- HOA fee: $20 annually
Location
- Region: Annapolis
Financial & listing details
- Price per square foot: $348/sqft
- Tax assessed value: $349,840
- Annual tax amount: $2,606
- Date on market: 4/3/2026
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
- Road surface type: Black Top
Price history
| Date | Event | Price |
|---|---|---|
| 5/26/2026 | Sold | $498,000$348/sqft |
Source:  Bright MLS #MDAA2141166 Report a problem | ||
| 4/20/2026 | Pending sale | $498,000$348/sqft |
Source: Bright MLS #MDAA2141166 Report a problem | ||
| 4/3/2026 | Listed for sale | $498,000+18.6%$348/sqft |
Source: Bright MLS #MDAA2141166 Report a problem | ||
| 6/6/2006 | Sold | $420,000+200%$293/sqft |
Source: Public Record Report a problem | ||
| 12/2/1994 | Sold | $140,000$98/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $4,787 +20.1% | $378,667 +4% |
| 2024 | $3,987 +4.4% | $364,133 +4.2% |
| 2023 | $3,818 +5% | $349,600 +0.5% |
| 2022 | $3,635 +0.5% | $347,800 +0.5% |
| 2021 | $3,616 +0.4% | $346,000 +0.5% |
| 2020 | $3,600 +2.6% | $344,200 |
| 2019 | $3,509 +6.1% | $344,200 +5.6% |
| 2018 | $3,306 +2.3% | $326,067 +2.9% |
| 2017 | $3,231 | $317,000 +4.6% |
| 2016 | -- | $303,133 +4.8% |
| 2015 | -- | $289,267 +5% |
| 2014 | -- | $275,400 |
| 2013 | -- | $275,400 |
| 2012 | -- | $275,400 -15% |
| 2011 | -- | $323,890 |
| 2010 | -- | $323,890 |
| 2009 | -- | $323,890 -7.4% |
| 2008 | -- | $349,840 +14.2% |
| 2007 | -- | $306,412 +16.5% |
| 2006 | -- | $262,986 +19.8% |
| 2005 | -- | $219,560 +13.5% |
| 2004 | -- | $193,472 +15.6% |
| 2003 | -- | $167,386 +18.5% |
| 2002 | -- | $141,300 +1.7% |
| 2001 | -- | $138,870 |
Find assessor info on the county website
Neighborhood: 21403
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Nearby schools
GreatSchools rating
- 9/10Hillsmere Elementary SchoolGrades: PK-5Distance: 0.3 mi
- 4/10Annapolis Middle SchoolGrades: 6-8Distance: 1.8 mi
- 5/10Annapolis High SchoolGrades: 9-12Distance: 4.7 mi
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.
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Estimated market value
$498,100
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$498,100
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