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$498,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 2 Beds
  • 2 Full Baths
  • 1,433 Sq. Ft.
  • Updated 6 hours ago
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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.

Full Property Details for 102 Oak Dr

General

  • Price: $498,000
  • HOA FEE: $2/month
  • HOA FEE FREQ.: Annually
  • Taxes: $2,606 (2005)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDAA2141166
  • Updated: 4/3/2026
  • Added to Site: 1 day(s) ago

Interior

  • Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Kitchen, Family Room, Bedroom 1, Laundry, Other, Utility Room, Attic
  • Interior Features: Kitchen - Table Space, Dining Area, Window Treatments, Wood Floors, Floor Plan - Open
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Fireplace(s): Screen
  • Appliances: Washer/Dryer Hookups Only, Dishwasher, Dryer, Stove, Washer

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Upper 2 - Full Baths: 1
  • Upper Floor Baths: 2
  • Upper - Full Baths: 2

Bedrooms

  • Total Bedrooms: 2
  • Bedrooms Upper: 2
  • Bedrooms-Up2: 2

Additional Information

  • Shared Amenities: Beach, Common Grounds, Pool - Outdoor, Tot Lots/Playground
  • Shared Pool: Yes
  • Pool: Yes

Parking

  • Carport Spaces: 1
  • Total Spaces: 1
  • Parking Type: Off Street, Attached Carport

Location

  • County: ANNE ARUNDEL
  • Subdivision: HILLSMERE ESTATES
  • Driving Directions: Please use GPS

School Information

  • School District: Anne Arundel County Public Schools

Community

  • Association: Yes

Heating & Cooling

  • Cooling Type: Ceiling Fan(s), Other
  • Cooling Fuel: Electric
  • Heating Type: Other, Radiator
  • Heating Fuel: Oil
  • Water Heater: Oil

Utilities

  • Sewer: Public Sewer
  • Water: Other, Well

Structural Information

  • Architectural Style: Split Level
  • Structure Type: Detached
  • Construction: Other
  • Foundation: Block
  • Walls/Ceilings: Cathedral Ceilings, Other
  • Windows: Screens
  • Doors: Storm
  • Stories Description: Lower 1, Lower 2, Main, Upper 1, Upper 2
  • Square Feet: 1,433
  • Sq. Ft. Source: Estimated
  • Living Area: 1,433 Sq. Ft.
  • Finished Above Grnd: 1,433 Sq. Ft.
  • Year Built: 1956
  • Year Built Source: Estimated

Additional Structures

  • Other Structures: Shed

Lot Features

  • Property View: Trees/Woods
  • Lot Size (Acres): 0.28
  • Lot Size (Sq. Ft.): 12,412
  • Lot Size Source: Estimated
  • Street/Road Desc.: Black Top
  • Zoning: R2
  • Lot Description: Backs to Trees, Trees/Wooded
  • Fencing (Description): Rear

Financial Considerations

  • Price Per Sq. Ft.: $347.52
  • Association Fee: $20
  • Assoc Fee Freq.: Annually
  • Assessment Year: 2005
  • County Tax: $2,331
  • County Tax Freq: Annually
  • Tax w/Assessment: $349,840
  • Tax Amount: $2,606
  • Tax Year: 2005

Disclosures and Reports

  • Ownership: Fee Simple
  • Section: 2
  • Lot Number: 8

Listed by Samson Properties, Amy L Presley and Samson Properties, Andrew Spagnolo

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Listing agents

— 102 Oak Dr —

  • Amy L Presley

    Samson Properties

  • Andrew Spagnolo

    Samson Properties

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 102 Oak Dr

School District:Anne Arundel County Public Schools
NameGradesDistance
Hillsmere Elementary School
3052 Arundel on the Bay Road, Annapolis, MD 21403
PK-50.3 mi
Annapolis Middle School
1399 Forest Drive, Annapolis, MD 21403
6-81.8 mi
Annapolis High School
2700 Riva Road, Annapolis, MD 21401
9-124.7 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 102 Oak Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/03/2026
Listed
$498,000
18.57%
MLS
6/02/2006
Sold
$420,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 102 Oak Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,787
25%
$378,667
4%
2023
$3,818
—
$364,133
4%
2023
$3,818
5%
$349,600
1%
2022
$3,635
10%
$347,800
1%
2018
$3,306
-22%
$346,000
1%
2021
$4,237
2%
$344,200
3%
2020
$4,145
5%
$335,133
3%
2019
$3,938
2%
$326,067
3%
2018
$3,862
3%
$317,000
5%
2017
$3,752
4%
$303,133
5%
2016
$3,625
4%
$289,267
5%
2015
$3,486
—
$275,400
—
2014
$3,476
—
$275,400
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 102 Oak Dr

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Samson Properties, Amy L Presley and Samson Properties, Andrew Spagnolo

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102 Oak Drive, Annapolis, MD 21403 (MLS# MDAA2141166) is a Single Family property with 2 bedrooms and 2 full bathrooms. 102 Oak Drive is currently listed for $498,000 and was received on April 03, 2026. Want to learn more about 102 Oak Drive? Do you have questions about finding other Single Family real estate for sale in Annapolis? You can browse all Annapolis real estate or contact a Coldwell Banker agent to request more information.

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