SIGN IN

100 Oak Drive, Annapolis, MD 21403

$815,000
  • 100 Oak Drive, Annapolis, MD 21403 Main Photo

49 Total Photos [Click to View All]

Price Reduced $30,000 on August 19th, 2026
BEDS4 BATHS3 full SQUARE FEET2,229 MLS#MDAA2149498
STATUSACTIVE PROPERTY TYPEResidential - Single Family SUBDIVISIONHILLSMERE ESTATES SCHOOLANNE ARUNDEL COUNTY PUBLIC SCHOOLS

Property Description

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.

100 Oak Drive | MLS# MDAA2149498

This single family home located at 100 Oak Drive, Annapolis, MD 21403 is currently listed for sale with an asking price of $815,000. This property was built in 1975 and has 4 bedrooms and 3 full baths with 2229 sq. ft. Oak Drive is located in the HILLSMERE ESTATES subdivision within the ANNE ARUNDEL COUNTY PUBLIC SCHOOLS school district. Search HILLSMERE ESTATES real estate on www.yermangainesteam.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Fully Finished
Cooling: Central A/C
Fireplaces: 1
Fuel Type: Electric
Garage: 1
Heating: Heat Pump - Electric BackUp
Home Style: Split Level
Lot Size: 0.29 Acres
Stories: 2.0
Taxes: $5,654
Year Built: 1975

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Exterior: Brick, Vinyl Siding
Exterior: Private Beach
Flooring: Ceramic Tile, Hardwood, Luxury Vinyl Plank
HOA Fee: $25.00/Annually
Lake Name: South River
Lot Dimensions: 0.29 Acre(S)
Parking Notes: 1 Total Parking Spaces
Sewer: Public Sewer
SQFT Above Finished: 1314
SQFT Below Finished: 915
SQFT Total Finished: 2229
Structure Type: Detached
Total Garage/Parking Spaces: 1
Water: Well
Water Access: Private Beach

Local Schools

School District: ANNE ARUNDEL COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Innovative Properties, Inc.
Agency Phone: 4102688400

IDX logo

Estimate Your Payment

Estimated Payment

$ 2,522.71 per month $1,813.84 Principal & Interest $471.17 Property Tax $237.71 Homeowner's Insurance

Change Payment Information

%
years/fixed
yearly
yearly (est.)
(Monthly PMI fees could increase payment if above 80% LTV)
Getting pre-qualified is the first step to buying a home! GET PREQUALIFIED NOW Home Mortgage Logo
Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 08/19/2026. The listing information on this page last changed on 08/19/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 08/19/2026 4:19:05 AM EST) or Bright MLS (last updated Tue 08/18/2026 9:54:27 AM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
Privacy Policy / DMCA Notice / ADA Accessibility
Federal Housing Equal Opportunity Realtor
Corporate Office - 215 S Centerville Rd. Lancaster, PA 17603
James J Hafer - West Virginia Broker of Record

©2026 BHH Affiliates, LLC. An independently owned and operated franchisee of BHH Affiliates, LLC. Berkshire Hathaway HomeServices and the Berkshire Hathaway HomeServices symbol are registered service marks of Columbia Insurance Company, a Berkshire Hathaway affiliate. Equal Housing Opportunity.


Agent License Information: 
Licensed in Maryland
The Gaines Group
Brandon Gaines, Jeffrey Gaines, Colin Gaines 

1425 Clarkview Road, Suite 700, Baltimore, MD 21209
410-583-0400

Login to Saved Search