Skip main navigation
For sale
  • Price cut: $16K (8/31)
    $799,000

    100 Oak Dr, Annapolis, MD 21403

    4beds
    2,229sqft
    : 
    $5,406/mo
    Get pre-qualified
    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
    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.
    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#: MDAA2149498MLS Logo

      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

        DateEventPrice
        8/31/2026Price change$799,000-2%$358/sqft
        Source: Bright MLS #MDAA2149498 Report a problem
        8/24/2026Listed for rent$4,250+13.3%$2/sqft
        Source: Zillow Rentals Report a problem
        8/19/2026Price change$815,000-3.6%$366/sqft
        Source: Bright MLS #MDAA2149498 Report a problem
        7/21/2026Listed for sale$845,000+48.2%$379/sqft
        Source: Bright MLS #MDAA2149498 Report a problem
        4/22/2025Listing removed$3,750$2/sqft
        Source: Zillow Rentals Report a problem
        2/18/2025Price change$3,750-5.1%$2/sqft
        Source: Zillow Rentals Report a problem
        1/9/2025Listed for rent$3,950$2/sqft
        Source: Zillow Rentals Report a problem
        12/10/2024Sold$570,000-2.6%$256/sqft
        Source: Bright MLS #MDAA2094460 Report a problem
        12/3/2024Pending sale$585,000$262/sqft
        Source: Bright MLS #MDAA2094460 Report a problem
        11/16/2024Contingent$585,000$262/sqft
        Source: Bright MLS #MDAA2094460 Report a problem
        10/27/2024Price change$585,000-1.7%$262/sqft
        Source: Bright MLS #MDAA2094460 Report a problem
        9/30/2024Price change$595,000-1.7%$267/sqft
        Source: Bright MLS #MDAA2094460 Report a problem
        9/25/2024Listed for sale$605,000+112.3%$271/sqft
        Source: Bright MLS #MDAA2094460 Report a problem
        4/1/2003Sold$285,000+99.3%$128/sqft
        Source: Public Record Report a problem
        3/24/1998Sold$143,000$64/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax 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.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 21403

        Getting around

        24 / 100
        Car-Dependent
        0 / 100
        No Nearby Transit
        37 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        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.

        A local agent can set up tours, give advice and negotiate with sellers.

        Browse local experts