For Sale
Price CutPrice Drop: $20K (10/02)
Single family home for sale at 100 Oak Dr, Annapolis, MD 21403 | MLS# MDAA2149498 | Listing updated on 2026-10-02
Photo 1 of Single family home for sale at 100 Oak Dr, Annapolis, MD 21403 | MLS# MDAA2149498 | Listing updated on 2026-10-02
Photo 2 of Single family home for sale at 100 Oak Dr, Annapolis, MD 21403 | MLS# MDAA2149498 | Listing updated on 2026-10-02
Photo 3 of Single family home for sale at 100 Oak Dr, Annapolis, MD 21403 | MLS# MDAA2149498 | Listing updated on 2026-10-02
Photo 4 of Single family home for sale at 100 Oak Dr, Annapolis, MD 21403 | MLS# MDAA2149498 | Listing updated on 2026-10-02
45+
Beds Icon

Street View

$749,900

Monthly Est:$3,733

  • Beds Icon4 Beds
  • Beds Icon
    3 Baths
  • Beds Icon2,229sqft

100 Oak Dr, Annapolis, MD 21403

$3,733/moEst:

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  • Single Family Residence

  • Built in 1975

  • $2.08/mo HOA

  • 12,600 sqft lot

  • $336/sq.ft

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.

  • Houzeo last checked: 12 hours ago
  • Listing updated: October 2, 2026 at 4:54 pm
  • Listing Provided by: Lauren R Dorsey (443) 775-7237 | Innovative Properties, Inc. (410) 268-8400
  • Source: Bright MLS-NJ | MLS#: MDAA2149498 Bright MLS-NJ

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Anne Arundel Md County

  • City

    Annapolis

  • Neighborhood

    --

  • Year Built

    1975

  • HOA Fees

    $2.08/mo

  • Finished Area

    2,229 sqft

  • Lot Size

    12,600 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Bright MLS

  • MLS Number

    MDAA2149498

  • MLS Status

    ACTIVE-BRIGHT

  • Days on Market

    73

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Location

HOA Management

HILLSMERE SHORES IMPROVEMENT ASSOCIATION

HOA Fees

$25/ Annually

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 3

Interior

  • Sewer

    Public Sewer

  • Heating

    Heat Pump Electric Back Up

  • Flooring

    Ceramic Tile, Hardwood, Luxury Vinyl Plank

  • Exterior Features

    Private Beach

  • Cooling

    Central A/c

Construction

  • Year Built

    Year Built: 1975

  • Home type

    Single Family Residence

  • Foundation Details

    Slab

  • Property Condition

    Excellent

  • Construction Materials

    Brick, Vinyl Siding

  • Architectural Style

    Split Level

Utilities & Energy

  • Basement

    Fully Finished

  • Water Source

    Well

Other Features

  • Subdivision Name

    Hillsmere Estates

Price History

DateEventPrice

09/25/2026

Source: mls_logoBright MLS-NJ #MDAA2149498

Off Market

$749,900 -2.60%

$336/sqft

09/16/2026

Source: mls_logoBright MLS-NJ #MDAA2149498

Listed for Sale

$769,900 +20430.67%

$345/sqft

09/14/2026

Source: mls_logoBright MLS-NJ #MDAA2156982

Off Market

$3,750 -99.53%

$2/sqft

08/31/2026

Source: mls_logoBright MLS-NJ #MDAA2149498

Price Decreased

$799,000 -1.96%

$358/sqft

08/19/2026

Source: mls_logoBright MLS-NJ #MDAA2149498

Price Decreased

$815,000 -3.55%

$366/sqft

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Nearby Homes

Based on information from Bright MLS through Oct 09, 2026, 02:30PM. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. IDX information is provided exclusively for 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 is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information

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