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- Property Details
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Street View
$749,900
Monthly Est:$3,733
4 Beds
- 3 Baths
3 full baths
2,229sqft
100 Oak Dr, Annapolis, MD 21403
$749,900
$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

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
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
| Date | Event | Price |
|---|---|---|
09/25/2026 Source: | Off Market | $749,900 -2.60% $336/sqft |
09/16/2026 Source: | Listed for Sale | $769,900 +20430.67% $345/sqft |
09/14/2026 Source: | Off Market | $3,750 -99.53% $2/sqft |
08/31/2026 Source: | Price Decreased | $799,000 -1.96% $358/sqft |
08/19/2026 Source: | Price Decreased | $815,000 -3.55% $366/sqft |
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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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