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$799,000 -$16,000 (-1.96%) Price Reduced

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 2,408 Sq. Ft.
  • 1 Car Garage
  • Updated 5 days ago
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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.

Full Property Details for 100 Oak Dr

General

  • Price: $799,000
  • HOA FEE: $2/month
  • HOA FEE FREQ.: Annually
  • Taxes: $5,654 (2027)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDAA2149498
  • Updated: 8/31/2026
  • Added to Site: 62 day(s) ago

Interior

  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Flooring: Ceramic Tile, Hardwood, Luxury Vinyl Plank

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3
  • Main Floor Baths: 2
  • Main - Full Baths: 2
  • Lower Floor Baths: 1
  • Lower - Full Baths: 1

Bedrooms

  • Total Bedrooms: 4
  • Bedrooms Lower: 1
  • Bedrooms Main & Up: 3

Additional Information

  • Shared Pool: Yes
  • Pool: Yes

Exterior

  • Exterior Features: Private Beach

Parking

  • Garage: Yes
  • Garage Spaces: 1
  • Total Spaces: 1
  • Parking Type: Attached Garage, Driveway
  • Garage Description: Garage - Front Entry

Location

  • County: ANNE ARUNDEL
  • Subdivision: HILLSMERE ESTATES
  • Driving Directions: 100 Oak Drive

School Information

  • School District: Anne Arundel County Public Schools

Community

  • Association: Yes
  • Assoc. Name: HILLSMERE SHORES IMPROVEMENT ASSOCIATION

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump - Electric BackUp
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Well

Structural Information

  • Architectural Style: Split Level
  • Structure Type: Detached
  • Construction: Brick, Vinyl Siding
  • Basement: Yes
  • Basement Desc.: Fully Finished
  • Foundation: Slab
  • Stories Description: Lower 1, Main
  • Square Feet: 2,408
  • Sq. Ft. Source: Estimated
  • Living Area: 2,229 Sq. Ft.
  • Finished Above Grnd: 1,314 Sq. Ft.
  • Finished Below Grnd: 915 Sq. Ft.
  • Year Built: 1975
  • Year Built Source: Assessor
  • Property Condition: Excellent

Unit Information

Unit 1

  • Bathrooms-Lower: 1
  • Bedrooms-Lower: 1

Lot Features

  • Lot Size (Acres): 0.29
  • Lot Size (Sq. Ft.): 12,600
  • Lot Size Source: Assessor
  • Zoning: R2

Water Features

  • Navigable Water: Yes
  • Water Access: Yes
  • Water Access Desc: Private Beach
  • Water Front Type: River
  • Water Front Name: South River

Financial Considerations

  • Price Per Sq. Ft.: $608.07
  • Association Fee: $25
  • Assoc Fee Freq.: Annually
  • Assessment Year: 2026
  • County Tax: $4,691
  • County Tax Freq: Annually
  • Tax w/Assessment: $444,600
  • Tax Amount: $5,654
  • Tax Year: 2027

Disclosures and Reports

  • Ownership: Fee Simple
  • Section: 2
  • Lot Number: 12

Listed by Innovative Properties, Inc., Lauren R Dorsey

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Listing agent

— 100 Oak Dr —

  • Lauren R Dorsey

    Innovative Properties, Inc.

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 100 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 100 Oak Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/31/2026
Price Reduced
$799,000
-1.96%
MLS
8/19/2026
Price Reduced
$815,000
-3.55%
MLS
6/22/2026
Listed
$845,000
48.25%
MLS
12/10/2024
Sold
$570,000
—
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 100 Oak Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,500
25%
$430,767
3%
2023
$4,402
—
$416,933
3%
2023
$4,402
6%
$403,100
2%
2022
$4,136
13%
$395,833
2%
2018
$3,653
-21%
$388,567
2%
2021
$4,625
2%
$381,300
3%
2020
$4,519
5%
$370,800
3%
2019
$4,285
2%
$360,300
3%
2018
$4,196
3%
$349,800
4%
2017
$4,087
3%
$335,700
4%
2016
$3,960
4%
$321,600
5%
2015
$3,825
—
$307,500
—
2014
$3,817
—
$307,500
—
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 100 Oak Dr

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

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Innovative Properties, Inc., Lauren R Dorsey

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100 Oak Drive, Annapolis, MD 21403 (MLS# MDAA2149498) is a Single Family property with 4 bedrooms and 3 full bathrooms. 100 Oak Drive is currently listed for $799,000 and was received on July 06, 2026. Want to learn more about 100 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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