996 Headwater Rd

Annapolis, MD 21403

$1,099,500
Price
4
Beds
2,288 Sq. Ft.
$481 / Sq. Ft.
2,288
Sq. Ft.
$481
per Sq. Ft.
Get preapproved with Rocket Mortgage1
Charming home by the serene waterway.
Bring your boat!
Welcome to 996 Headwater Rd
Serene waterside retreat awaits you.
Bright and airy living space.
Bright and airy living space awaits.
dining space overlooking the serene backyard
dining space looking into the living space
open concept living and kitchen
Breakfast nook with access to deck
kitchen and living with deck & backyard access
Serene deck amidst lush greenery.
living space with wood burning fireplace
Bright and airy kitchen oasis.
Modern kitchen with sleek finishes.
Modern kitchen with sleek finishes.
Powder room
main level laundry hook up with ramp access
Entry
Charming playroom with cozy vibes.
Bright and airy
Primary suite with hardwood flooring
primary suite with private balcony
Primary on-suite
Bedroom 2
Bright and airy bedroom retreat.
Bedroom 3
Bedroom 3
Hall bath
In-law kitchen with stove top and dishwasher
Lower level in-law suite living area
Lower level in-law suite
in-law suite living space
in-law suite bath with lower level laundry hookup
In-law suite bathroom with large walk-in shower
In-law suite living area
In-law suite living area
Charming home embraced by lush greenery.
Serene suburban oasis among trees.
Kitty creek to Duvall creek out to the south river
Easy access to Chesapeake Bay
Lush greenery surrounds serene waters.
Serene waterfront living awaits you.
Lush greenery on Kitty Creek
Charming home embraced by lush greenery.
grill out under the stars
Enjoy nature on the patio
Private dock on Kitty Creek
Tranquil path to your private dock on Kitty Creek
Back elevation. patio off in-law suite
Bonfire on the creek? perfect fall night
peaceful creek & easy access to south river & bay
Spacious second-floor layout design.
Spacious basement layout with wet bar.
Spacious floor plans for modern living.
Spacious floor plan for modern living.

Description

Annapolis Waterfront home located right off the South River with easy access to the Chesapeake Bay. This recently updated home offers the perfect blend of luxury, comfort, and waterfront living. Inside, you’re welcomed by refinished hardwood floors and abundant natural light. The updated kitchen features new GE stainless steel appliances and opens to a cozy living room with a wood-burning fireplace and direct access to the deck; ideal for dining under the stars overlooking the peaceful backyard and...Annapolis Waterfront home located right off the South River with easy access to the Chesapeake Bay. This recently updated home offers the perfect blend of luxury, comfort, and waterfront living. Inside, you’re welcomed by refinished hardwood floors and abundant natural light. The updated kitchen features new GE stainless steel appliances and opens to a cozy living room with a wood-burning fireplace and direct access to the deck; ideal for dining under the stars overlooking the peaceful backyard and creek. A main-level laundry/mudroom with side entrance and ramp adds everyday convenience. The primary suite is a true retreat, featuring a waterfront-facing design with a private balcony and updated en-suite bath. Three additional bedrooms with new carpet offer flexibility for guests, a home office, or growing needs. The fully finished walkout lower level provides a private in-law suite with its own entrance, full kitchen, large updated bath, and laundry hookup; perfect for extended stays or entertaining. Outside, enjoy 50 feet of waterfront with a private dock, kayak rack, and a spacious .41-acre lot offering plenty of room to relax, garden, or play. Ideally located with easy access to Historic Annapolis and Naval Academy, BWI, and DC, this home offers the best of peaceful waterfront living in Annapolis and everyday convenience.
  1. Listed by Amanda Joelle Greenfield • Engel & Volkers Annapolis
    P: (410)-991-2633 amanda.greenfield@engelvoelkers.com
  2. Listed by Deborah A Greenfield • Engel & Volkers Annapolis
    P: (410)-353-1605 debbie.greenfield@evrealestate.com

Property Details for 996 Headwater Road

Tax ID Number
020245090027513
Ownership
Fee Simple
Condo Coop Association
No
HOA
Yes
Entry Floor Number
-50
Structure Type
Detached
Style
Traditional, Transitional
Levels/Stories
2
LISTING UPDATED: 06/25/2026 02:54 PM

Property Details for 996 Headwater Road

StatusActive
MLS #MDAA2143898
Days on Market56
Taxes$8,067 / year
HOA Fees$230 / year
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Fee Simple
Year Built1986
Lot Size0.41 AC / 17,860 SF
CountyAnne Arundel County
Get preapproved with Rocket Mortgage1

Location

Listing Courtesy of Engel & Volkers Annapolis
Add your commute

Building Information for 996 Headwater Road

Stories2Year Built1986Building Size-Lot Size0.41 AC / 17,860 SF

Payment Calculator

Get preapproved with
OriginPoint Mortgage or Rocket Mortgage1

$6,170 per month

30 year fixed, 6.36% Interest

Principal and Interest

$5,479

Property Taxes

$672

HOA Dues

$19

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 996 Headwater Road

Location
Location
  • In City Limits: No
  • School District Name: ANNE ARUNDEL COUNTY PUBLIC SCHOOLS
  • School District County ID: 121140671932
  • County: ANNE ARUNDEL
Waterfront / Water Access
Waterfront / Water Access
  • Water View: Yes
  • Water Access: Yes
  • Water Oriented: Yes
  • Navigable Water: Yes
  • Tidal Water: Yes
  • Water Body Type: Creek
  • Water Frontage In Feet: 50.0
  • Docks Count: 1
  • Dock Type and Features: Private
  • Dock/Slip Conveys Y/N: true
  • Dock/Slip Conveyance: Physical Dock/Slip Conveys
  • Slips Count: 2
Association / Community Info
Association / Community Info
  • HOA Name: KITTY CREEK ASSOCIATION INC
  • HOA Phone: 4102803432
  • Property Manager Y/N: No
  • Senior Community: No
  • Association Recreation Fee Y/N: No
  • Type of Condo: Home Owner Association
Taxes and Assessment
Taxes and Assessment
  • Tax Year: 2026
  • Tax Assessed Value: $751,300
  • County Tax: $7,641
  • Zoning: R2
  • Zoning Dscrp: waterfront
  • School Tax: $0
  • Automatically Update Tax Values Y/N: Yes
Rooms
Main
  • # Bedrooms Count Main Level: 0
  • # Bathrooms Count Main Level: 1
  • # Bathrooms Full Main Level: 0
  • # Bathrooms Half Main Level: 1
All Upper Levels
  • # Bedrooms Count All Upper Levels: 4
  • # Bathrooms Count All Upper Levels: 2
  • # Bathrooms Full All Upper Levels: 2
Upper Level 1
  • # Bedrooms Count Upper Level: 4
  • # Bathrooms Count Upper Level: 2
  • # Bathrooms Full Upper Level: 2
All Lower Levels
  • # Bedrooms All Lower Levels: 0
  • # Bathrooms All Lower Levels: 1
  • # Bathrooms Full All Lower Levels: 1
Lower Level 1
  • # Bedrooms Lower Level: 0
  • # Bathrooms Lower Level: 1
  • # Bathrooms Full Lower Level: 1
Rooms
  • Stories: Lower 1, Main, Upper 1
Building Info
Building Info
  • Total Finished SQFT: 2,288.00
  • Total Finished SQFT Source: Assessor
  • Tax Total Finished SQFT: 2,288.00
  • Total SQFT: 2,288.00
  • Total SQFT Source: Assessor
  • Construction Materials: HardiPlank Type
  • Roof: Asphalt
  • Ext Main Mid-res: http://bright-media01.prd.brightmls.com/bright/images/0000/8050/3571/0656/805035710656_512_384_WM_BG8KkDHkwxq-fW-Z.jpg
  • Flooring Type: Hardwood, Carpet, Tile/Brick
  • Basement Type: English, Walkout Level, Rear Entrance
  • Foundation Details: Concrete Perimeter
  • Room and Floor: Bathrooms Half-Main Level-1, Bedrooms-Upper Level 1-1, Bedrooms-Upper Level 1-2, Bedrooms-Upper Level 1-3, Bedrooms-Upper Level 1-4, Bathrooms Full-Upper Level 1-1, Bathrooms Full-Upper Level 1-2, Bathrooms Full-Lower Level 1-1
  • # Bathrooms Full: 3
  • # Bathrooms Half: 1
  • Other Structure: Above Grade, Below Grade
Lot / Land Information
Lot / Land Information
  • Lot Size Source: Estimated
  • Fencing: Picket
  • Location Type: Creek/Stream
  • Parcel ID: 15184577
  • Ground Rent Exists: No
Parking
Parking
  • Type Of Parking: Driveway
Interior Features
Interior Features
  • Interior Features: 2nd Kitchen, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Breakfast Area, Ceiling Fan(s), Combination Kitchen/Living, Family Room Off Kitchen, Primary Bedroom - Bay Front, Primary Bath(s), Recessed Lighting, Skylight(s), Upgraded Countertops, Wood Floors
  • Fireplace: Yes
Exterior Features
Exterior Features
  • Pool: No Pool
Utilities
Utilities
  • Heating: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Hot Water: Electric
  • Water Source: Well
  • Sewer Septic: Public Sewer

Property History for 996 Headwater Road

DateEvent & SourcePriceAppreciation
Jun 11, 2026

Price Change

BRIGHT #MDAA2143898

$1,099,500—
Jun 3, 2026

Price Change

BRIGHT #MDAA2143898

$1,125,000—
May 9, 2026

Listed (Active)

BRIGHT #MDAA2143898

$1,150,000—
DateEvent & SourcePrice
06/11/2026

Price Change

BRIGHT #MDAA2143898

$1,099,500
06/03/2026

Price Change

BRIGHT #MDAA2143898

$1,125,000
05/09/2026

Listed (Active)

BRIGHT #MDAA2143898

$1,150,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 996 Headwater Road

Taxable ValueLand-Additions-Total-
Tax Record2025$8,166 ($680 / month)
Home Facts
Beds0Baths3.5Total Finished SqFt2,288 SqFtAbove Grade Finished SqFt1,700 SqFtFinished Basement SqFt588 SqFtStories2Lot Size18,119 SqFtStyleSingle Family ResidenceYear Built1986ZoningR2CountyANNE ARUNDELAPN02-450-90027513Fireplace TypeHas Fireplace

Schools near 996 Headwater Road

This home is within Anne Arundel County Public Schools.
Rating
School
Type
Grades
Distance
Hillsmere Elementary School
Public - PK to 5
Annapolis Middle School
Public - 6 to 8
Annapolis High School
Public - 9 to 12
Mary Moss at Adams Academy
Public - K to 12
Rating
School
Distance
Hillsmere Elementary School
PublicPK to 5

Annapolis Middle School
Public6 to 8

Annapolis High School
Public9 to 12

Mary Moss at Adams Academy
PublicK to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Explore Nearby Homes

More information about 996 Headwater Road, Annapolis, MD 21403

996 Headwater Road is a single family home for sale in Annapolis, MD 21403. This property was listed for sale on May 9, 2026 by Engel & Volkers Annapolis, it's currently listed at $1,099,500. It has been on the market for a total of 56 days and was last sold on October 21, 2016. This listing's school district is Anne Arundel County Public Schools. Nearby schools include Hillsmere Elementary School, Annapolis Middle School and Annapolis High School. 996 Headwater Road is a 4-bed, 4-bath, 2,288 sqft single family home built in 1986.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Engel & Volkers Annapolis

© 2026 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 06/25/2026 02:54 PM