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$1,099,500

4beds
|
4baths
|
2,288sqft
|
1986built
996 Headwater Road,Annapolis, MD 21403

Est.$7,230/moCustomize payment

What's special

$481/sqft

Price per square foot

Built in 1986

40 years old

Overview

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 convenienc...

Listing updated: June 25, 2026 at 6:54 PM

Listed by:

Amanda Joelle Greenfield 4109912633, Engel & Volkers Annapolis, Co-Listing Agent: Deborah A Greenfield 4103531605, Engel & Volkers Annapolis

Source: Bright MLS · MLS #MDAA2143898Bright MLS

Property details

Cost estimate

Est. monthly payment

$6,822/mo
Principal & interest
$5,764
Property tax
$672
Home insurance (est.)
$367
HOA fee
$19

Down payment

$219,90020% of list price
Adjust down payment20%
0%25%50%

Based on 20% down ($219,900), 6.85% interest rate, 30-year fixed. Insurance is an estimate. Actual costs may vary.

Rates provided by Mable Loans.

Customize scenario

Price history

DateEventPrice
Jun 11, 2026Price reduced$1,099,500($25,500)
Jun 3, 2026Price reduced$1,125,000($25,000)
May 9, 2026Listed for sale$1,150,000

Location

996 Headwater Road, Annapolis, MD 21403

Recently sold nearby

Similar homes sold within 0.5 miles in the last 90 days.

This home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.

Nearby homes

$1,099,500

4 beds · 4 baths · 2,288 sqft

Bright MLS

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Samson Properties participates, and is provided by BRIGHT through a licensing agreement. © 2026 Bright MLS, All Rights Reserved. Information deemed reliable but not guaranteed. The information provided by this website is for the personal, non-commercial use of consumers and 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 this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Data last updated: 7/2/2026.