Dustin Oldfather
Compass
(302) 393-2276
1,403 Total Sales
2 in Annapolis Neck
$615K - $859K Price Range
996 Headwater Rd Annapolis, MD 21403
Annapolis Neck AreaEstimated Value: $1,078,079
4
Beds
3.5
Baths
2,484
Sq Ft
$434/Sq Ft
Est. Value
Highlights
- 60 Feet of Waterfront
- Pier
- Open Floorplan
- 1 Dock Slip
- Fishing Allowed
- Colonial Architecture
About This Home
As of October 2016PRICE IMPROVEMENT!
Experience the best of Annapolis waterfront living with this beautifully updated home, complete with a private dock just off the South River and only minutes to the Chesapeake Bay. Bring your fishing rods, crab nets, kayaks, and boat; this is the waterfront lifestyle you've been waiting for.
Inside, refinished hardwood floors and abundant natural light create a warm, inviting atmosphere. The updated kitchen features new GE stainless steel appliances and opens seamlessly to the cozy living room with a wood-burning fireplace and direct access to the spacious deck; perfect for outdoor dining while overlooking the tranquil backyard. A convenient main-level laundry/mudroom with a side entrance and ramp adds everyday functionality. The waterfront primary suite is a true retreat, offering a private balcony and an updated en-suite bath. Three additional bedrooms with brand-new carpet provide plenty of space for family, guests, or a home office.
The fully finished walkout lower level offers exceptional flexibility with its own private entrance, full kitchen, spacious updated bathroom, and laundry hookup—ideal as an in-law suite, guest quarters, or entertaining space.
Outside, enjoy 50 feet of waterfront, a private dock, kayak rack, and a generous 0.41-acre lot with room to relax, garden, or entertain.
Conveniently located just minutes from Historic Annapolis, the U.S. Naval Academy, BWI Airport, and Washington, D.C., this home combines peaceful waterfront living with unbeatable accessibility.
Don't miss this incredible opportunity to own your own piece of Annapolis waterfront at an improved price!
Last Agent to Sell the Property
(410) 544-4000 amy@longandfoster.com Long & Foster Real Estate, Inc. Listed on: 06/10/2016
Last Buyer's Agent
(443) 292-6767 debbie.greenfield@evrealestate.com Engel & Völkers Annapolis License #528484
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Home Details
Home Type
- Single Family
Est. Annual Taxes
- $5,642
Year Built
- Built in 1986
Lot Details
- 18,119 Sq Ft Lot
- 60 Feet of Waterfront
- Home fronts navigable water
- Creek or Stream
- Cul-De-Sac
- Back Yard Fenced
- Property is in very good condition
- Property is zoned R2
HOA Fees
- $30 Monthly HOA Fees
Parking
- 1 Car Attached Garage
- Front Facing Garage
- Garage Door Opener
- Off-Street Parking
Home Design
- Colonial Architecture
- HardiePlank Type
Interior Spaces
- Property has 3 Levels
- Open Floorplan
- Wet Bar
- 1 Fireplace
- Window Treatments
- Family Room Off Kitchen
- Living Room
- Dining Room
- Game Room
- Wood Flooring
- Water Views
Kitchen
- Electric Oven or Range
- Dishwasher
- Upgraded Countertops
- Disposal
Bedrooms and Bathrooms
- 4 Bedrooms
- En-Suite Bathroom
- 3.5 Bathrooms
Laundry
- Front Loading Dryer
- Front Loading Washer
Finished Basement
- Walk-Out Basement
- Basement Fills Entire Space Under The House
- Rear Basement Entry
- Basement with some natural light
Outdoor Features
- Pier
- Canoe or Kayak Water Access
- Private Water Access
- 1 Dock Slip
- Physical Dock Slip Conveys
- 1 Powered Boats Permitted
- 3 Non-Powered Boats Permitted
- Balcony
- Deck
- Patio
- Porch
Location
- Property is near creek
Schools
- Hillsmere Elementary School
- Annapolis Middle School
- Annapolis High School
Utilities
- Central Air
- Heat Pump System
- Well
- Electric Water Heater
Listing and Financial Details
- Tax Lot 14
- Assessor Parcel Number 020245090027513
Community Details
Overview
- Kitty Creek Subdivision
Amenities
- Common Area
Recreation
- Fishing Allowed
Ownership History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Date
Name
Owned For
Owner Type
Purchase Details
Closed on
Mar 28, 2025
Sold by
Bought by
Current Estimated Value
Purchase Details
Closed on
May 28, 2019
Sold by
Bought by
Purchase Details
Listed on
Jun 10, 2016
Closed on
Oct 21, 2016
Sold by
Bought by
Seller's Agent
Amy Faust
Long & Foster Real Estate, Inc.
Buyer's Agent
Deborah Greenfield
Engel & Völkers Annapolis
List Price
$599,900
Sold Price
$549,000
Premium/Discount to List
-$50,900
-8.48%
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
7.14%
Original Mortgage
$526,556
Interest Rate
4.03%
Mortgage Type
FHA
Purchase Details
Closed on
Jun 27, 2001
Sold by
Bought by
Purchase Details
Closed on
Jun 15, 1987
Sold by
Bought by
Home Values in the Area
Average Home Value in this Area
Agents Specializing in Annapolis, MD
-
Dustin Oldfather
-
Kara Leddy
Kara Leddy
Coldwell Banker Realty
(443) 494-8169
62 Total Sales
10 in Annapolis Neck
$246K - $880K Price Range
-
Christopher Swade
Christopher Swade
Taylor Properties
(667) 771-4822
69 Total Sales
1 in Annapolis Neck
$330,000 Price
-
Sarah Miller
Sarah Miller
Hubble Bisbee Christie's International Real Estate
(443) 232-2586
20 Total Sales
1 in Annapolis Neck
$280,000 Price
-
Mahdi Salarfar
Mahdi Salarfar
RE/MAX Gateway, LLC
(571) 410-3574
56 Total Sales
2 in Annapolis Neck
$650K - $710K Price Range
-
Jamie Richardson
Jamie Richardson
RE/MAX United Real Estate
(202) 852-9903
57 Total Sales
1 in Annapolis Neck
$865,882 Price
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Buyer | Sale Price | Title Company |
|---|---|---|---|
| -- | None Listed On Document | ||
| -- | None Available | ||
| $549,000 | Church Circle Title & Escrow | ||
| $278,000 | -- | ||
| $157,100 | -- |
Source: Public Records
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Borrower | Loan Amount |
|---|---|---|---|
| Previous Owner | $526,556 |
Source: Public Records
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 08/05/2026 08/05/26 | Price Changed | $1,049,000 | -4.6% | $458 / Sq Ft |
| 06/11/2026 06/11/26 | Price Changed | $1,099,500 | -2.3% | $481 / Sq Ft |
| 06/03/2026 06/03/26 | Price Changed | $1,125,000 | -2.2% | $492 / Sq Ft |
| 05/09/2026 05/09/26 | For Sale | $1,150,000 | +109.5% | $503 / Sq Ft |
| 10/21/2016 10/21/16 | Sold | $549,000 | 0.0% | $221 / Sq Ft |
| 09/10/2016 09/10/16 | Pending | -- | -- | -- |
| 09/02/2016 09/02/16 | Price Changed | $549,000 | -4.5% | $221 / Sq Ft |
| 08/17/2016 08/17/16 | Price Changed | $575,000 | -4.2% | $231 / Sq Ft |
| 08/01/2016 08/01/16 | For Sale | $599,900 | +9.3% | $242 / Sq Ft |
| 07/21/2016 07/21/16 | Off Market | $549,000 | -- | -- |
| 06/28/2016 06/28/16 | Price Changed | $599,900 | 0.0% | $242 / Sq Ft |
| 06/10/2016 06/10/16 | For Sale | $599,999 | 0.0% | $242 / Sq Ft |
| 07/10/2014 07/10/14 | Rented | $3,000 | -3.2% | -- |
| 07/10/2014 07/10/14 | Under Contract | -- | -- | -- |
| 06/04/2014 06/04/14 | For Rent | $3,100 | -- | -- |
Source: Bright MLS
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $8,166 | $701,667 | ||
| 2024 | $7,642 | $652,033 | ||
| 2023 | $6,578 | $602,400 | $420,300 | $182,100 |
| 2022 | $6,725 | $602,400 | $420,300 | $182,100 |
| 2020 | $6,765 | $609,700 | $420,300 | $189,400 |
| 2019 | $12,930 | $580,500 | $0 | $0 |
| 2018 | $5,590 | $551,300 | $0 | $0 |
| 2017 | $5,715 | $522,100 | $0 | $0 |
| 2016 | -- | $519,200 | $0 | $0 |
| 2015 | -- | $516,300 | $0 | $0 |
| 2014 | -- | $513,400 | $0 | $0 |
Source: Public Records
Agents Affiliated with this Home
-
Amanda Greenfield
A
Seller's Agent in 2026
Amanda Greenfield
Engel & Völkers Annapolis
(410) 991-2633
14 Total Sales
-
Deborah Greenfield
Seller Co-Listing Agent in 2026
Deborah Greenfield
Engel & Völkers Annapolis
(410) 353-1605
25 Total Sales
-
Amy Faust
Seller's Agent in 2016
Amy Faust
Long & Foster
(410) 299-7650
40 Total Sales
-
Rachel Gontkovic
Seller's Agent in 2014
Rachel Gontkovic
EXP Realty, LLC
(410) 271-6246
136 Total Sales
-
J
Buyer's Agent in 2014
Joyce Hartnett
Coldwell Banker (NRT-Southeast-MidAtlantic)
Map
Source: Bright MLS
MLS Number: 1001625587
APN: 02-450-90027513
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement.
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.
Copyright 2026 Bright MLS, Inc.
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