Dustin Oldfather
Compass
(302) 393-2276
1,393 Total Sales
39 in Berlin
$100K - $886K Price Range
Waterfront investment opportunity in Ocean Pines! 2 Windjammer Rd represents an incredible chance to buy into a premier coastal location at a low waterfront price point and build instant equity through your own improvements. Please note: This is an trustee sale. The property is being sold strictly AS-IS and is priced accordingly.
Bring your vision and tools to this classic handyman special! The spacious main house features 2,258 square feet of potential, boasting a side porch with vinyl tech windows, and a rear deck perfect for entertaining. The unique layout offers incredible versatility with an open floor plan for the living/dining/kitchen areas. There are a total of 5 bedrooms and 2 full baths in the main house- 2 beds and 1 bath on entry level, 3 beds and 1 bath on upper level. The second-floor balcony provides private access (with additional steps from the ground level) to a separate room over the garage. This bonus area includes finished, climate-controlled guest quarters (approx 600 sq feet) complete with its own full bathroom, kitchenette, and stairs to loft area.
The over-sized 2 car garage is attached to the main home by a deck/breezeway and offers space for covered parking plus workshop area and additional storage.
Boaters and water lovers take note: the true highlight of this property is its prime waterfront location. Enjoy your own private dock with direct access out of the canal and into Assawoman Bay.
There is a long list of amenities in Ocean Pines, including: championship golf course, five swimming pools (including an indoor pool and the oceanfront Beach Club in Ocean City), two marinas, racquet sports, a yacht club, and multiple parks and trails. Positioned in an ideal coastal hub, you are just a short drive from the historic charm of downtown Berlin, the legendary beaches and boardwalk of Ocean City, MD, and the pristine, natural beauty of Assateague National and State Beaches. Don't miss this rare waterfront flip, rental asset, or dream coastal project!
Last Agent to Sell the Property
(410) 208-3500 oceanpines@penfedrealty.com Berkshire Hathaway HomeServices PenFed Realty - OP Brokerage Phone: 4102083500 License #611601 Listed on: 08/01/2026
Last Buyer's Agent
(410) 524-0919 ryan@ryanhaley.com Atlantic Shores Sotheby's International Realty License #525472
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Dustin Oldfather
Compass
(302) 393-2276
1,393 Total Sales
39 in Berlin
$100K - $886K Price Range
Laurie Cannon
ERA Martin Associates
(410) 936-3324
129 Total Sales
7 in Berlin
$310K - $724K Price Range
Tricia Wilson
Wilson Realty & Staging LLC
(443) 960-7224
123 Total Sales
1 in Berlin
$740,000 Price
Tony Golden
Berkshire Hathaway HomeServices PenFed Realty
(302) 248-4650
143 Total Sales
22 in Berlin
$171K - $1.2M Price Range
Holly Worthington
Worthington Realty Group, LLC
(443) 493-7652
166 Total Sales
8 in Berlin
$105K - $2.4M Price Range
Kimberly Bounds
Coldwell Banker Realty
(410) 896-1073
52 Total Sales
13 in Berlin
$253K - $975K Price Range
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 | Type | Sale Price | Title Company |
|---|---|---|---|
| Deed | -- | None Listed On Document | |
| Deed | $312,000 | -- | |
| Deed | $17,000 | -- |
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 | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $215,000 | Credit Line Revolving | |
| Previous Owner | $71,913 | No Value Available | |
| Previous Owner | $50,000 | Credit Line Revolving |
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 |
|---|---|---|---|---|
| 09/10/2026 09/10/26 | Sold | $500,000 | -8.3% | $221 / Sq Ft |
| 08/01/2026 08/01/26 | For Sale | $545,000 | -- | $241 / Sq Ft |
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 |
|---|---|---|---|---|
| 2026 | $4,025 | $457,167 | $0 | $0 |
| 2025 | $4,025 | $436,133 | $0 | $0 |
| 2024 | $3,955 | $415,100 | $163,900 | $251,200 |
| 2023 | $3,794 | $396,400 | $0 | $0 |
| 2022 | $3,528 | $377,700 | $0 | $0 |
| 2021 | $3,432 | $359,000 | $162,600 | $196,400 |
| 2020 | $3,334 | $350,133 | $0 | $0 |
| 2019 | $3,238 | $341,267 | $0 | $0 |
| 2018 | $3,047 | $332,400 | $159,900 | $172,500 |
| 2017 | $3,021 | $321,700 | $0 | $0 |
| 2016 | -- | $311,000 | $0 | $0 |
| 2015 | -- | $300,300 | $0 | $0 |
| 2014 | $2,863 | $300,300 | $0 | $0 |
Seller's Agent in 2026
Sally Todd Stout
Berkshire Hathaway HomeServices PenFed Realty - OP
(410) 726-3506
109 Total Sales
CA
Buyer's Agent in 2026
Chantal Apple
Atlantic Shores Sotheby's International Realty
(410) 524-0919
35 Total Sales
Source: Bright MLS
MLS Number: MDWO2040224
APN: 03-078795
Ask me questions while you tour the home.