Date
Details
Price
Change
Source
8/01/2026
Listed
$545,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$545,000 Just Listed
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Property Description
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!
Full Property Details
Full Property Details for 2 Windjammer Rd
General
- Price: $545,000
- HOA FEE: $132/month
- HOA FEE FREQ.: Annually
- Taxes: $4,043 (2025)
- Status: Active
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: MDWO2040224
- Updated: Today (8/1/2026)
- Added to Site: Today
Interior
- Rooms/Areas: Living Room, Dining Room, Kitchen
- Interior Features: Entry Level Bedroom, Ceiling Fan(s), Walk-in Closet(s), Combination Dining/Living, Family Room Off Kitchen, Floor Plan - Open
- Appliances: Dishwasher, Dryer, Oven/Range - Electric, Refrigerator, Washer
- Flooring: Laminate Plank, Laminated
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
- Upper Floor Baths: 1
- Upper - Full Baths: 1
- Main Floor Baths: 1
- Main - Full Baths: 1
Bedrooms
- Total Bedrooms: 5
- Bedrooms Upper: 3
- Bedrooms Main & Up: 2
Other Rooms
- Laundry: Main Floor
Additional Information
- Shared Amenities: Beach Club, Boat Ramp, Club House, Golf Course, Marina/Marina Club, Pool - Outdoor, Basketball Courts, Common Grounds, Community Center, Dog Park, Golf Course Membership Available, Jog/Walk Path, Pickleball Courts, Pier/Dock, Pool - Indoor, Pool Mem Avail, Racquet Ball, Recreational Center
- Shared Pool: Yes
- Pool: Yes
Exterior
- Porch/Patio/Deck: Deck(s), Screened, Porch(es), Breezeway, Balcony
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 6
- Parking Type: Detached Garage, Driveway
- Garage Description: Additional Storage Area, Garage - Front Entry, Oversized
Location
- Area: Worcester Ocean Pines
- Municipality: OCEAN PINES
- County: WORCESTER
- Subdivision: OCEAN PINES - NEWPORT
- Driving Directions: Enter Ocean PInes North Gate and follow Ocean Parkway, make a left on Windjammer, #2 is on the left
- Location Details: Canal
School Information
- School District: Worcester County Public Schools
- Elementary School: Berlin Intermediate School
- Middle School: Stephen Decatur
- High School: Stephen Decatur
Community
- Association: Yes
- Assoc. Name: OCEAN PINES ASSOCIATION
- Assoc. Fees Include: Common Area Maintenance, Management, Reserve Funds, Road Maintenance
- Pets Allowed: Yes
- Pets: No Pet Restrictions
Heating & Cooling
- Central air: Yes
- Cooling Type: Central A/C
- Cooling Fuel: Electric
- Heating Type: Heat Pump(s)
- Heating Fuel: Electric
- Water Heater: Electric
Utilities
- Sewer: Public Sewer
- Water: Public
Structural Information
- Architectural Style: Contemporary
- Structure Type: Detached
- Construction: Frame, Vinyl Siding, Stick Built
- Foundation: Block, Crawl Space
- Roof: Asphalt
- Walls/Ceilings: Cathedral Ceilings
- Stories Description: Main, Upper 1
- Square Feet: 2,258
- Sq. Ft. Source: Estimated
- Living Area: 2,258 Sq. Ft.
- Finished Above Grnd: 2,258 Sq. Ft.
- Year Built: 1984
- Year Built Source: Assessor
Unit Information
- Unit Floor in Bldg.: 2
Additional Structures
- Other Structures: Garage(s)
Lot Features
- Property View: Canal, Water
- Lot Size (Acres): 0.23
- Lot Size (Sq. Ft.): 9,953
- Lot Size Source: Assessor
- Zoning: R-3
- Lot Description: Bulkheaded, Cleared, Corner
Water Features
- Water Front: Yes
- Water View: Yes
- Navigable Water: Yes
- Water Access: Yes
- Water Access Desc: Private Access
- Water Front Type: Canal
Financial Considerations
- Price Per Sq. Ft.: $241.36
- Association Fee: $1,580
- Assoc Fee Freq.: Annually
- Other Fee: $200
- Other Fee Freq.: One Time
- Assessment Year: 2026
- City/TownTax Freq: Annually
- Tax w/Assessment: $457,167
- Tax Amount: $4,043
- Tax Year: 2025
- Tax Total Finished Sq. Ft.: 2415
Disclosures and Reports
- Ownership: Fee Simple
- Exclusions: staging items
- Inclusions: as shown
Listed by Berkshire Hathaway HomeServices PenFed Realty - OP, Sally Todd Stout
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agent
— 2 Windjammer Rd —
Sally Todd Stout
Berkshire Hathaway HomeServices PenFed Realty - OP
Listing Office Email: oceanpines@penfedrealty.com
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 2 Windjammer Rd
School District:Worcester County Public Schools
| Name | Grades | Distance |
|---|---|---|
Showell Elementary School 11318 Showell School Road, Berlin, MD 21811 | PK-3 | 2.2 mi |
Berlin Intermediate School 309 Franklin Avenue, Berlin, MD 21811 | 4-6 | 5.8 mi |
Stephen Decatur Middle School, Berlin, MD 9815 Seahawk Road, Berlin, MD 21811 | 7-8 | 4.8 mi |
Stephen Decatur High School 9913 Seahawk Road, Berlin, MD 21811 | 9-12 | 4.6 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 2 Windjammer Rd
Tax History
Tax History for 2 Windjammer Rd
Year
Property Taxes
Change
Tax Assessment
Change
2023
$3,794
—
$436,133
10%
2023
$3,794
11%
$396,400
5%
2021
$3,432
—
$377,700
5%
2021
$3,432
3%
$359,000
3%
2021
$3,334
3%
$350,133
3%
2020
$3,238
4%
$341,267
3%
2019
$3,112
3%
$332,400
3%
2018
$3,021
3%
$321,700
3%
2017
$2,931
3%
$311,000
4%
2016
$2,844
7%
$300,300
—
2015
$2,649
—
$300,300
—
2014
$2,649
—
$300,300
—
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
Estimate the Cost for 2 Windjammer Rd
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2 Windjammer Road, Ocean Pines, MD 21811 (MLS# MDWO2040224) is a Single Family property with 5 bedrooms and 2 full bathrooms. 2 Windjammer Road is currently listed for $545,000 and was received on August 01, 2026. Want to learn more about 2 Windjammer Road? Do you have questions about finding other Single Family real estate for sale in Ocean Pines? You can browse all Ocean Pines real estate or contact a Coldwell Banker agent to request more information.