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!
Sold for $500,000
$500,000
2 Windjammer Rd, Ocean Pines, MD 21811
5beds
2,258sqft
Single Family Residence
Built in 1984
9,953 Square Feet Lot
$533,900 Zestimate®
$221/sqft
$2,908 Estimated rent
Home value
$533,900
$507,000 - $561,000
$2,908/mo
Zestimate® history
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$2,908/mo
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$4,010/mo
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$4,010/mo
Est. payment
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Prime waterfront location
Zillow last checked:
Listing updated:
Listed by:
Sally Todd Stout 410-726-3506,
Berkshire Hathaway HomeServices PenFed Realty - OP
Bought with:
Chantal Apple, 525472
Atlantic Shores Sotheby's International Realty
Source: Bright MLS,MLS#: MDWO2040224
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 2
- Full bathrooms: 2
- Main level bathrooms: 1
- Main level bedrooms: 2
Rooms
- Room types: Living Room, Dining Room, Kitchen
Dining room
- Level: Main
Kitchen
- Level: Main
Living room
- Level: Main
Heating
- Heat Pump, Electric
Cooling
- Central Air, Electric
Appliances
- Included: Dishwasher, Dryer, Oven/Range - Electric, Refrigerator, Washer, Electric Water Heater
- Laundry: Main Level
Features
- Entry Level Bedroom, Ceiling Fan(s), Walk-In Closet(s), Combination Dining/Living, Family Room Off Kitchen, Open Floorplan, Cathedral Ceiling(s)
- Flooring: Laminate
- Has basement: No
- Has fireplace: No
Interior area
- Total structure area: 2,258
- Total interior livable area: 2,258 sqft
- Finished area above ground: 2,258
- Finished area below ground: 0
Property
Parking
- Total spaces: 6
- Parking features: Storage, Garage Faces Front, Oversized, Detached, Driveway
- Garage spaces: 2
- Uncovered spaces: 4
Accessibility
- Accessibility features: 2+ Access Exits
Features
- Levels: Two
- Stories: 2
- Patio & porch: Deck, Screened, Porch, Breezeway
- Exterior features: Balcony
- Pool features: Community
- Has view: Yes
- View description: Canal, Water
- Has water view: Yes
- Water view: Canal,Water
- Waterfront features: Private Dock Site, Canal, Private Access
- Frontage length: Water Frontage Ft: 70
Lot
- Size: 9,953 Square Feet
- Features: Bulkheaded, Cleared, Corner Lot
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 2403078795
- Zoning: R-3
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary
- Property subtype: Single Family Residence
Materials
- Frame, Vinyl Siding, Stick Built
- Foundation: Block, Crawl Space
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1984
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Subdivision: Ocean Pines - Newport
HOA
- Has HOA: Yes
- Amenities included: Beach Club, Boat Ramp, Clubhouse, Golf Course, Marina/Marina Club, Pool, Basketball Court, Common Grounds, Community Center, Dog Park, Golf Course Membership Available, Jogging Path, Pier/Dock, Indoor Pool, Pool Mem Avail, Racquetball, Recreation Facilities
- Services included: Common Area Maintenance, Management, Reserve Funds, Road Maintenance
- HOA fee: $1,580 annually
- HOA name: OCEAN PINES ASSOCIATION
Location
- Region: Ocean Pines
- Municipality: OCEAN PINES
Financial & listing details
- Price per square foot: $221/sqft
- Tax assessed value: $457,167
- Annual tax amount: $4,043
- Date on market: 8/1/2026
- Listing agreement: Exclusive Right To Sell
- Inclusions: As Shown
- Exclusions: Staging Items
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 9/10/2026 | Sold | $500,000-8.3%$221/sqft |
Source:  Bright MLS #MDWO2040224 Report a problem | ||
| 8/18/2026 | Contingent | $545,000$241/sqft |
Source: Bright MLS #MDWO2040224 Report a problem | ||
| 8/1/2026 | Listed for sale | $545,000+74.7%$241/sqft |
Source: Bright MLS #MDWO2040224 Report a problem | ||
| 10/22/2002 | Sold | $312,000$138/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $4,043 +1.8% | $436,133 +5.1% |
| 2024 | $3,973 +4.7% | $415,100 +4.7% |
| 2023 | $3,794 +5% | $396,400 -4.5% |
| 2022 | $3,615 +5.2% | $415,100 +15.6% |
| 2021 | $3,436 +2.5% | $359,000 +2.5% |
| 2020 | $3,351 +2.6% | $350,133 -2.5% |
| 2019 | $3,266 +3.8% | $359,000 +8% |
| 2018 | $3,148 +3.3% | $332,400 +3.3% |
| 2017 | $3,047 +6.4% | $321,700 +3.4% |
| 2016 | $2,863 | $311,000 +3.6% |
| 2015 | $2,863 | $300,300 |
| 2014 | $2,863 | $300,300 |
| 2013 | -- | $300,300 -15.6% |
| 2012 | -- | $355,600 |
| 2011 | -- | $355,600 |
| 2010 | -- | $355,600 -28.9% |
| 2009 | -- | $499,850 +10.4% |
| 2008 | -- | $452,610 +11.7% |
| 2007 | -- | $405,370 +13.2% |
| 2006 | -- | $358,130 +18.6% |
| 2005 | -- | $301,942 +22.9% |
| 2004 | -- | $245,756 +29.6% |
| 2003 | -- | $189,570 +9.8% |
| 2002 | -- | $172,596 +10.9% |
| 2001 | -- | $155,623 |
Find assessor info on the county website
Neighborhood: 21811
Nearby homes
- $502,400-- bd1 ba1.5k sqft5 White Sail Cir, Ocean Pines, MD 21811Off Market
- $465,100-- bd2 ba1.4k sqft4 Windjammer Rd, Ocean Pines, MD 21811Off Market
- $642,000-- bd2 ba1.5k sqft7 White Sail Cir, Ocean Pines, MD 21811Off Market
- $809,200-- bd2 ba2.6k sqft1 Windjammer Rd, Ocean Pines, MD 21811Off Market
- $378,6002 bd1 ba1k sqft23 Carriage Ln, Ocean Pines, MD 21811Off Market
- $727,5005 bd3 ba2.9k sqft21 Carriage Ln, Ocean Pines, MD 21811Off Market
- $604,000-- bd2 ba1.8k sqft9 White Sail Cir, Ocean Pines, MD 21811Off Market
- $499,0003 bd2 ba1.5k sqft101 White Sail Cir, Ocean Pines, MD 21811For Sale
Nearby schools
GreatSchools rating
- 8/10Showell Elementary SchoolGrades: PK-4Distance: 2.2 mi
- 10/10Stephen Decatur Middle SchoolGrades: 7-8Distance: 4.9 mi
- 7/10Stephen Decatur High SchoolGrades: 9-12Distance: 4.6 mi
Schools provided by the listing agent
- Elementary: Berlin Intermediate School
- Middle: Stephen Decatur
- High: Stephen Decatur
- District: Worcester County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$533,900
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$533,900
- Maryland
- Worcester County
- Berlin
- 21811
- 2 Windjammer Rd
