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2 WINDJAMMER RD, OCEAN PINES, MD 21811

5 Beds

2 Baths

2,258SqFt

Active

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!

Property Details
Price $545,000
Bedrooms 5
Full Baths 2
Total Baths 2
Property Style Contemporary
Lot Size 0.00 x 0.00
Lot Size Area Units Square Feet
Acres 0.23
Property Type Residential
Sub type SingleFamilyResidence
MLS Sub type Detached
Stories 2
Features Entry Level Bedroom,Ceiling Fan(s),Walk-in Closet(s),Combination Dining/Living,Family Room Off Kitchen,Floor Plan - Open
Year Built 1984
Subdivision OCEAN PINES - NEWPORT
View Canal,Water
Roof Asphalt
Heating Heat Pump(s)
Foundation Block,Crawl Space
Accessibility 2+ Access Exits
Lot Description Bulkheaded,Cleared,Corner
Garage spaces 2
Association Name OCEAN PINES ASSOCIATION
Association Fee 1580
Association 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
Geographic Data
Directions Enter Ocean PInes North Gate and follow Ocean Parkway, make a left on Windjammer, #2 is on the left
County WORCESTER
Latitude 38.40158
Longitude -75.15428
Market Area Worcester Ocean Pines
Address Information
Address 2 WINDJAMMER RD, OCEAN PINES, MD 21811
Postal Code 21811
City OCEAN PINES
Cross Street 0.00
State MD
Country United States
Listing Information
Listing Office Berkshire Hathaway HomeServices PenFed Realty - OP
Listing Office Email oceanpines@penfedrealty.com
Listing Agent Sally Todd Stout
Special listing conditions Standard
Ownership Fee Simple
Virtual Tour URL https://idx.imprev.net/i/21015/MDWO2040224/714/html/virtualtour/listing/idx/index.html
School Information
District WORCESTER COUNTY PUBLIC SCHOOLS
Elementary School BERLIN INTERMEDIATE SCHOOL
Middle School STEPHEN DECATUR
High School STEPHEN DECATUR
MLS Information
Days on market 14
MLS Status Active
Listing Date Aug 1, 2026
Listing Last Modified Aug 14, 2026
Tax ID 2403078795
Tax Year 2025
Tax Annual Amount 4043
MLS Area Worcester Ocean Pines
MLS # MDWO2040224

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Last updated: 2026-08-17T06:00:25.310118Z. Listing information is provided by Bright MLS. Listings are generated from various brokers who participate in IDX. Information is deemed reliable but not guaranteed.