2 Windjammer Rd
Ocean Pines, MD 21811

$545,000

Price

Beds

Baths

2,258 Sq. Ft.

$241 / Sq. Ft.

2,258

Sq. Ft.

$241

per Sq. Ft.

Get preapproved with Rocket Mortgage¹

Coming Soon

Waterfront property in coastal community

2nd floor (bedrm 4) w/ slider to balcony

2nd floor (bedrm 5) with slider to balcony

balcony between main house and garage/loft

screened porch off dining rm w/ vinyl tch windows

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,...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!

Listed by Sally Todd Stout • Berkshire Hathaway HomeServices PenFed Realty - OP
P: (410)-726-3506 sallytoddrealtor@yahoo.com

Property Details for 2 Windjammer Road

Tax ID Number

2403078795

Ownership

Fee Simple

Condo Coop Association

HOA

Yes

Structure Type

Detached

Style

Contemporary

Levels/Stories

Furnished

Partially

LISTING UPDATED: 07/31/2026 04:41 PM

Property Details for 2 Windjammer Road

Status	Coming Soon
MLS #	MDWO2040224
Days on Market	-
Taxes	$4,043 / year
HOA Fees	$1,580 / year
Condo/Co-op Fees	-
Property Type	Single Family
MLS Type	Residential / Fee Simple
Year Built	1984
Lot Size	0.23 AC / 9,953 SF
County	Worcester County

Get preapproved with Rocket Mortgage¹

Location

Listing Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Add your commute

Building Information for 2 Windjammer Road

Stories2Year Built1984Building Size-Lot Size0.23 AC / 9,953 SF

Payment Calculator

Get preapproved with
OriginPoint Mortgage or Rocket Mortgage¹

$3,239 per month

30 year fixed, 6.55% Interest

Principal and Interest

$2,770

Property Taxes

$337

HOA Dues

$132

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Property Information for 2 Windjammer Road

Location

In City Limits: No
Transportation: Airport less than 10 miles

School District Name: WORCESTER COUNTY PUBLIC SCHOOLS
School District County ID: 121138066543
SchoolDistrictSource: Listing Agent
Elementary School: BERLIN INTERMEDIATE SCHOOL (WORCESTER MD)
ElementarySchoolSource: Listing Agent
Middle Or Junior School: STEPHEN DECATUR (WORCESTER MD)
MiddleSchoolSource: Listing Agent
High School: STEPHEN DECATUR (WORCESTER MD)
County: WORCESTER
MLS Area: Worcester Ocean Pines

Waterfront / Water Access

Water View: Yes
Water Access: Yes

Water Access Features: Private Access
Water Oriented: Yes
Navigable Water: Yes
Water Body Type: Canal
Water Frontage In Feet: 70.0

Association / Community Info

HOA Name: OCEAN PINES ASSOCIATION
HOA Phone: 410-641-7717

HOA Condo Coop Fee Includes: Common Area Maintenance, Management, Reserve Funds, Road Maintenance
HOA Condo Coop 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
Property Manager Y/N: No
Other Fees: $200
Other Fees Frequency: One Time
Senior Community: No
Association Recreation Fee Y/N: No
Type of Condo: Home Owner Association

Taxes and Assessment

Tax Year: 2025
Tax Assessed Value: $457,167

Year Assessed: 2026
Improvement Assessed Value: $0
City Town Tax: $0
Land Assessed Value: $0
Clean Green Assessed: No
Land Use Code: R
Zoning: R-3
School Tax: $0
Automatically Update Tax Values Y/N: Yes

Lease Information

Pets Allowed: Yes
Pet Restrictions: No Pet Restrictions

Rooms

Main

# Bedrooms Count Main Level: 2
# Bathrooms Count Main Level: 1

# Bathrooms Full Main Level: 1

All Upper Levels

# Bedrooms Count All Upper Levels: 3
# Bathrooms Count All Upper Levels: 1

# Bathrooms Full All Upper Levels: 1

Upper Level 1

# Bedrooms Count Upper Level: 3
# Bathrooms Count Upper Level: 1

# Bathrooms Full Upper Level: 1

Rooms

Room List: Living Room, Dining Room, Kitchen
Stories: Main, Upper 1

Rooms Information

Room 1

Room Type: Living Room
Room Level: Main

Room Exists: Yes

Room 2

Room Type: Kitchen
Room Level: Main

Room Exists: Yes

Room 3

Room Type: Dining Room
Room Level: Main

Room Exists: Yes

Building Info

Total Finished SQFT: 2,258.00
Total Finished SQFT Source: Estimated

Tax Total Finished SQFT: 2,415.00
Total SQFT: 2,258.00
Total SQFT Source: Estimated
Floors In Unit Count: 2
Construction Materials: Frame, Vinyl Siding, Stick Built
Roof: Asphalt
Ext Main Mid-res: http://bright-media02.prd.brightmls.com/bright/images/0000/8052/1889/8834/805218898834_512_384_WM_lsgT7gfjZyEohBVq.jpg
Wall and Ceiling Types: Cathedral Ceilings
Flooring Type: Laminate Plank, Laminated
Foundation Details: Block, Crawl Space
Room and Floor: Bedrooms-Main Level-1, Bedrooms-Main Level-2, Bathrooms Full-Main Level-1, Bedrooms-Upper Level 1-1, Bedrooms-Upper Level 1-2, Bedrooms-Upper Level 1-3, Bathrooms Full-Upper Level 1-1
# Bathrooms Full: 2
Other Structure: Garage(s)

Lot / Land Information

Lot Size Source: Assessor
Lot Size Dimensions: 0.00 x 0.00

Lot Dimensions Source: Assessor
Lot Features: Bulkheaded, Cleared, Corner
Road Responsibility: Public
Location Type: Canal
Parcel ID: 5384711
Ground Rent Exists: No

Parking

Type Of Parking: Detached Garage, Driveway
Num of Detached Garage Spaces: 2

Driveway - # of Spaces: 4
Total Garage Spaces: 2
Garage Features: Additional Storage Area, Garage - Front Entry, Oversized

Interior Features

Interior Features: Entry Level Bedroom, Ceiling Fan(s), Walk-in Closet(s), Combination Dining/Living, Family Room Off Kitchen, Floor Plan - Open
Fireplace: No

Appliances: Dishwasher, Dryer, Oven/Range - Electric, Refrigerator, Washer
Accessibility Features: 2+ Access Exits
Laundry Type: Main Floor

Exterior Features

Outdoor Living Structures: Deck(s), Screened, Porch(es), Breezeway, Balcony
Pool: Yes - Community

Utilities

Heating: Yes
Cooling Type: Central A/C

Cooling Fuel: Electric
Heating Type: Heat Pump(s)
Heating Fuel: Electric
Hot Water: Electric
Water Source: Public
Sewer Septic: Public Sewer

Confidential Data

Listing Office

List Agent AOR: Coastal Association of REALTORS (MD)
List Agent URL: www.sallytoddstout.com

Property History for 2 Windjammer Road

Date	Event & Source	Price	Appreciation
Oct 22, 2002	Closed (Public Record) Public Record #103237622	$312,000,000	—
Oct 19, 2002	Closed BRIGHT #1000617846	$312,000	—
Sep 11, 2002	Pending BRIGHT #1000617846		—
Aug 19, 2002	Listed (Active) BRIGHT #1000617846	$309,900	—

Date	Event & Source	Price
10/22/2002	Closed (Public Record) Public Record #103237622	$312,000,000
10/19/2002	Closed BRIGHT #1000617846	$312,000
09/11/2002	Pending BRIGHT #1000617846	—
08/19/2002	Listed (Active) BRIGHT #1000617846	$309,900

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 2 Windjammer Road

Taxable ValueLand-Additions-Total-

Tax Record2023$3,794 ($316 / month)

Home Facts

Beds0Baths3Total Finished SqFt2,415 SqFtAbove Grade Finished SqFt2,415 SqFtStories2Lot Size9,953 SqFtStyleSingle Family ResidenceYear Built1984ZoningR-3CountyWORCESTERAPN03-078795Fireplace TypeHas Fireplace

Schools near 2 Windjammer Road

This home is within Worcester County Public Schools.


Rating	School	Type	Grades	Distance
8/10	Showell Elementary School	Public - Serves this home	PK to 4	2.2 mi
7/10	Berlin Intermediate School	Public - Serves this home	5 to 6	5.8 mi
10/10	Stephen Decatur Middle School	Public - Serves this home	7 to 8	4.8 mi
7/10	Stephen Decatur High School	Public - Serves this home	9 to 12	4.6 mi
NR	Worcester Technical High School	Public - Choice school	9 to 12	16.0 mi
NR	Cedar Chapel Special School	Public - Choice school	PK to 12	20.9 mi
NR	Most Blessed Sacrament Catholic School	Private - Nearby school	PK to 8	2.0 mi


Rating	School	Distance
8/10	Showell Elementary School PublicPK to 4 Serves this home	2.2 mi
7/10	Berlin Intermediate School Public5 to 6 Serves this home	5.8 mi
10/10	Stephen Decatur Middle School Public7 to 8 Serves this home	4.8 mi
7/10	Stephen Decatur High School Public9 to 12 Serves this home	4.6 mi
NR	Worcester Technical High School Public9 to 12 Choice school	16.0 mi
NR	Cedar Chapel Special School PublicPK to 12 Choice school	20.9 mi
NR	Most Blessed Sacrament Catholic School PrivatePK to 8 Nearby school	2.0 mi

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

New listings in 21811

$499,900 | 180 Teal Circle, Ocean Pines, MD 21811

1/88

Listed By Coldwell Banker RealtyOpen: 8/1 10:00AM - 12:00PM

$499,900

3
Bedrooms: 3
Bathrooms: 1,638
Square Feet: 0.17
Acres

180 Teal Circle, Ocean Pines, MD 21811

$469,900 | 39 King Richard Road, Ocean Pines, MD 21811

1/70

New

$469,900

3
Bedrooms: 3
Bathrooms: 1,740
Square Feet: 0.20
Acres

39 King Richard Road, Ocean Pines, MD 21811

$515,000 | 13121 Fancourt Lane, Unit 139, Berlin, MD 21811

1/92

Listed By Coldwell Banker RealtyNew

$515,000

4
Bedrooms: 3
Bathrooms: 2,218
Square Feet

13121 Fancourt Lane, Unit 139, Berlin, MD 21811

$1,749,900 | 538 Yacht Club Drive, Ocean Pines, MD 21811

1/137

Listed By Coldwell Banker RealtyOpen: 8/2 12:00PM - 02:00PM

$1,749,900

4
Bedrooms: 5
Bathrooms: 4,289
Square Feet: 0.50
Acres

538 Yacht Club Drive, Ocean Pines, MD 21811

$364,900 | 1218 Ocean Parkway, Ocean Pines, MD 21811

1/92

Virtual TourNew

$364,900

3
Bedrooms: 2
Bathrooms: 1,284
Square Feet: 0.17
Acres

1218 Ocean Parkway, Ocean Pines, MD 21811

$479,900 | 953 Yacht Club Drive, Ocean Pines, MD 21811

1/90

Coldwell Banker Realty Coming SoonOpen: 8/1 01:30PM - 03:30PM

$479,900

3
Bedrooms: 3
Bathrooms: 1,784
Square Feet: 0.07
Acres

953 Yacht Club Drive, Ocean Pines, MD 21811

$365,000 | 13 Hatteras Street, Ocean Pines, MD 21811

1/63

Open: 8/2 01:00PM - 04:00PM

$365,000

2
Bedrooms: 2
Bathrooms: 1,230
Square Feet: 0.11
Acres

13 Hatteras Street, Ocean Pines, MD 21811

$939,000 | 12120 Pimlico Lane, Berlin, MD 21811

1/140

Active Under Contract

$939,000

4
Bedrooms: 4
Bathrooms: 3,368
Square Feet: 0.24
Acres

12120 Pimlico Lane, Berlin, MD 21811

1/95

$759,000

4
Bedrooms: 4
Bathrooms: 3,234
Square Feet: 0.24
Acres

11654 Maid At Arms Lane, Berlin, MD 21811

Explore Nearby Homes

More information about 2 Windjammer Road, Ocean Pines, MD 21811

2 Windjammer Road is a single family home Coming Soon in Ocean Pines, MD 21811. This property is currently priced at $545,000. This listing's school district is Worcester County Public Schools. Nearby schools include Showell Elementary School, Berlin Intermediate School and Stephen Decatur Middle School. 2 Windjammer Road is a 5-bed, 2-bath, 2,258 sqft single family home built in 1984.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

© 2026 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 07/31/2026 04:41 PM

2 Windjammer RdOcean Pines, MD 21811

Know your buying power with a preapproval and custom rate in minutes

Explore Nearby Homes

Homes in Nearby Ocean Pines Neighborhoods

Homes in Nearby Ocean Pines Cities

Homes in Nearby Ocean Pines Zip Codes

More information about 2 Windjammer Road, Ocean Pines, MD 21811

2 Windjammer Rd
Ocean Pines, MD 21811