Sold on Sep 2026

$500,000

•

2,258

sq ft

2 Windjammer Rd, Ocean Pines, MD 21811

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About this home

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!

Single-familyProperty Type

1984Year Built

9,953 sq ftLot Size

$221Price/Sq.Ft.

$132/moHOA Dues

2 garage spacesParking

Listed by Sally Todd Stout • Berkshire Hathaway HomeServices PenFed Realty - OP

•410-208-3500 (broker)

•oceanpines@penfedrealty.com (broker)

Bought with Chantal Apple • Atlantic Shores Sotheby's International Realty

•410-524-0919 (broker)

•ryan@ryanhaley.com (broker)

Redfin checked: a minute ago

•Source:BRIGHT MLS #MDWO2040224

Redfin Estimate

$510,544

$11K since sold in September 2026$21K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 1.6% higher than the average sale price ($502K) of 6 comparable homes.

SOLD AUG 21, 2026
$350,000
A
3 beds2 baths1,738 sq ft
25 Seabreeze Rd, Ocean Pines, MD 21811
SOLD AUG 31, 2026
$425,000
B
4 beds3 baths1,900 sq ft
3 Mates Ct, Ocean Pines, MD 21811
SOLD JUL 6, 2026
$399,900
C
4 beds2 baths2,224 sq ft
29 Pinehurst Rd, Ocean Pines, MD 21811
SOLD MAY 19, 2026
$440,000
D
4 beds2 baths2,034 sq ft
289 Ocean, Ocean Pines, MD 21811
SOLD JUN 11, 2026
$650,000
E
4 beds3 baths2,157 sq ft
31 Brookside Rd, Ocean Pines, MD 21811
SOLD JUL 27, 2026
$750,000
F
3 beds2.5 baths2,176 sq ft
22 Harborview Dr, Berlin, MD 21811

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Market trends in 21811, MD

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

97.8%

0.3% MoM

Median sale price

$500K

$166 MoM

Avg. days on market

58d

1 days MoM

Recently sold homes

191

9 MoM

New listings for sale

$444,900
4 beds3 baths2,059 sq ft
12540 River Run Ln Unit 104 B, Berlin, MD 21811
(410) 208-9200
NEW 19 HRS AGO
$399,999
2 beds2 baths1,236 sq ft
12503 W Torquay Rd, Ocean City, MD 21842
(443) 275-7188
COMING SOON
$725,000
3 beds2 baths2,411 sq ft
102 Quillen Dr, Berlin, MD 21811
(410) 524-6400
VIDEO TOUR
$1,276,000
4 beds2.5 baths2,693 sq ft
14 Goldeneye Ct, Ocean Pines, MD 21811
(410) 524-1700
$360,000
3 beds2 baths1,608 sq ft
857 Ocean Pkwy, Ocean Pines, MD 21811
(410) 208-3500
COMING SOON
$309,900
4 beds1 bath1,056 sq ft
99 White Horse Dr, Berlin, MD 21811
(410) 641-5000
3D WALKTHROUGH
$329,900
3 beds2 baths1,056 sq ft
3 Dockside Dr, Berlin, MD 21811
(410) 520-2600
OPEN SAT, 11AM TO 1PM
$499,000
3 beds2 baths2,052 sq ft
63 Chatham Ct, Ocean Pines, MD 21811
(410) 208-3500
COMING SOON
$1,100,000
6 beds3 baths4,316 sq ft
33 Wood Duck Dr, Ocean Pines, MD 21811
(302) 539-9040
OPEN SAT, 10AM TO 12:30PM
$409,000
3 beds2 baths1,371 sq ft
13 Royal Oaks Dr, Ocean Pines, MD 21811
(410) 524-6400
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Rental estimate

Est. $3,847 per month, based on comparable rentals

Sale and tax history for 2 Windjammer Rd

Sale History
Tax History

Date

Event

Price

BRIGHT MLS #MDWO2040224

Sep 10, 2026

Sold

$500,000

$221/sq ft

Aug 18, 2026

Contingent

—

Aug 1, 2026

Listed

$545,000

$241/sq ft

Jul 31, 2026

Coming Soon

$545,000

$241/sq ft

BRIGHT MLS #1000617846

Oct 19, 2002

Sold

$312,000

$138/sq ft

Aug 19, 2002

Listed

$309,900

$137/sq ft

Public Records

Apr 29, 1981

Sold

$17,000

$8/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$4,219 (+4.8%)

2025

$4,025 (+1.8%)

2024

$3,955 (+4.7%)

2023

$3,777 (+7.0%)

2022

$3,528 (+2.8%)

2021

$3,432 (+2.9%)

2020

$3,334 (+3.0%)

$162,600 + $196,400

$359,000

2019

$3,238 (+4.0%)

2018

$3,112 (+3.0%)

$159,900 + $172,500

$332,400

2017

$3,021 (+6.2%)

2016

$2,843 (+7.4%)

$155,400 + $144,900

$300,300

2015

$2,648

$155,400 + $144,900

$300,300

2014

$2,649 (−15.6%)

2013

$3,136 (+9.6%)

2012

$2,863

2011

$2,863 (−28.9%)

2010

$4,024 (+9.5%)

2009

$3,675

Public record

Beds

—

Baths

Stories

Lot width

—

Lot depth

—

Lot size

9,953 Sq. Ft.

Year renovated

—

Sq. Ft.

2,415

Year built

1984

Style

Single Family Residential

County

Worcester County

APN

03 078795

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 21, 2026.

Property details

Parking

Parking Information
# of Detached Garage Spaces: 2
Garage Features: Additional Storage Area, Garage - Front Entry, Oversized
# of Total Garage and Parking Spaces: 6
Has Garage
# of Garage Spaces: 2
Driveway - # of Spaces: 4
Detached Garage, Driveway

Interior

Virtual Tour

Bedroom Information
# of Bedrooms On 1st Upper Level: 3
# of Bedrooms On Main Level: 2

Bathroom Information
# of Bathrooms (Full) On 1st Upper Level: 1
# of Bathrooms (Full) On Main Level: 1
# of Bathrooms (Full) On All Upper Levels: 1
# of Bathrooms (Full): 2

Interior Information
Appliances: Dishwasher, Dryer, Oven/Range - Electric, Refrigerator, Washer
Flooring Type: Laminate Plank, Laminated
Partially Furnished
Interior Features: Entry Level Bedroom, CeilngFan(s), Walk-in Closet(s), Combination Dining/Living, Family Room Off Kitchen, Floor Plan - Open
Living Area Sq.Ft. Source: Estimated
Wall & Ceiling Types: Cathedral Ceilings

Room Information
Living Room, Dining Room, Kitchen
Laundry Type: Main Floor

Basement Information
Basement: No

Exterior

Property Information
Federal Flood Zone
Total Below Grade Sq. Ft.: 0
Accessibility Features: 2+ Access Exits
Federal Flood Zone: X500, AE, X
# of Floors In Unit: 2
Ownership Interest: Fee Simple
Year Built Source: Assessor

Building Information
Building Name: NONE AVAILABLE
Construction Materials: Frame, Vinyl Siding, Stick Built
Foundation Details: Block, Crawl Space
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Deck(s), Screened, Porch(es), Breezeway, Balcony
Pets Allowed: Yes
Pet Restrictions: No Pet Restrictions
Roof: Asphalt
Structure Type: Detached
Other Structures: Garage(s)

Pool Information
Community Pool

Lot Information
Lot Features: Bulkheaded, Cleared, Corner
Lot Size Dimensions: 0.00 x 0.00
Lot Dimensions Source: Assessor
Navigable Water
Has Water View
Water Frontage In Feet: 70

Above Grade Information
Finished Sq.Ft.: 2,258
Finished Sq.Ft. Source: Estimated

Below Grade Information
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft. Source: Assessor

Financial

Tax Information
Tax Assessed Value: $457,167
Tax Year: 2025
Tax Annual Amount: $4,043

Assessments Information
Year Assessed: 2026

Utilities

Utilities Information
Central Air
Cooling Type: Central A/C
Cooling Fuel: Electric
Heat Pump(s)
Heating Fuel: Electric
Hot Water: Electric
Sewer Septic: Public Sewer
Water Source: Public

Location

Homeowners Association Information
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, Pier/Dock, Pool - Indoor, Pool Mem Avail, Racquet Ball, Recreational Center
HOA Fee: $1,580
HOA Fee Frequency: Annually
Other Fees: $200
Other Fees Frequency: One Time

School Information
Elementary School: BERLIN INTERMEDIATE SCHOOL
Middle Or Junior School: STEPHEN DECATUR
High School: STEPHEN DECATUR
School District Name: WORCESTER COUNTY PUBLIC SCHOOLS
Elementary School Source: Listing Agent
Middle School Source: Listing Agent
School District Source: Listing Agent

Location Information
Outside City Limits
Cross Street: 0.00
Directions: Enter Ocean PInes North Gate and follow Ocean Parkway, make a left on Windjammer, #2 is on the left
Location Type: Canal
Municipality: OCEAN PINES
Road Responsibility: Public
Transportation: Airport less than 10 miles

Waterfrontage Information
Water Access Features: Private Access
Water Access
Private Dock Site
On Waterfront
Water Oriented
Water Body Type: Canal

Public facts

Beds: —
Baths: 3.0
Sq. Ft.: 2,415
Stories: 2.0
Lot Size: 9,953 square feet
Style: Single Family Residential
Year Built: 1984
Year Renovated: —
County: Worcester County
APN: 03 078795

Home facts updated by county records on Aug 21, 2026

Around this home

Schools

Showell Elementary School

Public PreK-4 • Assigned • 2.2mi

8/10

Stephen Decatur Middle School

Public 7-8 • Assigned • 4.9mi

10/10

Stephen Decatur High School

Public 9-12 • Assigned • 4.6mi

7/10

Provided by GreatSchools

Climate risks

10/10 Flood Factor

Estimated 80%+ chance of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

8/10 Heat Factor

7 days above 102° expected this year, 17 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

2/10 Air Factor

2 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Ocean Pines, MD • 21811

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

91/ 100

Exceptional sunlight

Sunscore

This home receives average direct sun exposure in Ocean Pines. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.6 hrs

5.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$486,000 – $588,000

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New listings for sale in 21811

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(410) 208-9200

NEW 19 HRS AGO

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COMING SOON

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VIDEO TOUR

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COMING SOON

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3D WALKTHROUGH

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OPEN SAT, 11AM TO 1PM

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COMING SOON

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Home values near 2 Windjammer Rd

Data from public records.

Address	Redfin Estimate
1 Windjammer Rd, Ocean Pines, MD 4 Beds \| 2.5 Baths \| 2500 Sq. Ft.	$788,979
97 White Sail Cir, Ocean Pines, MD 3 Beds \| 2.5 Baths \| 2395 Sq. Ft.	$843,893

Address	Redfin Estimate
4 Windjammer Rd, Ocean Pines, MD - Beds \| 2 Baths \| 1440 Sq. Ft.	$425,240
6 White Sail Cir, Ocean Pines, MD - Beds \| 2.5 Baths \| 2300 Sq. Ft.	$553,062

Address	Redfin Estimate
3 Windjammer Rd, Ocean Pines, MD 4 Beds \| 2 Baths \| 1696 Sq. Ft.	$565,383
104 White Sail Cir, Ocean Pines, MD 4 Beds \| 2.5 Baths \| 2016 Sq. Ft.	$435,612

Property information provided by BRIGHT MLS when last listed in 2026. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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2 Windjammer Rd, Ocean Pines, MD 21811

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About this home

Redfin Estimate

Market trends in 21811, MD

Homeowner tools

Sale and tax history for 2 Windjammer Rd

Public record

Property details

Parking

Interior

Exterior

Financial

Utilities

Location

Public facts

Around this home

Schools

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 21811

Home values near 2 Windjammer Rd

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