OFF MARKET

Off Market Jun 2021 for $340K

$438,024

Est. refi paymentEst. refi $2,114/mo

•

1,550

sq ft

99 Windjammer Rd, Ocean Pines, MD 21811

About this home

Move in ready and being sold fully furnished! Popular 3 bedroom/2 bath split bedroom floor plan providing privacy for family & guests. Skylights, hardwood flooring, recessed lights, plant shelf and a cozy gas fireplace accent the wide open great room with cathedral ceiling. Rear deck leads to a large 3-season room with vinyl windows and screens that overlook the 6th Tee of the Golf course. Wonderfully landscaped front yard, including an irrigation system. Large asphalt paved driveway leads to the 2 car garage providing ample storage. HVAC unit (2015), encapsulated crawl space that is climate controlled & side door in garage. These sellers have lovingly maintained this beautiful home built by J. J. Reed. Enjoy all Ocean Pines has to offer including the Yacht Club and restaurant, new Golf Clubhouse with restaurant, 5 swimming pools (1 enclosed), Robert Trent Jones golf course, marina, community center, beach club, skateboard park, dog park, library, shopping, weekly farmers market, community police and fire departments. Playgrounds and athletic fields and more!

Single-familyProperty Type

1997Year Built

9,000 sq ftLot Size

$283Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Sonia Zaffiris • Hileman Real Estate-Berlin

•410-208-9200 (broker)

•debbie@hilemanrealestate.com (broker)

Bought with Julie Woulfe • ERA Martin Associates, Shamrock Division

•410-641-5000 (broker)

•joni@era.com (broker)

Redfin checked: a few seconds ago

•Source:BRIGHT MLS #MDWO122298

Redfin Estimate

$438,024

$98K since sold in June 2021$3,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 16.7% higher than the average sale price ($375K) of 6 comparable homes.

SOLD APR 21, 2026
$379,900
A
3 beds2 baths1,480 sq ft
125 Ocean Pkwy, Ocean Pines, MD 21811
SOLD MAY 29, 2026
$406,000
B
3 beds2 baths1,446 sq ft
1 Surfers Way, Ocean Pines, MD 21811
SOLD JUN 22, 2026
$390,000
C
3 beds2 baths1,722 sq ft
51 Newport Dr, Ocean Pines, MD 21811
SOLD JUN 5, 2026
$380,000
D
3 beds2 baths1,585 sq ft
48 Windjammer Rd, Ocean Pines, MD 21811
SOLD MAY 1, 2026
$309,000
E
3 beds2 baths1,290 sq ft
22 Rabbit Run Ln, Ocean Pines, MD 21811
SOLD JUL 1, 2026
$388,000
F
3 beds2 baths1,430 sq ft
40 Harbormist Cir, Ocean Pines, MD 21811

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Earn from this home

Sell

$165,797

Est. take-home

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Refinance

Est. cash available

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Rent

$2,767/mo

Redfin rental estimate

List your home for rent

Market trends in 21811, MD

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

97.8%

0.5% MoM

Median sale price

$490K

$15K MoM

Avg. days on market

59d

6 days MoM

Recently sold homes

204

11 MoM

New listings for sale

$470,000
7 beds4 baths2,768 sq ft
5 Church St, Berlin, MD 21811
(443) 552-7579
3D WALKTHROUGH
$785,000
3 beds3.5 baths2,471 sq ft
12911 Sand Bar Ln #1, Ocean City, MD 21842
(410) 208-3500
COMING SOON
$444,900
4 beds3 baths2,059 sq ft
12540 River Run Ln Unit 104 B, Berlin, MD 21811
(410) 208-9200
3D WALKTHROUGH
$485,000
3 beds2 baths1,892 sq ft
13 Catalpa Ln, Ocean Pines, MD 21811
(443) 552-7579
$510,500
3 beds2 baths2,048 sq ft
21 Castle Dr, Ocean Pines, MD 21811
(410) 208-9200
COMING SOON
$394,500
3 beds2 baths1,536 sq ft
14 Willow Way, Ocean Pines, MD 21811
(410) 208-9200
$1,050,000
4 beds3.5 baths3,342 sq ft
12121 Pimlico Ln, Berlin, MD 21811
(443) 552-7579
$419,900
3 beds2 baths1,456 sq ft
55 Martinique Cir, Ocean Pines, MD 21811
(410) 524-0919
$222,000
1 bed1 bath660 sq ft
392 Timberline Cir, Ocean Pines, MD 21811
(302) 360-0300
$485,000
4 beds3.5 baths2,765 sq ft
8663 Bat Creek Loop Ln #3, Berlin, MD 21811
(410) 723-1895
See all

Provided by Redfin

Sale history for 99 Windjammer Rd

Date

Event

Price

BRIGHT MLS #MDWO122298

Jun 11, 2021

Sold

$340,000

$219/sq ft

May 12, 2021

Pending

—

May 9, 2021

Listed

$329,000

$212/sq ft

BRIGHT MLS #1001853660

Oct 10, 2018

Sold

$265,000

$171/sq ft

Sep 7, 2018

Pending

—

Aug 31, 2018

Relisted

—

Aug 23, 2018

Pending

—

Aug 22, 2018

Price Changed

$265,000

$171/sq ft

Aug 13, 2018

Relisted

—

Jul 22, 2018

Pending

—

Jul 12, 2018

Relisted

—

Jun 26, 2018

Pending

—

Jun 14, 2018

Listed

$272,500

$176/sq ft

+35

NEW PRICE & MOTIVATED SELLER! Move in ready. Watch the birdies on the 6th tee of Ocean Pines Golf Course from this well maintained J. J. Reed built Contemporary home. Popular 3 bedroom/2 bath split bedroom floor plan with spacious living and dining areas located in the center. Skylights, hardwood flooring and a cozy gas fireplace accent this wide open space with cathedral ceiling. Wonderful eat-in breakfast room adjacent to kitchen. Rear deck, that has been recently painted, leads to a large 3-season room with vinyl windows that allow screen option as well. Wonderfully landscaped front yard, including an irrigation system. Large asphalt paved and sealed driveway that leads to the 2 car garage. 1 year HMS Home Warranty included for the new buyer. Upgrades include new HVAC unit (2015), encapsulated crawl space that is climate controlled & new service door in garage. All this adds to the beauty of this wonderfully maintained home . Private rear yard that overlooks the 6th Tee box on the Robert Trent Jones designed Golf Course. Come see and fall in love.

BRIGHT MLS #1000551624

Aug 20, 2014

Sold

$243,000

$157/sq ft

May 29, 2014

Listed

$249,900

$161/sq ft

+11

GOLF COURSE Custom built rancher was crafted by premier builder JJ Reed. This 3 bed/2 bath home has had major updates done in 2008 and in 2014. Upgrades include a updated kitchen with 42 inch high cabinets and GE Profile Stainless appliances, and brand new updated custom guest bath. In April 2014 a total remodel of the master bath was completed to include a solid surface shower with designer glass door, new commode, and new sink with granite. The great room features a cathedral ceiling, gas fireplace, recessed lights and a plant shelf. A 12 x 12 - 3 season room overlooks the 6th Tee of the Robert Trent Jones Golf course. The split floor plan provides privacy for family & guests and the 2 car garage provides ample storage. HMS Warranty provided by seller. Owner occupied, but easy to show.

Public Records

Nov 30, 1999

Sold

$143,000

$92/sq ft

BRIGHT MLS #1000594700

Sep 5, 1999

Listed

$145,500

$94/sq ft

BRIGHT MLS #1000580024

Jun 13, 1997

Listed

$136,000

$88/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$3,159 (+7.0%)

2025

$2,953 (+4.1%)

2024

$2,835 (+7.8%)

2023

$2,629 (+8.5%)

2022

$2,423 (+8.8%)

2021

$2,227 (+3.4%)

2020

$2,154 (+3.5%)

$82,000 + $150,700

$232,700

2019

$2,081 (+4.7%)

2018

$1,987 (+3.2%)

$77,000 + $132,800

$209,800

2017

$1,925 (+6.9%)

2016

$1,801 (+8.4%)

$77,000 + $113,200

$190,200

2015

$1,661 (+2.6%)

$77,000 + $113,200

$190,200

2014

$1,620 (−0.9%)

2013

$1,634 (+11.8%)

2012

$1,462 (+2.4%)

2011

$1,427 (+3.1%)

2010

$1,384 (+3.4%)

2009

$1,339

Tax history for 99 Windjammer Rd

Year

Property tax

Land + Additions

Assessment*

2026

$3,159 (+7.0%)

2025

$2,953 (+4.1%)

2024

$2,835 (+7.8%)

2023

$2,629 (+8.5%)

2022

$2,423 (+8.8%)

2021

$2,227 (+3.4%)

2020

$2,154 (+3.5%)

$82,000 + $150,700

$232,700

2019

$2,081 (+4.7%)

2018

$1,987 (+3.2%)

$77,000 + $132,800

$209,800

2017

$1,925 (+6.9%)

2016

$1,801 (+8.4%)

$77,000 + $113,200

$190,200

2015

$1,661 (+2.6%)

$77,000 + $113,200

$190,200

2014

$1,620 (−0.9%)

2013

$1,634 (+11.8%)

2012

$1,462 (+2.4%)

2011

$1,427 (+3.1%)

2010

$1,384 (+3.4%)

2009

$1,339

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

—

Baths

Stories

Lot width

—

Lot depth

—

Lot size

9,000 Sq. Ft.

Year renovated

—

Sq. Ft.

1,360

Year built

1997

Style

Single Family Residential

County

Worcester County

APN

03 048608

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 21, 2026.

Property details

Parking

Parking Information
# of Attached Garage Spaces: 2
Garage Features: Garage Door Opener
# of Total Garage and Parking Spaces: 4
Has Garage
# of Garage Spaces: 2
Driveway - # of Spaces: 2
Asphalt Driveway
Attached Garage, Driveway, Off Street

Interior

Bedroom Information
# of Bedrooms On Main Level: 3

Bathroom Information
# of Bathrooms (Full) On Main Level: 2
# of Bathrooms (Full): 2

Interior Information
Appliances: Built-In Microwave, Disposal, Dryer - Electric, Icemaker, Oven/Range - Electric, Refrigerator, Stainless Steel Appliances, Washer, Water Heater
Furnished
Interior Features: Carpet, CeilngFan(s), Combination Kitchen/Dining, Entry Level Bedroom, Master Bath(s), Walk-in Closet(s), Window Treatments, Wood Floors
Living Area Sq.Ft. Source: Estimated

Fireplace Information
Has Fireplace
Gas/Propane

Basement Information
Basement: No

Exterior

Property Information
Not Federal Flood Zone
Total Below Grade Sq. Ft.: 0
Ownership Interest: Fee Simple
Year Built Source: Assessor

Building Information
Building Name: NONE AVAILABLE
Construction Materials: Frame
Foundation Details: Block
Other Structures: Above Grade, Below Grade
Structure Type: Detached

Pool Information
Community Pool

Lot Information
Lot Size Dimensions: 0.00 x 0.00
Lot Dimensions Source: Assessor
Tidal Water: No

Above Grade Information
Finished Sq.Ft.: 1,550
Finished Sq.Ft. Source: Estimated

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

Financial

Tax Information
County Tax: $1,966
Tax Assessed Value: $232,700
Tax Year: 2020
Tax Annual Amount: $2,227

Assessments Information
Year Assessed: 2020

Utilities

Utilities Information
Cooling Type: Heat Pump(s)
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, Pier/Dock Maintenance, Road Maintenance, Snow Removal
HOA/Condo/Coop Amenities: Basketball Courts, Beach, Beach Club, Boat Ramp, Club House, Common Grounds, Community Center, Gift Shop, Golf Club, Golf Course, Golf Course Membership Available, Library, Marina/Marina Club, Picnic Area, Pool - Indoor, Pool - Outdoor, Pool Mem Avail, Racquet Ball, Swimming Pool, Tennis Courts, Tot Lots/Playground, Baseball Field, Jog/Walk Path
HOA Fee: $996
HOA Fee Frequency: Annually
Other Fees: $50
Other Fees Frequency: One Time

School Information
Elementary School: SHOWELL
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
High School Source: Listing Agent
School District Source: Listing Agent

Location Information
Outside City Limits
Directions: Ocean Pines North, right turn on Windjammer

Public facts

Beds: —
Baths: 2.0
Sq. Ft.: 1,360
Stories: 1.0
Lot Size: 9,000 square feet
Style: Single Family Residential
Year Built: 1997
Year Renovated: —
County: Worcester County
APN: 03 048608

Home facts updated by county records on Aug 21, 2026

Around this home

Schools

Showell Elementary School

Public PreK-4 • Assigned • 1.7mi

8/10

Stephen Decatur Middle School

Public 7-8 • Assigned • 4.2mi

10/10

Stephen Decatur High School

Public 9-12 • Assigned • 3.9mi

7/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk 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 103° 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

In this area, properties receive around 9.2 hours in June and 5.5 hours in December, which is comparable to the U.S. average for solar exposure.

9.2 hrs

5.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$417,000 – $504,000

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392 Timberline Cir, Ocean Pines, MD 21811

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Home values near 99 Windjammer Rd

Data from public records.

Address	Redfin Estimate
97 Windjammer Road, Berlin, MD - Beds \| 2.5 Baths \| 2058 Sq. Ft.	$460,063
108 Windjammer Road, Ocean Pines, MD 3 Beds \| 3 Baths \| 1728 Sq. Ft.	$394,599

Address	Redfin Estimate
111 Windjammer Road, Ocean Pines, MD 3 Beds \| 2.5 Baths \| 2823 Sq. Ft.	$634,141
87 Windjammer Road, Ocean Pines, MD 4 Beds \| 3.5 Baths \| 2982 Sq. Ft.	$653,488

Address	Redfin Estimate
110 Windjammer Road, Ocean Pines, MD - Beds \| 2 Baths \| 1232 Sq. Ft.	$367,395
91 Windjammer Road, Ocean Pines, MD 3 Beds \| 2.5 Baths \| 2075 Sq. Ft.	$466,748

Property information provided by BRIGHT MLS when last listed in 2021. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 21811, MD

Sale history for 99 Windjammer Rd

Tax history for 99 Windjammer Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 21811

Home values near 99 Windjammer Rd

More real estate resources