2 Windjammer Rd, Ocean Pines, MD 21811
SOLD
SEP 10, 2026

$533,900

Trulia Estimate
  • 5 Beds
  • 2 Baths
  • 2,258 sqft

2 Windjammer Rd, Ocean Pines, MD 21811

Refinance Your Home
Currently Off Market - Sold Sep 10, 2026 for $500,000 (8% below list price)

Home Value

Trulia Estimate
$534K
Since last month
Decreased$74K (-12.1%)
Since last year
Decreased$75K (-12.3%)
Since last sale
Increased$35K (+7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +39% in the last 10 years
MonthEstimated value
2026
September 2026$535K
August 2026$535K
July 2026$609K
June 2026$627K
May 2026$613K
April 2026$613K
March 2026$613K
February 2026$608K
January 2026$616K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
14 White Sail Cir, Ocean Pines, MD
0.07
Single-Family Home
$429,000
06/11/26
3
2
1,500
289 Ocean Pkwy, Ocean Pines, MD
0.35
Single-Family Home
$440,000
05/19/26
4
2
2,034
21 Seabreeze Rd, Ocean Pines, MD
0.28
Single-Family Home
$485,000
06/12/26
5
2.5
2,572
25 Seabreeze Rd, Ocean Pines, MD
0.27
Single-Family Home
$350,000
08/21/26
3
2
1,738
11 Clipper Ct, Ocean Pines, MD
0.18
Single-Family Home
$715,000
02/27/26
3
2.5
1,900
38 Grand Port Rd, Ocean Pines, MD
0.25
Single-Family Home
$735,000
11/06/25
4
3
1,872
32 Driftwood Ln, Ocean Pines, MD
0.41
Single-Family Home
$610,000
08/28/26
3
2
1,656
43 Grand Port Rd, Ocean Pines, MD
0.28
Single-Family Home
$422,900
02/06/26
3
2.5
1,928
258 Ocean Pkwy, Ocean Pines, MD
0.28
Single-Family Home
$370,000
05/26/26
3
2
1,238

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
60 White Sail Cir, Berlin, MD 21811
0.06
$452,100
3
2.5
2,145
Off Market
101 White Sail Cir, Ocean Pines, MD 21811
0.04
$499,000
3
2
1,584
For Sale
12 White Sail Cir, Ocean Pines, MD 21811
0.06
$250,000
2
1
720
Recently Sold
14 White Sail Cir, Ocean Pines, MD 21811
0.07
$429,000
3
2
1,500
Recently Sold
59 White Sail Cir, Ocean Pines, MD 21811
0.09
$1,033,500
5
3
2,534
Off Market
17 Carriage Ln, Ocean Pines, MD 21811
0.05
$708,800
3
2
1,520
Off Market
46 White Sail Cir, Ocean Pines, MD 21811
0.09
$461,200
4
2
2,496
Off Market
13 Carriage Ln, Ocean Pines, MD 21811
0.07
$679,800
3
2
1,350
Off Market
18 Widows Watch Ct, Ocean Pines, MD 21811
0.13
$1,071,000
4
3
2,002
Off Market
17 Widows Watch Ct, Ocean Pines, MD 21811
0.13
$880,000
3
1
2,116
Recently Sold
6 Carriage Ln, Ocean Pines, MD 21811
0.13
$650,000
4
3
1,856
Recently Sold

Local Information

  • Map ViewExplore the area around 2 Windjammer Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1984
2,258 sqft
$221/sqft
Garage
HOA $132/mo

About this House

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!
2 Windjammer Rd, Ocean Pines, MD 21811 is a 5 bedroom, 2 bathroom, 2,258 sqft single-family home built in 1984. It last sold for $500,000 on Sep 10, 2026 (8% below the $545,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $533,900, with a rent estimate of $2,908/month.
Last check for updates: about 2 hours ago
Listed by Sally Todd Stout, (410) 726-3506
Berkshire Hathaway HomeServices PenFed Realty - OP
Bought with: Chantal Apple, (203) 558-2662, Atlantic Shores Sotheby's International Realty
Source: Bright MLS, MLS#MDWO2040224

Home Details for 2 Windjammer Rd

Interior Features

Interior Details
Number of Rooms: 3Types of Rooms: Dining Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 5Main Level Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 2258 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Dryer, Oven/Range - Electric, Refrigerator, Washer, Electric Water HeaterDishwasherDryerLaundry: Main LevelRefrigeratorWasher
Heating & Cooling
Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Flooring: Laminate
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: 2+ Access ExitsFloors: Laminate
View
Has a ViewView: Canal, Water

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Deck, Screened, Porch, BreezewayOther Structures: Above Grade, Below GradeExterior: BalconyFoundation: Block, Crawl SpaceNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 4No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 6Parking: Storage,Garage Faces Front,Oversized,Detached,Driveway
Pool
Pool: Community
Frontage
WaterfrontWaterfront: Private Dock Site, Canal, Private AccessResponsible for Road Maintenance: Public Maintained RoadOn Waterfront
Water & Sewer
Sewer: Public Sewer
Farm & Range
Frontage Length: Water Frontage Ft: 70
Finished Area
Finished Area (above surface): 2258 Square Feet

Property Information

Year Built
Year Built: 1984
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Contemporary
Building
Building Name: None AvailableConstruction Materials: Frame, Vinyl Siding, Stick BuiltNot a New Construction
Property Information
Not Included in Sale: Staging ItemsIncluded in Sale: As ShownParcel Number: 2403078795

Price & Status

Price
List Price: $545,000Price Per Sqft: $221/sqft
Status Change & Dates
Off Market Date: Fri Sep 11 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Media

Location

Direction & Address
City: OCEAN PINESCommunity: Ocean Pines - Newport
School Information
Elementary School: Berlin Intermediate SchoolElementary School District: Worcester County Public SchoolsJr High / Middle School: Stephen DecaturJr High / Middle School District: Worcester County Public SchoolsHigh School: Stephen DecaturHigh School District: Worcester County Public Schools

Building

Building Area
Building Area: 2258 Square Feet

Community

Not Senior Community

HOA

HOA Fee Includes: Common Area Maintenance, Management, Reserve Funds, Road MaintenanceHOA Name: OCEAN PINES ASSOCIATIONHas an HOAHOA Fee: $1,580/Annually

Lot Information

Lot Area: 9953 sqft

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: MDWO2040224Municipality: OCEAN PINESWater ViewWater View: Canal, WaterAbove Grade Unfinished Area: 2258

Additional Information

HOA Amenities: 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 FacilitiesSource Internet Consumer Comment: NSource Internet Automated Valuation Display: YSource Internet Entire Listing Display: YSource Internet Address Display: Y

Price and Tax history

DateEventPrice
Sep 10, 2026
Source: Bright MLS #MDWO2040224
Sold
$500,000
Aug 18, 2026
Source: Bright MLS #MDWO2040224
Contingent
$545,000
Aug 1, 2026
Source: Bright MLS #MDWO2040224
Listed For Sale
$545,000
Oct 22, 2002
Source: N/A
Sold
$312,000

Market trends in Berlin

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$499K
$16.83KMoM
Sale-to-List Price
98.6%
Price per sq ft
$268
$4MoM
Available listings
262
10MoM

Around this home

What Locals Say about Berlin

At least 220 Trulia users voted on each feature.

  • 89 % Say car is needed

  • 89 % Say it's dog friendly

  • 82 % Say yards are well-kept

  • 81 % Say parking is easy

  • 80 % Say there's holiday spirit

  • 73 % Say it's quiet

  • 73 % Say people would walk alone at night

  • 66 % Say kids play outside

  • 63 % Say there's wildlife

  • 61 % Say neighbors are friendly

  • 53 % Say they plan to stay for at least 5 years

  • 49 % Say it's walkable to restaurants

  • 42 % Say there are community events

  • 38 % Say it's walkable to grocery stores

  • 30 % Say streets are well-lit

  • 25 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Henllysauldiazreyes
    "We have to be safe at home because is very important and I would like to have a places like that It would be good to have such a place it would be good to live at home that can be safe"
    1
    Flag
  • Leighannejohnsonphotography
    "It’s safe and schools are great. I’d recommend living here to anyone with a family. Also has perks being close to the beach and great restaurants! "
    0
    Flag
  • Tdannemann720
    "Simple and easy, not much traffic. Semi rural area makes it easy to get around to and from work, school, and shopping."
    0
    Flag
  • Trulia User
    "Need a car. These is no public transportation in Ocean Pines. Walking and biking to jobs are not recommended. "
    0
    Flag
  • Trulia User
    "Ocean city is wonderful. The schools are absolutely amazing they're all blue ribbons schools. I would highly recommended if you have children. It's just only if you want to buy because they're Arnold rentals they're. 8/3 they're putting out the locals."
    0
    Flag
  • Trulia User
    "Safe area, nice parks, 5 pools, low crime, shopping and restaurants are close by, fishing and other water sports nearby."
    0
    Flag
  • Trulia User
    "I believe that dog owners would be highly disapproving of the lack of sidewalks. Dog owners would also disapprove of the amount of litter that their dogs could accidentally ingest."
    0
    Flag
  • Trulia User
    "Friendly neighbors. Most have second homes, but a handful are year round. Neighbors all look out for each other"
    0
    Flag
  • Trulia User
    "I’m not a dog owner so not a good one to answer this question . From observing those that do have dogs, there are a lot of places to walk dogs - parks, streets and walk ways"
    0
    Flag
  • Trulia User
    "Our neighbors are all very welcoming and helpful and look out for each other. Could not ask for better neighbors!"
    0
    Flag
  • Christopher E
    "Many neighbors have dogs and all are thoughtful dog owners . Often dogs are walked from nearby streets and courts to our culdesac "
    0
    Flag
  • Charlie L.
    "I live in west Oc, very peaceful and quiet, I leave my door open often, and never worry about crime over here"
    0
    Flag
  • Sarah.schwind
    "Private police and safe quiet streets line Ocean Pines, Maryland. My family of seven, absolutely love where we live. My older children now know the streets better than ever, and they ride their bikes to everything our neighborhood has to offer. Fishing, skateboarding, farmers market, ice cream man, private parks, golfing...the list goes on. We love our special beach community! "
    0
    Flag
  • Alexis M.
    "Beautiful farm land! Very quite. Great place to get away from the hustle and bustle of Berlin but only 10mins away!"
    0
    Flag
  • Kimberlie F.
    "Walkable small historic town on the Eastern Shore of Maryland. Rated America’s Coolest Small Town in 2014. Berlin is pet friendly with parks for kids to play in."
    4
    Flag
  • Lauraltharp
    "Farmers market, live music at yacht club, very quiet and safe community with respectful and caring neighbors."
    0
    Flag
  • Bobby S.
    "Public transportation is fine and accessible to anyone in need. If not that luckily everything close enough to be within walking or biking distance "
    0
    Flag
  • Brian D.
    "Typically quiet neighborhood. The public space are kept up and the people are friendly. We live here year round and really enjoy it. "
    0
    Flag
  • Lindsey
    "Very neighborly and comforting. Small town feel with a vacation in your backyard every day, which is something you can’t beat!"
    0
    Flag
  • Harley B.
    "Showell elementary is amazing! Many activities and places to take the kids. Parks are clean and well kept"
    0
    Flag
  • Cschanno2909
    "Berlin is America’s Coolest Small Town. It always has fun activities for both adults and children. Awesome restaurants too! "
    0
    Flag
  • Julie F.
    "No sidewalks in the pines, old town Berlin has sidewalks and great for riding bikes and letting kids go play"
    0
    Flag
  • Jody P.
    "I drive to work. Traffic is not too bad except on Saturdays in the summer. Once you know how to get around the traffic it is not a problem. "
    0
    Flag
  • Jody P.
    "Everything is very close and you will learn to get around the traffic even though it is nothing compared to big city traffic "
    0
    Flag
  • Jonathan R.
    "I need to be close to public transportation, I do not have a vehicle right now plus I work in Ocean City."
    0
    Flag
  • Jody P
    "Voted coolest town in America. Safe Friendly town with great restaurants parking antique stores and a very cool historic hotel. Great celebrations for holidays"
    0
    Flag
  • Bonnie.russell
    "nice area to walk dogs and every one here is friendly but not noisie. people in this area are very nice "
    0
    Flag
  • Moonstars19
    "The neighborhood is quiet and the neighborhood is friendly. During the Summer months it’s very busy with a lot of tourists and vacationers.. "
    0
    Flag
  • Stacey M.
    "There is always a yard sale going on the weekends, as long as the weathers nice. You can just drive around and find a handful. There are always signs out. "
    0
    Flag
  • Johnny P.
    "It’s more the town festivals down the street from the community. After all, it is the coolest small town in America!"
    2
    Flag
  • Daniellemrossi
    "The association does a nice job keeping it look clean, you are right outside of ocean city, taxes are cheaper, friendly neighborhood "
    0
    Flag
  • Johnny P.
    "There are many dogs to become social towards, meaning many dog owners and potential puppy playmates!"
    1
    Flag
  • Emys E.
    "The neighborhood offers many options for get together on holidays. It helps to get to know the neighbors and keeps children safe as well."
    0
    Flag
  • Moonstars19
    "This is a close nit community and everyone helps each other out .. Lots of boaters and Golfers and plenty of things to do here "
    0
    Flag
  • Mydreamer1956
    "We were voted the coolest small town in America. Monthly events summer events Celebrations. Halloween. Christmas parade."
    1
    Flag
  • Treesa65
    "Yoga classes, nice neighborhoods, small town, good restaurants, friendly! Music in the streets. Great beer, "
    0
    Flag
  • Pattidevenny
    "Only about 50% of the neighborhood lives here year round so you do at least recognize your full time neighbors. "
    10
    Flag
  • Michael E.
    "Quiet,quiet, quiet. Low traffic factor. Friendly neighbors but allow space. All houses have waterfront property. Have to drive to bank, groceries, restaurants ,post office but not far."
    6
    Flag

LGBTQ Local Legal Protections

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

Frequently asked questions about 2 Windjammer Rd

  • What is 2 Windjammer Rd estimated to be worth?
    Trulia's estimated value for 2 Windjammer Rd in Ocean Pines, MD is $533,900.
  • What is the price history for 2 Windjammer Rd?
    2 Windjammer Rd in Ocean Pines, MD last sold for $500,000 in September 2026.
  • Is Ocean Pines a buyer's or seller's market?
    Ocean Pines is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Ocean Pines?
    The median sale price in Ocean Pines is $499K. That is up $16.83K from the prior month.
  • Does 2 Windjammer Rd have air conditioning?
    Yes, 2 Windjammer Rd in Ocean Pines, MD has air conditioning.
  • Does 2 Windjammer Rd have a pool?
    Yes, 2 Windjammer Rd in Ocean Pines, MD has a pool.

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Off Market Homes Near 2 Windjammer Rd

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