Is a car needed in Berlin, MD?

As of early 2026, 89% of users say car is needed

Is Berlin, MD dog-friendly?

As of early 2026, 89% of users say it's dog friendly

Are yards well-kept in Berlin, MD?

As of early 2026, 82% of users say yards are well-kept

Is parking easy in Berlin, MD?

As of early 2026, 81% of users say parking is easy

Does Berlin, MD show holiday spirit?

As of early 2026, 80% of users say there's holiday spirit

As of early 2026, 73% of users say it's quiet

Would people walk alone at night in Berlin, MD?

As of early 2026, 73% of users say people would walk alone at night

Do kids play outside in Berlin, MD?

As of early 2026, 66% of users say kids play outside

Is there wildlife in Berlin, MD?

As of early 2026, 63% of users say there's wildlife

Are neighbors friendly in Berlin, MD?

As of early 2026, 61% of users say neighbors are friendly

Do residents of Berlin, MD plan to stay at least 5 years?

As of early 2026, 53% of users say they plan to stay for at least 5 years

Is Berlin, MD walkable to restaurants?

As of early 2026, 49% of users say it's walkable to restaurants

Are there community events in Berlin, MD?

As of early 2026, 42% of users say there are community events

Is Berlin, MD walkable to grocery stores?

As of early 2026, 38% of users say it's walkable to grocery stores

Are the streets well-lit in Berlin, MD?

As of early 2026, 30% of users say streets are well-lit

Does Berlin, MD have sidewalks?

As of early 2026, 25% of users say there are sidewalks

NEW

COMING SOON 8/1

2 Windjammer Rd
Ocean Pines, MD 21811

5 Beds
2 Baths
2,258 sqft

$545,000

5 Beds

2 Baths

2,258 sqft

Home Highlights

Parking

Garage

Outdoor

Porch, Deck

Climate Control

Heating & Cooling

HOA

$132/Monthly

Price/Sqft

$241

Listed

Less than a day ago

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

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!

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

Days on Market
Days on Market: <1 day on Trulia

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: $241
Status Change & Dates Possession Timing: Close Of Escrow

Active Status
MLS Status: COMING SOON

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

Agent Information
Listing Agent Listing ID: MDWO2040224

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

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

Last check for updates: about 5 hours ago

Listing courtesy of Sally Todd Stout, (410) 726-3506

Berkshire Hathaway HomeServices PenFed Realty - OP, (410) 208-3500

Source: Bright MLS, MLS#MDWO2040224

Also Listed on Bright MLS.

Market trends in Berlin

Last updated June 2026

Avg. sale price

$469K

$15KMoM

Sale-to-List Price

99.2%

0.8%MoM

Price per sq ft

$249

$9MoM

Available listings

247

7MoM

Price History for 2 Windjammer Rd

Date	Price	Event	Source
10/22/2002	$312,000	Sold	N/A
Recording Date 10/22/2002 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$4,043
Assessment	$436,133

Home facts updated by county records

Comparable Sales for 2 Windjammer Rd

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
8 Grand Port Rd, Ocean Pines, MD	0.20	Single-Family Home	$603,000	09/03/25	5	3	2,548
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
44 Grand Port Rd, Ocean Pines, MD	0.30	Single-Family Home	$345,000	07/08/26	3	1.5	1,008
258 Ocean Pkwy, Ocean Pines, MD	0.28	Single-Family Home	$370,000	05/26/26	3	2	1,238
284 Ocean Pkwy, Ocean Pines, MD	0.33	Single-Family Home	$258,000	02/02/26	3	2	1,398
48 Windjammer Rd, Ocean Pines, MD	0.38	Single-Family Home	$380,000	06/05/26	3	2	1,585
38 Grand Port Rd, Ocean Pines, MD	0.25	Single-Family Home	$735,000	11/06/25	4	3	1,872
11 Clipper Ct, Ocean Pines, MD	0.18	Single-Family Home	$715,000	02/27/26	3	2.5	1,900

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RE/MAX Solutions

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Additional Cost

Assigned Schools

These are the assigned schools for 2 Windjammer Rd.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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
Resident
1y ago
"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
Resident
2y ago
"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
Resident
2y ago
"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
Prev. Resident
2y ago
"Need a car. These is no public transportation in Ocean Pines. Walking and biking to jobs are not recommended. "
0
Flag
Trulia User
Resident
3y ago
"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
Resident
3y ago
"Safe area, nice parks, 5 pools, low crime, shopping and restaurants are close by, fishing and other water sports nearby."
0
Flag
Trulia User
Resident
4y ago
"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
Resident
4y ago
"Friendly neighbors. Most have second homes, but a handful are year round. Neighbors all look out for each other"
0
Flag
Trulia User
Resident
4y ago
"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
Resident
5y ago
"Our neighbors are all very welcoming and helpful and look out for each other. Could not ask for better neighbors!"
0
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Christopher E
Resident
5y ago
"Many neighbors have dogs and all are thoughtful dog owners . Often dogs are walked from nearby streets and courts to our culdesac "
0
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Charlie L.
Resident
5y ago
"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
Resident
5y ago
"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
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Alexis M.
Resident
5y ago
"Beautiful farm land! Very quite. Great place to get away from the hustle and bustle of Berlin but only 10mins away!"
0
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Kimberlie F.
Resident
5y ago
"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
Resident
5y ago
"Farmers market, live music at yacht club, very quiet and safe community with respectful and caring neighbors."
0
Flag
Bobby S.
Resident
6y ago
"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
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Brian D.
Resident
6y ago
"Typically quiet neighborhood. The public space are kept up and the people are friendly. We live here year round and really enjoy it. "
0
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Lindsey
Resident
6y ago
"Very neighborly and comforting. Small town feel with a vacation in your backyard every day, which is something you can’t beat!"
0
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Harley B.
Resident
6y ago
"Showell elementary is amazing! Many activities and places to take the kids. Parks are clean and well kept"
0
Flag
Cschanno2909
Prev. Resident
6y ago
"Berlin is America’s Coolest Small Town. It always has fun activities for both adults and children. Awesome restaurants too! "
0
Flag
Julie F.
Resident
6y ago
"No sidewalks in the pines, old town Berlin has sidewalks and great for riding bikes and letting kids go play"
0
Flag
Jody P.
Resident
6y ago
"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. "
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Jody P.
Resident
6y ago
"Everything is very close and you will learn to get around the traffic even though it is nothing compared to big city traffic "
0
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Jonathan R.
Prev. Resident
6y ago
"I need to be close to public transportation, I do not have a vehicle right now plus I work in Ocean City."
0
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Jody P
Resident
7y ago
"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
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Bonnie.russell
Resident
7y ago
"nice area to walk dogs and every one here is friendly but not noisie. people in this area are very nice "
0
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Moonstars19
Resident
7y ago
"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
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Stacey M.
Resident
7y ago
"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
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Johnny P.
Resident
7y ago
"It’s more the town festivals down the street from the community. After all, it is the coolest small town in America!"
2
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Daniellemrossi
Resident
7y ago
"The association does a nice job keeping it look clean, you are right outside of ocean city, taxes are cheaper, friendly neighborhood "
0
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Johnny P.
Resident
7y ago
"There are many dogs to become social towards, meaning many dog owners and potential puppy playmates!"
1
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Emys E.
Resident
7y ago
"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
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Moonstars19
Resident
7y ago
"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
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Mydreamer1956
Resident
7y ago
"We were voted the coolest small town in America. Monthly events summer events Celebrations. Halloween. Christmas parade."
1
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Treesa65
Resident
7y ago
"Yoga classes, nice neighborhoods, small town, good restaurants, friendly! Music in the streets. Great beer, "
0
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Pattidevenny
Resident
7y ago
"Only about 50% of the neighborhood lives here year round so you do at least recognize your full time neighbors. "
10
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Michael E.
Resident
7y ago
"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
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LGBTQ Local Legal Protections

Sally Todd Stout, Berkshire Hathaway HomeServices PenFed Realty - OP, (410) 208-3500

Agent Phone: (410) 726-3506

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

2 Windjammer Rd, Ocean Pines, MD 21811 is a 5 bedroom, 2 bathroom, 2,258 sqft single-family home built in 1984. This property is currently available for sale and was listed by Bright MLS on Jul 31, 2026. The MLS # for this home is MLS# MDWO2040224.

2 Windjammer Rd Ocean Pines, MD 21811

$545,000

$545,000

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2 Windjammer Rd
Ocean Pines, MD 21811