199 Windjammer Rd, Ocean Pines, MD 21811
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Property image
OFF MARKET

199 Windjammer Rd
Ocean Pines, MD 21811

  • 3 Beds
  • 2.5 Baths
  • 1,882 sqft

$452,200

Trulia Estimate
as of Aug 25, 2026
Est. Refi. Payment $2,676/mo*
Refinance Your Home

$452,200

Trulia Estimate
as of Aug 25, 2026
Est. Refi. Payment $2,676/mo*
Refinance Your Home
3 Beds
2.5 Baths
1,882 sqft

Home Value

Trulia Estimate
$452K
Since last month
Decreased$7K (-1.6%)
Since last year
Increased$800 (+0.2%)
Since last sale
Increased$1K (+0.2%)
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 +88% in the last 10 years
MonthEstimated value
2026
August 2026$451K
July 2026$458K
June 2026$457K
May 2026$444K
April 2026$446K
March 2026$448K
February 2026$452K
January 2026$453K
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
4 Fantail Ct, Ocean Pines, MD
0.13
Single-Family Home
$428,000
06/16/26
4
2
1,766
17 Falcon Bridge Rd, Ocean Pines, MD
0.10
Single-Family Home
$340,000
05/15/26
3
2
1,343
65 Cresthaven Dr, Ocean Pines, MD
0.34
Single-Family Home
$450,000
04/20/26
3
2.5
2,025
30 Cresthaven Dr, Ocean Pines, MD
0.27
Single-Family Home
$405,000
10/02/25
3
2
2,315
8 Wharf Ct, Ocean Pines, MD
0.34
Single-Family Home
$412,000
12/05/25
3
2
1,816
76 Birdnest Dr, Ocean Pines, MD
0.22
Single-Family Home
$415,000
09/19/25
3
2
1,272
73 Birdnest Dr, Ocean Pines, MD
0.26
Single-Family Home
$409,000
08/25/25
3
2
1,608
50 Cresthaven Dr, Ocean Pines, MD
0.30
Single-Family Home
$344,900
09/12/25
3
2
1,418
1 Darby Ct, Ocean Pines, MD
0.29
Single-Family Home
$380,000
10/24/25
3
2
2,024
14 Liberty St, Ocean Pines, MD
0.43
Single-Family Home
$449,000
03/20/26
3
2
1,739

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
5 Falcon Bridge Rd, Ocean Pines, MD 21811
0.06
$389,999
3
2
1,224
For Sale
11 Falcon Bridge Rd, Ocean Pines, MD 21811
0.08
$339,000
3
2
1,068
Off Market
189 Windjammer Rd, Ocean Pines, MD 21811
0.07
$327,400
3
2
1,040
Off Market
207 Windjammer Rd, Ocean Pines, MD 21811
0.04
$476,200
3
2.5
1,558
Off Market
17 Falcon Bridge Rd, Ocean Pines, MD 21811
0.10
$340,000
3
2
1,343
Recently Sold
20 Falcon Bridge Rd, Ocean Pines, MD 21811
0.12
$426,500
3
2
1,550
Off Market
216 Windjammer Rd, Ocean Pines, MD 21811
0.10
$478,600
3
2
1,573
Off Market
4 Fantail Ct, Ocean Pines, MD 21811
0.13
$428,000
4
2
1,766
Recently Sold
25 Falcon Bridge Rd, Ocean Pines, MD 21811
0.14
$386,100
4
3
1,471
Off Market
38 Battersea Rd, Ocean Pines, MD 21811
0.11
$899,900
4
3
3,896
For Sale
22 Cresthaven Dr, Ocean Pines, MD 21811
0.13
$281,000
2
1
912
Recently Sold

Local Information

  • Map ViewExplore the area around 199 Windjammer Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2001
Living Area
1,882 sqft
Price/Sqft
$240
Parking
2 Car Garage
HOA
$73/Monthly

About this House

Price adjustment! Beautiful Turn-Key Contemporary home with golf course frontage comes fully furnished and with a new roof, refrigerator , washer, dryer & encapsulated crawl space. The two story great room has a corner gas fireplace and sliding door access to the large deck. Hardwood flooring highlights the dining and kitchen areas, featuring a breakfast bar and walk- in pantry. Three spacious bedrooms plus an extra bonus room promises room for everyone! Wood stained six panel doors add a touch of elegance, as does the second level “bridge” walkway overlooking the living area. A utility sink and Central Vacuum add cleaning ease. Top it off with a large screened porch, the perfect place for eating crabs or reading a book!
199 Windjammer Rd, Ocean Pines, MD 21811 is a 3 bedroom, 3 bathroom, 1,882 sqft single-family home built in 2001. It last sold for $450,000 on Aug 15, 2025 (4% below the $469,900 asking price). More recently, it was listed as a rental in September 2012 with an asking price of $1,600 per month. That rental listing was removed on November 9, 2012. It is currently off market. The Trulia Estimate is $452,200, with a rent estimate of $2,683/month.
Last check for updates: about 6 hours ago
Listed by Debbie E Hileman, (410) 208-9200
Hileman Real Estate-Berlin
Bought with: Anthony Golden, (410) 524-7625, Berkshire Hathaway HomeServices PenFed Realty
Co-Buyer's Agent: Carol Proctor, (443) 567-0650, Berkshire Hathaway HomeServices PenFed Realty
Source: Bright MLS, MLS#MDWO2029580

Home Details for 199 Windjammer Rd

Interior Features

Interior Details
Number of Rooms: 9Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Primary Bathroom, Bathroom 2, Bonus Room, Dining Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Main Level Bedrooms: 1Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1Number of Bathrooms (main level): 2
Dimensions and Layout
Living Area: 1882 Square Feet
Appliances & Utilities
Utilities: Cable Available, Natural Gas Available, Phone Available, Underground Utilities, CableAppliances: Microwave, Central Vacuum, Dishwasher, Disposal, Dryer, Exhaust Fan, Ice Maker, Self Cleaning Oven, Oven/Range - Electric, Refrigerator, Washer, Electric Water HeaterDishwasherDisposalDryerLaundry: Has Laundry,Dryer In Unit,Washer In UnitMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Heat Pump,Central,Zoned,ElectricHas CoolingAir Conditioning: Ceiling Fan(s),Central Air,Zoned,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Corner, Glass Doors, Gas/Propane, Mantel(s)Has a Fireplace
Gas & Electric
Electric: Circuit Breakers
Windows, Doors, Floors & Walls
Window: Double Hung, Insulated Windows, Vinyl Clad, Window TreatmentsDoor: Six Panel, Storm Door(s), Sliding GlassFlooring: Ceramic Tile, Hardwood, Carpet, Wood
Levels, Entrance, & Accessibility
Stories: 2.5Levels: Two and One HalfAccessibility: 2+ Access ExitsFloors: Ceramic Tile, Hardwood, Carpet, Wood
View
Has a ViewView: Garden, Golf Course, Street, Trees/Woods
Security
Security: Main Entrance Lock

Exterior Features

Exterior Home Features
Roof: Architectural ShinglePatio / Porch: Deck, Porch, ScreenedOther Structures: Above Grade, Below GradeFoundation: Block, Crawl SpaceNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 4No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 6Parking: Garage Faces Front,Garage Door Opener,Inside Entrance,Gravel,Private,Attached,Driveway
Pool
Pool: Community
Frontage
Frontage Type: Road FrontageRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1882 Square Feet

Property Information

Year Built
Year Built: 2001
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Contemporary
Building
Building Name: None AvailableConstruction Materials: Vinyl Siding, Stick BuiltNot a New Construction
Property Information
Not Included in Sale: Games, Flower Lamps, Metal Nautical Art, Bedding, Vw Bus Framed Art, Sail Boat.Included in Sale: Furnished With ExclusionsParcel Number: 2403050386

Price & Status

Price
List Price: $469,900
Status Change & Dates
Off Market Date: Fri Aug 15 2025Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Location

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

Building

Building Area
Building Area: 1882 Square Feet

Community

Community Features: PoolNot Senior Community

HOA

HOA Fee Includes: Common Area Maintenance, Management, Reserve Funds, Road Maintenance, Snow RemovalHOA Name: OCEAN PINES ASSOCIATIONHas an HOAHOA Fee: $875/Annually

Lot Information

Lot Area: 9000 sqft

Listing Info

Special Conditions: Standard

Offer

Contingencies: Financing Approval, Home InspectionListing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: MDWO2029580Above Grade Unfinished Area: 1882

Additional Information

HOA Amenities: Bar/Lounge,Baseball Field,Basketball Court,Beach Access,Beach Club,Bike Trail,Boat Dock/Slip,Boat Ramp,Cable TV,Clubhouse,Common Grounds,Community Center,Dining Rooms,Dog Park,Golf Club,Gift Shop,Golf Course,Golf Course Membership Available,Jogging Path,Lake,Library,Marina/Marina Club,Meeting Room,Non-Lake Recreational Area,Party Room,Picnic Area,Pier/Dock,Indoor Pool,Pool,Pool Mem Avail,Putting Green,Recreation Facilities,Racquetball,Retirement Community,Security,Soccer Field,Tennis Court(s),Tot Lots/Playground,Water/Lake Privileges

Price and Tax history

DateEventPrice
Aug 15, 2025
Source: Bright MLS #MDWO2029580
Sold
$450,000
Jul 8, 2025
Source: Bright MLS #MDWO2029580
Contingent
$469,900
Jul 8, 2025
Source: Bright MLS #MDWO2029580
Pending
$469,900
Jun 25, 2025
Source: Bright MLS #MDWO2029580
PriceChange
$469,900
Price decreased by 2%
Jun 9, 2025
Source: Bright MLS #MDWO2029580
PriceChange
$479,900
Price decreased by 4%

Market trends in Berlin

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$482K
$13.5KMoM
Sale-to-List Price
98.6%
0.6%MoM
Price per sq ft
$263
$14MoM
Available listings
251
4MoM

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

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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 199 Windjammer Rd

  • What is 199 Windjammer Rd estimated to be worth?
    Trulia's estimated value for 199 Windjammer Rd in Ocean Pines, MD is $452,200.
  • What is the price history for 199 Windjammer Rd?
    199 Windjammer Rd in Ocean Pines, MD last sold for $450,000 in August 2025.
  • 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 $482K. That is up $13.5K from the prior month.
  • Does 199 Windjammer Rd have air conditioning?
    Yes, 199 Windjammer Rd in Ocean Pines, MD has air conditioning.
  • Does 199 Windjammer Rd have a pool?
    Yes, 199 Windjammer Rd in Ocean Pines, MD has a pool.

Explore by feature - Pet Friendly

11 pet-friendly rentals in Ocean Pines, MD

Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Pool

13 rentals with a pool in Ocean Pines, MD

Explore by feature - Washer/dryer

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Apartments for Rent

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Off Market Homes Near 199 Windjammer Rd

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