99 Windjammer Rd, Ocean Pines, MD 21811
OFF MARKET

99 Windjammer Rd
Ocean Pines, MD 21811

  • 3 Beds
  • 2 Baths
  • 1,550 sqft

$429,500

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $2,532/mo*
Refinance Your Home

$429,500

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $2,532/mo*
Refinance Your Home
3 Beds
2 Baths
1,550 sqft

Local Information

  • Map ViewExplore the area around 99 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
1997
Living Area
1,550 sqft
Price/Sqft
$277
Parking
Garage

About this House

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.
99 Windjammer Rd, Ocean Pines, MD 21811 is a 3 bedroom, 2 bathroom, 1,550 sqft single-family home built in 1997. It last sold for $340,000 on Jun 15, 2021. It is currently off market. The Trulia Estimate is $429,500, with a rent estimate of $2,378/month.

Home Details for 99 Windjammer Rd

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 1
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: Other
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1997
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 8999 sqft

Price History for 99 Windjammer Rd

DatePriceEventSource
06/15/2021$340,000Sold
N/A
10/24/2018$265,000Sold
N/A
08/22/2018$265,000PriceChange
Agent Provided
07/12/2018$272,500Listed For SaleAgent Provided
08/26/2014$243,000Sold
N/A
05/30/2014$249,900Listed For SaleAgent Provided
11/30/1999$143,000Sold
N/A
12/02/1997$135,000Sold
N/A
06/20/1997$18,000Sold
N/A

Market trends in Berlin

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$469K
$15KMoM
Sale-to-List Price
99.2%
0.8%MoM
Price per sq ft
$249
$9MoM
Available listings
247
7MoM
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Property Tax and Assessment

Year2025
Tax$2,966
Assessment$319,967
Home facts updated by county records

Comparable Sales for 99 Windjammer Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
102 Windjammer Rd, Ocean Pines, MD
0.04
Single-Family Home
$423,750
10/20/25
3
2
1,711
22 Rabbit Run Ln, Ocean Pines, MD
0.17
Single-Family Home
$309,000
05/01/26
3
2
1,290
4 Surfers Way, Ocean Pines, MD
0.21
Single-Family Home
$360,000
12/16/25
3
2
1,496
1 Surfers Way, Ocean Pines, MD
0.22
Single-Family Home
$406,000
05/29/26
3
2
1,446
13 Drawbridge Rd, Ocean Pines, MD
0.22
Single-Family Home
$316,593
04/13/26
3
2
1,376
48 Moonraker Rd, Ocean Pines, MD
0.25
Single-Family Home
$387,500
10/10/25
3
2
1,200
48 Windjammer Rd, Ocean Pines, MD
0.30
Single-Family Home
$380,000
06/05/26
3
2
1,585
51 Newport Dr, Ocean Pines, MD
0.35
Single-Family Home
$390,000
06/22/26
3
2
1,722
125 Ocean Pkwy, Ocean Pines, MD
0.38
Single-Family Home
$379,900
04/27/26
3
2
1,480
125 Ocean Parkway Pnes, Berlin, MD
0.38
Single-Family Home
$379,900
04/21/26
3
2
1,480

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 99 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
    "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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Apartments for Rent

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Explore by feature - Pet Friendly

7 pet-friendly rentals in Ocean Pines, MD

Explore by feature - Garage

8 rentals with a garage in Ocean Pines, MD

Explore by feature - Air Conditioning

23 rentals with air conditioning in Ocean Pines, MD

Explore by feature - Pool

10 rentals with a pool in Ocean Pines, MD

Explore by feature - Washer/dryer

20 rentals with a washer/dryer in Ocean Pines, MD

Homes for sale near 99 Windjammer Rd

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Off Market Homes Near 99 Windjammer Rd

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Frequently asked questions about 99 Windjammer Rd

  • What is 99 Windjammer Rd estimated to be worth?
    Trulia's estimated value for 99 Windjammer Rd in Ocean Pines, MD is $429,500.
  • What is the price history for 99 Windjammer Rd?
    99 Windjammer Rd in Ocean Pines, MD last sold for $340,000 in June 2021.
  • 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 $469K. That is up $15K from the prior month.
  • Does 99 Windjammer Rd have air conditioning?
    Yes, 99 Windjammer Rd in Ocean Pines, MD has air conditioning.
  • Does 99 Windjammer Rd have laundry facilities?
    Yes, 99 Windjammer Rd in Ocean Pines, MD has in-unit laundry.