59 Windjammer Rd, Ocean Pines, MD 21811
OFF MARKET

59 Windjammer Rd
Ocean Pines, MD 21811

  • 3 Beds
  • 3 Baths
  • 2,716 sqft

$639,200

Trulia Estimate
as of May 11, 2026
Est. Refi. Payment $3,579/mo*
Refinance Your Home

$639,200

Trulia Estimate
as of May 11, 2026
Est. Refi. Payment $3,579/mo*
Refinance Your Home
3 Beds
3 Baths
2,716 sqft

Homes for sale near 59 Windjammer Rd

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Apartments for Rent

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Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

An exquisite home with a superb view of the Par 5 fourth hole of the Robert Trent Jones Golf Course. This custom built home is positioned behind the green gazing down this challenging 590 yard hole. Wide open floor plan with wide doorways and hallways. Custom features include heated ceramic tile floors in all 3 bathrooms, kitchen and sunroom; walk in kitchen pantry, wine room, walk in attic, enclosed and conditioned crawl space. Also enjoy the gas fireplace, expansive loft currently used as office and den area, large kitchen w/granite countertops, two master suites along with a third bedroom and bath, exercise room, central station alarm system. Most rooms are wired for stereo. Exterior features include a deck and patio overlooking the golf course, a paved drive and two car garage. Directions: North Gate,Ocean Parkway to Right on Windjammer
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 59 Windjammer Rd

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 1.5
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: Other
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2002
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 10018 sqft

Price History for 59 Windjammer Rd

DatePriceEventSource
06/24/2011$362,500Sold
N/A
06/21/2011$399,000Listed For SaleAgent Provided
04/27/2011$399,000ListingRemovedAgent Provided
03/31/2011$399,000PriceChange
Agent Provided
01/28/2011$400,000PriceChange
Agent Provided
11/28/2010$429,900Listed For SaleAgent Provided
05/04/2000$56,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$3,436
Assessment$482,267
Home facts updated by county records

Comparable Sales for 59 Windjammer Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
57 Drawbridge Rd, Ocean Pines, MD
0.09
Single-Family Home
$530,000
02/25/26
4
2.5
2,586
19 Brookside Rd, Ocean Pines, MD
0.21
Single-Family Home
$500,000
01/02/26
4
2.5
2,544
3 Sailors Way, Ocean Pines, MD
0.23
Single-Family Home
$350,000
06/18/25
3
3
1,734
216 Ocean Pkwy, Ocean Pines, MD
0.18
Single-Family Home
$445,000
05/30/25
3
2
1,750
102 Windjammer Rd, Ocean Pines, MD
0.24
Single-Family Home
$423,750
10/20/25
3
2
1,711
1 Tiller Ln, Ocean Pines, MD
0.17
Single-Family Home
$850,000
10/17/25
4
3
2,900
15 Essex Ct, Ocean Pines, MD
0.20
Single-Family Home
$550,000
10/06/25
5
3
2,833
43 Grand Port Rd, Ocean Pines, MD
0.41
Single-Family Home
$422,900
02/06/26
3
2.5
1,928
9 Sailors Way, Ocean Pines, MD
0.27
Single-Family Home
$469,000
04/30/26
6
3
2,928
37 Moonraker Rd, Ocean Pines, MD
0.41
Single-Family Home
$465,000
06/20/25
5
3
2,496

Assigned Schools

These are the assigned schools for 59 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 219 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

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
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  • 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
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  • 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
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  • 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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Homes for rent near 59 Windjammer Rd

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Off Market Homes Near 59 Windjammer Rd

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59 Windjammer Rd, Ocean Pines, MD 21811 is a 3 bedroom, 3 bathroom, 2,716 sqft single-family home built in 2002. This property is not currently available for sale. 59 Windjammer Rd was last sold on Jun 24, 2011 for $362,500. The current Trulia Estimate for 59 Windjammer Rd is $639,200.