59 Windjammer Rd, Ocean Pines, MD 21811
OFF MARKET

$637,200

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 2,716 sqft

59 Windjammer Rd, Ocean Pines, MD 21811

Est. Refi. Payment $3,936/mo*
Refinance Your Home
Currently Off Market - Sold Jun 24, 2011 for $362,500

Home Value

Trulia Estimate
$637K
Since last month
Increased$5K (+0.8%)
Since last year
Increased$25K (+4.1%)
Since last sale
Increased$273K (+75.3%)
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 +111% in the last 10 years
MonthEstimated value
2026
September 2026$635K
August 2026$630K
July 2026$630K
June 2026$633K
May 2026$636K
April 2026$636K
March 2026$629K
February 2026$628K
January 2026$622K
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
63 Drawbridge Rd, Ocean Pines, MD
0.07
Single-Family Home
$415,000
09/14/26
4
3
3,041
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
70 Capetown Rd, Ocean Pines, MD
0.27
Single-Family Home
$446,500
09/01/26
4
3
2,894
48 Windjammer Rd, Ocean Pines, MD
0.10
Single-Family Home
$380,000
06/05/26
3
2
1,585
51 Newport Dr, Ocean Pines, MD
0.20
Single-Family Home
$390,000
06/22/26
3
2
1,722
220 Ocean Pkwy, Ocean Pines, MD
0.18
Single-Family Home
$380,000
08/21/26
4
3
1,353
40 Harbormist Cir, Ocean Pines, MD
0.15
Single-Family Home
$388,000
07/01/26
3
2
1,430
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

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
67 Windjammer Rd, Ocean Pines, MD 21811
0.05
$448,000
3
2
1,706
Off Market
63 Drawbridge Rd, Ocean Pines, MD 21811
0.07
$415,000
4
3
3,041
Recently Sold
69 Windjammer Rd, Ocean Pines, MD 21811
0.06
$362,900
3
2
1,568
Off Market
4 Brookton Ln, Ocean Pines, MD 21811
0.06
$356,200
3
2
1,344
Off Market
62 Drawbridge Rd, Ocean Pines, MD 21811
0.08
$444,200
2
2
1,606
Off Market
19 Newport Dr, Ocean Pines, MD 21811
0.07
$335,100
2
2
1,296
Off Market
3 Harbormist Cir, Ocean Pines, MD 21811
0.08
$339,800
4
2
1,536
Off Market
33 Newport Dr, Ocean Pines, MD 21811
0.09
$349,100
3
2
1,740
Off Market
10 Newport Dr, Ocean Pines, MD 21811
0.10
$380,900
3
2.5
1,485
Off Market
48 Windjammer Rd, Ocean Pines, MD 21811
0.10
$380,000
3
2
1,585
Recently Sold
47 Drawbridge Rd, Ocean Pines, MD 21811
0.16
$364,700
3
2
1,242
Off Market
6 White Cap Ln, Ocean Pines, MD 21811
0.12
$382,400
3
2
1,700
Off Market

Local Information

  • Map ViewExplore the area around 59 Windjammer Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2002
2,716 sqft
$235/sqft
Garage

About this House

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
59 Windjammer Rd, Ocean Pines, MD 21811 is a 3 bedroom, 3 bathroom, 2,716 sqft single-family home built in 2002. It last sold for $362,500 on Jun 24, 2011. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $637,200, with a rent estimate of $3,352/month.

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 and Tax history

DateEventPrice
Jun 24, 2011
Source: N/A
Sold
$362,500
Jun 21, 2011
Source: Agent Provided
Listed For Sale
$399,000
Apr 27, 2011
Source: Agent Provided
ListingRemoved
$399,000
Mar 31, 2011
Source: Agent Provided
PriceChange
$399,000
Price decreased by 0%
Jan 28, 2011
Source: Agent Provided
PriceChange
$400,000
Price decreased by 7%

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

Frequently asked questions about 59 Windjammer Rd

  • What is 59 Windjammer Rd estimated to be worth?
    Trulia's estimated value for 59 Windjammer Rd in Ocean Pines, MD is $637,200.
  • What is the price history for 59 Windjammer Rd?
    59 Windjammer Rd in Ocean Pines, MD last sold for $362,500 in June 2011.
  • 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 59 Windjammer Rd have a pool?
    Yes, 59 Windjammer Rd in Ocean Pines, MD has a pool.
  • How big is the lot at 59 Windjammer Rd?
    The lot at 59 Windjammer Rd in Ocean Pines, MD is about 0.23 acres (10,018 sq ft).

Explore by feature - Pet Friendly

8 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

8 rentals with a pool in Ocean Pines, MD

Explore by feature - Washer/dryer

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