266 Windjammer Rd, Ocean Pines, MD 21811
OFF MARKET

$385,600

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 1,329 sqft

266 Windjammer Rd, Ocean Pines, MD 21811

Est. Refi. Payment $2,417/mo*
Refinance Your Home
Currently Off Market - Sold Jul 23, 2015 for $198,000

Home Value

Trulia Estimate
$386K
Since last month
Decreased$2K (-0.5%)
Since last year
Decreased$21K (-5.1%)
Since last sale
Increased$188K (+94.7%)
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 +92% in the last 10 years
MonthEstimated value
2026
September 2026$386K
August 2026$388K
July 2026$392K
June 2026$397K
May 2026$394K
April 2026$393K
March 2026$395K
February 2026$396K
January 2026$394K
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
35 Tail Of The Fox Dr, Ocean Pines, MD
0.11
Single-Family Home
$203,000
03/27/26
3
2
1,398
79 Brandywine Dr, Ocean pines, MD
0.18
Single-Family Home
$100,000
01/23/26
3
2
1,358
65 Cresthaven Dr, Ocean Pines, MD
0.20
Single-Family Home
$450,000
04/20/26
3
2.5
2,025
818 Ocean Pkwy, Ocean Pines, MD
0.40
Single-Family Home
$185,000
02/13/26
3
2
1,200
82 Battersea Rd, Ocean Pines, MD
0.10
Single-Family Home
$555,000
11/21/25
3
2.5
2,402
33 Liberty St, Ocean Pines, MD
0.32
Single-Family Home
$364,500
03/19/26
3
2
1,316
6 Sundial Cir, Ocean Pines, MD
0.30
Single-Family Home
$444,000
04/02/26
3
2.5
1,932
84 Brandywine Dr, Ocean Pines, MD
0.14
Single-Family Home
$480,000
05/29/26
3
2
1,722
8 Pelican Ct, Ocean Pines, MD
0.24
Single-Family Home
$354,607
05/28/26
3
2
1,680
1 Darby Ct, Ocean Pines, MD
0.10
Single-Family Home
$380,000
10/24/25
3
2
2,024

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
270 Windjammer Rd, Ocean Pines, MD 21811
0.02
$335,000
3
2
960
For Sale
259 Windjammer Rd, Ocean Pines, MD 21811
0.05
$519,800
3
2
2,039
Off Market
1 Darby Ct, Ocean Pines, MD 21811
0.10
$388,600
3
2
2,024
Off Market
43 Tail Of The Fox Dr, Ocean Pines, MD 21811
0.10
$460,000
3
2.5
2,210
Recently Sold
35 Tail Of The Fox Dr, Ocean Pines, MD 21811
0.11
$389,900
3
2
1,398
For Sale
277 Windjammer Rd, Ocean Pines, MD 21811
0.08
$624,990
3
2.5
1,840
For Sale
243 Windjammer Rd, Ocean Pines, MD 21811
0.13
$466,300
3
2.5
2,244
Off Market
82 Battersea Rd, Ocean Pines, MD 21811
0.10
$566,800
3
2.5
2,402
Off Market
44 Tail Of The Fox Dr, Ocean Pines, MD 21811
0.15
$411,700
3
2
1,330
Off Market
74 Battersea Rd, Ocean Pines, MD 21811
0.14
$527,900
4
2.5
2,204
Off Market
70 Battersea Rd, Ocean Pines, MD 21811
0.14
$571,500
3
2.5
2,404
Off Market
50 Tail Of The Fox Dr, Ocean Pines, MD 21811
0.16
$610,490
4
3.5
2,120
Recently Sold

Local Information

  • Map ViewExplore the area around 266 Windjammer Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1998
1,329 sqft
$290/sqft
Garage

About this House

Custom granite counters, 1st floor master bedroom with custom walk in closet and spacious bath with whirlpool tub. Skylights, open floor plan, beautifully maintained. Truly a must see home.
266 Windjammer Rd, Ocean Pines, MD 21811 is a 3 bedroom, 3 bathroom, 1,329 sqft single-family home built in 1998. It last sold for $198,000 on Jul 23, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $385,600, with a rent estimate of $2,290/month.

Home Details for 266 Windjammer Rd

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Tile, Carpet

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: VinylPorch
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Property Information

Year Built
Year Built: 1998
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 9212 sqft

Price and Tax history

DateEventPrice
Jul 23, 2015
Source: N/A
Sold
$198,000
Apr 23, 2015
Source: Agent Provided
PriceChange
$214,900
Price decreased by 2%
Apr 9, 2015
Source: Agent Provided
PriceChange
$219,900
Price decreased by 2%
Mar 29, 2015
Source: Agent Provided
Listed For Sale
$224,900
Nov 24, 2010
Source: N/A
Sold
$185,000

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 266 Windjammer Rd

  • What is 266 Windjammer Rd estimated to be worth?
    Trulia's estimated value for 266 Windjammer Rd in Ocean Pines, MD is $385,600.
  • What is the price history for 266 Windjammer Rd?
    266 Windjammer Rd in Ocean Pines, MD last sold for $198,000 in July 2015.
  • 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 266 Windjammer Rd have air conditioning?
    Yes, 266 Windjammer Rd in Ocean Pines, MD has air conditioning.
  • Does 266 Windjammer Rd have laundry facilities?
    Yes, 266 Windjammer Rd in Ocean Pines, MD has in-unit laundry.

Explore by feature - Pet Friendly

8 pet-friendly rentals in Ocean Pines, MD

Explore by feature - Garage

11 rentals with a garage in Ocean Pines, MD

Explore by feature - Air Conditioning

30 rentals with air conditioning in Ocean Pines, MD

Explore by feature - Pool

8 rentals with a pool in Ocean Pines, MD

Explore by feature - Washer/dryer

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

Apartments for Rent

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Off Market Homes Near 266 Windjammer Rd

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