4 Windward Ct, Ocean Pines, MD 21811
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Property image
OFF MARKET

4 Windward Ct
Ocean Pines, MD 21811

  • 4 Beds
  • 2.5 Baths
  • 1,856 sqft

$605,300

Trulia Estimate
as of Aug 1, 2026

$605,300

Trulia Estimate
as of Aug 1, 2026
4 Beds
2.5 Baths
1,856 sqft

Local Information

  • Map ViewExplore the area around 4 Windward Ct.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1987
Living Area
1,856 sqft
Price/Sqft
$326
Parking
1 Car Garage
HOA
$125/Monthly

About this House

*****This may just be THE BEST WATERFRONT BUY IN OCEAN PINES RIGHT NOW***** Welcome to TEAL BAY! *****Beautiful Wide Open, DEEP WATER CANAL***** *****NO Boating traffic, and NO car traffic on a quiet Court!***** This charming home is located on a peaceful, quiet court on the canal that takes you straight out to the Bay! ***NO BOAT TRAFFIC***NO CAR TRAFFIC***NO BRIDGES TO NAVIGATE THROUGH*** 4 bedrooms and 2.5 baths, Garage! Watch the ducks from your private deck off the Main Bedroom as you sip your morning coffee! The garage can hold all the toys, workshop, and plenty of storage! The warm, cozy wood-burning fireplace is great for those cool evenings. There's a screened in porch, perfect for some HOT Steamed Crabs and COLD beer, or Grill on the Open Deck, which leads to a nice rear yard and your *** 1 year NEW DOCK with 45 FEET of BULKHEAD*** Boating, Jet Skis, Paddle Boarding, Kayak... right outside your back door. Stainless Steel Appliances (New to 2 years old), Gutter Guards... ******PRICE JUST REDUCED $12K TO ACCOMODATE CARPET, DECKS, DRIVEWAY****** Ocean Pines offers an Ocean Front Beach Club on 50th St. just 10 minutes away in Ocean City, a Yacht Club, Championship Golf Course, Tennis, Pickleball, Indoor and Outdoor Pools, Dog Park, walking trails and more, Welcome Home!
4 Windward Ct, Ocean Pines, MD 21811 is a 4 bedroom, 3 bathroom, 1,856 sqft single-family home built in 1987. It last sold for $550,000 on Aug 28, 2024 (13% below the $635,000 asking price). It is currently off market. The Trulia Estimate is $605,300, with a rent estimate of $2,679/month.

Home Details for 4 Windward Ct

Interior Features

Interior Details
Number of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 1856 Square Feet
Appliances & Utilities
Appliances: Microwave, Dishwasher, Disposal, Dryer, Refrigerator, Washer, Stainless Steel Appliance(s), Electric Water HeaterDishwasherDisposalDryerLaundry: Main LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Glass DoorsHas a Fireplace
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: None
View
Has a ViewView: Canal

Exterior Features

Exterior Home Features
Patio / Porch: Deck, Enclosed, ScreenedOther Structures: Above Grade, Below GradeExterior: BalconyFoundation: Crawl SpaceNo Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageHas an Attached GarageParking Spaces: 1Parking: Garage Faces Front,Inside Entrance,Attached
Pool
Pool: Community
Frontage
WaterfrontWaterfront: CanalOn Waterfront
Water & Sewer
Sewer: Public Sewer
Farm & Range
Frontage Length: Water Frontage Ft: 46
Finished Area
Finished Area (above surface): 1856 Square Feet

Property Information

Year Built
Year Built: 1987
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Colonial
Building
Building Name: None AvailableConstruction Materials: FrameNot a New Construction
Property Information
Condition: GoodParcel Number: 2403041735

Price & Status

Price
List Price: $635,000
Status Change & Dates
Off Market Date: Wed Aug 28 2024Possession Timing: Immediate

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: OCEAN PINESCommunity: Ocean Pines - Teal Bay
School Information
Elementary School District: Worcester County Public SchoolsJr High / Middle School District: Worcester County Public SchoolsHigh School District: Worcester County Public Schools

Building

Building Area
Building Area: 1856 Square Feet

Community

Community Features: PoolNot Senior Community

HOA

HOA Name: OCEAN PINES HOAHas an HOAHOA Fee: $1,498/Annually

Lot Information

Lot Area: 8851 sqft

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: MDWO2019910Water ViewWater View: CanalAbove Grade Unfinished Area: 1856

Additional Information

Pool
Last check for updates: about 21 hours ago
Listed by Craig Hyatt, (443) 235-7455
Coldwell Banker Realty
Bought with: Bethany Drew, (410) 208-9200, Hileman Real Estate-Berlin
Source: Bright MLS, MLS#MDWO2019910

Price History for 4 Windward Ct

DatePriceEventSource
08/28/2024$550,000Sold
Bright MLS #MDWO2019910
08/01/2024$635,000ContingentBright MLS #MDWO2019910
07/05/2024$635,000PriceChange
Bright MLS #MDWO2019910
05/23/2024$647,000PriceChange
Bright MLS #MDWO2019910
05/05/2024$655,000PriceChange
Bright MLS #MDWO2019910
04/17/2024$658,000PriceChange
Bright MLS #MDWO2019910
03/26/2024$664,900Listed For SaleBright MLS #MDWO2019910
10/29/2021$559,500Sold
Bright MLS #MDWO2002164
10/19/2021$564,900PendingBright MLS #MDWO2002164
09/15/2021$564,900PriceChange
Bright MLS #MDWO2002164
09/04/2021$579,900Listed For SaleBright MLS #MDWO2002164
12/08/2009$357,000Sold
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$3,969
Assessment$428,200
Home facts updated by county records

Comparable Sales for 4 Windward Ct

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
143 Teal Cir, Ocean Pines, MD
0.09
Single-Family Home
$500,000
08/29/25
4
3
1,650
148 Teal Cir, Ocean Pines, MD
0.04
Single-Family Home
$545,000
04/24/26
3
2.5
1,824
1 Windward Ct, Ocean Pines, MD
0.03
Single-Family Home
$381,600
01/16/26
3
3
1,728
140 Teal Cir, Ocean Pines, MD
0.08
Single-Family Home
$725,000
10/22/25
4
3
2,636
240 Teal Cir, Ocean Pines, MD
0.06
Single-Family Home
$589,000
07/01/26
3
3
2,757
3 Beach Ct, Ocean Pines, MD
0.20
Single-Family Home
$715,000
05/15/26
4
3
2,400
414 Ocean Pkwy, Ocean Pines, MD
0.24
Single-Family Home
$575,000
06/11/26
3
2
1,498
385 Ocean Pkwy, Ocean Pines, MD
0.18
Single-Family Home
$733,000
12/05/25
3
3
1,882
178 Teal Cir, Ocean Pines, MD
0.08
Single-Family Home
$550,000
01/30/26
3
3.5
3,028

Nearby homes

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Assigned Schools

These are the assigned schools for 4 Windward Ct.
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 - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Washer/dryer

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Homes for sale near 4 Windward Ct

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Off Market Homes Near 4 Windward Ct

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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