1 Windward Ct, Ocean Pines, MD 21811
Property image
Property image
SOLD
JAN 16, 2026

$381,700

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 1,728 sqft

1 Windward Ct, Ocean Pines, MD 21811

Refinance Your Home
Currently Off Market - Sold Jan 16, 2026 for $381,600 (17% below list price)

Home Value

Trulia Estimate
$382K
Since last month
Decreased$4K (-1%)
Since last year
Decreased$85K (-18.3%)
Since last sale
$0 (0%)
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 +30% in the last 10 years
MonthEstimated value
2026
August 2026$382K
August 2026$381K
July 2026$385K
June 2026$385K
May 2026$379K
April 2026$380K
March 2026$381K
February 2026$382K
January 2026$382K
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
148 Teal Cir, Ocean Pines, MD
0.07
Single-Family Home
$545,000
04/24/26
3
2.5
1,824
240 Teal Cir, Ocean Pines, MD
0.04
Single-Family Home
$589,000
07/01/26
3
3
2,757
2 Waters Edge Ct, Ocean Pines, MD
0.23
Single-Family Home
$500,000
06/12/26
3
3
1,220
178 Teal Cir, Ocean Pines, MD
0.08
Single-Family Home
$550,000
01/30/26
3
3.5
3,028
6 Sundial Cir, Ocean Pines, MD
0.40
Single-Family Home
$444,000
04/02/26
3
2.5
1,932
5 Laport Ct, Ocean Pines, MD
0.14
Single-Family Home
$725,000
10/27/25
3
2.5
1,744
368 Ocean Pkwy, Ocean Pines, MD
0.30
Single-Family Home
$730,000
03/06/26
3
3
1,714

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
4 Windward Ct, Ocean Pines, MD 21811
0.03
$611,300
4
2.5
1,856
Off Market
241 Teal Cir, Ocean Pines, MD 21811
0.01
$621,900
3
3
1,840
Off Market
148 Teal Cir, Ocean Pines, MD 21811
0.07
$545,000
3
2.5
1,824
Recently Sold
240 Teal Cir, Ocean Pines, MD 21811
0.04
$589,000
3
3
2,757
Recently Sold
253 Teal Cir, Ocean Pines, MD 21811
0.06
-
-
-
-
Off Market
22 Windward Ct, Ocean Pines, MD 21811
0.09
$938,900
5
3
2,444
Off Market
140 Teal Cir, Ocean Pines, MD 21811
0.11
$725,700
4
3
2,636
Off Market
186 Teal Cir, Ocean Pines, MD 21811
0.07
$405,300
3
2
1,318
Off Market
188 Teal Cir, Ocean Pines, MD 21811
0.07
$640,600
4
2.5
2,647
Off Market
178 Teal Cir, Ocean Pines, MD 21811
0.08
$550,000
3
3.5
3,028
Recently Sold
180 Teal Cir, Ocean Pines, MD 21811
0.07
$489,900
3
3
1,638
For Sale

Local Information

  • Map ViewExplore the area around 1 Windward Ct.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1989
1,728 sqft
$221/sqft
4 Open Spaces
HOA $122/mo

About this House

Welcome to 1 Windward Ct, Ocean Pines, MD – where waterfront living meets unmatched community amenities! This charming split-level home boasts 3 bedrooms, 3 full baths, and 1,728 square feet of thoughtfully designed living space. The large living room has strong natural light, while the kitchen offers a serene view of the water out back – perfect for savoring the moments while cooking and preparing food. The primary bedroom features its own full bathroom for added convenience. A cozy fireplace warms the downstairs family room, which connects to a walk-out basement with sliding doors. Enjoy the tranquil surroundings from the screened-in porch or the spacious rear deck, both ideal for relaxation and entertaining. Nestled in the coveted Ocean Pines community, this home offers access to a variety of exclusive amenities. Boating and water enthusiasts will appreciate the fishing marina with boat slips, as well as the Ocean Pines Beach Club on 49th St. in Ocean City. Residents enjoy the Ocean Pines Golf Club, outdoor pools, tennis and pickleball courts, basketball courts, and soccer fields. For families and outdoor lovers, the community includes kids' play areas, walking and jogging trails, and several parks. Social opportunities abound, from dining at the Yacht Club overlooking the marina to participating in events like ice cream socials, bingo nights, and community yard sales. Located just minutes from the beach, dining, shopping, and top-notch golf courses, this property also offers unbeatable convenience. Less than 4 miles away, you'll find groceries, restaurants, and Veterans Memorial Park, while the Ocean City Beach at 62nd St. is just a quick drive under 10 miles. Across the street from the community, enjoy a vibrant farmers market, craft shows, live music under the pavilion, and a large playground. This home is ready to provide the perfect blend of coastal living and everyday convenience!
1 Windward Ct, Ocean Pines, MD 21811 is a 3 bedroom, 3 bathroom, 1,728 sqft single-family home built in 1989. It last sold for $381,600 on Jan 16, 2026 (17% below the $460,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $381,700, with a rent estimate of $2,746/month.
Last check for updates: about 9 hours ago
Listed by Broc Schmelyun, (717) 880-0393
Keller Williams Keystone Realty
Bought with: Laura Diamantoni, (717) 538-2629, Realty ONE Group Unlimited
Source: Bright MLS, MLS#MDWO2027250

Home Details for 1 Windward Ct

Interior Features

Interior Details
Basement: Finished,Heated,Exterior Entry,Walk-Out Access,ShelvingNumber of Rooms: 8Types of Rooms: Primary Bedroom, Primary Bathroom, Dining Room, Family Room, Kitchen, Laundry, Living Room, Screened Porch
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 1728 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Dryer, Oven/Range - Electric, Refrigerator, Washer, Water Heater, Electric Water HeaterDishwasherDryerLaundry: Laundry RoomRefrigeratorWasher
Heating & Cooling
Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Mantel(s), Wood Burning StoveHas a Fireplace
Windows, Doors, Floors & Walls
Flooring: Carpet, Laminate
Levels, Entrance, & Accessibility
Stories: 2Levels: Multi/Split, TwoAccessibility: NoneFloors: Carpet, Laminate
View
No View

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Deck, Porch, Screened, Screened PorchOther Structures: Above Grade, Below GradeExterior: Lighting, OtherFoundation: PermanentNo Private Pool
Parking & Garage
Open Parking Spaces: 4No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 4Parking: Gravel,Driveway
Pool
Pool: Community
Frontage
WaterfrontWaterfront: Boat - Powered, Canoe/Kayak, Private Access, CanalOn Waterfront
Water & Sewer
Sewer: Public SewerWater Body: Saint Martin River
Farm & Range
Frontage Length: Water Frontage Ft: 2
Finished Area
Finished Area (above surface): 1728 Square Feet

Property Information

Year Built
Year Built: 1989
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Detached
Building
Building Name: None AvailableConstruction Materials: Vinyl SidingNot a New Construction
Property Information
Parcel Number: 2403061221

Price & Status

Price
List Price: $460,000Price Per Sqft: $221/sqft
Status Change & Dates
Off Market Date: Fri Jan 16 2026Possession Timing: Close Of Escrow

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: 1728 Square Feet

Community

Not Senior Community

HOA

HOA Name: OCEAN PINESHas an HOAHOA Fee: $1,465/Annually

Lot Information

Lot Area: 7991 sqft

Listing Info

Special Conditions: Standard

Offer

Contingencies: Appraisal, Financing ApprovalListing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: MDWO2027250Above Grade Unfinished Area: 1728

Additional Information

HOA Amenities: Bar/Lounge,Beach Access,Beach Club,Boat Ramp,Community Center,Golf Course,Golf Course Membership Available,Jogging Path,Library,Marina/Marina Club,Meeting Room,Picnic Area,Pier/Dock,Pool,Tennis Court(s),Tot Lots/PlaygroundSource Internet Entire Listing Display: Y

Price and Tax history

DateEventPrice
Jan 16, 2026
Source: Bright MLS #MDWO2027250
Sold
$381,600
Dec 30, 2025
Source: Bright MLS #MDWO2027250
Pending
$460,000
Dec 10, 2025
Source: Bright MLS #MDWO2027250
Contingent
$460,000
Nov 25, 2025
Source: Bright MLS #MDWO2027250
PendingToActive
$460,000
Oct 29, 2025
Source: Bright MLS #MDWO2027250
Pending
$460,000

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

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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

Frequently asked questions about 1 Windward Ct

  • What is 1 Windward Ct estimated to be worth?
    Trulia's estimated value for 1 Windward Ct in Ocean Pines, MD is $381,700.
  • What is the price history for 1 Windward Ct?
    1 Windward Ct in Ocean Pines, MD last sold for $381,600 in January 2026.
  • 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 1 Windward Ct have air conditioning?
    Yes, 1 Windward Ct in Ocean Pines, MD has air conditioning.
  • Does 1 Windward Ct have a pool?
    Yes, 1 Windward Ct in Ocean Pines, MD has a pool.

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