37 Windjammer Rd, Ocean Pines, MD 21811
Property image
Property image
FOR SALE

$329,900

  • 3 Beds
  • 2 Baths
  • 1,232 sqft

37 Windjammer Rd, Ocean Pines, MD 21811

Est. Mortgage $2,070/mo*
Get Pre-Qualified
We estimate this home will sell faster than 99% nearby.

Home Highlights

Single-Family Home
Built in 1984
$268/sqft
Open Parking
HOA $71/mo

Local Information

  • Map ViewExplore the area around 37 Windjammer Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Cozy electric fireplaceFront and rear yardModern appliancesOutbuilding for additional storageGravel drivewayPrivate parking
This charming 3-bedroom, 2-bathroom ranch-style home in Ocean Pines offers a solid investment opportunity with a spacious 1,232 sq ft layout. The interior features a combination kitchen/dining area, an eat-in kitchen with pantry, and a cozy electric fireplace, enhancing its appeal for potential renters. The home boasts modern appliances, including a dishwasher, washer/dryer, and water heater, ensuring low maintenance costs. The exterior showcases a well-maintained lot of 0.21 acres with a front and rear yard, complemented by a screened porch and outbuilding for additional storage. Community amenities include pools, tennis courts, and a beach club, enhancing rental desirability. With a gravel driveway and private parking, this property is positioned for strong rental returns in a sought-after area. The serene views of gardens and wooded surroundings add to its charm, making it an attractive option for both long-term and vacation rentals.
Last check for updates: about 3 hours ago
Listing courtesy of Diana L. Whitney, (410) 726-7886
Whitney-Wallace Commercial Real Estate Services, LLC, (410) 548-5484
Co-Listing Agent: Paul J Whitney, (410) 430-7752
Whitney-Wallace Commercial Real Estate Services, LLC, (410) 548-5484
Source: Bright MLS, MLS#MDWO2042190
We estimate this home will sell faster than 99% nearby.

Home Details for 37 Windjammer Rd

Interior Features

Interior Details
Number of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 3Main Level Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2Number of Bathrooms (main level): 2
Dimensions and Layout
Living Area: 1232 Square Feet
Appliances & Utilities
Utilities: Cable Available, Natural Gas Available, Phone Available, Underground UtilitiesAppliances: Dishwasher, Disposal, Dryer, Exhaust Fan, Ice Maker, Oven/Range - Electric, Range Hood, Refrigerator, Washer, Water Heater, Electric Water HeaterDishwasherDisposalDryerLaundry: Has Laundry,Dryer In Unit,Washer In UnitRefrigeratorWasher
Heating & Cooling
Heating: Heat Pump,Electric,CentralHas CoolingAir Conditioning: Ceiling Fan(s),Central Air,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Electric, Mantel(s)Has a FireplaceNo Spa
Gas & Electric
Electric: Circuit Breakers
Windows, Doors, Floors & Walls
Window: Double Hung, Insulated Windows, Wood Frames, Window TreatmentsDoor: Six Panel, Sliding Glass, Storm Door(s)Flooring: Laminate, Vinyl, Marble
Levels, Entrance, & Accessibility
Stories: 1Levels: OneAccessibility: 2+ Access ExitsFloors: Laminate, Vinyl, Marble
View
Has a ViewView: Garden, Street, Trees/Woods
Security
Security: Main Entrance Lock

Exterior Features

Exterior Home Features
Roof: Architectural ShinglePatio / Porch: Porch, ScreenedOther Structures: Above Grade, Below Grade, OutbuildingFoundation: Block, Crawl SpaceNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking: Gravel,Private,Driveway
Pool
Pool: Community
Frontage
Frontage Type: Road FrontageRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Farm & Range
Not Allowed to Raise Horses
Finished Area
Finished Area (above surface): 1232 Square Feet

Days on Market

Days on Market: 8

Property Information

Year Built
Year Built: 1984
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Ranch/Rambler
Building
Building Name: None AvailableConstruction Materials: Aluminum SidingNot a New ConstructionNo Additional Parcels
Property Information
Not Included in Sale: NoneIncluded in Sale: Appliances, ShedParcel Number: 2403044211

Price & Status

Price
List Price: $329,900Price Per Sqft: $268
Status Change & Dates
Possession Timing: Close Of Escrow

Active Status

MLS Status: ACTIVE

Location

Direction & Address
City: OCEAN PINESCommunity: Ocean Pines - Newport
School Information
Elementary School: ShowellElementary School District: Worcester County Public SchoolsJr High / Middle School: Berlin Intermediate SchoolJr High / Middle School District: Worcester County Public SchoolsHigh School: Stephen DecaturHigh School District: Worcester County Public Schools

Agent Information

Listing Agent
Listing ID: MDWO2042190

Building

Building Area
Building Area: 1232 Square Feet

Community

Community Features: PoolNot Senior Community

HOA

HOA Fee Includes: Common Area Maintenance, Management, Reserve Funds, Road Maintenance, Snow RemovalHOA Name: OCEAN PINES ASSOCIATIONHas an HOAHOA Fee: $850/Annually

Lot Information

Lot Area: 9113 sqft

Listing Info

Special Conditions: Standard

Offer

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

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: MDWO2042190Above Grade Unfinished Area: 1232

Additional Information

HOA Amenities: Bar/Lounge,Baseball Field,Basketball Court,Beach Access,Beach Club,Bike Trail,Boat Dock/Slip,Boat Ramp,Cable TV,Clubhouse,Common Grounds,Community Center,Dining Rooms,Dog Park,Gift Shop,Golf Club,Golf Course,Golf Course Membership Available,Jogging Path,Lake,Library,Marina/Marina Club,Meeting Room,Non-Lake Recreational Area,Party Room,Picnic Area,Pier/Dock,Indoor Pool,Pool,Pool Mem Avail,Putting Green,Racquetball,Recreation Facilities,Retirement Community,Security,Soccer Field,Tennis Court(s),Tot Lots/Playground,Water/Lake PrivilegesInternet Listing Display Prices: YSource Internet Automated Valuation Display: YSource Internet Consumer Comment: YSource Internet Entire Listing Display: YInternet Listing Display: Full Distribution - YesInternet Listing Display Days On Site: YInternet Listing Display Historical Prices: YSource Internet Address Display: Y

Price and Tax history

DateEventPrice
Oct 31, 2026
Source: Bright MLS #MDWO2042190
Listed For Sale
$329,900
Jan 18, 2026
Source: Zillow Rentals
ListingRemoved
$2,000
Dec 27, 2025
Source: Zillow Rentals
Listed For Rent
$2,000
Apr 18, 2024
Source: Bright MLS #MDWO2019536
Sold
$315,000
Mar 18, 2024
Source: Bright MLS #MDWO2019536
Contingent
$319,900

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

Market trends in Berlin

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$511K
$11.67KMoM
Sale-to-List Price
98.2%
0.4%MoM
Price per sq ft
$256
$12MoM
Available listings
256
6MoM
Sourced by Trulia Market Trends

Home Value

Trulia Estimate
$322K
Since last month
Decreased$16K (-4.7%)
Since last year
Decreased$3K (-1%)
Since last sale
Increased$7K (+2.3%)
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 +76% in the last 10 years
MonthEstimated value
2026
November 2026$322K
October 2026$335K
September 2026$338K
August 2026$338K
July 2026$339K
June 2026$341K
May 2026$344K
April 2026$345K
March 2026$341K
February 2026$342K
January 2026$337K
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
258 Ocean Pkwy, Ocean Pines, MD
0.05
Single-Family Home
$370,000
05/26/26
3
2
1,238
48 Windjammer Rd, Ocean Pines, MD
0.08
Single-Family Home
$380,000
06/05/26
3
2
1,585
284 Ocean Pkwy, Ocean Pines, MD
0.12
Single-Family Home
$258,000
02/02/26
3
2
1,398
40 Harbormist Cir, Ocean Pines, MD
0.11
Single-Family Home
$388,000
07/01/26
3
2
1,430
12 Sailors Way, Berlin, MD
0.26
Single-Family Home
$330,000
04/17/26
3
2
1,176
44 Grand Port Rd, Ocean Pines, MD
0.25
Single-Family Home
$345,000
07/08/26
3
1.5
1,008
3 Crows Nest Ln, Ocean Pines, MD
0.12
Single-Family Home
$225,000
06/12/26
3
2
896
62 Newport Dr, Ocean Pines, MD
0.28
Single-Family Home
$354,900
07/23/26
3
2
1,170
51 Newport Dr, Ocean Pines, MD
0.21
Single-Family Home
$390,000
06/22/26
3
2
1,722
306 Ocean Pkwy, Ocean Pines, MD
0.29
Single-Family Home
$285,000
08/21/26
3
2
1,388

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
35 Windjammer Rd, Ocean Pines, MD 21811
0.01
$441,500
3
2
1,450
Off Market
39 Windjammer Rd, Ocean Pines, MD 21811
0.01
$382,000
3
2.5
1,443
Off Market
15 Harbormist Cir, Ocean Pines, MD 21811
0.02
$299,000
3
2
1,120
Off Market
41 Windjammer Rd, Ocean Pines, MD 21811
0.03
$386,400
Studio
2
1,704
Off Market
262 Ocean Pkwy, Ocean Pines, MD 21811
0.03
$330,600
3
2
1,296
Off Market
264 Ocean Pkwy, Ocean Pines, MD 21811
0.03
$286,000
3
2
1,208
Off Market
266 Ocean Pkwy, Ocean Pines, MD 21811
0.03
$247,800
3
1
832
Off Market
13 Harbormist Cir, Ocean Pines, MD 21811
0.03
$309,400
3
2
1,024
Off Market
2 Frigate Run, Ocean Pines, MD 21811
0.03
$457,800
4
3.5
2,100
Off Market
19 Harbormist Cir, Ocean Pines, MD 21811
0.04
$413,500
Studio
1
1,776
Off Market
270 Ocean Pkwy, Ocean Pines, MD 21811
0.04
$302,200
Studio
2
1,568
Off Market
1 Frigate Run, Ocean Pines, MD 21811
0.04
$431,000
4
3
1,750
Off Market
43 Windjammer Rd, Ocean Pines, MD 21811
0.04
$285,400
Studio
2
1,208
Off Market
260 Ocean Pkwy, Ocean Pines, MD 21811
0.05
$382,800
4
2
1,720
Off Market
11 Harbormist Cir, Ocean Pines, MD 21811
0.05
$374,500
4
2.5
1,632
Off Market
4 Frigate Run, Ocean Pines, MD 21811
0.05
$325,100
Studio
2
1,172
Off Market
258 Ocean Pkwy, Ocean Pines, MD 21811
0.05
$370,000
3
2
1,238
Recently Sold
44 Windjammer Rd, Ocean Pines, MD 21811
0.05
$347,800
Studio
2
1,306
Off Market
272 Ocean Pkwy, Ocean Pines, MD 21811
0.05
-
-
-
-
Off Market
45 Windjammer Rd, Ocean Pines, MD 21811
0.05
-
-
-
-
Off Market

LGBTQ Local Legal Protections

Diana L. Whitney, Whitney-Wallace Commercial Real Estate Services, LLC, (410) 548-5484
Agent Phone: (410) 726-7886
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

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Frequently asked questions about 37 Windjammer Rd

  • What is the estimated monthly payment for 37 Windjammer Rd?
    Based on a $329,900 list price with 20% down at today's rates, the estimated monthly payment for 37 Windjammer Rd in Ocean Pines, MD is approximately $2,062 (about $1,778 principal & interest, $209 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 37 Windjammer Rd compare to homes in Ocean Pines?
    37 Windjammer Rd in Ocean Pines, MD is listed at $329,900, about 35% below the $511K median sale price in Ocean Pines.
  • What do residents say about Ocean Pines?
    Residents describe Ocean Pines, MD as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See homes for sale in Ocean Pines, MD.
  • What are the closest schools to 37 Windjammer Rd?
    The closest schools to 37 Windjammer Rd in Ocean Pines, MD are Berlin Intermediate School (Elementary, rated 8/10), Showell Elementary School (Pre-K, rated 8/10), Stephen Decatur High School (rated 7/10).
  • Does 37 Windjammer Rd have air conditioning?
    Yes, 37 Windjammer Rd in Ocean Pines, MD has air conditioning.
  • Does 37 Windjammer Rd have a pool?
    Yes, 37 Windjammer Rd in Ocean Pines, MD has a pool.
37 Windjammer Rd, Ocean Pines, MD 21811 is a 3 bedroom, 2 bathroom, 1,232 sqft single-family home built in 1984. This property is currently available for sale and was listed by Bright MLS on Oct 22, 2026. The MLS # for this home is MLS# MDWO2042190.