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$1,299,999 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1,775 Sq. Ft.
  • Updated 1 day ago
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Welcome to this beautiful five-bedroom, two-and-a-half-bath single-family home in the sought-after Caine Keys II community of Ocean City, Maryland. Perfect for boaters and beach lovers alike, this home features a private boat slip right outside your back door, providing easy access to the water. Enjoy the coastal lifestyle with a large balcony offering scenic views, a cozy gas fireplace, and plenty of parking, Located just minutes from Ocean City's stunning beaches, this home is ideal for year-round living or a relaxing vacation retreat. Don't miss this rare opportunity to own a spacious waterfront home in one of Ocean City's most desirable neighborhoods! Home Extras: Central Vac, Gas stove, 2 large waterfront decks, gas fireplace, and in home stereo speakers ***NEW ROOF April 2026***

Full Property Details for 103 Winter Harbor Dr

General

  • Price: $1,299,999
  • Taxes: $7,112 (2026)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDWO2037044
  • Updated: 3/18/2026
  • Added to Site: 2 day(s) ago

Interior

  • Interior Features: Carpet, Ceiling Fan(s), Primary Bath(s), Window Treatments
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Dishwasher, Dryer, Microwave, Refrigerator, Washer, Water Heater, Oven/Range - Gas
  • Furnished: Yes
  • Flooring: Carpet, Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Upper Floor Baths: 1
  • Upper - Full Baths: 1
  • Main Floor Baths: 2
  • Main - Full Baths: 1
  • Main - 1/2 Baths: 1

Bedrooms

  • Total Bedrooms: 5
  • Bedrooms Upper: 3
  • Bedrooms Main & Up: 2

Exterior

  • Exterior Features: Outside Shower, Sidewalks
  • Porch/Patio/Deck: Patio(s), Deck(s)

Parking

  • Total Spaces: 4
  • Parking Features: Concrete Driveway
  • Parking Type: Driveway

Location

  • Area: Bayside Waterfront (84)
  • Municipality: Ocean City
  • County: WORCESTER
  • Subdivision: CAINE KEYS II
  • Driving Directions: Coastal Hwy to Winter Harbor Dr, Turn West, house on Left
  • Location Details: Canal
  • City Limits: Yes

School Information

  • School District: Worcester County Public Schools

Community

  • Pets Allowed: Yes
  • Pets: Dogs OK, Cats OK

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump - Electric BackUp
  • Heating Fuel: Electric
  • Water Heater: Natural Gas

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Coastal
  • Structure Type: Detached
  • Construction: Frame
  • Foundation: Block
  • Stories Description: Main, Upper 1
  • Square Feet: 1,775
  • Sq. Ft. Source: Assessor
  • Living Area: 1,775 Sq. Ft.
  • Finished Above Grnd: 1,775 Sq. Ft.
  • Year Built: 2002
  • Year Built Source: Assessor
  • Property Condition: Very Good

Lot Features

  • Property View: Canal
  • Lot Size (Acres): 0.17
  • Lot Size (Sq. Ft.): 7,500
  • Lot Size Source: Assessor
  • Zoning: R1
  • Lot Description: Bulkheaded

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Navigable Water: Yes
  • Water Access: Yes
  • Water Front Type: Lagoon
  • Dock/Slip Conveys: Yes
  • Docks: 2

Financial Considerations

  • Price Per Sq. Ft.: $732.39
  • City/TownTax: $2,298
  • City/TownTax Freq: Annually
  • Tax w/Assessment: $564,600
  • Tax Amount: $7,112
  • Tax Year: 2026

Disclosures and Reports

  • Ownership: Fee Simple
  • Exclusions: Personal Items
  • Inclusions: Furniture
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

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— 103 Winter Harbor Dr —

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 103 Winter Harbor Dr

School District:Worcester County Public Schools
NameGradesDistance
Ocean City Elementary School
12828 Center Drive, Ocean City, MD 21842
PK-45.5 mi
Stephen Decatur Middle School, Berlin, MD
9815 Seahawk Road, Berlin, MD 21811
7-89 mi
Stephen Decatur High School
9913 Seahawk Road, Berlin, MD 21811
9-128.8 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 103 Winter Harbor Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/18/2026
Listed
$1,299,999
766.67%
MLS
9/06/2001
Sold
$150,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 103 Winter Harbor Dr

Year
Property Taxes
Change
Tax Assessment
Change
2023
$6,042
—
$519,267
21%
2023
$6,042
1%
$428,600
1%
2021
$5,969
—
$425,500
1%
2021
$5,969
1%
$422,400
1%
2021
$5,924
-1%
$419,300
—
2020
$5,965
1%
$419,300
—
2019
$5,923
-1%
$419,300
-1%
2018
$5,961
-1%
$422,000
—
2017
$5,991
—
$422,000
—
2016
$6,014
5%
$422,000
-1%
2015
$5,742
—
$424,600
—
2014
$5,749
—
$424,600
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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103 Winter Harbor Drive, Ocean City, MD 21842 (MLS# MDWO2037044) is a Single Family property with 5 bedrooms, 2 full bathrooms and 1 partial bathroom. 103 Winter Harbor Drive is currently listed for $1,299,999 and was received on March 18, 2026. This property is listed by Jamie Caine from our Ocean City - 123rd Office.Want to learn more about 103 Winter Harbor Drive? Do you have questions about finding other Single Family real estate for sale in Ocean City? You can browse all Ocean City real estate or contact a Coldwell Banker agent to request more information.

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