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103 Winter Harbor Dr, 
Ocean City, MD 21842

$1,299,999


5

Beds


3

Baths


1,775

Sq Ft


Single Family

Active

Listed by

Jamie Caine

Last updated:

March 22, 2026, 01:44 PM

MLS#

MDWO2037044

Source:

BRIGHTMLS

Company Logo

About This Home

103 Winter Harbor Dr

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***

Home Facts

Single Family

3 Baths

5 Bedrooms

Built in 2002

Price Summary

1,299,999

$732 per Sq. Ft.

MLS #:

MDWO2037044

Last Updated:

March 22, 2026, 01:44 PM

Added:

4 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

2

Interior

Living Area:

1,775 Sq. Ft.


Structure

Structure

Architectural Style:

Coastal

Building Area:

1,775 Sq. Ft.

Year Built:

2002


Lot

Lot Size (Sq. Ft):

7,405


Finances & Disclosures

Finances

Price:

$1,299,999

Price per Sq. Ft:

$732 per Sq. Ft.

103 Winter Harbor Dr
Source:BRIGHTMLS
The information being provided by Bright Mls is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Bright Mls All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.