118 WINTER HARBOR DRIVE, OCEAN CITY, MD 21842

$724,000

What happens when Ocean City stops numbering the streets... and starts naming them? You find rare waterfront retreats like this house on Winter Harbor Dr. Tucked into the Caine Keys section of North Ocean City, just a few short blocks where the streets suddenly trade numbers for names, this waterfront… Read More cul-de-sac feels different than the rest of town. More relaxed. More personal. More like the version of beach life people remember.... and people want more of. Affordable waterfront living! It's disappearing fast. 118 Winter Harbor is a 3-bedroom, 2-bath waterfront home offering direct canal frontage with immediate access to the Assawoman Bay, along with something buyers are struggling to find anymore... a move-in-ready waterfront property, with a dock, at a price point that still feels attainable. The home itself has been thoughtfully updated and exceptionally well cared for, with coastal finishes, updated bathrooms, updated decor, a newer roof, updated vinyl bulkheading, and an updated rear deck overlooking the canal. Inside, the space feels comfortable, easy, bright, vibrant, and charming. And then you step outside... for more! Step onto the back deck and your private dock is right there, ready for your boat, pontoon, or jet skis, with direct bay access for days spent on the water instead of sitting in traffic wondering why you didn't buy a place like this sooner. Meanwhile, directly across Coastal Highway... the Atlantic Ocean and Ocean City's world famous white sand beaches. Not ''a short drive away.'' Not ''close enough.'' Right there... just a short distance across Coastal Highway! You've finally found a place in Ocean City where you genuinely get both worlds... waterfront boating lifestyle on one side, and easy access to Ocean City's famous beaches on the other. And there's another detail longtime owners in this area know about, and treat it like they're little secret. At the eastern end of the street, situated on the oceanfront, sits the Golden Sands Condominium, whose oceanfront bar/grill and public restrooms become an unexpectedly convenient part of everyday beach life. Grab lunch or a drink without leaving the beach, use the facilities, and avoid the constant back-and-forth trips home that most beachgoers deal with all summer long. That's the kind of every-day-use you don't think about upfront. Until you become a local. The location also puts you close to some of North Ocean City's favorite spots, like the Original Green Turtle, The Gold Coast Mall, and lots of dining and entertainment options... all while still giving you the slower pace and residential feel that makes Caine Keys so desirable. Whether you're looking for a personal beach retreat, a waterfront getaway, or a strong rental property with broad appeal, this home checks boxes that are becoming harder and harder to find together. Waterfront. Move-in ready. No HOA. Direct bay access. Steps from the beach. New Roof in 2020 & HVAC in 2022. That combination used to be normal in Ocean City. Now it's becoming RARE. Where will you be 5-years from now? And will you be regretting not buying this? Read Less

Courtesy of Grant K Fritschle, Keller Williams Realty Delmarva 410-524-6400

Listing Snapshot

Days Online

Last Updated

May 24, 2026

Property Type

Single Family Residential

Beds

Full Baths

Square Ft.

1,248

Lot Size

0.17 Acres

Year Built

1967

MLS Number

MDWO2038188

Additional Details

Appliances & Equipment

Dishwasher, Dryer, Exhaust Fan, Freezer, Microwave, Oven/Range - Electric, Refrigerator, Washer

Building

Built in 1967, Living area: 1248, Levels: 1, Entry level: 1, Construction Materials: Frame, Metal Siding, Stick Built

Cooling

Central A/C

Accessibility Features

None

Exterior Features

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

Floors

Carpet, Laminated

Foundation

Block

Heating

Forced Air, Heat Pump(s)

Interior Features

Bathroom - Stall Shower, Carpet, Combination Kitchen/Dining, Crown Moldings, Dining Area, Entry Level Bedroom, Window Treatments

Lot

0.17 acres, Dimensions: 0.00 x 0.00

Property

Other structures: Above Grade, Below Grade

Roof

Architectural Shingle

Sewer

Public Sewer

Taxes

Annual Amount: $5,898, Lot: 57, Year: 2025, Zoning: R-1

Utilities

Water Source: Public

Water Features

Private Dock Site

Windows

Insulated, Screens

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118 WINTER HARBOR DRIVE

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