Chesapeake Beach, MD Homes for Sale with Pool

For those seeking privacy and tranquility, this residence presents an ideal opportunity. Meticulously maintained and upgraded. Upon entering, one is immediately impressed by the inherent elegance of the property. Spanning over 2,600 square feet, this home features four bedrooms and three and a half bathrooms. The main level showcases a beautifully appointed kitchen with granite countertops and

Indera Coggins CENTURY 21 New Millennium

Nestled along the tranquil shores of Chesapeake Beach, this stunning four-bedroom, four-and-a-half-bath waterfront townhome offers 2,632 square feet of thoughtfully designed living space for those who appreciate the beauty of life on the water. Expansive decks on every level provide uninterrupted views, where you can savor gentle breezes and watch local crab boats set out at sunrise. Also, the

Greg Beckman Coldwell Banker Realty

***OFFER DEADLINE is Monday, May 18, 2026, at 2:00 p.m.***Experience unparalleled WATERFRONT LUXURY in the highly sought-after Windward Key community on the Chesapeake Bay. This exceptional four-level end-unit garage townhome has been extensively updated with stunning coastal-modern finishes and offers breathtaking panoramic Bay views from nearly every room. With the Chesapeake Bay quite

Doug Smith RE/MAX Realty Group

Experience an elevated waterfront lifestyle in the coveted Windward Key community, ideally positioned along the shores of the Chesapeake Bay in the heart of Chesapeake Beach. This exceptional four-level townhome blends refined design with water views, offering 3 bedrooms, 4 full baths, and 1 half bath across thoughtfully designed living spaces. Sunlight pours through expansive windows,

Doug Smith RE/MAX Realty Group

COASTAL LUXURY MEETS EVERYDAY VACATION LIVING in Windward Key on the Chesapeake Bay. Experience the ultimate waterfront lifestyle in this four-level townhome nestled in the sought-after Windward Key community in the heart of Chesapeake Beach. Whether you are searching for a full-time residence or the perfect weekend retreat, this exceptional home offers resort-style living with water views and

Doug Smith RE/MAX Realty Group

Discover coastal living at its finest at 8048 Windward Key Dr, Chesapeake Beach! This "as-is" gem offers breathtaking views of the canal and the iconic Chesapeake Bay, placing you right in the heart of everything this charming waterfront town has to offer. Located just steps away from the renowned Rod 'N' Reel Resort, you'll enjoy the convenience of walking to local restaurants, marina boat

Chris Moore Compass