Welcome to 1244 Pine Avenue, a charming Chesapeake Bay waterfront retreat in Shady Side, Maryland, offering beautiful water and marina views, generous indoor-outdoor living, and a peaceful setting rooted in the boating lifestyle of southern Maryland The offering encompasses approximately 0.34 acres across Lots 16, 17, and 28, providing additional land and versatility rarely found in a waterfront community. Lots 16 and 17 are currently taxed together, while Lot 28 is separately deeded. Set within an established waterfront community, this inviting home offers the rare opportunity to enjoy everyday life just moments from the water, with a marina approximately one block (slips available for rent) away and a waterfront community center, playground, and picnic area nearby. Inside, the welcoming living and dining spaces are anchored by a fireplace and framed by picture windows that draw the surrounding water views into the home. The classic kitchen is thoughtfully appointed with green cabinetry, granite countertops, stainless steel appliances, and a gas range, creating a bright and functional space for everyday cooking and entertaining. Just beyond the kitchen, a screened-in porch extends the living space outdoors and provides an ideal setting for al fresco dining, morning coffee, or crisp fall evenings overlooking the peaceful surroundings. An expansive family room at the rear of the home offers additional space to gather and relax, with large windows capturing views toward the bay and sliding glass doors opening directly to the deck and backyard. A main-level bedroom adds valuable flexibility as a guest suite, home office, or additional living space. Upstairs, three generously proportioned bedrooms provide comfortable accommodations, including a spacious primary bedroom spanning one side of the home and offering lovely Chesapeake Bay views. Well appointed bathrooms throughout complete this turn-key home. Outside, the deck and yard create an effortless extension of the home, while a large storage shed provides additional functionality. Perfectly positioned in Shady Side, Maryland, 1244 Pine Avenue offers the relaxed character and natural beauty of Chesapeake Bay living with convenient access to the water, the nearby marina, Cedarhurst community amenities, and the surrounding towns of southern Anne Arundel County. Whether you're seeking a primary residence, weekend retreat, or a home that embraces the region's celebrated waterfront lifestyle, this distinctive property combines water views, flexible living space, multiple outdoor areas, and exceptional proximity head out on the Chesapeake Bay.