View Homes for Sale in Shady Side

Welcome to Shady Side, Anne Arundel County

Shady Side sits along the western edge of the Chesapeake Bay in southern Anne Arundel County. It offers a peaceful setting with deep ties to the water. Life here moves at a slower pace. The smell of salt air and the sound of gulls shape daily routines. This small community draws people who want simplicity, nature, and strong neighborhood bonds.

A Heritage on the Water

Shady Side began as a waterman’s village. That legacy still shapes the local culture. Many of the homes reflect this past—ranging from early 20th-century cottages to modern custom builds. Neighborhoods like Idlewilde, Cedarhurst on the Bay, and Snug Harbor offer piers, beaches, and boat ramps. Residents here don’t just live near the water—they live with it. Boating, fishing, and crabbing are part of everyday life.

Nature at Every Turn

The Chesapeake Bay gives Shady Side its character. From shaded creeks to wide open water, the scenery invites outdoor activity. Franklin Point State Park and Jack Creek Park sit close by with trails and marsh views. Birdwatchers often visit, and kayakers glide through the calm creeks. This is a place where evenings end with sunset walks by the shore.

A Close Community with Room to Breathe

Though small, Shady Side feels complete. Local marinas, seafood markets, and community centers bring people together. Events and local gatherings build strong ties between neighbors. The town remains quiet but connected to nearby hubs like Deale and Edgewater for shopping and daily needs. Annapolis lies just a short drive away, and Washington DC remains within reach via MD-2 and MD-214.

A Chesapeake Lifestyle

Shady Side suits those who want water, nature, and a slower rhythm. Whether you’re downsizing, retiring, or seeking a weekend home, this community gives you space, peace, and a deep sense of place. With its quiet roads, coastal breezes, and timeless charm, Shady Side captures the spirit of life on the Chesapeake.

Explore homes for sale in Shady Side below: