There is truly no place like Annapolis. A modern city nestled on the Chesapeake Bay, our capital city located at the mouth of Maryland’s Severn River offers a picturesque setting for waterfront living.

Luxury Waterfront Homes in Annapolis

A luxury waterfront home in Annapolis is a destination that offers a variety of incredible, limitless views of the Severn River and the Chesapeake Bay. The view can awaken the dreams of a serene getaway from city life. From providing recreation to reducing stress, water is a mood booster: research shows that people need just as much blue space as they do green for peak psychological health. The Chesapeake Bay and Severn River can all offer respite and a personal oasis.

Whether your pastime is water sports, sailing, or beach lounging, these are just a few of the perks that make the Annapolis waterfront lifestyle worth pursuing.

Fall in Annapolis 2021 Annapolis Waterfront Homes

Along with the water comes some of the area’s most breathtaking views. Appreciate the scenery poolside at this Annapolis waterfront home overlooking the Severn River in Annapolis, Maryland. Image copyright ©2021 StahleyThompson Homes.

The Chesapeake Bay and the Severn river and streams that feed it are the largest estuary in the United States and third-largest in the world. The Maryland Eastern Shore region consists of nine counties and lies predominantly around the eastern side of the Chesapeake Bay. It features the most shoreline and points of public waterway access sites of any region in Maryland – with hundreds of coves, bays, rivers, and islands that dot the many waterfront communities.

An Area with a rich History

Way back in 1608, Captain John Smith explored the Sassafras River, eventually landing at Tockwogh village near present-day Rock Hall.  He noted that “Heaven and earth never agreed better to frame a place for man’s habitation,” while exploring the Eastern Shore.

The Eastern Shore has long been known for its Chesapeake Bay Blue Crabs and crab feasts. For thousands of years, the delectable Oyster has been an integral part of the Chesapeake Bay’s history. To learn more about the history of Chesapeake Oysters, the book “Chesapeake Oysters” by Kate Livie is an interesting read with historic photos.

Fall in Annapolis 2021 Annapolis Waterfront Homes

A boater enjoys an early morning trip across the Severn River. Image copyright ©2021 StahleyThompson Homes. 


The Annapolis lifestyle includes a wide variety of opportunities to actively embrace the great outdoors – even while being close to the city life. Waterfront homes with sweeping views and deep water docks are great for boaters while cottages nestled in the woods on creeks are perfect for kayaks.

Among the many settings to choose from are waterfront condos, residences with breathtaking sunset views of the Chesapeake Bay and other tributaries, hunting farms, and waterfront communities. The Severn and Magothy rivers offer great places for day trips and weekend getaways to visit the many scenic waterfront villages and historic towns along the waterways. Other destinations may include The United States Naval Academy (USNA) or a visit to one of the Annapolis Historical Society’s many locations.

Fall brings a crisp change to the air every year and Annapolis plays host to some amazing vistas – if you know where to look. Enjoy these aerials taken during early October.