8 Best Places To Retire On The Chesapeake Bay

The Chesapeake Bay offers retirees the dream of retiring on the water, which comes with a peaceful yet active lifestyle. Fortunately, the largest estuary in the United States dabbles as a major source of seafood, specifically blue crabs, a species known for their sweet and succulent meat. Keep in mind that Maryland is tax-friendly toward retirees, especially considering it does not tax Social Security income. Starting with Crisfield, Maryland, discover the 8 best places to retire in the Chesapeake Bay.

Crisfield, Maryland

With its endless water and biking opportunities, Crisfield provides retirees with a lively relaxation and adventure menu. Expect beautiful sunset views, interesting historic homes, and one of the most spellbinding outdoor venues in the area: Janes Island State Park. This park features over 30 miles of water trails, a network of saltwater marshes, and several tranquil campsites. Moreover, a retiree here will enjoy evening rides to the Crisfield City Dock, exploring the Crisfield's Arts and Entertainment District, and floating down the Daugherty Creek Canal. The highly rated TidalHealth Peninsula Regional is next door in Salisbury while the median house listing price is an unbelievable $243,267. On the social side, Crisfield residents have a median age of 35.8, meaning a retiree has ample chance to mingle with both the old and young.

Chestertown, Maryland

Washington College gives Chester town special energy while its Saturday Farmers Market offers residents a fantastic opportunity to mingle and shop. Keep in mind that you have a nice, historic downtown peppered with inviting restaurants and locally owned shops. You also have an intimate movie theatre with comfortable recliner seats and the Chester River for boating and other recreational activities. On healthcare access, you have the University of Maryland Shore Medical Center at your doorstep, so no need to make an out-of-town trip. Chestertown residents have a median age of 32, implying a social scene that leans on the livelier, burblier side of life. Finally, houses in Chestertown fetch a median listing price of $354,633, a price point that many will want to jump at.

St. Michaels, Maryland

St. Michaels, with its lookout points and white-sand beaches, is a nice, friendly town with a vibrant culinary scene. A retiree here enjoys access to the Waterfront Park on Miles River, which has benches for watching heart-stirring sunsets; Chesapeake Bay Maritime Museum, a mind-rousing, 18-acre waterfront venue that offers boat rides and insightful exhibits, and a stand-out wine spot: the 5-star rated Bordeleau Winery at St. Michaels. Considering that the University of MD Shore Medical Center at Easton is a doorbell away — and that the median age of residents grazes the 50-year mark, a retiree here will have few complaints, if any. Houses in St Michaels have a median listing price of $665,000

Easton, Maryland

Easton is a quiet, family-friendly town with a strong sense of community. It is in the tidewater region along the eastern shore of Chesapeake Bay. You have a historical downtown loved for its charming Colonial and Victorian architecture, the Tred Avon River, famous for its association with fresh oysters, the Amish Country Farmer's Market for all kinds of fresh fruit and vegetables, and the Academy Art Museum, a cultural hub for the Eastern Shore.

The annual Waterfowl Festival, which electrifies the town every November, often draws visitors from across the region. Keep in mind that with the award-winning University of MD Shore Medical Center at your doorstep, there is scarcely any need to make the short trip to Annapolis for your healthcare needs. Also, Easton residents have a median age of 45.6, which many empty nesters will view as alluringly calm. Finally, homes in Easton fetch a median listing price of $535,167.

Lewes, Delaware

Lewes is a small, peaceful town that provides access to the highly rated Savannah Beach, where a retiree can walk out ankle-deep and view tons of sea life. Junction and Breakwater Trail is every biker’s dream while Cape Henlopen State Park — with its mature maritime forests — speaks to the town’s alluring outdoor appeal. Beebe Medical Center, which has been serving area residents since 1916, is a 2025 recipient of the America’s 100 Best Hospitals for Coronary Intervention Award. It is on Savannah Road a few steps from Lloyd's Market, the go-to spot for fresh apples and groceries. The latest data from Zillow shows that homes in Lewes fetch a median listing price of $606,000. But this is the most exciting part: Lewes residents have a median age of 67.3, meaning almost everyone here is a fellow empty nester.

Annapolis, Maryland

Annapolis — known across the globe as America's Sailing Capital — is also the capital of Maryland. This fun, artsy community is conveniently located between Washington DC and Baltimore, meaning a retiree can easily access all kinds of desirable amenities, including some of the best hospitals in the mid-Atlantic. You will enjoy cool parks like Truxton, which features lovely trails with water views; evening walks to the city Dock and the harbor; and mood-lifting performances at the historic Colonial Players Theater, a fantastic local community theatre in a 180-seat arena. Considering the convenience it provides, a median listing price of $651,317 is good value for money. Finally, Annapolis residents have a median age of 40.9, just where life begins.

Stevensville, Maryland

Many people dream of retiring on a secluded island; to be surrounded by water and to enjoy the sound of crashing waves. This makes Stevensville, a small, friendly town on Kent Island, a much sought-after retirement destination. You will live in a quiet and laid-back environment, yet be only 20 minutes from Annapolis, the capital of the U.S. state of Maryland. There is a lot to enjoy at Terrapin Nature Park, including the dreamy views it provides; Matapeake Park (if you don’t mind the presence of jellyfish), and the Blue Heron Golf Course, a beautifully maintained space with good greens and well-redesigned fairways.

On healthcare access, the award-winning Luminis Health Anne Arundel Medical Center is a short drive away in Annapolis, so no need to worry about a midnight medical emergency. On the social side, residents here have a median age of 42.2, implying a social scene that is calm but not lifeless. According to data from Zillow, houses in Stevensville have a median listing price of $553,316.

Pasadena, Maryland

A retiree in Pasadena is a short, 25-minute drive from downtown Baltimore, implying fantastic access to big-city amenities (including hospitals ) and a long list of interesting cultural attractions. Moreover, she is also surrounded by Stoney Creek, Nabbs Creek, and Curtis Creek, the site of one of Baltimore's most unique military facilities: The U.S. Coast Guard shipyard. One thing is guaranteed: you will enjoy Pasadena’s small hometown feel. Keep in mind that Pasadena residents have a median age of 35.4, a sweet spot between the old and young and in a sense, the best of both worlds. The prices of homes are not over the roof either, especially considering that the median listing price — according to Zillow’s January 2025 data — is just $486,742.

The Takeaway

If you are looking for thrilling outdoor adventures, fantastic access to excellent medical facilities, and more importantly — scenic waterfront views — it is time you considered retiring in the Chesapeake Bay. Besides the dream-like nautical charm that pervades the entire stretch, the Chesapeake Bay is strewn with small, charming towns where life is beautiful, slow, and relaxed. Some are vibrant and artsy, like Annapolis, while others look like a big tent gathering of retirees, like Lewes, Delaware. Whichever town you choose, one thing is certain: you will enjoy being close to the water.