Annapolis, Maryland: What to Do and Where to Live

Downtown Annapolis has historic homes, museums, arts, and plenty of opportunities to have fun on the water.

As the capital of Maryland, Annapolis is a calm, yet happening place to live. The historic center of the city is small and walkable, with most shops, restaurants, and museums located between the state capitol building and the waterfront.

The broader Annapolis area offers malls and big box stores, with new and old developments with homes for sale that tend to be slightly higher in price than other areas in Central Maryland. Here are some highlights of Annapolis, and great 55+ communities nearby.  

Explore the History

The Maryland State House capitol building in Annapolis, Maryland.

Annapolis is steeped in history, and many museums and houses pay tribute to historic Marylanders and the state’s past.

The Banneker-Douglass Museum, named after Benjamin Banneker and Frederick Douglass, shares African American history in Maryland and celebrates contemporary artists. Historic homes like the William Paca House and Gardens and the James Brice House attempt to interpret life in 17th and 18th century Maryland.

At the Annapolis Maritime Museum, visitors can expand their knowledge of the Chesapeake Bay, the largest estuary in the U.S. The museum is free, and offers programming and events throughout the year.

Annapolis is also home to the Naval Academy, so don’t be surprised to see midshipmen in uniform exploring the streets or a lot of traffic on game days. Visitors can tour the grounds of the Academy with a valid ID (for security reasons) and stop into the visitor’s center for the history of this famous institution.

Experience Arts and Culture

The skyline at Chesapeake Bay with the United States Naval Academy Chapel dome in Annapolis, Maryland.

The first Sunday of the month is the best day to get the full experience of Annapolis’s arts and culture scene. The First Sundays Arts Festival brings together musicians and bands, craft vendors, and fine art dealers from May to November.

At other times, visitors can see the galleries in town like the McBride Gallery or see what’s playing at the Annapolis Symphony.

Get on the Water

The Annapolis Harbor at dusk in Annapolis, Maryland.

Just standing at the waterfront in Annapolis will make visitors want to be on a boat. Watermark offers tours of the Chesapeake Bay on small cruising ships, while Schooner Woodwind Sailing Cruises sets sail on a 74-foot sailboat for a variety of tours. Local marinas also provide places to dock boats or load into the water.

At nearby Quiet Waters Park, visitors can walk wooded trails and enjoy expansive green lawns. Sandy Point State Park provides visitors the opportunity to experience the Bay up close with a beach area and boat launch.

Here are four communities in and around Annapolis.

55+ Communities in Annapolis

The golf course at Heritage Harbour in Annapolis, Maryland on a sunny day.

Mid $300s - Low $800s

Residents of Heritage Harbour don’t need to leave their community to get out on the water. The amenities of this large community of 1,600 homes include a boat dock, boat storage, a pier, and boat launch.

This community provides residents with the experience that many people want living in or near Annapolis. Homes are just minutes from the center of the city, but the woods and views of the water offer a peaceful place to call home.

The active adult community includes condos, attached, and single-family homes that vary widely in size and price, offering plenty of options for various budgets.

Mid $300s - Mid $400s

Located across the Severn River on the north side of Annapolis, Four Seasons at Saint Margaret’s is a condo community with 166 homes offered for resale.

The community’s amenities include a clubhouse with lounge, meeting rooms, a billiards room, and card room. Outside, residents can enjoy the outdoor pool and patio, or the wooded surroundings of this quiet neighborhood. Within minutes, residents can walk to parks and the waterfront.

Mid $400s - Mid $1Ms

Chesapeake Harbour is an active lifestyle community of 378 homes situated on the Chesapeake Bay. This gated community offers residents a low-maintenance lifestyle and many amenities, including a deep-water marina with private boat slips.

Developed from 1985 to 1998, Chesapeake Harbour is divided into four villages. First Village condominiums range from 1,003 to 1,748 square feet, and Second Village condos offer 1,023 to 1,769 square feet. Also, attached homes in Townhome Village range from 1,230 to 3,136 square feet, while Harbour Marina Village features attached homes that range from 1,830 to 2,321 square feet.

Low $400s - High $600s

An up-and-coming 55+ community, Element at Mill Creek will have 140 condos upon completion. The community also offers amenities such as a state-of-the-art fitness center, a social lounge, and pickleball courts. 

Construction began in 2022, and the planned condo homes will range from 1,076 to 1,853 square feet with one to three bedrooms, two or two-and-a-half bathrooms, and outdoor parking. Also, the community’s location is within 15 minutes of Downtown Annapolis and 45 minutes of Baltimore. 

Can you spot the $207,744 difference between these identical homes?

Financing is the difference!

Get the details in The 62+ Loan Homebuyers Guide.

55places Mortgage is a joint venture between Mutual of Omaha Mortgage and 55places.com.
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