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

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 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 Fin Art or the McBride Gallery, or see what’s playing at the Annapolis Symphony.

Get on the Water

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.

Heritage Harbour – Annapolis

Low $200s – High $700s

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.

Four Seasons at Saint Margarets – Annapolis

Low $200s – Low $400s

Located across the Severn River on the north side of Annapolis, Four Seasons at Saint Margarets 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.  

The Hamlets at South River Colony – Edgewater

High $300s – Low $400s

Just south of Annapolis in Edgewater, the Hamlets at South River Colony offers active adults attached homes and condos within the larger planned community of South River Colony.

Residents have access to the clubhouse, outdoor pools, tennis courts, and greenspaces in the community, but also have their own clubhouse exclusively for the residents of the Hamlets. The wooded and green neighborhood is just steps from the waterfront and the Historic London Town and Gardens museum and park.

McKinsey Park

High $200s – Low $300s

North of Annapolis on the way to Baltimore, McKinsey Park offers active adults maintenance-free living in an intimate condo community.

While McKinsey Park does have a small clubhouse and community patio, residents enjoy the area around the community. Both are steps from the water and a shopping center that includes fast-casual dining, big box stores, grocery stores, and the local library. These homes feel more like a neighborhood than a retirement community.

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