Retirement Cities in Maryland

Boats along Dock Street and the harbor in Annapolis, Maryland.

Annapolis, Maryland, United States

Budget · $5,353/mo

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Berlin, Maryland, United States

Budget · $4,382/mo

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Cambridge, Maryland, United States

Budget · $3,800/mo

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Chestertown, Maryland, United States

Budget · $4,456/mo

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An aerial photograph of Cumberland, Maryland in October 2022.

Cumberland, Maryland, United States

Budget · $3,422/mo

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A downtown alley on Dover Street in Easton, Maryland.

Easton, Maryland, United States

Budget · $4,074/mo

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An aerial photograph of Frederick, Maryland's city hall in 2022.

Frederick, Maryland, United States

Budget · $5,016/mo

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Downtown Hagerstown, Maryland looking west on Franklin Street. Image slightly edited to crop out hood of vehicle and blur license plates.

Hagerstown, Maryland, United States

Budget · $3,805/mo

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The Havre de Grace waterfront in September 2025.

Havre de Grace, Maryland, United States

Budget · $4,002/mo

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A view of the beach in Ocean City, Maryland looking north from the pier.

Ocean City, Maryland, United States

Budget · $4,416/mo

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Salisbury, Maryland, United States

Budget · $4,039/mo

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Old Inn in Saint Michaels, Maryland, USA

St. Michaels, Maryland, United States

Budget · $3,903/mo

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Westminster, Maryland, United States

Budget · $4,596/mo

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Retirement cities in Maryland