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Originally “Hilsmere Farm” in the early 1900’s, Hillsmere is a quiet waterfront community with around 1,200 homes. It is located 3 miles away from Historic Downtown Annapolis and walking distance from Quiet Waters Park, the Bay Ridge Plaza shopping center, the Eastport-Annapolis Library and Hillsmere Elementary School. Found within the neighborhood is The Key School campus, founded in 1958, home of the Obezags. Many of the campuses buildings were incorporated from the original farm including the main dairy barn and Manor House. Amenities of the neighborhood are plentiful, including but not limited to a private marina on the South River, community pool, multiple playgrounds, and a beach with waterfront pavilions.


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