There are several resort-style and waterfront retirement community options on Maryland’s Eastern Shore, ranging from continuing care retirement communities (CCRCs) to active 55+ lifestyle communities. Popular options include:

• Heron Point of Chestertown (Chestertown, MD) – An Acts community set on 66 acres along the Chester River, offering true waterfront living with easy access to boating, kayaking, and scenic river views, along with wellness and social amenities on campus.
• Bayleigh Chase (Easton, MD) – Another Acts community on the Eastern Shore, located near downtown Easton with water access nearby and shoreline recreation just outside the community. It’s convenient to healthcare and lifestyle amenities, with care services available on campus.

While not CCRCs, these communities appeal to active retirees who want amenities and coastal or water-oriented living:

• Four Seasons at Kent Island (Chester, MD) – A resort-style 55+ active adult community on Kent Island.
• The Parke at Ocean Pines (near Ocean City, MD) – A popular 55+ active adult community close to beaches and the boardwalk.

Unlike a CCRC, these retirement communities do not offer assisted living and skilled nursing services on the same campus.