Top 10 Places to Retire in Annapolis, Maryland


Welcome to Annapolis, Maryland, a picturesque city steeped in history, culture, and maritime charm, making it an ideal destination for retirees seeking a blend of relaxation and excitement in their golden years. As we explore the question, "Is Annapolis, Maryland a good place to retire?" join us in uncovering the best neighborhoods and retirement communities that offer retirees a fulfilling and enriching lifestyle. From waterfront vistas to historic districts, Annapolis beckons retirees to discover the perfect place to call home during retirement.


Historic District

Annapolis' Historic District, nestled along the shores of the Chesapeake Bay, is a charming and vibrant neighborhood renowned for its colonial architecture and maritime heritage. Retirees in the Historic District can stroll along the cobblestone streets and explore landmarks like the Maryland State House, the oldest state capitol still in continuous legislative use. The neighborhood offers a plethora of dining options, from cozy cafes to upscale restaurants, and hosts cultural events like the Annapolis Film Festival. With its waterfront parks and bustling downtown scene, the Historic District provides retirees with a lively and culturally rich retirement experience.



Eastport, located across Spa Creek from downtown Annapolis, is a waterfront neighborhood known for its maritime character and laid-back atmosphere. Retirees in Eastport can enjoy panoramic views of the Chesapeake Bay and participate in sailing and boating activities at the Annapolis Maritime Museum. The neighborhood boasts a variety of dining establishments, including dockside eateries and seafood restaurants. With its community events like the Eastport Yacht Club Lights Parade and proximity to downtown amenities, Eastport offers retirees a relaxed and nautical retirement lifestyle.


Murray Hill

Murray Hill, situated west of downtown Annapolis, is a prestigious residential neighborhood known for its tree-lined streets and elegant homes. Retirees in Murray Hill can explore the lush gardens of the William Paca House and Garden, a National Historic Landmark. The neighborhood offers proximity to boutique shops and art galleries along Maryland Avenue and West Street. With its tranquil ambiance and historic charm, Murray Hill provides retirees with a refined and sophisticated retirement setting.


West Annapolis

West Annapolis, located across the Severn River from downtown, is a quaint and welcoming neighborhood known for its small-town charm and community spirit. Retirees in West Annapolis can explore the boutiques and cafes along Annapolis Street and enjoy outdoor concerts at nearby Navy-Marine Corps Memorial Stadium. The neighborhood offers a mix of housing options, from historic homes to waterfront properties along Weems Creek. With its family-friendly atmosphere and close-knit community, West Annapolis provides retirees with a warm and inviting retirement environment.


Bay Ridge

Bay Ridge, situated on the southeastern tip of Annapolis, is an exclusive waterfront community known for its scenic beauty and private amenities. Retirees in Bay Ridge can enjoy access to private beaches, marinas, and tennis courts, along with community events like the Bay Ridge Fourth of July Parade. The neighborhood offers stunning views of the Chesapeake Bay and easy access to outdoor recreation at Quiet Waters Park. With its secluded ambiance and resort-style amenities, Bay Ridge provides retirees with a luxurious and tranquil retirement experience.


Admiral Heights

Admiral Heights, located northwest of downtown Annapolis, is a sought-after neighborhood known for its waterfront properties and community amenities. Retirees in Admiral Heights can enjoy access to private marinas and waterfront parks, such as Truxtun Park, which offers walking trails and recreational facilities. The neighborhood hosts social events like the Admiral Heights Summer Concert Series and provides easy access to downtown Annapolis' dining and cultural attractions. With its waterfront lifestyle and active community, Admiral Heights offers retirees a scenic and engaging retirement experience.



Germantown, situated in the heart of Annapolis, is a historic neighborhood known for its charming streetscapes and diverse architecture. Retirees in Germantown can explore landmarks like St. Anne's Episcopal Church and the Hammond-Harwood House Museum, showcasing the area's rich heritage. The neighborhood offers proximity to downtown shopping districts and cultural venues like the Maryland Hall for the Creative Arts. With its historic ambiance and cultural offerings, Germantown provides retirees with a vibrant and enriching retirement lifestyle.



Hillsmere, a serene neighborhood nestled along the Chesapeake Bay, offers retirees a picturesque retreat with its waterfront living and strong community bonds. The neighborhood also hosts regular events and activities, including holiday celebrations, picnics, and yoga classes, providing retirees with opportunities to stay active and engaged within the community. Residents enjoy breathtaking views of the bay, abundant outdoor activities, and a close-knit atmosphere that fosters a vibrant retirement lifestyle. From leisurely walks along private beaches to community events and convenient access to downtown Annapolis, Hillsmere provides retirees with an idyllic setting to enjoy their golden years.


Presidents Hill

Presidents Hill, located south of downtown Annapolis, is a historic neighborhood known for its Federal-style homes and cobblestone streets. Retirees in Presidents Hill can explore landmarks like the William Paca House and Garden and enjoy waterfront dining along Spa Creek. The neighborhood offers a mix of residential properties and boutique shops along Maryland Avenue. With its historic charm and scenic vistas of the State House dome, Presidents Hill provides retirees with a quaint and picturesque retirement environment.



Homewood, situated east of downtown Annapolis, is a residential neighborhood known for its leafy streets and proximity to the Naval Academy. Retirees in Homewood can enjoy walks along College Creek and attend events at the Naval Academy's Chapel and Alumni Hall. The neighborhood offers a mix of architectural styles and easy access to downtown amenities. With its close-knit community and academic ambiance, Homewood provides retirees with a tranquil and intellectually stimulating retirement experience.


In conclusion, Annapolis, Maryland, stands as a remarkable choice for retirees seeking a blend of history, waterfront living, and vibrant community life. Whether it's the colonial charm of the Historic District, the maritime allure of Eastport, the elegance of Murray Hill, the small-town appeal of West Annapolis, or the waterfront luxury of Bay Ridge, each neighborhood offers retirees a unique and fulfilling retirement experience. With its rich cultural heritage, scenic landscapes, and welcoming community, Annapolis invites retirees to embrace a rewarding and enjoyable retirement journey. Explore these top places to retire in Annapolis and discover the perfect setting for your golden years.


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