Annapolis Neck

Hillsmere Shores, Annapolis Neck Neighborhood

Hillsmere Shores is a peaceful neighborhood offering a serene setting with low noise levels throughout the area. The community features a predominance of single detached homes, many with three or four bedrooms, providing spacious living options. Residents benefit from convenient parking and well-maintained streets, supporting easy vehicular movement. This area provides excellent opportunities for biking, with suitable infrastructure available. Several public green spaces and nearby parks contribute to the neighborhood’s inviting outdoor environment, allowing for plenty of recreational possibilities close to residences. The calm atmosphere combined with access to local dining options creates a comfortable and appealing living environment.

Hillsmere Shores offers a calm atmosphere and will appeal to those who enjoy spending time in green spaces. This area is very quiet, as there tend to be low levels of noise from traffic. Finally, a lot of locations within the neighborhood have fairly good access to parks, including Quiet Waters Park, since reaching one from most homes for sale is very easy and there are a few public green spaces nearby for residents to enjoy.

Highlights of Hillsmere Shores

Parks, schools, dining, and what makes this neighborhood special

🏞️ Hillsmere Beach & Marina

The private community beach and marina at the end of Hillsmere Drive offer residents exclusive access to the Chesapeake Bay with sandy shores, picnic areas, and boat slips—perfect for swimming, kayaking, and enjoying waterfront sunsets.

🌳 Quiet Waters Park

Located right at the edge of Hillsmere Shores on Quiet Waters Park Road, this beloved county park features miles of biking and walking trails, scenic water views, dog parks, playgrounds, an ice rink in winter, and outdoor summer concerts.

🏫 Hillsmere Elementary School

Situated conveniently within the neighborhood on Hillsmere Drive, this highly-rated public elementary school is walkable for many families and is a hub for community events and activities.

🛥️ Key School

This renowned independent school on Hillsmere Drive draws families from all over Annapolis, offering outstanding academics from pre-K through grade 12, and a vibrant campus life right in the heart of Hillsmere Shores.

🍦 Shady Side Ice Cream Stand

Just outside the Hillsmere Shores entrance on Forest Drive, this beloved family-run ice cream spot has been serving up cones, shakes, and sundaes since 1979—a favorite treat for locals on warm evenings and after park visits.

Hillsmere Shores

This October in Hillsmere Shores

Things to do, events, and what's happening this month

October 8–11, 2026

Annapolis Powerboat Show

Downtown Annapolis Waterfront

A convenient waterfront outing from Hillsmere Shores, this major Annapolis tradition lets visitors tour powerboats, browse marine gear, and enjoy the harbor atmosphere. It is especially appealing to local families and boating enthusiasts who want a seasonal activity without traveling far from Annapolis Neck.

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October 15–18, 2026

Annapolis Sailboat Show

Downtown Annapolis Waterfront

Residents of Hillsmere Shores can easily make this a half-day or full-day waterfront excursion. The show features sailboats, nautical equipment, exhibitors, and harbor scenery, offering a distinctly local Annapolis experience for families, sailors, and anyone who enjoys spending time around the Chesapeake.

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October 21, 2026

STEAM Wednesday: Indigenous Ingenuity

Eastport-Annapolis Neck Community Library • 3:30 PM

This hands-on library program is particularly convenient for Annapolis Neck residents and offers children an engaging after-school activity close to home. Participants explore Indigenous innovation and design a water-based farm inspired by Aztec chinampas, making it a creative, educational choice for families.

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October 25, 2026

Autumn Jazz in the Garden

William Paca House and Garden • 3:00 PM–5:00 PM

This relaxed afternoon concert pairs live music by the Annapolis Jazz Collective with the historic Paca Garden setting. It is a nearby, low-key cultural outing for Hillsmere Shores adults, couples, and families who want to enjoy fall weather, gardens, and local music in downtown Annapolis.

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October 31, 2026

Very Superstitious! Paca House and Garden Tour

William Paca House and Garden • 11:00 AM–12:00 PM or 4:00 PM–5:00 PM

A Halloween-day history experience within easy reach of Hillsmere Shores, this guided tour explores colonial beliefs, folklore, protective rituals, and superstitions. It offers a seasonal alternative to standard Halloween activities and can fit conveniently into a day of downtown Annapolis sightseeing.

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From the Neighborhood

Stories, updates, and things to know in Hillsmere Shores

Know Your Neighborhood

Local characteristics and demographics for Hillsmere Shores

Neighborhood Characteristics

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Demographics

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