Cherry Point, Annapolis, MD

Cherry Point Neighborhood Overview

Overview

Cherry Point is a serene, waterfront-centric neighborhood located on a peninsula in Annapolis, Maryland, just south of the city's historic downtown. It is bounded by Glebe Bay to the north, Back Creek to the east, and the Chesapeake Bay to the south, offering residents expansive water views and a distinct maritime atmosphere. The area's history is rooted in its connection to the water, originally developed as a summer cottage community in the early-to-mid 20th century, with many homes built to take advantage of the breezes and recreational opportunities of the Chesapeake.

Today, Cherry Point retains its quiet, residential character, feeling removed from the bustle of downtown while being only a short drive or bike ride away. The neighborhood is defined by winding, tree-lined streets, modest-to-luxury homes, and numerous community piers and beaches. Its location provides a perfect blend of secluded waterfront living with convenient access to the amenities, culture, and employment centers of Annapolis and the broader Washington-Baltimore corridor.

Housing & Real Estate

The housing stock in Cherry Point is predominantly single-family homes, ranging from original mid-century ramblers and cottages to substantial, modern custom-built residences designed to maximize water views. Lot sizes are generally generous, with many properties featuring deep, wooded yards that lead to private or community waterfront access. Architectural styles are varied, but the most sought-after homes are those with direct deep-water slips or sandy beaches.

Real estate prices in Cherry Point are among the highest in the Annapolis area, reflecting the premium for waterfront and water-access property. Homes typically range from the high $800,000s for a smaller home with community water access to several million dollars for a large, updated estate with a private pier. The market is overwhelmingly owner-occupied, with very few rental properties available. Recent trends show strong demand and rising values, as buyers seek homes that offer outdoor living space and private recreational amenities.

Schools & Education

Cherry Point is served by the Anne Arundel County Public School system. Students typically attend Hillsmere Elementary School, which is located just outside the neighborhood to the north. From there, students progress to Annapolis Middle School and then Annapolis High School. The Annapolis cluster schools have diverse programs and have seen significant investment, with Annapolis High School offering the International Baccalaureate (IB) Diploma Programme alongside a variety of Advanced Placement (AP) courses and career academies.

There are also several well-regarded private and parochial school options in the greater Annapolis area, including St. Mary's Elementary and High School, Key School, and Indian Creek School. For higher education, the neighborhood is within a reasonable commute to the United States Naval Academy, St. John's College, and Anne Arundel Community College, providing a range of collegiate and continuing education opportunities.

Parks & Recreation

The primary recreational focus in Cherry Point is the water. Residents enjoy boating, kayaking, paddleboarding, and fishing directly from community beaches or their own piers. The neighborhood maintains several common areas, including small beaches and piers on Glebe Bay and the Chesapeake Bay, which serve as social hubs and launch points. The Cherry Point Property Owners Association often organizes community events like picnics and beach clean-ups, fostering a strong neighborhood connection.

While the neighborhood itself is quiet, it is adjacent to larger green spaces. Quiet Waters Park, a 340-acre county park, is just a few minutes away and offers hiking and biking trails, picnic pavilions, a dog beach, kayak rentals, and an ice rink in the winter. For sailors and boaters, the proximity to Back Creek provides easy access to marinas, yacht clubs, and the open waters of the Chesapeake Bay, making it a premier location for maritime enthusiasts.

Local Dining & Shopping

Cherry Point itself is strictly residential, with no commercial establishments within its boundaries. However, its location provides quick and easy access to a variety of dining and shopping options. The nearby Annapolis Towne Centre at Parole, just a 10-minute drive north, offers a large selection of national retailers, grocery stores like Whole Foods and Trader Joe's, and a diverse array of restaurants and a cinema.

For a more local flavor, residents frequently head to the historic downtown Annapolis district or the Eastport neighborhood, just across the Spa Creek Bridge. These areas are renowned for their vibrant dining scenes, featuring everything from fresh seafood and Chesapeake Bay cuisine to international fare and casual pubs. Local marinas and the Eastport shopping corridor provide boutique shopping, marine supply stores, and essential services, ensuring residents have everything they need within a short drive.

Who Lives Here

Cherry Point attracts a demographic that values privacy, natural beauty, and an active outdoor lifestyle. The community is a mix of established families, empty-nesters, and professionals who appreciate the peaceful setting. Many residents have a strong affinity for the water, including sailors, boaters, fishermen, and those simply seeking the tranquility of waterfront living. The neighborhood fosters a low-key, friendly atmosphere where neighbors often know each other through community association activities and shared use of the waterfront amenities.

The overall vibe is one of understated affluence and community-mindedness. Residents are drawn to the unique combination of a secluded, almost rural feel with the convenience of urban amenities nearby. It is a neighborhood for those who want to come home to a retreat-like environment, where the sound of lapping water and views of stunning sunsets over the Chesapeake are part of daily life, all while being connected to

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