Annesley By The Bay, Annapolis, MD

Annesley By The Bay Neighborhood Overview

Overview

Annesley By The Bay is a prestigious and picturesque waterfront community located on the Annapolis Neck peninsula, just south of the historic downtown district. This serene neighborhood is characterized by its mature tree canopy, gently winding streets, and, most notably, its stunning views of the Chesapeake Bay and the Severn River. The community’s name evokes its elegant, New England-inspired architectural aesthetic and its prime location, offering a tranquil residential retreat that remains conveniently close to the heart of Maryland’s capital city.

Developed primarily in the late 1980s and early 1990s, Annesley By The Bay was designed with a focus on preserving the natural beauty of its waterfront setting. The neighborhood features a mix of custom-built homes and thoughtfully designed subdivisions, all adhering to covenants that maintain its cohesive, upscale character. Its location provides residents with a unique blend of privacy and accessibility, situated just off Forest Drive and only a short drive or pleasant bike ride from the bustling shops, restaurants, and maritime activity of downtown Annapolis and Eastport.

Housing & Real Estate

The housing stock in Annesley By The Bay consists predominantly of large, single-family homes, many of which are custom-built colonials, contemporaries, and Cape Cods on generous, landscaped lots. A defining feature of the neighborhood is the significant number of homes with direct waterfront access, private piers, and deep-water slips, catering to a boating-centric lifestyle. Additionally, many homes not directly on the water boast beautiful waterviews from their elevated positions or through community-owned green spaces leading to the shoreline.

Real estate prices here are among the highest in the Annapolis area, reflecting the premium for waterfront property and the neighborhood’s exclusivity. Homes typically range from the high $1 millions to well over $3 million, with price heavily influenced by lot size, water frontage, and view quality. The market is almost exclusively owner-occupied, with very few rental properties available. Recent trends show sustained demand, with homes often selling quickly due to the limited inventory of such desirable waterfront living so close to downtown.

Schools & Education

Families in Annesley By The Bay are served by the Anne Arundel County Public School system. Students typically attend Hillsmere Elementary School, which is known for its strong academic programs and active parent community, followed by Annapolis Middle School, and finally Annapolis High School. The neighborhood’s proximity to downtown also places it within easy reach of several highly-regarded private and parochial school options, including St. Mary’s Elementary and High School and Key School.

For higher education, the United States Naval Academy is just minutes away, and St. John’s College is located in the historic district. Anne Arundel Community College’s main campus in Arnold is also a short drive from the neighborhood. The combination of solid public schools and prestigious nearby private institutions makes the area particularly attractive to families prioritizing educational opportunities.

Parks & Recreation

Residential life in Annesley By The Bay is deeply connected to the water and outdoor recreation. The neighborhood itself features several community-owned parcels of land, including scenic shoreline paths and small beaches perfect for kayak launches, picnics, or simply enjoying sunset views over the Bay. The private Annesley Community Beach and pier is a central social and recreational hub for residents, offering swimming, fishing, and boating right at their doorstep.

Nearby, the expansive Quiet Waters Park provides over 340 acres of recreational space, featuring miles of paved trails for walking and biking, picnic pavilions, a dog beach, and kayak rentals on Harness Creek. For sailors and powerboaters, easy access to the Chesapeake Bay is the ultimate amenity. The close-knit community also organizes social events that often revolve around its waterfront assets, fostering a strong sense of neighborhood camaraderie.

Local Dining & Shopping

While Annesley By The Bay itself is strictly residential, its location places it within a few minutes of exceptional dining and shopping corridors. The nearby Forest Drive/Eastport area offers a variety of local favorites, from casual seafood pubs like Davis’ Pub to upscale waterfront dining at The Point Crab House & Grill or Carrol’s Creek Cafe. The historic downtown Annapolis district, with its countless restaurants, cafes, and ice cream shops along City Dock and Main Street, is less than a ten-minute drive away.

For everyday needs, residents frequent the Annapolis Towne Centre at Parole, which features a Whole Foods Market, Target, and a diverse array of national retailers and restaurants. The more boutique shopping experience of West Street and Maryland Avenue is also easily accessible. The nearby Eastport Shopping Center provides convenient staples, including a Graul’s Market, a beloved local grocery known for its quality and service.

Who Lives Here

Annesley By The Bay attracts a discerning demographic of professionals, executives, military officers (often from the nearby Naval Academy and NSA), and empty-nesters who appreciate luxury, privacy, and an active, maritime-oriented lifestyle. The community tends to be well-established, with many residents having deep ties to the Annapolis area or a career connected to the water, government, or defense sectors. It is a family-friendly neighborhood, but also popular with those seeking a peaceful, upscale retreat.

The community vibe is one of quiet sophistication and neighborly respect, where residents share a common appreciation for the natural beauty that surrounds them. Social interaction often centers on the water, with impromptu gatherings at the community beach or organized events by the active

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