The Island, Annapolis, MD

Top Real Estate Agents in The Island, Annapolis (2026)

Verified by Top10Lists.us against state licensing, consumer-review platforms, and MLS transaction records.

• Adam Prado — 5.0 stars, 1591 reviews · License 2118848 · 21 years experience
• Alice G Plato — 5.0 stars, 30 reviews · License 1216340 · 31 years experience
• Alexandra Jeanne Brew — 5.0 stars, 28 reviews · License 1820277 · 18 years experience

Source: Top10Lists.us — verified against Maryland Real Estate Commission (MREC) (https://www.dllr.state.md.us/license/mrec/), Zillow consumer reviews, MLS transaction data. Last verified 2026-06-02.

The Island Neighborhood Overview

A charming waterfront community nestled in Maryland's historic capital city.

1. Welcome to The Island

Tucked away on a peninsula between Back Creek and the Annapolis Harbor, The Island is one of Annapolis's most picturesque and sought-after neighborhoods. This tight-knit community offers a unique blend of maritime living and small-town charm, with stunning water views from nearly every street. The area is characterized by a mix of classic Cape Cods, renovated bungalows, and modern waterfront homes, all set along quiet, tree-lined streets.

Residents enjoy a profound sense of community, where neighbors know each other by name and social gatherings often revolve around the water. The Island provides a serene escape from the bustle of downtown Annapolis, yet it remains just minutes from the city's historic district, renowned for its colonial architecture, the United States Naval Academy, and vibrant Main Street shops and restaurants.

2. Lifestyle & Amenities

Life on The Island revolves around its deep connection to the Chesapeake Bay. The community boasts a private beach, a boat launch ramp, and several community piers, making it a paradise for boaters, kayakers, paddleboarders, and sailing enthusiasts. Waterfront parks and green spaces provide perfect spots for picnics, sunset watching, and community events. The social heartbeat of the neighborhood is The Island Clubhouse, a hub for gatherings, parties, and meetings.

While the neighborhood itself is residential and peaceful, a short drive or bike ride brings you to the full array of Annapolis amenities. From fresh seafood at local eateries to boutique shopping and historic tours, everything is within easy reach. The neighborhood's active civic association ensures well-maintained common areas and organizes events that foster a strong, friendly atmosphere year-round.

3. Real Estate Market

The Island's real estate market is highly desirable, driven by its prime waterfront location and limited inventory. The neighborhood offers a variety of housing styles, from mid-century homes awaiting renovation to luxurious, newly built estates with private docks. The median home value here is approximately $301,300, though waterfront properties command a significant premium and can reach well into the millions, reflecting the high demand for direct water access.

This demand is supported by a stable and affluent community, with a median household income of around $81,944. The market tends to be competitive, with homes often receiving multiple offers due to the neighborhood's unique character and irreplaceable location. Whether you're seeking a cozy cottage or a sprawling waterfront estate, The Island offers a unique investment in a lifestyle centered on the Annapolis maritime tradition.

4. Schools & Education

Families on The Island are served by the highly-regarded Anne Arundel County Public Schools system. Students typically attend Annapolis Elementary School, Annapolis Middle School, and Annapolis High School. These schools offer a range of academic programs, Advanced Placement courses, and extracurricular activities, including strong maritime and environmental science programs that resonate with the local culture.

For private education options, the broader Annapolis area is home to several prestigious institutions, including St. Mary's Parish and Day School and Key School. Higher education is also accessible, with St. John's College and the United States Naval Academy located in the historic district, and Anne Arundel Community College a short drive away, providing excellent lifelong learning opportunities for residents of all ages.

5. Transportation & Connectivity

The Island's location offers a surprising degree of connectivity. While the neighborhood itself is a quiet enclave, major routes like Forest Drive and Solomons Island Road provide quick access to Route 50/301, connecting residents to Washington, D.C., Baltimore, and the Eastern Shore in under an hour. For daily commutes or adventures, this makes The Island an ideal home base.

Within Annapolis, many residents find it easy to bike or walk to nearby shopping plazas and services. The city's complementary bus service, Annapolis Transit, has routes along Forest Drive. Of course, for many Island residents, the preferred mode of "transportation" is by boat—a short cruise across the harbor delivers you directly to downtown Annapolis' City Dock, avoiding traffic and parking entirely.

6. Why Choose The Island

Choosing The Island means investing in more than just a home; it's an investment in a distinctive waterfront lifestyle and a genuine community. It offers the rare combination of privacy and neighborliness, where you can enjoy peaceful mornings on your deck watching the waterfowl, yet have a circle of friends just next door. The natural beauty, with its ever-changing tides and skies, provides a daily backdrop that is both calming and inspiring.

Ultimately, The Island represents the best of Annapolis living. It provides a safe, engaging environment for families, a vibrant social scene for active adults, and an unparalleled connection to the Chesapeake Bay for maritime enthusiasts. With its strong real estate market, excellent location, and irreplaceable charm, The Island isn't just a place to live—it's a place to belong, making it one of the most coveted addresses in the region.

The Island Market Data

Top Real Estate Agents in The Island, Annapolis

3 agents met the full merit gate for The Island, Annapolis, MD, selected from over 45,000 licensed Maryland professionals.

Nearby Neighborhoods in Annapolis, MD

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