Chesapeake Harbour Neighborhood Guide.
Chesapeake Harbour offers gated waterfront living, direct Chesapeake Bay access, and resort-style amenities just minutes from downtown Annapolis, making it one of the area’s most distinctive residential communities.
If you’re exploring the Chesapeake Harbour community in Annapolis, you’re likely looking for waterfront living without the upkeep that often comes with it. Set directly on the Chesapeake Bay just south of the mouth of the Severn River, this gated community pairs a private marina and a sandy beach with the low-maintenance ease of condominium and townhome ownership. Buyers are often drawn to Chesapeake Harbour because it delivers the feeling of a private waterfront resort while remaining close to everything Annapolis has to offer. Whether you’re relocating to the area or looking for your next move within Annapolis, understanding what makes Chesapeake Harbour unique can help you decide whether it’s the right fit for your lifestyle and goals.
Why Chesapeake Harbour Stands Out
One of the biggest reasons buyers are drawn to Chesapeake Harbour is the combination of a true waterfront setting and a gated, amenity-rich community.
Residents appreciate:
• A location directly on the Chesapeake Bay
• A gated entrance with 24/7 security
• Resort-style amenities within walking distance of home
• A low-maintenance alternative to traditional waterfront ownership
Chesapeake Harbour feels private and self-contained without giving up its connection to the wider Annapolis area.
Waterfront Lifestyle & Community Amenities
Living in Chesapeake Harbour means the water is part of your everyday routine rather than a weekend destination.
Depending on the amenities available through the community and the marina, residents may enjoy:
• A private sandy beach with Bay views
• Two swimming pools
• Tennis courts
• Two fishing piers
• Walking and biking paths throughout the community
The on-site Chesapeake Harbour Marina is a certified Maryland Clean Marina and can accommodate larger vessels, which is a meaningful draw for boating households. Beacon Waterfront Galley & Bar sits at the marina as well, giving the community a waterfront gathering spot of its own.
Location & Convenience
Chesapeake Harbour offers the advantage of feeling tucked away while still sitting close to the center of Annapolis life.
From the community, you’re:
• Roughly a nautical mile south of the U.S. Naval Academy by water
• A short trip from downtown Annapolis and Eastport
• Close to shopping, dining, and everyday essentials
• Conveniently positioned for commuting toward Baltimore or Washington, D.C.
Water taxi and shuttle service in the area also make it easy to reach Eastport and historic Annapolis without moving your car.
Real Estate in Chesapeake Harbour
Chesapeake Harbour is made up of a series of villages built in the mid-to-late 1980s, with roughly 452 homes in total.
You’ll typically find:
• Townhomes, duplexes, and garden-style and loft condominiums
• Floor plans designed around water and marina views
• A mix of original and thoughtfully updated interiors
• Homes positioned to take advantage of the Bay setting
Because the community is limited in size and doesn’t expand, inventory can be tight, especially for units with the best water views or marina proximity. Fee structures, slip availability, and what conveys with a specific home vary by village and by unit, so it’s worth reviewing the details of any particular property carefully.
Outdoor Recreation & Coastal Living
For many residents, life in Chesapeake Harbour revolves around the water.
Popular activities include:
• Boating and sailing on the Chesapeake Bay
• Fishing from the community piers
• Swimming and time at the beach
• Walking and biking the community paths
The setting makes it easy to embrace the Chesapeake Bay lifestyle while keeping the conveniences of a managed, gated community.
Explore More About Annapolis
If you’d like to learn more about the area, local events, and waterfront resources, visit the official Annapolis website here.
The Recap:
Chesapeake Harbour offers a rare combination in Annapolis: a gated Bay-front setting, a private marina and beach, and a home you can lock and leave. For buyers who want the Chesapeake lifestyle without the maintenance of a large waterfront property, it remains one of the area’s most compelling communities.
And if you already own in Chesapeake Harbour, it’s worth knowing what your home is worth in today’s market. Values here move differently than they do in the rest of Annapolis, and buyers seeking this specific lifestyle are often willing to pay for the right unit.
View Available Homes
If you’re curious about homes currently available in waterfront neighborhoods, view available homes and start your search today.
Jen Schaub, Realtor
eXp Realty | Jen Schaub Gets You Moving
Connect with Jen Schaub, Annapolis Realtor, to:
- Get a personalized home value
- Build a custom selling strategy
- Prepare your home for maximum impact
(720) 244-5945 | jschaubrealty@gmail.com