Discover Eastport: Annapolis’s Nautical Gem
Welcome to Eastport—a vibrant waterfront community that perfectly blends laid-back coastal charm with the energy of downtown Annapolis just a footbridge away. Known for its friendly spirit, local eateries, and unbeatable access to the Chesapeake Bay, Eastport is a place where every day feels like a getaway.

The Eastport Lifestyle
Eastport isn’t just a neighborhood—it’s a way of life. Residents wake up to the sound of boat horns and end their evenings with sunsets over the marina. Here, you’ll find neighbors gathering for Wednesday Night Races, sipping coffee at Oscar’s, or enjoying the legendary crab cakes at local favorites like Boatyard Bar & Grill. Walkable streets, dog-friendly parks, and a calendar full of community events make Eastport one of the most sought-after addresses in Annapolis.

Homes for Sale in Eastport
Eastport’s real estate offers a diverse mix, from charming cottages and classic bungalows to luxury waterfront homes with private docks. Whether you dream of living steps from the water, want a turnkey condo, or are searching for your next investment property, there’s something for everyone in Eastport.

As local experts, The Jen Holden Group has an inside track on both on-market and off-market opportunities. We’ve helped buyers secure homes even when inventory is tight, and our strategic approach gets sellers top results.

Why Choose The Jen Holden Group
Local insight: We live and work in the greater Annapolis area and understand what makes Eastport truly special.
Expert Negotiation: Our proven track record includes securing homes for buyers in competitive situations and negotiating favorable terms for sellers.
Community Connections: From yacht clubs to neighborhood socials, we’re connected and committed to helping you plug into the Eastport lifestyle.
 
Ready to experience life in Eastport?
Let’s talk about your real estate goals. Whether you’re buying, selling, or just curious about this unique waterfront community, The Jen Holden Group is here as your trusted resource.