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Annapolis Yachts for Sale – New & Used Yachts in the Sailing Capital of America
Searching for Annapolis yachts for sale? Welcome to the heart of American yachting. Nestled on the shores of the Chesapeake Bay, Annapolis, Maryland is a legendary boating destination — home to world-famous sailing regattas, premier yacht shows, and a passionate community of boat owners.
Whether you're in the market for a bluewater sailboat, weekend cruiser, sport yacht, or trawler, YachtWay offers exclusive access to Annapolis’s finest new and used yacht listings, along with expert brokers who understand the local waters and the sophistication of Chesapeake boating.
Yachts for Sale in Annapolis – Market Highlights
Annapolis boasts one of the most balanced and vibrant yacht markets in the country, with strong offerings for both power and sail:
- Large inventory of sailing yachts, from performance racers to luxury cruisers
- Expansive motor yacht selection, including trawlers, express cruisers, and flybridge yachts
- Listings concentrated around Annapolis Harbor, Eastport, Spa Creek, and the Severn River
- Top brands include Beneteau, Jeanneau, Sabre, Catalina, Grand Banks, Hinckley, Pursuit, and Sea Ray
- Many yachts are professionally maintained, due to the area’s expert service yards and strong boating infrastructure
Luxury Yachts in Annapolis – Price Range Overview
Annapolis offers a versatile market with a full spectrum of price points, ideal for both seasoned yachtsmen and first-time buyers:
- Entry-Level Yachts: Starting around $20,000–$50,000, great for daysailing or river cruising
- Performance Sailboats & Cruising Yachts: Commonly priced from $100,000–$400,000
- Luxury Motor Yachts & Liveaboard Options: Ranging from $500,000–$2 million+, with high-end finishes and long-range capability
- Average Price: Many Annapolis yacht listings fall in the $200,000–$600,000 range, offering premium value for quality vessels
Why Buy a Yacht in Annapolis?
There’s a reason Annapolis is known as the Sailing Capital of America — and it goes far beyond regattas and racing:
- Prime Chesapeake Bay access, with thousands of miles of protected coastline to explore
- A thriving boating culture, with yacht clubs, marina events, and boat shows year-round
- Proximity to Washington D.C., Baltimore, and the Eastern Shore
- World-class service yards and refit specialists, with a deep bench of marine expertise
- A sailor’s town at heart, but with full support for serious powerboat ownership too
Whether you're headed to St. Michaels, the Eastern Shore, or planning a longer run south down the ICW, Annapolis is the perfect home port.
Explore Annapolis Yachts for Sale Today
At YachtWay, we connect you with the most trusted brokers and finest yacht listings in Annapolis, from locally loved sailboats to fully outfitted cruising motor yachts. With full data privacy, smart search tools, and direct access to professional insights — we make the yacht-buying process smarter and smoother.