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Search Annapolis Yachts for Sale

Which Yacht?$10,001 - $340,000,000  •  Length
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Annapolis, Maryland, US

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Kufner Yachts 54 2024
$729,000
New
Annapolis, Maryland
Sail Drive
54.5 ft
+1
Connection Kufner Yachts USA
Kufner Yachts USA
Dragonfly Trimarans 28 2023
$259,000
Pre-Owned
Annapolis, Maryland
Outboard
29.53 ft
+1
Connection Dragonfly Trimarans Northeast
Dragonfly Trimarans Northeast
Sea Ray 310 Sundancer 2000
$35,950
Pre-Owned
Fort Washington, Maryland
Inboard
31.5 ft
Connection Yacht Sales International
Yacht Sales International
Bayliner Avanti 3488 1996
$18,500
Pre-Owned
Tracys Landing, Maryland
Inboard
34.5 ft
Connection Yacht Sales International
Yacht Sales International
Silverton 330 Sport Bridge 2002
$84,000
Pre-Owned
Pasadena, Maryland
Inboard
35.33 ft
Connection Yacht Sales International
Yacht Sales International
Sumerset Houseboat 2017
$750,000
Pre-Owned
Chestertown, Maryland
Sterndrive
70 ft
Connection Yacht Sales International
Yacht Sales International
Mainship 34 Pilot 2003
$130,000
Pre-Owned
Annapolis, Maryland
Inboard
34.17 ft
Connection Yacht Sales International
Yacht Sales International
Kufner Yachts 50 2024
Contact for Pricing
New
Annapolis, Maryland
Sail Drive
49 ft
+1
Connection Kufner Yachts USA
Kufner Yachts USA
Kufner Yachts USA 45 2025
Contact for Pricing
New
Annapolis, Maryland
Sail Drive
46 ft
+1
Connection Kufner Yachts USA
Kufner Yachts USA
Hatteras 50' Sport Deck 1996
$295,000
Pre-Owned
Annapolis, Maryland
Inboard
50.83 ft
Connection Yacht Sales International
Yacht Sales International
Technohull Alpha 40 2025
$698,000
New
Annapolis, Maryland
Outboard
39.7 ft
Connection KMB Yachting, LLC.
KMB Yachting, LLC.
SeaTek 36 Express 2017
$350,000
Pre-Owned
Annapolis, Maryland
Inboard
36 ft
Connection Yacht Sales International
Yacht Sales International
Greenline Yachts 45 Fly Hybrid 2023
$1,250,000
Pre-Owned
Annapolis, Maryland
Pod Drive
51.1 ft
Connection Yacht Sales International
Yacht Sales International
Catalina Yachts 400 1995
$110,000
Pre-Owned
Tracys Landing, Maryland
Inboard
40.52 ft
+1
Connection Yacht Sales International
Yacht Sales International
Greenline Yachts 45 Fly Hybrid 2024
$1,591,150
New
Annapolis, Maryland
Straight Shaft
51.1 ft
Connection Yacht Sales International
Yacht Sales International
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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.