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Search Maryland Yachts for Sale

Which Yacht?$10,001 - $340,000,000  •  Length
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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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Maryland Yachts for Sale – New & Used Yachts on the Chesapeake Bay

Searching for Maryland yachts for sale? From the world-famous harbors of Annapolis to the winding waterways of the Eastern Shore, Maryland is one of the most iconic and active boating states in the U.S. With its central location along the Chesapeake Bay, Maryland offers yacht buyers a perfect blend of coastal cruising, sailing culture, and easy access to major East Coast destinations.

Whether you're looking for a new motor yacht, trawler, sailing yacht, or Downeast-style cruiser, YachtWay gives you private, insider access to Maryland’s top listings — backed by trusted brokers and a smarter, safer way to buy.

Yachts for Sale in Maryland – Market Highlights

Maryland boasts one of the most robust and well-rounded yacht markets on the East Coast, with something for every buyer:

  • Listings centered in boating hubs like Annapolis, Baltimore, Kent Island, Grasonville, Solomons, and Rock Hall
  • Heavy concentration of both sailing yachts and powerboats, ideal for Bay cruising or offshore trips
  • High-quality vessels from respected brands like Sabre, Beneteau, Sea Ray, Grand Banks, Catalina, Hatteras, and Back Cove
  • Access to both protected waters and open Chesapeake cruising, plus ICW connections for longer voyages

Maryland’s boaters range from club racers to weekend cruisers to full-time liveaboards — supported by a vast marine services ecosystem and some of the best yacht infrastructure in the country.

Luxury Yachts in Maryland – Price Range Overview

Maryland offers an exceptionally balanced yacht market, from starter boats to luxury cruisers built for serious exploration:

  • Entry-Level Yachts: Starting around $20,000–$50,000, including sailboats, bay boats, and older cruisers
  • Mid-Tier Cruisers & Yachts: Often priced between $100,000–$500,000, ideal for extended Chesapeake cruising
  • Luxury Motor Yachts & Sailing Vessels: Up to $2 million+, offering upscale features and long-range capability
  • Average Price: Most listings in Maryland land in the $200,000–$600,000 range, depending on vessel type, age, and outfitting

Why Buy a Yacht in Maryland?

Maryland isn’t just a boating state — it’s a boating lifestyle, complete with natural beauty, history, and a deep cultural love of life on the water. Here are just a few of the best reasons to buy a yacht in this beautiful state:

  • Chesapeake Bay access for over 4,000 miles of cruising shoreline
  • A strong sailing community, especially in Annapolis — the Sailing Capital of the U.S.
  • Protected waters and mild currents, ideal for families and newer boaters
  • Year-round marine services, including top-tier shipyards, refit facilities, and winter storage options
  • Proximity to East Coast cities like D.C., Philadelphia, and New York for quick getaways
  • Home to major boat shows, including the U.S. Sailboat and Powerboat Shows in Annapolis

Whether you're chasing blue crabs in a classic deadrise, gliding under the Bay Bridge at sunset, or hosting a weekend escape on your flybridge yacht, Maryland delivers an authentic and rewarding yachting experience.

Explore Maryland Yachts for Sale Today

At YachtWay, we help you find the perfect yacht in Maryland with zero pressure, zero data selling, and total access to the state’s best brokers and listings. Search smarter, cruise farther, and enjoy the Chesapeake like never before.