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2016 Monte Carlo Yachts MCY 65
from $7,128/Mo
2025 Seawind Catamarans 1600 Passagemaker
2025 Seawind Catamarans 1170
2025 Seawind Catamarans 1370
2024 Nuova Jolly Prince 38 CC
from $2,217/Mo
2025 Seawind Catamarans 1160XL
2006 Carver Voyager
from $2,244/Mo
2023 Dragonfly Trimarans 28
from $1,367/Mo
1996 Grand Banks Yachts Eastbay 40
from $1,188/Mo
1996 Bayliner Avanti 3488
2002 Silverton 330 Sport Bridge
2017 Sumerset Houseboat
from $3,960/Mo
2003 Mainship 34 Pilot
from $686/Mo
1996 Hatteras 50' Sport Deck
from $1,452/Mo
2025 Technohull Alpha 40
from $3,685/Mo
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.