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    Within 100 Miles Of
    Chester, Maryland

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Yacht boats for sale in Chester Maryland

There are 6 new and used Yacht boats for sale in Chester, Maryland. Explore Yacht brands like Steiger Craft, Other, Regal, and Sea Ray on BoatCrazy. View a wide selection of Yacht boats from $29,000 to $159,900.
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    Within 100 Miles Of
    Chester, Maryland
6 boats found within 100 miles from Chester, Maryland
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  • 2004 Regal Commodore 3860

    2004 Regal Commodore 3860

    $84,900
    Chester, MD
    • Chester, MD
    • Yacht
    • 0'
    • 2004 / Used
    • $84,900

    2004 Reagl Commodore 3860 Introducing the Regal Commodore 3860, a stunning 40.08-foot cruiser built in 2004, designed for those who appreciate both performance and comfort. This... View Details

    View 21 Photos and Details Contact Seller
    $84,900
    VIEW DETAILS
  • 2027 Steiger Craft 255 Annapolis

    2027 Steiger Craft 255 Annapolis

    Call for price
    Chester, MD
    • Chester, MD
    • Yacht
    • 0'
    • 2027 / New
    • Call for price

    Introducing the stunning 2027 Steiger Craft 255 Annapolis, a remarkable pilothouse boat that embodies both elegance and performance. With an overall length of 25.5 feet, this new... View Details

    View 22 Photos and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2027 Steiger Craft 255 Miami

    2027 Steiger Craft 255 Miami

    Call for price
    Chester, MD
    • Chester, MD
    • Yacht
    • 0'
    • 2027 / New
    • Call for price

    2027 Steiger Craft 255 Miami Introducing the stunning 2027 Steiger Craft 255 Miami, a new Cuddy Cabin boat that promises an exhilarating experience on the water. With an overall... View Details

    View 22 Photos and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2027 Steiger Craft 28 Annapolis

    2027 Steiger Craft 28 Annapolis

    Call for price
    Chester, MD
    • Chester, MD
    • Yacht
    • 0'
    • 2027 / New
    • Call for price

    2027 Steiger Craft 28 Annapolis Introducing the 2027 Steiger Craft 28 Annapolis, a remarkable pilothouse boat that combines performance and comfort. With an overall length of 28... View Details

    View 27 Photos and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2005 Other Matthews Brothers Blackwater 29

    2005 Other Matthews Brothers Blackwater 29

    $159,900
    Chester, MD
    • Chester, MD
    • Yacht
    • 0'
    • 2005 / Used
    • $159,900

    Blackwater 29Proudly custom built in Maryland, the Blackwater 29 combines local craftsmanship with a design suited for the Chesapeake Bay lifestyle. This boat has been further enh... View Details

    View 23 Photos and Details Contact Seller
    $159,900
    VIEW DETAILS
  • Price Drop 1996 Sea Ray 370 Sedan Bridge

    1996 Sea Ray 370 Sedan Bridge

    $29,000
    Deale, MD
    • Deale, MD
    • Yacht
    • 37'
    • 1996 / Used
    • $29,000

    Stock #503782 Reason for selling is "Bought another boat". This Sea Ray has been on the market for more than 30 days (Aug 26th). If you are thinking of making an offer, submit it... View Details

    View 10 Photos and Details Contact Seller
    $29,000
    VIEW DETAILS
Showing 1 to 6 of 6 boats found.

Yacht Boats on Boatcrazy

Yachts represent the pinnacle of luxury, performance, and comfort on the water. Ranging from sleek sport cruisers to opulent motor yachts and long-range expedition vessels, yachts are designed for extended cruising, entertaining, and relaxation—often with all the amenities of a high-end home. They typically feature multiple staterooms, full galleys, spacious salons, and flybridges or enclosed helm stations for all-weather navigation.

Whether privately owned or crewed, yachts can serve as weekend retreats, liveaboard homes, or global explorers. From harbor-hopping to crossing oceans, these vessels offer unmatched elegance, power, and prestige.

Explore our inventory of new and used yachts from leading manufacturers. Whether you're seeking a stylish express cruiser or a fully equipped luxury yacht, you'll find the perfect vessel for your lifestyle and ambitions.

Yacht Boats manufacturers on Boatcrazy

When looking to buy a premium Yacht, consider these leading Yacht Manufacturers

Beneteau, Azimut, Princess Yachts.

Yacht Boats For Sale by State

Yacht Boats Frequently Asked Questions

What exactly qualifies as a yacht?

A yacht is a pleasure craft—either sail or motor—typically over ~33 ft with cabins for overnight cruising, built for recreation, sport, or luxury cruising.

Major yacht categories include Sailing Yachts, Motor Yachts, Explorer or Expedition Yachts, Sports Yachts, and Luxury Flybridge models—each with unique capabilities and lifestyle appeal.

Yachts generally start around 33 ft and go up to hundreds of feet. Motor yachts cruise between 12–20 knots; high-performance or sport models can exceed 30 knots.

Entry-level 30–35 ft yachts may cost around $100K, while luxury yachts run into the millions. Maintenance and operating costs typically average ~10% of the purchase price annually.

Yes. Many yachts offer spacious cabins, lounges, and amenities designed for family comfort—ideal for coastal and offshore cruising in style and safety.

Today’s yacht buyers—especially younger and eco-conscious—are demanding sustainability, multifunctional layouts, remote-work friendly spaces, and efficient, hybrid propulsion systems.