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    Within 100 Miles Of
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Cruiser boats for sale in Leesburg Florida

There are 12 new and used Cruiser boats for sale in Leesburg, Florida. Explore Cruiser brands like Cobalt, Regal, Sea Ray, Monterey, and Chris Craft on BoatCrazy. View a wide selection of Cruiser boats from $4,000 to $434,950.
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  • Cruiser
    Within 100 Miles Of
    Leesburg, Florida
12 boats found within 100 miles from Leesburg, Florida
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  • Price Drop 2018 Regal 1900 ES Bowrider

    2018 Regal 1900 ES Bowrider

    $23,995
    Leesburg, FL
    • Leesburg, FL
    • Cruiser
    • 20'
    • 2018 / Used
    • $23,995

    2018 Regal 1900 ESw/ Volvo Penta 4.3L V6 – TrailerPrice: $23,995354 ENGINE HOURS • VOLVO PENTA V6 • OPEN-BOW SEATING • TRAILER INCLUDEDThe 2018 Regal 1900 ES is a 19'10" fiberglass... View Details

    View 11 Photos and Details Contact Seller
    $23,995
    VIEW DETAILS
  • 2001 Monterey 240 Explorer Sport

    2001 Monterey 240 Explorer Sport

    $14,995
    Leesburg, FL
    • Leesburg, FL
    • Cruiser
    • 24'
    • 2001 / Used
    • $14,995

    2001 Monterey 240 Explorer Sportw/ 5.7L Volvo Penta V8 – Performance TrailerPrice: $14,995405 ENGINE HOURS • V8 VOLVO PENTA POWER • DUAL STAINLESS-STEEL COUNTER-ROTATING PROPELLERS... View Details

    View 27 Photos and Details Contact Seller
    $14,995
    VIEW DETAILS
  • Price Drop 2026 Cobalt R6B

    2026 Cobalt R6B

    $164,781
    Daytona Beach, FL
    • Daytona Beach, FL
    • Cruiser
    • 25'
    • 2026 / New
    • $164,781

    The 2026 Cobalt R6 Outboard is the kind of boat that feels like it was designed for people who want to do it all on the water. With room for up to 14, it’s the ultimate social hub—... View Details

    View 32 Photos and Details Contact Seller
    $164,781
    VIEW DETAILS
  • 2027 Cobalt R4

    2027 Cobalt R4

    $158,213
    Daytona Beach, FL
    • Daytona Beach, FL
    • Cruiser
    • 24'
    • 2027 / New
    • $158,213

    Designed for social sun-seekers, day-cruisers, and water sports lovers, the Cobalt R4 Outboard is the ultimate entertainer’s platform on the water. With a certified capacity for up... View Details

    View 25 Photos and Details Contact Seller
    $158,213
    VIEW DETAILS
  • 2026 Cobalt R6

    2026 Cobalt R6

    $174,674
    Daytona Beach, FL
    • Daytona Beach, FL
    • Cruiser
    • 25'
    • 2026 / New
    • $174,674

    If you are the ultimate weekend host who loves nothing more than gathering a lively crew for long, sun-drenched days on the water, the Cobalt R6 Outboard is your next obsession. Th... View Details

    View 29 Photos and Details Contact Seller
    $174,674
    VIEW DETAILS
  • 2022 Regal 26 XO

    2022 Regal 26 XO

    $129,900
    Tampa, FL

    Regal 26 XO - Reliable and Efficient Cruising The Regal 26 XO is a versatile cruiser designed for those who value performance and comfort. This 2022 model is crafted with precisio... View Details

    View 35 Photos and Details Contact Seller
    $129,900
    VIEW DETAILS
  • Price Drop 2010 Monterey 280 SCR

    2010 Monterey 280 SCR

    $52,950
    Palm Harbor, FL
    • Palm Harbor, FL
    • Cruiser
    • 29'
    • 2010 / Used
    • $52,950

    Very Well Kept, Always Dry Stored Under Cover 2010 Monterey 280 Sport Cruiser with Only 442 Hours On Volvo 8.1 375HP and Dual Prop Drive. Garmin Electronics With Radar, A/C/ Heat,... View Details

    View 78 Photos and Details Contact Seller
    $52,950
    VIEW DETAILS
  • 2021 Regal 38 XO

    2021 Regal 38 XO

    $434,950
    Clearwater Beach, FL
    • Clearwater Beach, FL
    • Cruiser
    • 38'
    • 2021 / Used
    • $434,950

    The 2021 Regal 38 XO is a luxury sport yacht that combines style, performance, and comfort. It offers a spacious design both above and below deck, making it a great choice for crui... View Details

    View 22 Photos and Details Contact Seller
    $434,950
    VIEW DETAILS
  • Price Drop 1984 Chris Craft #217 scorpion

    1984 Chris Craft #217 scorpion

    $4,000
    Largo, FL

    21 foot Chris Craft with a 1999 150 hp Yamaha Motor and a 1995 Troi Trailer. Used all in good shape In good shape uses non ethanol gas recently added new yamaha carburator. Thermo... View Details

    View 3 Photos and Details Contact Seller
    $4,000
    VIEW DETAILS
  • 2005 Sea Ray 420 Sundancer

    2005 Sea Ray 420 Sundancer

    $239,900
    Ruskin, FL
    • Ruskin, FL
    • Cruiser
    • 45'
    • 2005 / Used
    • $239,900

    2005 Sea Ray 420 Sundancer "NaviGator" | Twin Cummins Diesels | 1,903 Hours | Simrad Electronics | Fully Documented Service | SIONYX Nightwave™ Ultra Low-Light Marine CameraNaviGat... View Details

    View 59 Photos and Details Contact Seller
    $239,900
    VIEW DETAILS
  • 1998 Sea Ray 330 Sundancer

    1998 Sea Ray 330 Sundancer

    $29,977
    Bradenton, FL
    • Bradenton, FL
    • Cruiser
    • 33'
    • 1998 / Used
    • $29,977

    1998 Sea Ray 330 Sundancer – Repowered Luxury Cruising at Boater’s World BradentonExperience the timeless appeal of a true cruising classic with this used 1998 Sea Ray 330 Sundance... View Details

    View 27 Photos and Details Contact Seller
    $29,977
    VIEW DETAILS
  • 2000 Sea Ray 290 AMBERJACK

    2000 Sea Ray 290 AMBERJACK

    $14,977
    Bradenton, FL
    • Bradenton, FL
    • Cruiser
    • 29'
    • 2000 / Used
    • $14,977

    2000 Sea Ray 290 Amberjack – Repowered Family CruisingDiscover a classic built for adventure with this used 2000 Sea Ray 290 Amberjack, now available at Boater’s World Bradenton. T... View Details

    View 20 Photos and Details Contact Seller
    $14,977
    VIEW DETAILS
Showing 1 to 12 of 12 boats found.

Cruiser Boats on Boatcrazy

Cruisers are versatile powerboats designed for comfort, extended trips, and overnight stays on the water. Offering the perfect blend of performance and livability, cruisers typically feature spacious cabins, galleys, sleeping quarters, and enclosed heads—making them ideal for weekend getaways, coastal cruising, or even liveaboard life.

Available in a range of sizes—from compact express cruisers to luxurious cabin cruisers—these boats often include features like air conditioning, generator power, swim platforms, and entertainment systems. Many models also offer flybridges, hardtops, or sunpads for added versatility and style.

Explore our selection of new and used cruisers from leading brands. Whether you're looking for a family-friendly cruiser or a sleek performance model for harbor-hopping, you'll find a boat that balances comfort and adventure.

Cruiser Boats manufacturers on Boatcrazy

When looking for a comfortable and capable Cruiser boat, consider these top-tier Cruiser Manufacturers

Sea Ray, Regal, Cruisers Yachts, Beneteau, Tiara Yachts, Boston Whaler

Cruiser Boats For Sale by State

Cruiser Boats Frequently Asked Questions

What is a cruiser boat?

A cruiser boat—also referred to as a cabin cruiser—is a powerboat typically between 21 ft and 45 ft in length, equipped with sleeping berths, a galley, and a head—designed for overnight cruising in comfort.

Most cruisers range from 21 to 45 ft, with cabins located in the bow and amenities like berths, galley, enclosed head, and open cockpit or helm area for both comfort and day-use flexibility.

Typical cabin cruisers cruise at around 20–30 knots. Larger models and luxury cruisers can exceed 30 knots, while fuel-efficient models offer long-range capabilities style-wise akin to small yachts.

Cruisers combine indoor-outdoor living with amenities like cabins, galleys, heads, comfortable cockpits, and often flybridge or sun decks—making them ideal for entertaining, weekend cruising, and family overnight outings.

Prices vary widely—from around $100,000 for modest used models up to $700,000 or more for modern, well-equipped cabin cruisers. Luxury or larger models may exceed $1 million.

Cruiser boats are ideal for boating couples, families, or weekenders who want overnight ability, onboard comfort, and multi-day flexibility without the size or expense of a full yacht.