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Boats for sale in Chesapeake, Virginia

445 Boats Available

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Palm Beach Motor Yachts Palm Beach 70

2026

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The Palm Beach 70 embodies the perfect blend of timeless aesthetics and advanced design techniques. When underway the yacht demonstrates an impressive cruising speed of 28 knots, offering a sporty thrill while still excelling at efficiency. Expertly designed with all the comforts and amenities for long-range cruising and smooth performance in most sea conditions, the Palm Beach 70 delivers on all its promises. Available in Sedan, Extended Sedan, Flybridge, Skylounge and Extended Flybridge models, the current flagship of the fleet boasts expansive volume for livability without compromise.

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22

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Formula 430 All Sport Crossover

2026

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The Formula 430 All Sport Crossover is the latest of the revolutionary 430 Super Sport Crossover. True to the Formula Crossover mission of providing a platform where boaters truly can have the best of all worlds, the 430 ASC is an unprecedented fusion of dayboat versatility, overnight capabilities and sporting accommodations, where playing hard no longer means hard work or compromise for anyone aboard. At 43’ in length with a 12’ beam, the 430 ASC retains all of the SSC’s comfort amenities forward with a generous shot of offshore adventure aft.

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23

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Sunreef 70 NEXT

2026

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The Sunreef 70 stands as a masterfully engineered electric sailing catamaran that harmonizes elegance, sustainability, and performance. With a design ethos rooted in extreme comfort and advanced marine technology, this model redefines modern yachting for discerning owners seeking more than just a vessel — but a true home on the water. Crafted for those who seek personalized perfection, the 70ft yacht is fully customizable, offering an infinite array of layouts, décors, and functional configurations on top of showstopping features like the generous aft deck with a concealed garage and foldout bulwark platforms.Inspired by the forward-thinking design language of the Sunreef NEXT line, the Sunreef 70 features a hull and superstructure engineered to maximize onboard volume, delivering an exceptional sense of openness and spatial harmony. The yacht’s sleek exterior, combined with an intuitive yacht interior flow, ensure that every space is optimized for both luxury and practicality, creating a seamless balance between form and function.Reflecting the refined ambiance seen in Sunreef’s NEXT generation, this sailing yacht boasts yacht interiors bathed in natural light, thanks to strategic structural cut-outs and panoramic glazing. The spacious hulls allow for light-filled guest accommodations and lavish master suites that feature spa-inspired bathrooms and optional freestanding bathtubs. On deck, the flybridge and bow terrace invite relaxation, with customizable arrangements for sun-lounging, alfresco dining, or even wellness-focused setups, ensuring every moment at sea is one of comfort and serenity.Combining tailor-made interiors, environmentally conscious technologies, and top tier sailing performance, the 70ft yacht establishes a distinctive class of its own. Whether embarking on a global voyage or enjoying a coastal retreat, it offers a next-generation yachting experience — one that blends beauty, flexibility, and intelligent design into a seamless and unforgettable journey. Available in classic and solar versions, the Sunreef 70 integrates traditional craftsmanship with cutting-edge yachting innovation.

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25

Manufacturer Specification
Formula 360 Crossover Bowrider I/O

2026

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An exciting new generation of Formula dayboats has arrived with the Formula 360 Crossover Bowrider. From the stepped FAS3Tech hull to the stylish glass-sunroof hardtop, this leap in day venture offerings is a refreshing, innovative choice for dayboaters. 36ʹ long with a generous 11' 3" beam, the 360 CBR heralds the arrival of the new generation of open-bow dayboats, the first driven by Formula Designer Michael Young, a John Adams-mentored new creative force in luxury-boating architecture. True to its Formula CBR lineage, the 360 boasts an open bow with a single-level, flush cockpit and a true stand-up cabin with overnight accommodations and a spacious head compartment.

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22

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Sponsored Boats
Regal 38 SAV

Chesapeake, Virginia

2024

$610,000

Private Seller

29

Chaparral 246 SSi

Chesapeake, Virginia

2019

$90,000

Seller Joshua Hodge

7

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Chaparral GTS 6

2026

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The GTS series represents the next generation of the Surf series, offering enhanced multi-sport capabilities along with the performance that Chaparral is known for. Equipped with the GT Surf system, these boats feature customizable wake and wave generation technologies, which include Malibu Surf Gates and a touchscreen display to manage your rider's settings. Designed with safety in mind for swimmers and watersports enthusiasts, the GTS 6 is powered by a forward-facing drive and boasts a spacious cockpit with plenty of storage.

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8

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Intrepid 438 Evolution

2026

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With a cabin twice as large as an inboard of similar size, this sleek, big-water day boat is the complete package – on a more compact and fuel-efficient platform. State-of-the-art accommodations invite you cruise the islands for a week at a time. The spacious helm accommodates all the latest flat-screen electronics, while an optional power sunroof overlooks wraparound, club-style seating that inspires joyful camaraderie.A spacious, Euro-styled cabin is flooded with natural sunlight during the day and appointed with world-class amenities. The large settee with high-low table converts to a roomy V-berth at the touch of a button. The private head compartment features a separate shower. The galley includes a microwave and sink. The cozy cabin even features a pop-up television for catching your favorite shows…when you’re not catching a falling star on another perfect night aboard your custom 438 Evolution sport yacht.

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20

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Robalo R317 Dual Console

2025

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The R317 has an overall length of 31 feet making it not only the largest Robalo afloat, but also the largest dual console Robalo. A perfect blend of versatility for both the die-hard fishing enthusiast and the family minded angler. Sleek lines and loaded with standard features, the R317 is the boat you have been waiting for.

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25

Manufacturer Specification
Robalo R230 Center Console

2026

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The Robalo R230 is designed to satisfy all of your fishing and performance needs. Outfitted with our Hydro Lift™ multi angle hull design, horizontal tubed rod storage, SeaStar tilt hydraulic steering, and a 25 gallon live well. The R230 is perfect for those with the desire for endless possibilities.

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10

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East Marine 300

2026

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The East Marine 300 series stands out as the pinnacle of design and innovation, featuring a sleek aesthetic combined with unparalleled lightweight construction. Compact, efficient, and perfectly designed for solo rides or small group outings, the 300 Ultra Light Model features a lightweight yet durable aluminum hull and premium comfort enhancements.

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5

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Chaparral 30 Surf

2026

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With 30 feet of length, Malibu Surf Gates™, and enough seating capacity for the entire crew, don't just pretend to wake surf, surf like you mean it with the 30 Surf from Chaparral. The 30 Surf was designed with the most advanced technology afloat today. Dual touch screen "Glass Dash" helm is NMEA compatible and offers navigation, engine management, full gauge compliment, and can be customized to your personal preferences. Additionally, to make surfing effortless, the 30 Surf features a Simrad touchscreen interface to control all surf related functions like ballast and the Malibu Surf Gates (TM).

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18

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Robalo R207 Dual Console

2026

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The amazing R207 invites you to double your pleasure and double your fun on a boat that showcases everything that's right about owning a dual console outboard. Equal parts fishing machine and multi-purpose family sport boat, the R207 with F150 Yamaha power might be the best value in Robalo's 2020 fleet. An aluminum tandem axle trailer is included in the Reel Deal price. In the cockpit, a lockable head compartment provides welcome privacy. Add an optional porta-pottie because overboard isn't always an option. On the water, an 18-degree variable deadrise Hydro Lift bottom is stable while trolling, balanced under shifting weight loads and efficient going back-and-forth from your favorite fishing spot. A ski tow bar is a must have option for wakeboarding and pulling tubes.

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15

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Ocean Alexander 27 Revolution Skylounge

2026

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Ocean Alexander and Evan K. Marshall have once again partnered together to masterfully combine world-class engineering with extraordinary design. We don’t believe in taking shortcuts when creating a masterpiece. This is evident in every aspect of the 27R. The vertical bow expands living space without compromising the incomparable performance and efficiency we’re known for. Exotic-wood panels conveniently hide the vessel’s ample storage space. And enormous windows in the salon give commanding views of the endless stretches of sea around you. The impressive master stateroom boasts phenomenal views of its own, and the finishings in the stone-clad master head are pure perfection. Both the skylounge and flybridge options provide you with the ultimate entertainment space. Each are complete with comfortable seating areas, a wet bar and a custom-made grill. And the glass-enclosed beach club serves as the perfect hideaway for a relaxing afternoon lounge or a satisfying late-night cocktail.

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18

Manufacturer Specification
Robalo 266 Cayman SD

2026

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The 266 Cayman SkyDeck has been designed from the ground up to help you catch fish. The bow features an elevated casting deck that smoothly transitions to the wide gunnels that run around the boat. Cushioned seats and an enclosed head help keep you comfortable on all-day trips. The second station, from where the SkyDeck gets its name, gives you an unbeatable vantage point that is great for both navigation and fishing. Rod holders and storage compartments have been built into every surface of this boat so you can use all of your deck space for fishing. From offshore to narrow creeks, this bay boat will keep you in the middle of the action.

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21

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Chaparral 28 Surf

2026

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With a LOA of 28 feet, Malibu Surf Gates™, and an Infinity Power Step swim platform, don't just pretend to wake surf, surf like you mean it with the 28 Surf from Chaparral. The 28 Surf is available with our most popular package ever - the Black Edition. The Black Edition package elevates the entire boating experience and all starts with premium Black Gelcoated Hullsides and Hullbottom paired with black metal finishes around the windshield. Moving to the interior, the new soft Silicone Cayenne interior with black accents will be sure to be envied by others.

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23

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Chaparral 270 OSX

2026

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Chaparral is re-writing the rules on outboard boating. The 270 OSX is a trendsetter in design, performance, and function. The helm features a glass dash with dual touch screen Simrad displays. The cockpit is open, and spacious and features a multi-position sun lounger aft. The open-concept design carries forward into the bow area which features hinged storage beneath luxuriously appointed upholstery. Chaparral went to great lengths to create a powerful and agile craft that will provide a smooth ride in any kind of water. The 270 OSX was designed with the most advanced technology afloat today. Our Standard Dual 7" inch Simrad touchscreen displays with controls are NMEA compatible and offer navigation, engine management, full gauge compliment, and can be customized to your personal preferences.

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15

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East Marine 320

2026

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It is the ace of the East Marine 300 series offering sleek design & ultra light weight. This lightweight tender is designed for both performance and portability. Whether you need it shipped or plan to pick it up yourself, we make the process easy and flexible.

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7

Manufacturer Specification
Robalo R317 Dual Console

2026

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The R317 has an overall length of 31 feet making it not only the largest Robalo afloat, but also the largest dual console Robalo. A perfect blend of versatility for both the die-hard fishing enthusiast and the family minded angler. Sleek lines and loaded with standard features, the R317 is the boat you have been waiting for.

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25

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