2026 Grady-White Freedom 285 Boat in Annapolis, MD 21403 US
Freedom 285
2 Engines (2x Yamaha)
28 feet
Gas
Fiberglass/Reinforced
Offered Exclusively by Tri-State Marine, Maryland, DC and Virginia's #1 Grady-White dealer. Providing expert sales and service from two locations on the Chesapeake Bay in Annapolis and Deale, MD for 65 years. Experience the Tri-State Marine service advantage by purchasing direct from us, one of the top Grady-White dealers in the United States.
2026 Grady-White Freedom 285
Luxury Dual Console. Legendary Grady-White Performance.
The 2026 Grady-White Freedom 285 is where premium craftsmanship meets versatile comfort. Designed for both serious anglers and discerning families, this dual console delivers unmatched quality, seaworthiness, and attention to detail - all powered by Grady-White's proven SeaV²® hull for the smoothest, driest ride in its class.
Premium Options & Features
Jet Top with Underside in White - Sleek, clean aesthetic with durable overhead protection.
Twin Yamaha F300 XSB FM Outboards - Digital Electronic Controls deliver quiet, effortless power and precision handling.
Painted Hull in Seaport Blue - Distinctive and modern with a refined coastal look.
Side Bar with Corian Countertop & Sink - Perfect for entertaining on the water, with easy access to refreshments.
Ivory Bow Cover - Adds a layer of sun protection and elegant style for relaxing up front.
Sun Platform Insert with Cushion - Converts the bow area into a spacious sun lounge for family enjoyment.
Refrigerator in Bar - Keep your drinks and snacks cool all day while cruising or entertaining.
Ivory Hardtop Drop Curtain - Shields the cockpit for extended comfort in cooler or breezy conditions.
Electric SureShade Top in Oyster - Extendable shade system for customizable protection at the touch of a button.
Performance & Design
From early-morning fishing runs to sunset cocktail cruises, the Freedom 285 delivers the versatility today's boaters demand. Its open layout, premium finishes, and thoughtful features make it ideal for Chesapeake Bay adventures - balancing offshore capability with refined onboard living.
INCLUDES: FREIGHT, PREP, FUEL & ORIENTATION
The Company offers the details of this vessel in good faith but cannot guarantee or warrant the accuracy of this information nor warrant the condition of the vessel. A buyer should instruct his agents, or his surveyors, to investigate such details as the buyer desires validated. This vessel is offered subject to prior sale, price change, or withdrawal without notice.
2026 Grady-White Freedom 285 Video Tours
Overview from around the web 2026 Grady-White Freedom 285
The 2026 Grady-White Freedom 285 is receiving praise from customers for its versatility, comfort, and performance
Many boaters admire its spacious layout, which seamlessly blends fishing and family-friendly features, making it ideal for both leisurely outings and serious angling adventures. Customers highlight the ample seating and cabin space, perfect for entertaining guests or enjoying a day out on the water with family. The innovative design includes a well-equipped helm, easy access to the bow, and a spacious cockpit that enhances the overall experience. Performance-wise, the Freedom 285 boasts impressive handling and stability, even in choppy waters. Its powerful engines provide both speed and efficiency, making it a reliable choice for all types of outings. The attention to detail in craftsmanship and high-quality materials further earns the model high marks, ensuring durability and longevity. Overall, users appreciate the Freedom 285 for its ability to offer a luxurious boating experience while maintaining the functionality needed for fishing, making it a sought-after choice among boat enthusiasts.
The Biggest Pros and Cons
2026 Grady-White Freedom 285: Pros and Cons
Pros
Versatile Design: The Freedom 285 combines the best features of a center console and a dual console, providing flexibility for both fishing and family outings. Its spacious layout caters to various activities, from cruising to water sports.
Exceptional Performance: Grady-White is renowned for building boats that handle exceptionally well in various sea conditions. The Freedom 285 is equipped with powerful engine options that ensure impressive speed and agility.
Luxurious Comfort: With ample seating, a well-structured helm, and comfortable bow seating, the Freedom 285 ensures a pleasurable experience for all passengers. The added touches like Marine-grade upholstery and thoughtful storage solutions enhance comfort.
Fishing Features: For avid anglers, the boat comes equipped with features such as live wells, rod holders, and a customizable tackle station, making it a fishing powerhouse.
Safety and Build Quality: Grady-White boats are known for their robust construction and attention to safety. The Freedom 285's deep-V hull provides stability and minimizes the risk of taking on water in rough seas.
Customizable Options: Buyers have the opportunity to personalize their boats with a variety of options and upgrades, ensuring the Freedom 285 meets their specific needs.
Cons
Price Point: Grady-White boats are premium vessels, often reflected in their price tag. The Freedom 285 may be considered expensive compared to other models in its class.
Maintenance Costs: Owning a high-quality boat like the Freedom 285 can come with higher maintenance and insurance costs, which potential buyers should factor into their budget.
Size and Handling: While the spaciousness is a major plus, the boat's larger size might be challenging for novice boaters to handle, particularly in tight spaces or during docking maneuvers.
Fuel Efficiency: Powerful engines and bigger hulls typically mean higher fuel consumption. Although performance is enhanced, fuel costs can add up during extended outings.
Limited Overnight Capabilities: While the Freedom 285 does offer some creature comforts, it isn't primarily designed for overnight stays. Those seeking true overnight accommodations may find it lacking in sleeping space. The 2026 Grady-White Freedom 285 offers a delightful blend of performance, comfort, and versatility, making it a strong contender for both anglers and families alike, but prospective buyers should weigh the cons against their specific needs and budget.
Made For
The 2026 Grady-White Freedom 285 is designed for boaters who appreciate both versatility and luxury on the water. Ideal for families and fishing enthusiasts alike, this model combines the best features of a powerboat and a fishing vessel. Whether you're cruising with friends for a sunset dinner or setting out for a day of deep-sea fishing, the Freedom 285 is built to accommodate a range of activities. The spacious cockpit offers ample seating and storage for all your gear, while the comfortable, well-appointed cabin provides a retreat with modern amenities for quick getaways. Operators who value safety will appreciate the Grady-White's renowned stability and seaworthiness, while those who prioritize technology will find advanced navigation and entertainment systems seamlessly integrated. With an emphasis on quality craftsmanship and performance, the Freedom 285 caters to those who seek adventure without sacrificing comfort. It is the perfect choice for those looking to create lasting memories on the water.
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| Price on request | Price on request | Price on request | Price on request | Price on request | Price on request |
| Annapolis | Annapolis | Annapolis | Annapolis | Annapolis | Annapolis |
| 28' | 21' | 34' | 31' | 27' | 25' |
| Yamaha | Yamaha | Yamaha | Yamaha | Yamaha | Yamaha |
| 300 hp | 200 hp | 450 hp | 350 hp | 200 hp | 200 hp |
| 150 | 229 | 11 | 11 | 396 | 192 |
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Address
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Contact Tri-State Marine - Annapolis about 2026 Grady-White Freedom 285
222 Severn Avenue #12 , Annapolis, MD, 21403























