2008 Grady-White Freedom 275 Boat in Naples, FL 34104 US
Freedom 275
2 Engines (2x --)
27.4 feet
--
Fiberglass/Reinforced
2008 Grady-White 275 Freedom
Enjoy versatile family cruising, fishing, and watersports aboard this 2008 Grady-White 275 Freedom. This well-appointed dual console combines Grady-White's quality construction and comfortable layout with desirable onboard amenities.
Highlights include:
Garmin GPSMAP 4214 chartplotter
Freshwater head
Kenwood stereo unit with speakers
Bow filler cushion
Lewmar windlass
Engine and bow covers
Powered portside sun lounger
Approximately 680 engine hours
The 275 Freedom offers generous seating, a flexible cockpit, and the confidence-inspiring ride Grady-White is known for. Whether heading out for a day of fishing, relaxing at the sandbar, or cruising with family and friends, this boat is set up to make the most of your time on the water.
Contact for additional details, pricing, and to arrange a showing.
World Cat of South Florida and Naples:
The Nation's leading dealership for World Cat sales and service for over 15 years.Your 5-Star Service Dealer, Award Winning Dealer of the Year, Customer Service Award Winner.
Now proud to bring this award winning 5-star team with custom options, premium service and quality products to Collier County. World Cat of Naples serving Marco Island, Naples and surrounding areas with World Cat Sales and Service in addition to the South Florida (Palm Beach, Broward and Dade Counties) and the Caribbean. That's right - We Export! Top is Sales to the Caribbean.
Contact us before you decide to buy another boat. The proof is in the ride and if you have never ridden a World Cat, our no pressure sales team will sign you up for your Ultimate Sea Trial.
Monday through Friday 9am - 6pm
Saturday 10am - 2pm
Sunday by Appointment
QUALITY TRADES CONSIDERED AND FINANCING AVAILABLE!
Price History
| Date | Event | Price |
|---|---|---|
| 7/30/26 | Initial price | $60,000 |
Videos from World Cat of South Florida on this 2008 Grady-White Freedom 275
2008 Grady-White Freedom 275 Video Tours
Overview
The Grady White 275 Freedom is a versatile dual-console boat that combines the brand's renowned fishing capabilities with a family-friendly layout. Designed to accommodate fishing, entertaining, and watersports such as towing boarders, this model offers flexibility for a variety of recreational activities. Its deep V-bottom hull and twin-engine configuration enable it to navigate waters that many bowriders would avoid, emphasizing its rough water pedigree.
Exterior Design and Construction
Measuring 26 feet 11 inches in length overall with an 8 foot 6 inch beam, the 275 Freedom features a hull constructed from 100% hand-laid fiberglass complemented by composite stringers, transom, and bulkheads. The hull incorporates Grady White's CV2 technology, which utilizes a continuously variable degree deadrise bottom starting at 18.5 degrees at the transom and sharpening to nearly 30 degrees at midship. This design enhances performance in rough conditions. The boat also employs a self-bailing deck system that drains water overboard, ensuring safety even if the bilge pump fails. Proper propeller operation requires at least 20 inches of water depth due to the boat's displacement of nearly 6,500 pounds.
Power and Performance
Grady White offers the 275 Freedom with four different outboard propulsion options, ranging from a single 350 horsepower engine to twin configurations between 150 and 250 horsepower. For the test, the boat was equipped with twin 200 horsepower Yamaha outboards, carrying two people and half tanks of fuel and water, totaling a test weight of 6,632 pounds. Under these conditions, the boat reached plane in 6.5 seconds and achieved 30 miles per hour in 7.9 seconds. Cruising speed at 4,000 RPM delivered 31.5 miles per hour with a fuel burn of 14.3 gallons per hour. At wide-open throttle of 5,800 RPM, the boat averaged 48.9 miles per hour while consuming 38.8 gallons per hour. Despite rough test conditions with high winds, the 275 Freedom handled choppy water and tight turns smoothly and quietly. The Yamaha engines provided rapid acceleration and solid overall performance, though some propeller adjustments might optimize performance based on load.
Helm and Controls
The helm console of the 275 Freedom impressed the test team with its modern design and functionality. It features an all-digital dash with a 12-inch touchscreen monitor displaying navigation and engine data. The boat is equipped with digital drive controls and hydraulic steering via a responsive Seastar system. While the steering felt precise at speed, it required more effort when maneuvering at slow speeds. For enhanced control, especially in slow-speed situations, Grady White offers a 250-horsepower model equipped with Yamaha's Helm Master system, which includes electro-hydraulic steering, joystick control, and integrated autopilot capabilities.
Conclusion
The Grady White 275 Freedom demonstrates a well-rounded combination of fishing prowess, family-friendly design, and solid performance in challenging conditions. Its advanced hull design and robust construction provide confidence in rough water, while the twin-engine setup delivers respectable speed and handling. The modern helm with digital instrumentation and available advanced steering options enhances usability. Overall, the 275 Freedom stands out as a versatile boat suitable for anglers and recreational boaters seeking dependable performance and comfort.
Overview from around the web 2008 Grady-White Freedom 275
Customers consistently praise the 2008 Grady-White Freedom 275 for its impressive blend of performance, comfort, and versatility
Many owners highlight its spacious dual-console layout, which provides ample seating for family and friends while maintaining a sleek, stylish design. The Freedom 275 is often commended for its smooth, stable ride, even in choppy waters. Users appreciate the boat's robust construction and excellent handling, making it suitable for both leisurely cruising and fishing trips. The combination of a reliable Yamaha engine and Grady-White’s renowned quality ensures a dependable and enjoyable boating experience. Customers are also impressed by the boat's well-thought-out storage solutions and amenities, such as the conveniently located head and the ample deck space for activities. The option for various configurations and features allows owners to customize their boats to fit their lifestyle, whether for fishing, family outings, or entertaining. Overall, the 2008 Grady-White Freedom 275 receives high marks for its craftsmanship, functionality, and the satisfying feel of being out on the water. It's a favored choice among boating enthusiasts who value quality and versatility.
The Biggest Pros and Cons
The 2008 Grady-White Freedom 275 is a versatile and well-regarded boat, known for its combination of performance, comfort, and functionality. Below are some pros and cons to consider:
Pros
Dual-Function Design: The Freedom 275 features a unique dual-console design, ideal for both fishing and family cruising. This versatility appeals to a wide range of boaters.
Quality Construction: Grady-White is known for its high-quality craftsmanship and durable materials, ensuring longevity and reliability on the water.
Spacious Layout: The interior offers ample seating for family and friends, along with a well-designed helm and galley area, making it great for day trips.
Excellent Ride: The boat is known for its smooth ride and stability, even in choppy waters, thanks to its deep-V hull design.
Storage Options: With various storage compartments and live wells, the Freedom 275 is practical for anglers with gear to stow away.
Performance: Equipped with powerful twin outboard engines, the boat delivers impressive speed and fuel efficiency, making it suitable for both leisure and longer journeys.
Comfort Features: The inclusion of a comfortable cabin area with a head (bathroom) enhances the overall boating experience for longer outings.
Cons
Price Point: Being a premium brand, Grady-White boats generally come with a higher price tag, which may not fit every budget.
Weight: The fiberglass construction, while durable, contributes to the boat's weight, which can affect towing and maneuverability.
Maintenance Costs: As with most quality boats, the maintenance and upkeep can be higher due to the need for premium parts and service.
Limited Fishing Features: While designed for both fishing and cruising, serious anglers might find the fishing-specific features (like rod storage and tackle space) somewhat limited compared to dedicated fishing boats.
Fuel Capacity: Depending on usage, some owners might find the fuel capacity less than optimal for extended excursions without frequent refueling stops.
Made For
The 2008 Grady-White Freedom 275 is designed for boating enthusiasts who appreciate versatility and quality. This dual console vessel is the perfect choice for families and friends looking for a comfortable day on the water or fishing adventures. It’s ideal for those who enjoy socializing, as the spacious layout accommodates gatherings, picnics, and leisurely cruises. With its robust construction and renowned Grady-White reliability, this boat appeals to both seasoned sailors and newcomers. The Freedom 275 caters to anglers seeking an effective fishing platform with ample storage for gear, as well as amenities for fun-filled days on the water. Whether you're pursuing adrenaline-filled watersports or seeking a relaxing boat ride, the Freedom 275 delivers in performance and comfort, making it suitable for a wide range of boating lifestyles.
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2008 Grady-White Freedom 275 | ||||||
|---|---|---|---|---|---|---|
| Price | $60,000 | $59,900 | $75,800 | $160,000 | $175,500 | $199,000 |
| Location | Naples | Saint Petersburg | Palmetto | Sarasota | Naples | Longboat Key |
| Nominal Length | 27' | 22' | 27' | 28' | 28' | 30' |
| Engine Make | - | YAMAHA | Yamaha | Yamaha | Yamaha | Yamaha |
| Total Engine Power | 225 hp | 300 hp | 250 hp | 300 hp | 250 hp | - |
| Days on Market | 22 | 304 | 37 | 97 | 104 | 113 |
| Get in touch |
Other 2008 Grady-White Freedom 275 For Sale in Florida, United States
Other Grady-White Freedom 275 boats for sale in Florida, United States
Other Grady-White boats for sale in Florida, United States
Meet the Broker

Address
Boat Location
Contact World Cat of South Florida about 2008 Grady-White Freedom 275
2541 West State Road 84, Fort Lauderdale, FL, 33312

























































