Chaparral 285 Boats for sale

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2002 Chaparral 285 SSI

2002 Chaparral 285 SSI

$18,000

Dania Beach, Florida

Year 2002

Make Chaparral

Model 285 SSI

Category Cuddy Cabin Boats

Length 28

Posted 1 Week Ago

Boat is well maintained and shed stored for the last three years. Engines just serviced and new zincs installed. Hull has a few scrapes and needs a good detail, but cockpit and cabin in good condition. All seating in great condition. Stock #178821 Good condition 285 SSI! Plenty of storage spaces! Loaded and ready to cruise! If you are in the market for an express cruiser, look no further than this 2002 Chaparral 285 SSI, just reduced to $18,000 (offers encouraged). This boat is located in Dania Beach, Florida and is in great condition. She is also equipped with twin Mercruiser engines that have 770 hours.

2006 Chaparral 285 SSI

2006 Chaparral 285 SSI

$47,800

Bradenton, Florida

Year 2006

Make Chaparral

Model 285 SSI

Category Cuddy Cabin Boats

Length 28

Posted 2 Weeks Ago

This Chaparral is in good overall condition just needs some TLC. The vinyl cushions are all supple but could use a good cleaning as well as the boat. The seller works out of town and does not have the time right now. The engines are maintained by at the marina it is stored at. The port engine was replaced in August 2015. The cabin AC does not work and the Captain's choice exhaust does not work. Stock #185585 Speedy sharp looking 285 SSI sportboat with Mercruiser engines, SeaDek Flooring! Intelligently designed, comfortable & great for overnighting! If you are in the market for a cuddy cabin, look no further than this 2006 Chaparral 285 SSI, priced right at $47,800 (offers encouraged). This boat is located in Bradenton, Florida and is in good condition. She is also equipped with twin Mercruiser engines that have only 105 hours. Reason for selling is not using enough.

2002 Chaparral 285

2002 Chaparral 285

$32,900

Pittsburgh, Pennsylvania

Year 2002

Make Chaparral

Model 285

Category Powerboats

Length 28'

Posted Over 1 Month

2002 Chaparral 285 THIS IS A LARGE CUDDY CABIN WITH TWIN ENGINES AND READY TO DO ANYTHING YOU WOULD LIKE TO DO FROM WATER SPORTS TO TRAVELING BY WATER - 285 SSI

2000 Chaparral 285 SSi

2000 Chaparral 285 SSi

$28,500

Mooresville, North Carolina

Year 2000

Make Chaparral

Model 285 SSi

Category Cuddy Cabin Boats

Length 29'

Posted Over 1 Month

2000 Chaparral 285 SSi 2000 Chaparral 285ssi  in  excellent condition with only 180 hours. 454 MPI   Magnum 385 horsepower Bravo Three. Always stored on a lift or rack. Cabin features include enclosed vacuum flush head with pressurized water system and sink. Removable V-birth table with cushion inserts for overnight. Microwave, shore power, JVC stereo with 12 CD changer. Cockpit features include galley with sink, AC/DC refrigerator, under seat ice chest, snap-in carpets, and removable table with cushion. Canvas options include cockpit cover, bimini tops, full coverage storage cover, and unused camper canvas package. Other options include twin batteries with charger, automatic fire protection system, Quick and Quiet Selectable Thru-Hull Exhaust, additional depth finder and full stainless steel trim package. Original owner, and the boat has been operated only in fresh water. $28500 OBO  Additional contact information,cell/text (704)953-2945, baarcher@outlook.com

2001 Chaparral 285 SSi

2001 Chaparral 285 SSi

$29,901

Port Clinton, Ohio

Year 2001

Make Chaparral

Model 285 SSi

Category Cuddy Cabin Boats

Length 29'

Posted Over 1 Month

2001 Chaparral 285 SSi This 285 SSI is Ready for you and the family. Modular designed for ease of use, functional fun! This boat is equipped with twin 5.7 Mercruisers Bravo lll drives. There is also a cockpit refrigerator/ bar area. No need to move from the helm when wanting to turn up the radio because you have a radio control right at your finger tips!  Very spacious cabin with marine head/shower.  Call today for more information and to scheduled a showing!

2003 Chaparral 285 SSi

2003 Chaparral 285 SSi

$50,000

Gilford, New Hampshire

Year 2003

Make Chaparral

Model 285 SSi

Category Cuddy Cabin Boats

Length 28'

Posted Over 1 Month

2003 Chaparral 285 SSi This Chaparral 285 is a new listing. The owner has used it here only in fresh water in Lake Winnipesaukee. It has been in a covered slip, and it shows. Yard maintained, this boat shows very well, and is worth a viewing. Well appointed, with many extras.

2013 Chaparral 285SSX

2013 Chaparral 285SSX

$79,900

Fort Lauderdale, Florida

Year 2013

Make Chaparral

Model 285SSX

Category Cuddy Cabin Boats

Length 28'

Posted Over 1 Month

2013 Chaparral 285SSX Chaparral 285 SSX - Low Hours - Hoist KeptDependable Volvo Power - 380 HPLots of Extras - Ready to Go!  Part sport boat, part luxury suite and all Chaparral. That's the Classic 285 SSX, a one-of-a-kind marvel of space and performance. This Chaparral 285 SSX is powered with the all-new 380HP Volvo Penta DP - only 90 hours since new. Hoist stored. Maintained to the highest standards.

2000 Chaparral 285 SSi

2000 Chaparral 285 SSi

$37,900

Michigan City, Indiana

Year 2000

Make Chaparral

Model 285 SSi

Category Cuddy Cabin Boats

Length 28'

Posted Over 1 Month

2000 Chaparral 285 ssI, Twin MerCruiser 5.0L EFI 240HP with 360 hours. Auto pilot, Depth sounder, GPS, VHF radio, Horn, Trim tabs, Stereo. Cold water pressure, Stove, Anchor & line, Fenders, Windlass, Mooring lines, Boat & Engine manuals, Swim platform, Bimini top, Side & Aft curtains, Camper top, Cockpit cover. Windshield cover, Co system, Engine alarm, Life Jackets, Life rings, Head System, Hold/Vac, Battery switch, Windshield wipers, Stored Inside summer and winter, enclosed head, Shore power, 2015 Venture Aluminum trailer.

2003 Chaparral 285 SSi

2003 Chaparral 285 SSi

$39,000

Verona Beach, New York

Year 2003

Make Chaparral

Model 285 SSi

Category Cuddy Cabin Boats

Length 29'

Posted Over 1 Month

2003 Chaparral 285 SSi, Please call 315-533-5693, 315-886-6083(c), 315-886-9239(c)2003 CHAPARRAL 285 SSi & TrailerBoat is in the WATER and available for Test Drives (with deposit)!- Twin Volvo Penta 5.7 Liter with D.P. Drives (320 H.P. each)- 310 Total Fresh Water Hours- Spinelli Brothers Custom Made S.S. Duoprops(4)- Factory Duoprops(4)- Bennett Trim Tabs- Fire Suppression System- Stored inside during Winter- Tie bar- 3 batteries- Extended Swim Platform with Custom Couch- Full canvas (Camper, Fast Back & Mooring)- Deck Seating for 7-8 (Double Helm)- Sink & Refrigerator on Deck- Deck Dinette converts to Tanning Lounge or Single Berth- Snap-in Carpet (2 Sets, 1 Berber)- VHF- Compass- Docking Lights- Power Inverter- Shore Power with Cord- Cabin Dinette Converts to Queen Berth- Custom V-berth Sheets- Microwave in Cabin- Cedar Storage Locker & Drawer- 3 Opening Ports- New Stereo with iPod/iPhone connection , 3 Operating Locations/Remotes- Amplifier- Enclosed Head with Vacu-Flush Toilet, Holding Tank & Indicator,Sink & Opening Port- Macerator- 2 Anchors (1 Custom made SS)- Fenders & Dock Lines- Load Rite Tandem Axle Trailer - $39000

2000 Chaparral 285 SSi

2000 Chaparral 285 SSi

$32,995

Okoboji, Iowa

Year 2000

Make Chaparral

Model 285 SSi

Category Cuddy Cabin Boats

Length 28'

Posted Over 1 Month

2000 Chaparral 285 SSi 2000 Chaparral 285 SSI One of a kind local trade Chaparral with upgraded speaker system. You have to see this boat to believe it!

2003 Chaparral 285 SSi

2003 Chaparral 285 SSi

$32,900

Occoquan, Virginia

Year 2003

Make Chaparral

Model 285 SSi

Category Cuddy Cabin Boats

Length 28'

Posted Over 1 Month

2003 Chaparral 285 SSi 2003 Chaparral 285 SSI NIce boatel kept boat powered by twin 5.0L Volvo's with DP drives this boat has 450 hours and is professionally maintained. This boat has capatin choice, GPS, VHF, cockpit cover, dual bimini's, cockpit carpet, cockpit fridge, windlass, remote spotlight, and docking lights. In the cabin you will find a microwave full head with vacu flush, and a berth that converts to a dining area.

2015 Chaparral 285 SSX

2015 Chaparral 285 SSX

Request Price

Hayden, Idaho

Year 2015

Make Chaparral

Model 285 SSX

Category Bowrider Boats

Length 28'

Posted Over 1 Month

2015 Chaparral 285 SSX, 2015 Chaparral 285 SSX, Volvo V8 DP (430 hp), Carbon Series White, Full canvas package (Black), Cockpit cover (black), Convenience package, Premium package, Overnight package, VHT Vacuflush system, Snap in carpet, Stainless transom shower, Swim platform l

2001 Chaparral 285 SSi

2001 Chaparral 285 SSi

$29,900

Pewaukee, Wisconsin

Year 2001

Make Chaparral

Model 285 SSi

Category Cuddy Cabin Boats

Length 28'

Posted Over 1 Month

2001 Chaparral 285 SSI, You don't get to see these come along everyday, and when they do, they disappear quickly. The 285 SSI has set the bar for performance cuddies since its creation and continues to do so today. she's a 50+ MPH boat that is a performer in the most adverse conditions. It's a perfect big water boat, and for the Great Lakes or off-shore application, her hull was designed for the "rough stuff". Sporting a 22 degree transom deadrise and high rake, you'd swear you were in a go-fast unit as she slices and dices with the best of them. Priced aggressively for quick sale. Call today! Trades considered.

2001 Chaparral 285 SSi ONLY 54 hours

2001 Chaparral 285 SSi ONLY 54 hours

$36,900

Oldsmar, Florida

Year 32767

Make Chaparral

Model 285 SSi

Category Cuddy Cabin Boats

Length 29.0

Posted Over 1 Month

ONLY 54 hours Up for sale is our 2001 Chaparral that we have had for almost 2 years now. Dont let the pics fool you, its a nice big boat. With the swim deck she is roughly 31 feet and perfect for over night stays.The Chaparral 285 SSi is Powerboat Magazine's Boat of the Year for 2001. Underneath, a 22-degree Extended V-Plane bottom design is bold enough for big water, yet tame enough for weekends on the river. Inside, a double-wide adjustable helm seat complements wrap-around aft seating. This cruiser-style seating is an extra, not usually found on a cuddy cabin sportboat of this size.Loaded with amenities Hydraulic Trim and Tilt, plus a convenient Power engine Hatch (brand NEW). Stunning two tone Graphics accent the hull, Wet Bar with Sink, Cocktail/Dining table that converts the lounge to a Sun pad, Swim Step with Ladder, Transom Shower, A double-wide adjustable helm seat/captains chair with Tilt Steering wheel complements wrap-around aft seating, Walk Thru Windshield, and even a Vacuum Flush Head with Sink and pressure water system, Electronic/hydraulic Trim Tabs with indicators, Twin Bimini's with new eyes and glass, BIG rear Swin deck, fridge, Fresh water and sinks, New macerator and freshwater pumps, toilet, USD power, 110 Volt power, Awesome stereo system with subs and amps, SERIUS XM ready, Live well, CB radio, Garmin GPS/NAV, $3000 canvas custom boat cover, Stainless BBQ, life jackets and safety gear. Front and rear anchors and ropes. Nice cabin with LED rope lights, factory down lights. USB charging ports/ 12 Volt charging port. Plenty of concealed storage compartmentsOnly 54 hours on a brand new 496 Merc engine ($15,000) and NEW Bravo 3 out drive with stainless steel Twin prop($9,300) That was fitted close to 2 years ago and only used for last season. This year we have only used it for 3 days $24,000 worth of receipts on new engine and out drive AloneRecently had some extra things added. 4 new batteries. ($759) (1 for start, 2 for house and one spare) LED swim lights ($1600) New Sea pump ($898), New fuel pumps ($890) New tensioner pulleys and serpentine belt ($350) New Ignition system and waterproof fuses ($650) Engine hatch hydraulic lift ($850) There is ZERO corrosion anywhere in the electrical system as I had a boat electrician go through the boat when we first got it and clean and replace pretty well everything and seal it ($1100). Most of the list of things above were done purely for prevention rather than replacement. There is roughly the asking price in upgradesPowerboat Magazine named Chaparral 285 SSi a Boat of the Year winner for good reason - it combines offshore performance with cruiser comforts and Chaparral quality. She has been VERY well maintained (as you can see and with receipts) No expense has been spared when it comes to maintaining our boat and it is TURN KEY ready for a new owner. NADA list price is $72,832, Low end value $37,285, Average Value $42,055. We believe we have priced it accordingly. The Chaparral 285SSI does not come up for sale very often as they are a very popular boat and when they do, they don't last long on the marketThis is a great family boat / party boat / all weekend boat. It can sleep 4 people comfortably, seat 12 on deck, 14 in total. Deck can transform into a large lounge/sundeck or a large family dining table. On the bow you can safely sunbake as well as on the rear seat or rear swim deck so its perfect for the ladies chasing that summer tan. As big as the boat is, it can still sit comfortable in 3-4 feet of water so its perfect for pulling up to islands and beachesA 2004 custom triple axle Aluminium trailer with new LED lights comes with the boat for FREE. SPECS:Beam: 9' 3"Min. Draft: 21"Max. Draft: 35"Deadrise: 22 deg.Weight: 7,200 lbsWater Capacity: 30 galsBridge Clearance: 5' 6"Waste Capacity: 9 galsEngine Make: MercruiserEngine Model: 496 Engine Hours: 54Engine Type: Inboard/outboardEngine Size: 496Fuel Type: GasolineFuel Tank: 143 galsPropeller: Twin prop Stainless SteelCruising Speed: 35 mphMaximum Speed: 67 mphDrive Make: MercruiserCabin Headroom: 5 ftNumber of Heads: 1NOTE: The picture showing the cabin bed converted into a dining area are from the Chaparral websiteHappy to take a part trade for a classic muscle car but would rather sell outrightIf you need any more information, please email me

2001 Chaparral 285 SSi

2001 Chaparral 285 SSi

$29,999

Dallas, Texas

Year -

Make -

Model -

Category -

Length -

Posted Over 1 Month

2001 Chaparral 285 SSi PRICED BELOW BOOK!  TWIN MERCRUISER 5.7EFI's!CAPTAINS CALL EXHAUST! COMPLETE WITH TRIPLE AXLE TRAILER!BOAT OF THE YEAR IN 2001!   This is your chance to own a great performing 285SSi that is priced BELOW dealer trade-in value! She is powered by TWIN 300hp Mercruiser 5.7 EFI engines with Bravo Threes duo prop drives.  Both engines were replaced in 2010 and now have about 300 hours.  Other options include, Bimini top, Cockpit table, In-floor ski locker, Cockpit cover, Windlass anchor system, Battery charger, Battery switch, Three batteries, Depth sounder, Walk thru windshield, CD sound system with speakers, Galley, Pressure water, M/W, AC/DC refrigerator, Shore power, Vacuflush head w/pump out, Large swim platform with swim ladder, Cooler storage, Hydraulic trim tabs, Captains Call thru-hull exhaust, Trim indicator, Trim tabs, Hydraulic engine hatch, Automatic fire extinguishing system, Transom shower and more.  Gelcoat is in great condition. Cockpit vinyl has a couple of areas that need attention (see photos) but overall in decent shape.  Cabin is in good condition.  Boats runs and sounds great.  The NADA blue book average is $38.6K with trailer and the BUC blue book is $38.8K with trailer!  You simply can't buy this model boat with a triple axle trailer anywhere in the USA at this price!     PRICED WELL BELOW ALL BOOK VALUES AND BELOW DEALER TRADE-IN VALUE!!