Boat Trailers for Sale in Winnetka, IL: Boating Trailers & Transportation Clear filtersBoat ConditionNew BoatsUsed BoatsLocationCape Coral61resultsElkhorn98resultsJohnsburg70resultsLake Geneva1resultsNaples47resultsNashotah57resultsPort Charlotte50resultsSister Bay37resultsThree Lakes58resultsWhitewater16resultsManufacturerAAD Custom1resultsAqua Patio5resultsAquaPatio1resultsAxis1resultsBayliner3resultsBennington103resultsBoston Whaler30resultsCarolina Skiff2resultsCenturion1resultsChaparral2resultsShow more CategoryAluminum Fish3resultsBay30resultsBowrider70resultsCenter Cockpit1resultsCenter Console73resultsCruiser4resultsCuddy Cabin2resultsDeck Boat48resultsDual Console5resultsFreshwater Fishing12resultsJet2resultsPontoon157resultsRunabout1resultsSki and Wakeboard Boat70resultsPriceto$to$Lengthto13 ft.75 ft.YeartoGoEngine Hoursto1 hr1,119 hrStatusINTERNET SPECIAL!10resultsIn Stock355resultsJUST SOLD!1resultsSALE PENDING25resultsSPECIAL SAVINGS!104resultsSearch boats...Searching…Sort ByRecently AddedPrice: Low to HighPrice: High to LowYear: Newest FirstYear: Oldest FirstShowing 495 Results Share SearchFeaturedNewFeatured2024 Sportsman 267 Masters OE Request PriceStatusSALE PENDINGLocationPort Charlotte, FLManufacturerSportsmanStock #SPO25559-B1 ADDITIONAL FEATURES * Masters 267 OE w/ Single Yamaha XF450 (White Engine Only) * Limited Package * Hull Side-Storm Cloud / Hull ... READ MORE Check AvailabilityView Boat Quick LookLength26Weight4600Fuel Capacity116Person CapacityYacht CertifiedFuel TypeGasolineDriveSingle OutboardBeam9'2"Draft15Used2020 Bennington 23SSBXD$54,999$425/mo.Get FinancingStatusIN STOCKLocationElkhorn, WIHours118Stock #UBA1125-B3-L ADDITIONAL FEATURES * Yamaha F200XB Engine * Power Bimini * Rockford Fosgate Stereo * Table with Cup Holders * Pop Up Cleats *... READ MORE Check AvailabilityView Boat Quick LookLength23Hours118Hull TypeAluminumFuel TypeGasolineEngine Horsepower175PowerYamaha 175DriveSingle OutboardUsed2022 FourWinns HD2 I/O$44,999$347/mo.Get FinancingStatusIN STOCKLocationElkhorn, WIHours139Stock #UBC2725-B1-B ADDITIONAL FEATURES * Mercruiser 4.5L Engine * Custom Trailer * Extended Swim Platform * Bimini * Kicker Stereo * Walk Thru Su... READ MORE Check AvailabilityView Boat Quick LookLength20Weight2700Fuel Capacity40Person Capacity10Hours139Fuel TypeGasolineDriveSingle I/ONew2024 Cobalt R6 Request PriceStatusIN STOCKLocationCape Coral, FLManufacturerCobaltStock #COB456517-B1 STANDARD FEATURES * 250 Verado w/PAS * Accessory Power Plug - 12 Volt (dual) * Composite Helm Eyebrow, Custom Stitching * Depth ... READ MORE Check AvailabilityView Boat Quick LookLength26Weight5,300Fuel Capacity80Person Capacity14Fuel TypeGasolineDriveOutboardBeam8' 6"Used2019 Bennington 20SSRCX$24,499$189/mo.Get FinancingStatusSALE PENDINGLocationSister Bay, WIHours265Stock #UBA1025-B2-H STANDARD FEATURES * All in One Kicker Speaker System (KMC1) * Console Courtesy Light * Custom Sterling Gauge Package: Fuel, Tacho... READ MORE Check AvailabilityView Boat Quick LookLength20Weight1761Fuel Capacity21.4 GalHours265Hull TypeAluminumFuel TypeGasolineDriveOutboardBeam8' 6"Draft10-12"Used2017 Crest 220SLRD$37,999$293/mo.Get FinancingStatusIN STOCKLocationElkhorn, WIManufacturerCrestStock #UBA1125-B1-G ADDITIONAL FEATURES * 2017 Suzuki DF150 Engine * Bimini w/ Dome Light * Ski Tow * Navigation Lights * Docking Lights * Boardin... READ MORE Check AvailabilityView Boat Quick LookLength22Weight2450Person Capacity12Hull TypeAluminumFuel TypeGasolineEngine Horsepower150PowerSuzuki 150hpDriveSingle OutboardBeam8'6"New2025 Bennington 22SSR-SPS Request PriceStatusIN STOCKLocationElkhorn, WIManufacturerBenningtonStock #BEN927900-B1-Stock STANDARD FEATURES * 12 Volt Receptacle USB A/C * Console Courtesy Light * Custom Sterling Gauge Package: Fuel, Tachometer and Tri... READ MORE Check AvailabilityView Boat Quick LookLength22Weight3017Fuel Capacity23.9 gallonsPerson Capacity12Hull TypeAluminumFuel TypeGasolineEngine Horsepower150DriveOutboardBeam8' 6"New2025 Boston Whaler 170 Montauk Request PriceStatusIN STOCKLocationSister Bay, WIManufacturerBoston WhalerStock #BWH2743928-B1-Stock STANDARD FEATURES * 170 Montauk Base Package (17mtk) 90 Exlpt Efi Command Thrust 4-Stroke Mercury Engine, 25 Gallon Capacity Int... READ MORE Check AvailabilityView Boat Quick LookLength17Weight1700Fuel Capacity25Person Capacity7Hull TypeFiberglassFuel TypeGasolineEngine Horsepower115DriveOutboardBeam7'3''Draft12New2025 Boston Whaler 170 Montauk Request PriceStatusIN STOCKLocationSister Bay, WIManufacturerBoston WhalerStock #BWH2743919-B1-Stock STANDARD FEATURES * 170 Montauk Base Package (17mtk) 90 Exlpt Efi Command Thrust 4-Stroke Mercury Engine, 25 Gallon Capacity Int... READ MORE Check AvailabilityView Boat Quick LookLength17Weight1700Fuel Capacity25Person Capacity7Hull TypeFiberglassFuel TypeGasolineEngine Horsepower115DriveOutboardBeam7'3''Draft12New2025 Boston Whaler 250 Dauntless Request PriceStatusIN STOCKLocationSister Bay, WIManufacturerBoston WhalerStock #BWH2744373-B1-Stock STANDARD FEATURES * 250 DAUNTLESS BASE PACKAGE (25DNT): 250 XXL V8 (DTS) 4-STROKE MERCURY ENGINE, 90 GALLON INTEGRATED FUEL TANK... READ MORE Check AvailabilityView Boat Quick LookLength25Weight5600Fuel Capacity90Person Capacity10Hull TypeFiberglassFuel TypeGasolineEngine Horsepower300DriveOutboardBeam8'6''Draft15New2025 Moomba Craz (MS) Request PriceStatusIN STOCKLocationElkhorn, WIManufacturerMoombaStock #MOO589348-M1-STOCK STANDARD FEATURES * 2025 Indmar 6.2L Ford Raptor 400, Catalyst w/1.7 trans V-drive * Boatmate Tandem Axle ADDITIONAL FEATURES ... READ MORE Check AvailabilityView Boat Quick LookLength22Weight4,700 lbsFuel Capacity70Person Capacity15Fuel TypeGasolineEngine Horsepower350DriveInboard-VBeam102"Draft27.5"New2025 Monaco 235SFL$75,834$585/mo.Get FinancingStatusIN STOCKLocationJohnsburg, ILManufacturerMonacoStock #MON242680-B1-Stock STANDARD FEATURES * Docking Lights: LED * Extended Deck w/ SS Safety Barrier * Ski Tow - Deluxe - Cage Style - Extended Deck * H... READ MORE Check AvailabilityView Boat Quick LookLength23Weight2694Fuel Capacity30Person Capacity12Hull TypeAluminumFuel TypeGasolineEngine Horsepower200PowerYamaha F200XCDriveOutboardBeam8'6"Draft12"New2025 Bennington 20SSB Request PriceStatusIN STOCKLocationThree Lakes, WIManufacturerBenningtonStock #BEN927898-B1-Stock STANDARD FEATURES * 12 Volt Receptacle USB A/C * Console Courtesy Light * Custom Sterling Gauge Package: Fuel, Tachometer and Tri... READ MORE Check AvailabilityView Boat Quick LookLength20Weight2317Fuel Capacity23.9 gallonsPerson Capacity10Hull TypeAluminumFuel TypeGasolineEngine Horsepower90DriveOutboardBeam8' 6"New2025 Bennington 22SSB Request PriceStatusIN STOCKLocationThree Lakes, WIManufacturerBenningtonStock #BEN927902-B1-Stock STANDARD FEATURES * 12 Volt Receptacle USB A/C * Console Courtesy Light * Custom Sterling Gauge Package: Fuel, Tachometer and Tri... READ MORE Check AvailabilityView Boat Quick LookLength22Weight2801Fuel Capacity23.9 gallonsPerson Capacity10Hull TypeAluminumFuel TypeGasolineEngine Horsepower115DriveOutboardBeam8' 6"New2025 Bennington 20SSR Request PriceStatusIN STOCKLocationThree Lakes, WIManufacturerBenningtonStock #BEN927897-B1-Stock STANDARD FEATURES * 12 Volt Receptacle USB A/C * Console Courtesy Light * Custom Sterling Gauge Package: Fuel, Tachometer and Tri... READ MORE Check AvailabilityView Boat Quick LookLength20Weight2317Fuel Capacity23.9 gallonsPerson Capacity10Hull TypeAluminumFuel TypeGasolineEngine Horsepower90DriveOutboardBeam8' 6"New2025 Bennington 22SSR Request PriceStatusIN STOCKLocationThree Lakes, WIManufacturerBenningtonStock #BEN927901-B1-Stock STANDARD FEATURES * 12 Volt Receptacle USB A/C * Console Courtesy Light * Custom Sterling Gauge Package: Fuel, Tachometer and Tri... READ MORE Check AvailabilityView Boat Quick LookLength22Fuel Capacity23.9 gallonsHull TypeAluminumFuel TypeGasolineEngine Horsepower115DriveOutboardBeam8' 6"New2025 Bennington 21SSR Request PriceStatusIN STOCKLocationThree Lakes, WIManufacturerBenningtonStock #BEN927899-B1-Stock STANDARD FEATURES * 12 Volt Receptacle USB A/C * Console Courtesy Light * Custom Sterling Gauge Package: Fuel, Tachometer and Tri... READ MORE Check AvailabilityView Boat Quick LookLength21Weight2278Fuel Capacity23.9 gallonsPerson Capacity10Hull TypeAluminumFuel TypeGasolineEngine Horsepower115DriveOutboardBeam8' 6"New2025 Bennington 22MSB-SPS Request PriceStatusIN STOCKLocationElkhorn, WIManufacturerBenningtonStock #BEN927903-B1-Stock STANDARD FEATURES * 12 Volt Receptacle * Console Courtesy Light * Console Footrest * Locking Side Access Console Door * Locking... READ MORE Check AvailabilityView Boat Quick LookLength22Fuel Capacity33Person Capacity12Hull TypeAluminumFuel TypeGasolineEngine Horsepower200DriveOutboardBeam8' 6"Used2023 Harris Flote Boat 250 GM SLEC TT$104,999$811/mo.Get FinancingStatusIN STOCKLocationNashotah, WIManufacturerHarrisStock #UBK1924-B1-HCheckout the 2023 Harris Flote Boat 250 GM SLEC TT by The Boat House at Nashotah, WI location... READ MORE Check AvailabilityView Boat Quick LookLength25Hull TypeAluminumFuel TypeGasolineDriveSingle OutboardUsed2022 Cobia 237 CC$82,995$641/mo.Get FinancingStatusIN STOCKLocationNaples, FLHours236Stock #UBC2625 ADDITIONAL FEATURES * Digital Yamaha 300XSB * Minnekota Trolling motor with charger * Garmin GPS w/transom mount transducer * Si... READ MORE Check AvailabilityView Boat Quick LookLength24Weight4515Fuel Capacity128Person Capacity10Hours236Fuel TypeGasolineEngine Horsepower300PowerYamaha F300NSBDriveSingle OutboardBeam8'10Draft30 inShow MoreFiltersClear filtersClear filtersBoat ConditionNew BoatsUsed BoatsLocationCape Coral61resultsElkhorn98resultsJohnsburg70resultsLake Geneva1resultsNaples47resultsNashotah57resultsPort Charlotte50resultsSister Bay37resultsThree Lakes58resultsWhitewater16resultsManufacturerAAD Custom1resultsAqua Patio5resultsAquaPatio1resultsAxis1resultsBayliner3resultsBennington103resultsBoston Whaler30resultsCarolina Skiff2resultsCenturion1resultsChaparral2resultsShow more CategoryAluminum Fish3resultsBay30resultsBowrider70resultsCenter Cockpit1resultsCenter Console73resultsCruiser4resultsCuddy Cabin2resultsDeck Boat48resultsDual Console5resultsFreshwater Fishing12resultsJet2resultsPontoon157resultsRunabout1resultsSki and Wakeboard Boat70resultsPriceto$to$Lengthto13 ft.75 ft.YeartoGoEngine Hoursto1 hr1,119 hrStatusINTERNET SPECIAL!10resultsIn Stock355resultsJUST SOLD!1resultsSALE PENDING25resultsSPECIAL SAVINGS!104results The Boat House in Winnetka, IL is dedicated to ensuring that the boating lifestyle is comprehensive, offering more than just the perfect boat. It’s about having the right tools and equipment to enjoy every moment on the water, no matter where you are. A high quality boat trailer is essential for any boater looking to embark on new adventures with confidence. With a range of new and used boat trailers for sale, each designed to secure and protect your watercraft, you can explore the Winnetka, IL waterways with peace of mind. Enhance Your Boating Experience in Winnetka, IL With the Right Boat Trailer for Sale Boat trailers play a crucial role in expanding your boating possibilities. With numerous lakes, rivers, and coastal areas to explore across the Winnetka, IL, the right trailer allows you to transport your boat safely and easily. Offering a selection of new and used trailers for sale, each tailored to different boat types, ensures that every journey starts and ends smoothly in Winnetka, IL. From single axle trailers for smaller boats to tandem axle options for larger watercrafts, there's a solution for every need. Choosing the Perfect Trailer for Your Boat in Winnetka, IL Partnering with trusted brands ensures that each boat trailer for sale is built to last, providing durability and reliability on the Winnetka, IL road. Therefore, our knowledgeable team is ready to assist in finding the ideal trailer that fits your boat’s size, weight, and specific boating needs, all while providing you with a quality brand you can trust. Whether you're cruising the waters of the Winnetka, IL or beyond, the right trailer ensures your boating experience is seamless and enjoyable. Reach out today to explore our inventory and receive personalized guidance on selecting the perfect boat trailer for sale for all your adventures. Other Boat Trailers in Winnetka, IL Boats Locations Boat Trailers in Winnetka, IL Boats in Illinois Boat Trailers in Winnetka, IL Boats in Wisconsin Boat Trailers in Winnetka, IL Boats in Minnesota Boat Trailers in Winnetka, IL Boats in Iowa Boat Trailers in Winnetka, IL Boats in Florida