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    Within 200 Miles Of
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Sailboat boats for sale in Naperville Illinois

There are 16 new and used boats for sale in Naperville Illinois. Find boats of all types and price ranges on BoatCrazy.com. We offer boats for sale by owner and dealers. Browse through Fishing Boats, Center Consoles, Pontoons, Cruisers, PWCs and more in Naperville Illinois.
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    Within 200 Miles Of
    Naperville, Illinois
16 boats found within 200 miles from Naperville, Illinois

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  • 1993 Catalina 42 MKI

    1993 Catalina 42 MKI

    $60,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 42' / 14'
    • 1993 / Used
    • $60,000

    1993 Catalina 42 MKIThis vessel is equipped with a Dodger, Bimini and connector. Refrigerator, VHF, Stereo System have been upgraded. An AIS system and Garmin GPS/Depth Sounder has... View Details

    View 53 Photos and Details Contact Seller
    $60,000
    VIEW DETAILS
  • 1986 Krogen 38 Cutter

    1986 Krogen 38 Cutter

    $60,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 44' / 12'
    • 1986 / Used
    • $60,000

    1986 Krogen Cutter 38"Intrepid"Intrepid has had two owners and has resided on the freshwater of Lake Michigan since 2012. Designed by James S. Krogen and built by Kady-Krogen Yacht... View Details

    View 56 Photos and Details Contact Seller
    $60,000
    VIEW DETAILS
  • 2024 Dufour D470

    2024 Dufour D470

    $695,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 48' / 15'
    • 2024 / New
    • $695,000

    2024 DuFour 470• 3 cabins 2 heads, toilets equipped with holding tanks• Infused hull• LED interior lights + indirect light• Upgrade to 75 hp engine - Saildrive• 4 blades folding pr... View Details

    View 8 Photos and Details Contact Seller
    $695,000
    VIEW DETAILS
  • 2000 Hunter 410

    2000 Hunter 410

    $116,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 43' / 13'
    • 2000 / Used
    • $116,000

    2000 Hunter 410 - "Cabaret"This Hunter has been maintained very well over its life, kept on the Great Lake Michigan. Take your family sailing in comfort and let your worries sail a... View Details

    View 50 Photos and Details Contact Seller
    $116,000
    VIEW DETAILS
  • 1994 Pacific Seacraft 34

    1994 Pacific Seacraft 34

    $110,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 34' / 10'
    • 1994 / Used
    • $110,000

    1994 Pacific Seacraft 34"Esmerelda"This William Crealock designed 1994 Pacific Seacraft cutter is ready for your next sailing adventure. The vessel has been stored indoors througho... View Details

    View 65 Photos and Details Contact Seller
    $110,000
    VIEW DETAILS
  • 1983 O Day 34

    1983 O Day 34

    $35,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 34' / 11'
    • 1983 / Used
    • $35,000

    1983 O'Day 34"Dawn Treader"The O'Day 34. This boat offers plenty of comfortable room below deck and a spacious cockpit which make this a great weekend cruiser and daysailer! Winter... View Details

    View 50 Photos and Details Contact Seller
    $35,000
    VIEW DETAILS
  • 2019 Beneteau Oceanis 35.1

    2019 Beneteau Oceanis 35.1

    $164,699
    Racine, WI
    • Racine, WI
    • Sailboat
    • 34' / 12'
    • 2019 / Used
    • $164,699

    2019 Beneteau Oceanis 35.1GENERAL SPECIFICATIONSOverall Length (L.O.A): (without bowsprit): 34’3’’Hull length: 32’9’’L.W.L.: 31’10’’Hull Beam: 12’2’’Light displacement: 13,149 lbsS... View Details

    View 24 Photos and Details Contact Seller
    $164,699
    VIEW DETAILS
  • 1987 Bayfield 32C

    1987 Bayfield 32C

    $30,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 32' / 10'
    • 1987 / Used
    • $30,000

    1987 Bayfield 32CEmbark on your next adventure with this beautifully crafted Bayfield Yachts cutter rig, a timeless vessel built in Ontario, Canada. Designed for durability and per... View Details

    View 45 Photos and Details Contact Seller
    $30,000
    VIEW DETAILS
  • 1987 Oyster 46.5

    1987 Oyster 46.5

    $145,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 46' / 14'
    • 1987 / Used
    • $145,000

    1987 Oyster 46.5"Here Be Dragons"LOA: 46ft 2inBEAM: 14ftDRAFT: 6ft 6inDISPLACEMENT: 32,000 LbsFUEL: 120 GalFRESH WATER: 220-250 Gal (With Water Heater!)HOLDING: ~26 GalOwner's Desc... View Details

    View 45 Photos and Details Contact Seller
    $145,000
    VIEW DETAILS
  • 1982 Campion C320

    1982 Campion C320

    $15,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 32' / 10'
    • 1982 / Used
    • $15,000

    1982 Campion C-320 Pilot House"LINDISFARNE"LOA: 32ftBeam: 10ft 1inBridge Clearance: 52ftEngine:17hp Volvo Diesel Model: MD7BEngine hours: 804 hrsRadarVHF RadioHood mainsail - fair... View Details

    View 57 Photos and Details Contact Seller
    $15,000
    VIEW DETAILS
  • 1983 Marlow Hunter 27 Cherubini

    1983 Marlow Hunter 27 Cherubini

    $15,500
    Racine, WI
    • Racine, WI
    • Sailboat
    • 27' / 9'
    • 1983 / Used
    • $15,500

    This 1983 Hunter 27 (Tall Rig) has been cared for and loved for many years. The boat has been maintained to a very high level, which will leave a lucky new owner with less headache... View Details

    View 57 Photos and Details Contact Seller
    $15,500
    VIEW DETAILS
  • 2019 Beneteau Oceanis 41.1

    2019 Beneteau Oceanis 41.1

    $289,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 40' / 13'
    • 2019 / Used
    • $289,000

    2019 Beneteau Oceanis 41.1**Listing currently under construction, More pictures coming soon** Your Next Dream Starts Here!Step aboard this beautifully maintained 2019 Beneteau Ocea... View Details

    View 10 Photos and Details Contact Seller
    $289,000
    VIEW DETAILS
  • 1985 C & C Landfall 39

    1985 C & C Landfall 39

    $59,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 39' / 12'
    • 1985 / Used
    • $59,000

    C&C Landfall 39A proven offshore cruising yacht with a balance of performance and comfort, this C&C Landfall 39 is fully equipped and extensively upgraded. Built by C&C Yachts, she... View Details

    View 57 Photos and Details Contact Seller
    $59,000
    VIEW DETAILS
  • 2020 Beneteau Oceanis 41.1

    2020 Beneteau Oceanis 41.1

    $309,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 40' / 0'
    • 2020 / Used
    • $309,000

    2020 Beneteau Oceanis 41.1KEEL: 5’6”HULL COLOR: WhiteFUEL CAPACITY: 53 GallonsFRESH WATER CAPACITY: 63 Gallon main tank plus 87 Gallon extra tank for extended cruisingWASTE CAPACIT... View Details

    View 12 Photos and Details Contact Seller
    $309,000
    VIEW DETAILS
  • 2012 Beneteau Oceanis 45

    2012 Beneteau Oceanis 45

    $283,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 45' / 14'
    • 2012 / Used
    • $283,000

    2012 Beneteau Oceanis 45US Elegance Pack: Simrad IS20 Graphic Displays (Log, Speed, Depth & Wind System @ Starboard & Port Helm; Cockpit Shower; Indirect Lighting With LED Interior... View Details

    View 44 Photos and Details Contact Seller
    $283,000
    VIEW DETAILS
  • 1978 American Spirit 23

    1978 American Spirit 23

    $6,400
    Reedsburg, WI
    • Reedsburg, WI
    • Sailboat
    • 23' / 0'
    • 1978 / Used
    • $6,400

    Stock #298982 Video of this vessel available at www [dot] popsells [dot] com/view/298982 Reason for selling is "Not using enough". ANY and ALL offers will be put in front of our... View Details

    View 10 Photos and Details Contact Seller
    $6,400
    VIEW DETAILS
Showing 1 to 16 of 16 boats found.

Sailboat Boats On Boatcrazy

As the name suggests, sailboats rely partly or entirely on the power of the wind for propulsion and use large cloth or synthetic sails for this purpose.

We have many kinds of Sailboats for Sale and as they differ by use, size and strength – it’s important to consider carefully which type of sailboat is best for your intended use.

Sailboat Boats On Boatcrazy

When looking to buy a quality Sailboat consider these top Sailboat Manufacturers

Hallberg-Rassy, Dufour, Beneteau, Brewer, Bluewater, Irwin, Herve, Endeavour, Corsair, Sabre, Hardin, Gulfstar, Willard.

Sailboat Boats For Sale by State

Sailboat Boats Frequently Asked Questions

How much does an average Sailboat cost?

Cruising sailboat prices vary. The average cost of new cruising sailboats is about $250K; however they range from around 100k all the way up to 500k For used models you should expect an expense between 10k-100k

To date, the average price for sailboat insurance has been around $250 to $1500 per year. This varies based on what type of policy and how much coverage you need- but it's usually cheaper than power boat insurance!

Obviously, the best time to buy a Sailboat is when the time is right for your budget! But there is never a bad time, as long as you are ready to handle the responsibility of owning such a boat, and on Boatcrazy, we have plenty to choose from! Each season also has its advantages and disadvantages, so understanding what each season presents can be of great help in finding a better deal.

Cruising Sailboats are the ultimate way to explore long distances, but for a Sailboat to travel a long journey, the boat needs to be livable, should have the right amenities and plenty of storage space, and should be able to travel at a decent speed. Moreover, it should be strong and durable.

Sailing through the Indian Ocean has come to be a challenging task owing to its characteristic of being one of the most deadly ocean waters in the world.

Centerboards are an essential part of any boat, but they're especially important on smaller vessels that don't have the weight or power to self-propel. Centerboard equipped boats range in length from 12 - 25 feet and work as both stability and steering systems.