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Boats for sale in Chester Connecticut

There are 250 new and used boats for sale in Chester, Connecticut. Browse Pontoon, Express Cruiser, Fishing, Center Console, Walkaround, and Sailboat from brands like Sea Ray, Other, Premier, Bennington, Yamaha, and Chaparral on BoatCrazy. View a wide selection of boats from $4,500 to $799,999.
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  • Boats
  • Within 100 Miles Of
    Chester, Connecticut
250 boats found within 100 miles from Chester, Connecticut
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  • 2002 Mastercraft X30

    2002 Mastercraft X30

    $32,250
    Newtown, CT
    • Newtown, CT
    • Ski & Wake
    • 30' / 0'
    • 2002 / Used
    • $32,250

    Stock #332247 Reason for selling is "Too busy & kids have all grown up & moved out". ANY and ALL offers will be put in front of our seller! Submit your offer today! 330HP INDMAR... View Details

    View 7 Photos and Details Contact Seller
    $32,250
    VIEW DETAILS
  • 1985 O Day 35

    1985 O Day 35

    $28,550
    Port Jefferson, NY
    • Port Jefferson, NY
    • Sailboat
    • 35' / 0'
    • 1985 / Used
    • $28,550

    Stock #393959 ANY and ALL offers will be put in front of our seller! Submit your offer today! This 1985 O'day 35 is very special in that it is rigged for racing with a larger mas... View Details

    View 10 Photos and Details Contact Seller
    $28,550
    VIEW DETAILS
  • 2003 J Boats J/120

    2003 J Boats J/120

    $156,000
    Port Jefferson, NY
    • Port Jefferson, NY
    • Sailboat
    • 40' / 0'
    • 2003 / Used
    • $156,000

    Stock #467988 Reason for selling is "Sellers are done with boating for now". This J Boats has now been on the market a couple months. Looking for any offers! 2003 J BOAT J/120!... View Details

    View 10 Photos and Details Contact Seller
    $156,000
    VIEW DETAILS
  • 1987 Symbol 44 MKII Sundeck

    1987 Symbol 44 MKII Sundeck

    $100,000
    Center Moriches, NY
    • Center Moriches, NY
    • Yacht
    • 44' / 0'
    • 1987 / Used
    • $100,000

    Stock #267969 Video of this vessel available at www [dot] popsells [dot] com/view/267969 Reason for selling is "Purchased a smaller boat". ANY and ALL offers will be put in fron... View Details

    View 11 Photos and Details Contact Seller
    $100,000
    VIEW DETAILS
  • Price Drop 1998 Sea Ray 310 sundancer

    1998 Sea Ray 310 sundancer

    $29,999
    Center Moriches, NY

    Stock #375503 Reason for selling is "Buying something else". ANY and ALL offers will be put in front of our seller! Submit your offer today! 1998 Searay 310 Sundancer. Mercruise... View Details

    View 10 Photos and Details Contact Seller
    $29,999
    VIEW DETAILS
  • Price Drop 2018 Glastron GS259

    2018 Glastron GS259

    $55,000
    Center Moriches, NY

    Stock #469596 Video of this vessel available at www [dot] popsells [dot] com/view/469596 Reason for selling is "No longer using boat getting out of boating". ANY and ALL offers... View Details

    View 10 Photos and Details Contact Seller
    $55,000
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  • 1979 Privateer 21 Roamer

    1979 Privateer 21 Roamer

    $20,000
    Moriches, NY
    • Moriches, NY
    • Pilothouse
    • 21' / 0'
    • 1979 / Used
    • $20,000

    Stock #257828 Video of this vessel available at www [dot] popsells [dot] com/view/257828 Reason for selling is "Purchased a smaller boat". ANY and ALL offers will be put in fron... View Details

    View 10 Photos and Details Contact Seller
    $20,000
    VIEW DETAILS
  • Price Drop 2011 Chaparral 215 SSI

    2011 Chaparral 215 SSI

    $18,000
    Port Jefferson Station, NY
    • Port Jefferson Station, NY
    • Cuddy Cabin
    • 21' / 0'
    • 2011 / Used
    • $18,000

    Stock #459695 Video of this vessel available at www [dot] popsells [dot] com/view/459695 Reason for selling is "Change in plans". ANY and ALL offers will be put in front of our... View Details

    View 11 Photos and Details Contact Seller
    $18,000
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  • 2004 Aquasport 275 Explorer

    2004 Aquasport 275 Explorer

    $39,995
    Mastic Beach, NY
    • Mastic Beach, NY
    • Walkaround
    • 27' / 0'
    • 2004 / Used
    • $39,995

    Stock #445676 Reason for selling is "Buying something else". ANY and ALL offers will be put in front of our seller! Submit your offer today! Well-maintained boat with updated ca... View Details

    View 10 Photos and Details Contact Seller
    $39,995
    VIEW DETAILS
  • 2021 Monterey 378SE

    2021 Monterey 378SE

    $329,000
    Patchogue, NY
    • Patchogue, NY
    • Bowrider
    • 37' / 0'
    • 2021 / Used
    • $329,000

    Stock #363953 Reason for selling is "The seller does not use". ANY and ALL offers will be put in front of our seller! Submit your offer today! Beautiful 2021 Monterey 378se Many... View Details

    View 10 Photos and Details Contact Seller
    $329,000
    VIEW DETAILS
  • 2019 Prestige 520 Flybridge

    2019 Prestige 520 Flybridge

    $799,999
    Westport, CT
    • Westport, CT
    • Yacht
    • 52' / 0'
    • 2019 / Used
    • $799,999

    FOR QUESTIONS CONTACT: JOSH 929-274-1641 or prestige520forsale@gmail.com 2019 Prestige 520 Flybridge with Hardtop First sold/commissioned in 2020! Volvo warranties into July 2025!... View Details

    View 38 Photos and Details Contact Seller
    $799,999
    VIEW DETAILS
  • Price Drop 2013 Mirage PH32

    2013 Mirage PH32

    $149,500
    Peace Dale, RI
    • Peace Dale, RI
    • Pilothouse
    • 32' / 0'
    • 2013 / Used
    • $149,500

    Stock #434088 Reason for selling is "Moving Up". ANY and ALL offers will be put in front of our seller! Submit your offer today! 2013 Mirage Pilothouse 32 w/ low hour Yamaha 300... View Details

    View 10 Photos and Details Contact Seller
    $149,500
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  • 2007 Sea Ray 270 Amberjack

    2007 Sea Ray 270 Amberjack

    $49,900
    East Greenwich, RI

    Stock #390711 ANY and ALL offers will be put in front of our seller! Submit your offer today! Great for cruising or fishing, lower hours, must see! This 2007 Sea Ray 270 Amberja... View Details

    View 10 Photos and Details Contact Seller
    $49,900
    VIEW DETAILS
  • 1981 Mainship 34

    1981 Mainship 34

    $34,950
    East Greenwich, RI
    • East Greenwich, RI
    • Commercial
    • 34' / 0'
    • 1981 / Used
    • $34,950

    Stock #424959 Reason for selling is "Moving Up". ANY and ALL offers will be put in front of our seller! Submit your offer today! Classic Mainship 34 with desirable 200hp Perkins... View Details

    View 10 Photos and Details Contact Seller
    $34,950
    VIEW DETAILS
  • 2024 Sea Hunt Ultra 234

    2024 Sea Hunt Ultra 234

    $86,700
    Holbrook, NY

    Stock #470329 Video of this vessel available at www [dot] popsells [dot] com/view/470329 Reason for selling is "Looking to Upgrade". This Sea Hunt has now been on the market mor... View Details

    View 10 Photos and Details Contact Seller
    $86,700
    VIEW DETAILS
  • Price Drop 2017 Bennington 21SSRX

    2017 Bennington 21SSRX

    $31,900
    Chepachet, RI
    • Chepachet, RI
    • Pontoon
    • 21' / 0'
    • 2017 / Used
    • $31,900

    Stock #456889 ANY and ALL offers will be put in front of our seller! Submit your offer today! Good and Clean Condition! Well Maintained! Fresh Water Only! Low Hours! If you are... View Details

    View 10 Photos and Details Contact Seller
    $31,900
    VIEW DETAILS
  • 2005 Polar 2300 WA

    2005 Polar 2300 WA

    $31,000
    Dudley, MA
    • Dudley, MA
    • Walkaround
    • 23' / 0'
    • 2005 / Used
    • $31,000

    Stock #361307 Reason for selling is "Bought another boat.". ANY and ALL offers will be put in front of our seller! Submit your offer today! 2005 POLAR 2300 WA WALKAROUND, YAMAHA... View Details

    View 10 Photos and Details Contact Seller
    $31,000
    VIEW DETAILS
  • Price Drop 2012 Robalo R180 CC

    2012 Robalo R180 CC

    $28,000
    North Kingstown, RI

    Stock #479083 Reason for selling is "Moving Up". This Robalo has been on the market for more than 30 days (Feb 2nd). If you are thinking of making an offer, submit it today and l... View Details

    View 10 Photos and Details Contact Seller
    $28,000
    VIEW DETAILS
  • 2026 Premier 230 Intrigue GT RLO CL

    2026 Premier 230 Intrigue GT RLO CL

    Call for price
    Webster, MA
    • Webster, MA
    • Pontoon
    • 0' / 0'
    • 2026 / New
    • Call for price

    Premier Intrigue featuring GT styling with Open Water Panels and a Convertible Rear Lounge/Bed with Bow Starboard and Port Side Couches. Stand out on the water with a Fiberglass Bo... View Details

    View 3 Photos and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2026 Other 523CS

    2026 Other 523CS

    Call for price
    Webster, MA
    • Webster, MA
    • Pontoon
    • 0' / 0'
    • 2026 / New
    • Call for price

    500 Series 23' Convertible Stern in Platinum Blue with Evolution Red Accent. This Tritoon will be powered by the Yamaha 200hp V-Max SHO Outboard. Features include Roan Bronze Inter... View Details

    View 2 Photos and Details Contact Seller
    Call for price
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  • 2020 Bennington SXP Series 23

    2020 Bennington SXP Series 23

    $57,995
    Webster, MA
    • Webster, MA
    • Pontoon
    • 24' / 0'
    • 2020 / Used
    • $57,995

    This 23' Bennington Tritoon powered by the ultra-reliable Yamaha 200hp Outboard is in excellent condition and delivers strong performance with a smooth, stable ride. Boat has been... View Details

    View 12 Photos and Details Contact Seller
    $57,995
    VIEW DETAILS
Showing 43 to 63 of 250 boats found.
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