Search below used Annapolis catamaran and sailboats for sale near you, in Maryland, and across the Chesapeake Bay,  including sail boat brands and models available globally by builder, length, price, year, and more.

Browse all Used Sailboats for Sale

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AYS Exclusive
LONELY GIRL 312303
LONELY GIRL
$152,900

MLS ID: 312303

Category: Cruising Sailboat

Length: 43.16"(13.15m)

Location: Annapolis, Maryland, United States

Broker: Brenden Tillman

AYS Exclusive
CELTIC CROSS 312425
CELTIC CROSS
$114,500

MLS ID: 312425

Category: Cruising Sailboat

Length: 38.16"(11.63m)

Location: Annapolis, Maryland, United States

Broker: Brenden Tillman

AYS Exclusive
CATALINA 380 310791
CATALINA 380
$83,500

MLS ID: 310791

Category: Cruising/Racing Sailboat

Length: 38"(11.58m)

Location: Annapolis, Maryland, United States

Broker: Brenden Tillman

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JUGGERNAUT 273167
JUGGERNAUT
$90,000

MLS ID: 273167

Category: Cruising/Racing Sailboat

Length: 37.75"(11.5m)

Location: Annapolis, Maryland, United States

Broker: Matt Weimer

Sale Pending
SHE'S A PEACH 310893
SHE'S A PEACH
$290,000

MLS ID: 310893

Category: Catamaran

Length: 37.66"(11.48m)

Location: Annapolis, Maryland, United States

Broker: Andre De Klerk

AYS Exclusive
CARPE VENTUM 313263
CARPE VENTUM
$99,500

MLS ID: 313263

Category: Cruising Sailboat

Length: 36.91"(11.25m)

Location: Annapolis, Maryland, United States

Broker: Matt Weimer

AYS Exclusive
TRITON 308407
TRITON
$32,500

MLS ID: 308407

Category: Cruising/Racing Sailboat

Length: 36.5"(11.12m)

Location: Annapolis, Maryland, United States

Broker: Brenden Tillman

AYS Exclusive
NO NAME 311651
NO NAME
$179,900

MLS ID: 311651

Category: Cruising Sailboat

Length: 35"(10.66m)

Location: Annapolis, Maryland, United States

Broker: Matt Weimer

AYS Exclusive
PAU HANA 313261
PAU HANA
$60,000

MLS ID: 313261

Category: Cruising Sailboat

Length: 35"(10.66m)

Location: Annapolis, Maryland, United States

Broker: Matt Weimer

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HAKUNA MATATA 311925
HAKUNA MATATA
$67,900

MLS ID: 311925

Category: Cruising Sailboat

Length: 33.83"(10.31m)

Location: Annapolis, Maryland, United States

Broker: Brenden Tillman

AYS Exclusive
KONA WIND 313029
KONA WIND
$99,995

MLS ID: 313029

Category: Cruising Sailboat

Length: 33.5"(10.21m)

Location: Annapolis, Maryland, United States

Broker: Andre De Klerk

AYS Exclusive
BUONA FORTUNA 276632
BUONA FORTUNA
$39,995

MLS ID: 276632

Category: Cruising Sailboat

Length: 27.08"(8.25m)

Location: Annapolis, Maryland, United States

Broker: Jeff Nicklason