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

Sort By:
AYS Exclusive
SEABBATICAL 314227
SEABBATICAL
$185,000

MLS ID: 314227

Category: Cruising Sailboat

Length: 46.91"(14.3m)

Location: Annapolis, Maryland, United States

Broker: Andre De Klerk

AYS Exclusive
CASCADIA CURRENT 314847
CASCADIA CURRENT
$149,500

MLS ID: 314847

Category: Cruising/Racing 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

AYS Exclusive
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

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
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

AYS Exclusive
TIKI THYME 314313
TIKI THYME
$87,500

MLS ID: 314313

Category: Cruising Sailboat

Length: 35"(10.66m)

Location: Annapolis, Maryland, United States

Broker: Andre De Klerk

Sale Pending
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

Sale Pending
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