Sailboats for sale

- New Arrival
1987 Bristol 41.1 Aft Cockpit
$85,000
St Augustine, FL 32084 | Edwards Yacht Sales
- In-Stock
1987 Island Packet 38
$58,500
Norfolk, VA 23518 | Beaufort Yacht Sales
1986 Cape Dory Motorsailer 300
$39,000
LaPointe, WI 54850 | Big Water Boats
- Price Drop
1995 Beneteau Oceanis 440
$69,000
↓ Price Drop
Vero Beach, FL 34950 | Private Seller
- New Arrival
2002 Beneteau Oceanis 393
$115,000
Annapolis, MD 21401 | North Point Yacht Sales
1998 Beneteau Oceanis 50
$149,000
Lake Worth Beach, FL 33462 | United Yacht Sales
2003 Leopard 47
$210,000
Fajardo, PR 00773 | The Multihull Company
1986 Krogen 38
$60,000
Racine, WI 53402 | Racine Riverside Marine, Inc.
1990 Catalina 30
$19,000
Pick City, ND 58545 | Private Seller
2017 Beneteau Oceanis 37
$165,000
$1,229/mo*
San Diego, CA 92101 | Marine Servicenter
1989 Custom Schooner Liveaboard
$169,000
Shady Side, MD 20778 | YachtSalesInternational.Com
1995 Catalina C270
$19,000
Coconut Grove, FL 33133 | Private Seller
- Price Drop
2001 Catalina 320
$29,800
↓ Price Drop
Washington, NC 27889 | Private Seller
- Sponsored
2026 Tracker Pro Guide V-175 Combo
$38,065
$331/mo*
Columbus, OH 43224 | Sizzle Marine
- Sponsored
2025 Yamaha WaveRunner VX Cruiser HO
$13,399
Columbus, OH 43224 | Sizzle Marine
- Sponsored
2024 Godfrey SWEETWATER 2286 SFL
$57,995
$432/mo*
Columbus, OH 43224 | Sizzle Marine
1992 Hans Christian 33 Traditional
$125,900
Northport, ME 04849 | Private Seller
- Price Drop
- In-Stock
1986 Sabre 36
$25,000
↓ Price Drop
Beaufort, NC 28516 | Beaufort Yacht Sales
- New Arrival
1984 Tayana 37
$54,900
Palm Coast, FL 32164 | United Yacht Sales
- Price Drop
1974 Bristol 40
$5,000
↓ Price Drop
Coltons Point, MD 20626 | Private Seller
- Price Drop
1977 Cape Dory 25
$3,000
↓ Price Drop
Reedville, VA 22539 | Private Seller
1980 Cape Dory 27
$12,000
Cape Elizabeth, ME 04107 | Private Seller
1971 Nautor Swan 43 Sloop
$63,000
Portsmouth, RI 02871 | Luke Brown Yachts
2016 J Boats J/70
$45,000
$392/mo*
Annapolis, MD 21403 | North Point Yacht Sales
2006 Lagoon 500
$399,000
$2,972/mo*
Charleston, SC 29412 | The Multihull Company
- New Arrival
2018 Nautor Swan 54
$1,450,000
$10,802/mo*
Annapolis, MD 21401 | North Point Yacht Sales
2022 Bali 4.8
$220,000
$1,639/mo*
Tortola, FL 33101 | Private Seller
- Price Drop
2005 Lagoon 440
$230,000
↓ Price Drop
$1,713/mo*
Saco, ME 04072 | The Multihull Company
- New Arrival
2009 Brooklin Boat Yard 2009
$2,850,000
$21,232/mo*
Newport, RI 02840 | Northrop and Johnson
- Available Soon
2026 Fountaine Pajot 44
$856,000
$6,377/mo*
San Diego, CA 92106 | ACY Yachts
2004 PCI Gemini 105mc
$83,000
Kemah, TX 77565 | Private Seller
2008 Oyster 46
$599,000
$4,462/mo*
Greenport, NY 12534 | Northrop and Johnson
2015 MacGregor 26M
$29,990
$261/mo*
Hutchinson Island, FL 34949 | Private Seller
1981 Sam Crocker 286
$17,500
New Harbor, ME 04554 | Private Seller

Sailboats

Sailboats are propelled partly or entirely by sails and include a variety of types from cutters to sloops and catboats to schooners. Traditionally sailboats are monohull displacement hulls, but catamarans and multi-hulls are becoming more common. There are many kinds of sailboats and they carry different rigs (masts, supporting shrouds and stay, and sail combinations). Sloops have one mast and generally two sails – a mainsail and a headsail called a jib or genoa. If there are two headsails, the boat is usually called a cutter rig. Ketches have two masts with the aft mast shorter than the main mast. Yawls also have a shorter aft mast but it’s farther back on deck than a ketch. A schooner can have two or three masts with the forward-most one being shorter. Sailboats differ by size, use and strength of build – so it’s important to consider carefully which type of sailboat is best for your intended use. Once you understand the different options available, you can make an educated choice.

1987 Bristol 41.1 Aft Cockpit

1987 Island Packet 38

1986 Cape Dory Motorsailer 300

1995 Beneteau Oceanis 440

2002 Beneteau Oceanis 393

1998 Beneteau Oceanis 50

2003 Leopard 47

1986 Krogen 38

1990 Catalina 30

2017 Beneteau Oceanis 37

1989 Custom Schooner Liveaboard

1995 Catalina C270

2001 Catalina 320

2026 Tracker Pro Guide V-175 Combo

2025 Yamaha WaveRunner VX Cruiser HO

2024 Godfrey SWEETWATER 2286 SFL

1992 Hans Christian 33 Traditional

1986 Sabre 36

1984 Tayana 37

1974 Bristol 40

1977 Cape Dory 25

1980 Cape Dory 27

1971 Nautor Swan 43 Sloop

2016 J Boats J/70

2006 Lagoon 500

2018 Nautor Swan 54

2022 Bali 4.8

2005 Lagoon 440

2009 Brooklin Boat Yard 2009

2026 Fountaine Pajot 44

2004 PCI Gemini 105mc

2008 Oyster 46

2015 MacGregor 26M

1981 Sam Crocker 286

Sailboats

Expert Sailboats Reviews