New and Used Sailboats For Sale

Sailboats have cruised the world’s lakes and oceans for centuries and remain popular among many skilled and dedicated watermen and women. They require a degree of skill and an awareness of the wind and weather while offering a traditional and exhilarating boating experience. Search for new or use... learn more about Sailboats

4,957 New and Used Sailboats

Moody 41 DS

Newport, Rhode Is... (United States of America)

41.08 ft.

2025

New

Like her bigger sisters, the Moody DS41 displays all the attributes of the Moody DS45 and DS54: ease of handling, the option of twin powered headsails, excellent all-...

Berthon International logo

P.O.A. *

Beneteau 36

North Beach, Mary... (United States of America)

36.42 ft.

2000

Used

The Beneteau 361 is a powerful and seafaring sailboat which will take you wherever you wish, with elegance and style. Innovative in terms of sailing pleasure and comf...

$55,000

Catalina 42'

Marina Del Rey, CA (United States of America)

137.8 ft.

2003

Used

Arlion Boat | 42' Catalina 2003 Second Owner after Catalina Yacht owner Inflatable Dinghy and 20hp Outboard Dinghy Davits New Strato Glass on Dodger ...

$175,000

Catalina 33

Kemah, Texas (United States of America)

32.74 ft.

2007

Used

Accomodations The interior of the 309 feels much larger than her 31 feet. There is an easy descent (no steep ladder) into a very spacious main salon and galley are...

$74,900

Beneteau Oceanis Clipper 423

Deltaville, Virginia (United States of America)

41.99 ft.

2007

Used

The Beneteau 423 is a classic.It’s the last generation of Beneteau to sport the Cherry finish on the interior woodwork.The interior exudes warmth, thanks ...

YaZu Yachting logo

$152,000

Pacific Seacraft "CREALOCK" 34

Green Cove Spring... (United States of America)

33.99 ft.

1987

Used

Beautiful Blue Water Sailer!! Wonderful Care!! Tiller Steering!! If you're searching for a sailboat that combines classic beauty with unmatched performance, look no...

POP Sells logo

$72,900

Pacific Seacraft Orion 27

Beaufort (United States of America)

27.0 ft.

1990

Used

“The Orion 27 sails well in all sea conditions and sports a well-balanced sailplan that makes it fast on and off the wind. Responsive and maneuverable are words often...

$39,500

Caliber 33

New Bern, North C... (United States of America)

33.01 ft.

1989

Used

1989 Caliber 33 Sailboat The Caliber 33 is a big boat tucked into a small package. Designed by company co-founder, Michael McCreary, the Caliber 33 is a solidly buil...

$35,000

Oyster 53

Marblehead, (United States of America)

52.99 ft.

2003

Used

DESCRIPTION DREAM AGAIN II is a great example of the Oyster 53. She shows very well and has benefitted from a constant professional maintenance program. The safe, ...

$465,000

Jeanneau Sun Odyssey 36i

Stuart, Florida (United States of America)

35.76 ft.

2010

Used

2010 Jeanneau Sun Odyssey 36i We are very pleased to add this well kept 2010 Jeanneau Odyssey 36i to our sailing fleet of offerings. Designed by Marc Lombard, the 3...

$109,000

Fountaine Pajot 44'

Puerto Vallarta, ... (United States of America)

144.36 ft.

2014

Used

Bisou Boat | 44' Fountaine Pajot 2014 Fountaine Pajot Helia 44 - Owners Version Ready to Cruise - Located in Puerto Vallarta, Mexico Australian Registere...

$525,000

Catalina 320

Bay Shore, New York (United States of America)

31.99 ft.

1996

Used

Beautiful Catalina 320 -- ready to create some great memories? This 1996 Catalina 320 is a well-maintained sailboat, perfect for those seeking both cruising comfort...

POP Sells logo

$35,600

Vagabond 39

Jacksonville, Flo... (United States of America)

39.07 ft.

1985

Used

Ideal size for long distance cruising, she can be handled by one experienced sailor, yet comfortably accommodate a family of four.Storage space is ample as well...

Sunshine Cruising Yachts logo

$44,500

Dettling Express Cruiser 51

Deltaville, Virginia (United States of America)

50.98 ft.

2003

Used

This Dettling 51, Blue Zone (#12 of 17 built), is a rare offering of a fine express cruising yacht with sleek lines, sea-kindly motion, extremely well appointed and c...

YaZu Yachting logo

$629,000

Hunter Passage 42

Daytona Beach, Fl... (United States of America)

42.49 ft.

1993

Used

Whether you dream of cruising around the world or simply spending weekends onboard in tranquility, the Hunter 42 might just be the perfect sailboat. The Hunter 42 of...

Sunshine Cruising Yachts logo

$109,900

Lagoon 380 S2
Lagoon 380 S2 Lagoon 380 S2 Lagoon 380 S2

Punta Gorda, FL (United States of America)

37.99 ft.

2005

Used

*Rare Opportunity: 2005 Lagoon 380 S2 Catamaran Spacious 3-Cabin Owner's Version* This popular catamaran with extensive upgrades offers a perfect blend of performance and comfort for cruising enthusiasts. The owners suite occupies the starboard hull, providing a spacious private cabin ...

The Multihull Company logo

$245,000

Catalina 355

Kemah, Texas (United States of America)

35.43 ft.

2012

Used

Preliminary Listing Subject to Owner's Approval Yanmar Diesel with Only 227 Hours Lead Keel with 4’ 6” Draft New Dripless Shaft Seal February 2022 New Custom Cock...

$194,900

Jeanneau 35

Kemah, Texas (United States of America)

35.24 ft.

2005

Used

Updates Recent additions within theLast two years Jib Sunbrella Sun Cover replaced 33 lb Rocna self-righting anchor 140 ft chain rode and chain...

$83,900

Jeanneau Sun Fast 30 One Design

Newport,RI, (United States of America)

34.09 ft.

2024

New

Description The newly launched Jeanneau Sun Fast 30 One Design is an affordable, innovative, powerful, and versatile 30-foot sailboat that aims to make offsho...

P.O.A.

Jeanneau SUN FAST 3300

Newport,RI, (United States of America)

33.17 ft.

2023

New

Description #1 DOUBLEHANDED RACE BOAT IN THE USA! A unique opportunity to own a "Performance Race Optimized" ex-demo, mint condition Sun Fast 3300 that has be...

$349,500

Leopard 40

Deltaville, VA (United States of America)

39.99 ft.

2019

Used

We are Proud to Present the Exceptional 2019 Leopard 40 Owners Version "Haven", Ready to Sail Away anywhere now!! 2019 ROBERTSON AND CAINE LEOPARD 40 – "Haven" BROK...

$499,000

Jeanneau Sun Odyssey 54 DS

North Kingstown, ... (United States of America)

54.92 ft.

2004

Used

The 54 Deck Salon is the Flagship of the manufacturer and a luxurious performance cruiser. The condition of Panache is immaculate. Full Specifications Accommodati...

$325,000

Beneteau Oceanis Clipper 361

North Kingstown, ... (United States of America)

36.42 ft.

2001

Used

Builders comments; The Clipper 361 is a powerful and seafaring sail boat which will take you wherever you wish, in the best possible conditions. Innovative in terms ...

$95,900

Nonsuch 30 ULTRA

Greenport, New York (United States of America)

30.25 ft.

1987

Used

Accommodations Forward you have a double berth to port with a hanging locker and dresser to starboard. Aft to starboard is the enclosed head with access from the m...

$45,000

Clock Sale pending
Nautor Swan Swan 80

, Florida (United States of America)

82.35 ft.

2012

Used

BROKER COMMENTS The Nautor’s Swan 80FD is just as well suited to gliding through a regatta or set sail for a family adventure. The Swan 80-102 is designed fo...

$3,254,449 *

O'day Boats 34 SL

Oyster Bay, New York (United States of America)

33.99 ft.

1984

Used

1984 O'Day 34. Well maintained. Ready for the next adventure! This O'Day 34, located on the North Shore of Long Island, New York, is a well-maintained sloop that tr...

POP Sells logo

$25,250

Beneteau Oceanis 300

Westbrook, Connec... (United States of America)

29.99 ft.

1995

Used

Well maintained 1995 Beneteau Oceanis 300! Ready to sail! This 1995 Beneteau Oceanis 300 has been lovingly cared for in her travels from her home port in CT to Mart...

POP Sells logo

$44,450

Nautor Swan 56

Marblehead, Massa... (United States of America)

56.33 ft.

1998

Used

One of our favourite Swans, a great cruiser/racer design. Our office sold Nautor Swan 56, TRAMONTANA as new, and we were involved with her construction and her launch...

Berthon International logo

$450,000

* Price displayed is based on today's currency conversion rate of the listed sales price.

ABOUT SAILBOATS

Sailboats have cruised the world’s lakes and oceans for centuries and remain popular among many skilled and dedicated watermen and women. They require a degree of skill and an awareness of the wind and weather while offering a traditional and exhilarating boating experience. Search for new or used sailboats for sale in your area in all sizes and prices to begin your journey.

 

Main Characteristics of Sailboats

A sailboat is classified as any boat that harnesses the power of the wind for propulsion. In real terms, this covers a huge variety of vessels, from small sailing dinghies to daysailers, single-masted boats, twin-masted boats, racing sailboats, and sailing superyachts. Depending on the size of the sailboat, it might have cabins, a galley, one or more heads, or more simply a small covered space for storage. 

Sailboats were traditionally constructed of wood, and it is still possible to find brands producing classic wooden hulls. However, these days most sailboats are made from materials such as fiberglass, aluminum, and even carbon fiber. 

When it comes to sails, rigging configurations are widely varying and are used to further classify sailboats into their relevant categories. Likewise, the keel of a sailboat can vary, from a full keel to a fin keel, or catamarans which have twin hulls with or without significant keels or daggerboards.

 

Types of Sailboat

 

Sloop

Sloops make up the largest segment of sailboats and are characterized by a single mast rig that commonly has a triangular mainsail and a headsail. They are popular with beginners who find their rig simple to handle, but also with sailing pros who enjoy their ease of maneuverability. They are also frequently seen as racing boats thanks to their speed and good windward performance. They can be of any length from an 8-foot pram to a 258-foot superyacht and are often versatile with regards to their layout and ability to cruise in many conditions. 

 

Cutter

Although similar in appearance to the sloop, a cutter has markedly different rigging with two headsails (a headsail and a staysail). This allows for good control and stability, especially in adverse weather, although it makes it a little more complicated to sail. Cutters also commonly have a spar extending from the bow known as a bowsprit. 

 

Schooner

Large schooners have been around for centuries and are characterized by their multiple masts. They were originally designed for fishing or offshore voyages and able to handle even the roughest of sea conditions but often require more crewmembers to handle the complex rigging. 

 

Ketch and Yawl

These two-masted sailboats are similar in their appearance as they have a mainmast in front that is taller than the mizzenmast behind it. The difference lies in the positioning of the mizzen—behind the rudder post on the yawl and forward of it on the ketch. In general they are not as fast upwind as a sloop sailboat, but because of their shorter masts and smaller sails they often better suited to handling rough sea conditions. They can vary in size and often make good long-range sailboats. 

 

Daysailer and Dinghy

The smallest sailboats are dinghies and daysailers, which are ideal for beginners or fun days out on protected waters. They are easily trailerable and simple to rig and handle. Dinghies are 8 to 18 feet in overall length, while daysailers can be small or quite a bit larger, accommodating more passengers. Both have a single mast, although the rigging can vary widely.  

 

Motorsailer

The motorsailer uses a combination of wind power and engine power. While these are less common than sailboats and motorboats thanks to their higher price, they can offer the best of both worlds with the space and ability to power against the wind like a motor boat and the wind power of a sailboat that can increase its range and even invite its sailors to turn off the engine when conditions are right. They are popular for long-range cruising and long-term living. 

 

Catamaran Sailboat

Catamarans are double-hulled vessels with a shallower draft than monohull sailboats. Small catamarans are fun and fast, sailing right off the beach. Larger catamarans provide much more deck and interior space thanks to their wide beam, and larger models have cabins in both hulls with a spacious living area above the waterline. They don’t heel or tip the way monohulls do and are typically more stable except in extreme windy or wavy conditions

 

Best Sailboat Brands

Listing the best sailboats brands is no easy feat as there are hundreds of excellent builders to choose from. There are brands currently producing new sailboats as well as those many that are no longer in operation but whose boats are available on the used market.

Some of the top brands of sailboats include long-time builders such as Catalina, Jeanneau, Tartan, Beneteau, and Hallberg-Rassy, the latter who are known for their blue water yachts. 

Other brands worth mentioning are Hobie and their ultra-popular dinghy catamarans, Lagoon Catamarans, Hinckley Yachts, and Dufour to name just a few. 

 

FAQs

 

Why Choose a Sailboat?

Sailboats give sailors the quintessential boating experience. They offer the chance to learn new skills together as a family, whether it’s on a small dinghy-sized sailboat for beginners, or a larger yacht that you might one day sail you around the world. Sailboats can be purchased for very different price points and styles to suit all skill levels. 

 

 

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