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

6,118 New and Used Sailboats

Lagoon 440

Cardinal, Virginia (United States of America)

44.42 ft.

2009

Used

OWNER VERSION! NEVER CHARTERED! EXTREMELY CLEAN & WELL MAINTAINED. The Lagoon 440 is an ideal family boat, or perfect for a couple that loves the cruising lifes...

YaZu Yachting logo

$399,000

Colvin Gazelle Junk Schooner

Baltimore, Maryland (United States of America)

41.99 ft.

1979

Used

A true head-turner, Summer Wind is a classic Tom Colvin Gazelle schooner with a unique junk rig, built tough with 1/4" steel for serious cruising. Designed for advent...

BVI Yacht Sales Ltd. logo

$100,000

SLOCUM Pilothouse 43

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

42.49 ft.

1986

Used

She can be piloted from both inside and out, and her living accommodations are truly overstated for a boat of this size and style. "Madison Ann" is located in northea...

Sunshine Cruising Yachts logo

$85,000

Custom 100'

Marina Del Rey, CA (United States of America)

100.0 ft.

1996

Used

Christine Yacht | 100' Custom 1996 The family is ready to let this magnificent boat go. They have enjoyed it for the past 27 years. Personally built by the owner...

$135,000

Hunter E36
Hunter E36 Hunter E36 Hunter E36

Annapolis, MD (United States of America)

35.93 ft.

2011

Used

Boat Overview Hunter created the e36 ("e" stands for extended cockpit) for a comfortable, easy-to-handle boat that is affordable. Bay Dream is perfect for sailors looking for a pocket size boat that offers comfortable amenities with a shoal draft. The e36's extra wide beam is carried...

The Multihull Company logo

$105,000

Freedom 40 Cat-Ketch
Freedom 40 Cat-Ketch Freedom 40 Cat-Ketch Freedom 40 Cat-Ketch

Charleston, SC (United States of America)

39.99 ft.

1979

Used

S/V "Sophie" Overview S/V "Sophie" is a distinctive and well-maintained blue water Ketch style monohull, cherished by her owner for the past 25 years. Designed by the innovative minds of Garry Hoyt and Ted Hood, the Freedom 40 was conceived with a focus on simplicity and ease of hand...

The Multihull Company logo

$60,000

Beneteau Custom

Clear Lake Shores... (United States of America)

50.0 ft.

1997

Used

Boat Overview NEVER-BEEN-CHARTERED! Three Stateroom, Three Head Interior Layout Three Zone Air Conditioning with Reverse Cycle Heat Yanmar 4JH2 DTE 88 HP (343...

Little Yacht Sales logo

$269,000

Leopard 50
Leopard 50 Leopard 50 Leopard 50

St. Thomas, Virgi... (United States of America)

50.0 ft.

2023

Used

Salty Dog is one of the most successful crewed yacht charter boats currently operating in the Virgin Islands.She is not only well equipped from the factory, but has been maintained with an open checkbook and under the watchful eye of the premiere crewed yacht charter management f...

Catamaran Central logo

$1,250,000

Lagoon 50
Lagoon 50 Lagoon 50 Lagoon 50

St. Thomas, Virgi... (United States of America)

50.0 ft.

2020

Used

Video Tour

Since new, Esperanza II has been fully maintained by a professional crew and is part of a successful crewed yacht charter program. She is truly a turnkey operation with crew in place, charters on the books, and yacht management in place. She is well-optioned from the factory with some...

Catamaran Central logo

$899,999

Leopard 42
Leopard 42 Leopard 42 Leopard 42

Brunswick, Georgia (United States of America)

41.99 ft.

2022

Used

Video Tour

Proof that you can have it all.The Leopard 42 is the organic evolution into the new generation of our award-winning line of yachts. Built by Robertson & Caine and designed by Naval Architects, Simonis & Voogd, together we have created a revolutionary design that has excee...

Catamaran Central logo

$670,000

Moody 41 Ds

Charleston, South... (United States of America)

41.08 ft.

2022

Used

Boat Overview This thoroughly modern Moody DS41 was launched in 2022 and incorporates all of the clever design details that have made the Moody Decksaloon yachts po...

Berthon International logo

$695,000

Abeking & Rasmussen Concordia Yawl

Stamford, Connect... (United States of America)

39.83 ft.

1952

Used

Boat Overview Discover the timeless elegance of PRAXILLA, a 1952 Concordia Yawl. This iconic 39'10" wooden sailboat, hull number 10 of 103 produced, embodies the le...

Berthon International logo

$94,500

Hallberg Rassy 53
Hallberg Rassy 53 Hallberg Rassy 53 Hallberg Rassy 53

Galveston, Texas (United States of America)

53.9 ft.

2000

Used

Video Tour

Manufacturer's Description GRACEFUL ELEGANCE The Hallberg-Rassy 53 was built for fifteen years between 1992 and 2006 in 88 units. This yacht with graceful elegance offers lots of elbow space and room for comfort equipment. At the time she was introduced, in 1992, she was the larges...

Murray Yacht Sales logo

$495,000

Beneteau Sense 55
Beneteau Sense 55 Beneteau Sense 55 Beneteau Sense 55

Galesville, Maryland (United States of America)

56.43 ft.

2015

Used

Video Tour

2015 Beneteau Sense 55 2013 Cruising World's Boat of the Year and SAIL's Best Boats The innovative concept of this range of cruisers is fully expressed in the Sense 55. Built on a one-level floor plan, the day and night living spaces are distinctly separate and the cabins resemble ...

Murray Yacht Sales logo

$360,000

Clock Sale pending
Catalina 42 MK 1

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

41.99 ft.

1989

Used

Welcome aboard Legacy, a 1989 Catalina 42 MK 1.Everything about this boat is the perfect blend of performance and luxury.She is a cruiser, designed for lo...

$95,000

Prout 37 Snowgoose

Stuart, Florida (United States of America)

37.01 ft.

1983

Used

1983 Prout 37 Snowgoose Sailing Catamaran The Prout Snowgoose is the original production cruising catamaran. Built in England for the North Sea, it is renowned for ...

$69,000

Leopard 48
Leopard 48 Leopard 48 Leopard 48

Saint Pete, Florida (United States of America)

48.43 ft.

2015

Used

Jubilee is one of the nicest 4 cabin Leopard 48's to come to market in 2025.Her original owner purchased her from Belize before she could even go into bareboat charter.He then sailed her to Fort Lauderdale for upgrades before placing her into private charter with a full tim...

Catamaran Central logo

$549,000

Lagoon 46
Lagoon 46 Lagoon 46 Lagoon 46

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

46.0 ft.

2024

Used

The Lagoon 46 has been regarded as one of the best sailing catamarans in her class.With a wide beam and more freebaord than other boats in her class she feels much larger than most 46ft catamarans.Don't let her volume fool you into thinking she can't sail.With a power...

Catamaran Central logo

$999,999

Sabre 38

Bridgeport, Conne... (United States of America)

37.99 ft.

1985

Used

The Sabre 38 is a diesel auxiliary masthead sloop designed by the Sabre Design Group and built in fiberglass by Sabre Yachts between 1981 and 1987. 100 yachts were bu...

$59,000

Corsair 28
Corsair 28 Corsair 28 Corsair 28

Nokomis, Florida (United States of America)

27.99 ft.

2001

Used

Beautiful and rare 2001 Corsair 28 in good condition, ready to sail! Trailer is included. This 2001 Corsair 28 Trimaran gives you a great combination of a family cruiser and offshore racer, and with her trailer-ability, you can take her anywhere you want to go! Trailering also offers...

Pop Sells logo

$68,900

Freedom 40-40

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

40.42 ft.

1998

Used

Boat Description Spruce is an excellent example of a timeless Freedom 40/40. Her freestanding rig is not only easy to sail but reduces weight aloft and the stress o...

$119,900

Bristol 38.8

Tracy's Landing, ... (United States of America)

38.25 ft.

1985

Used

ACCOMMODATION As you come down the companionway you are struck by the high quality and quantity of teak cabinetry. The varnished teak & holly sole and varnished ...

$77,500

Jeanneau Sun Odyssey

St Thomas, Virgin... (United States of America)

45.18 ft.

2002

Used

Boat Overview The Jeanneau Sun Odyssey 45 is a well-regarded cruising sailboat that combines performance, comfort, and seaworthiness. Designed by renowned naval arc...

BVI Yacht Sales Ltd. logo

$70,000

Sabre 28

Bridgeport, Conne... (United States of America)

27.99 ft.

1986

Used

For Sale, Bridgeport CT, 28 ft Sabre 28, 1986 Westerbeke diesel auxiliary sloop with new Quantum Dacron sails. It is reported that this hull was the last Sabre 28 bui...

$18,000

Jeanneau Sun Odyssey 349

Anacortes, WA (United States of America)

33.99 ft.

2019

Used

2019 Jeanneau Sun Odyssey 349 - Pristine, Performance-Oriented Cruiser Seaglass is a meticulously maintained, one-owner 2019 Jeanneau Sun Odyssey 349 with a perfect...

$199,900

Southerly 420
Southerly 420 Southerly 420 Southerly 420

Charleston, South... (United States of America)

43.64 ft.

2026

New

Exploring Where Others Can’t The Southerly 420 has all the elements you would expect of an ocean-going yacht: the tried and tested variable draft swing keel, twin helm rudder arrangement, and a smartly designed deck layout with a comfortable cockpit and cockpit arch for the main trav...

S&J Yachts logo

P.O.A. *

Concordia Yawl

Hopkington, Rhode... (United States of America)

39.83 ft.

1962

Used

Commissioned and launched and to be found at her mooring in Stonington Harbour.Woodwindis a handsome example of the successful and elegant Concordia yawl ...

$85,000

Dickerson aft cockpit cutter

Westport, Connect... (United States of America)

37.01 ft.

1983

Used

For sale, Westport, CT, 1983 37ft Dickerson shoal draft diesel auxiliary cutter in great condition. Beautiful Classic Lines, Quality Build and Cruising Performance, ...

$35,000

* 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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