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
5,776 New and Used Sailboats
Rock Hall, Maryland (United States of America)
41.5 ft.
1988
Used
This Island Packet has been one of the most popular IP models among cruisers. With her being the first 2 head models and a owners cabin with private head, an abundance of storage and a very comfortable salon. She is as comfortable at anchor as she is underway. Joyful Wings is a one own...
$125,000
Austin, Texas (United States of America)
39.17 ft.
2025
New
Video Tour
OCEANIS 37.1 The new 37-footer capitalizes on the innovations of the seventh generation of Oceanis Cruisers, which it completes. The Oceanis 37.1 is the eighth model launched since 2017 and it has all the line’s hallmarks and offers more sustainable eco-friendly sailing.The Ocea...
P.O.A.
Yorktown, Virginia (United States of America)
35.01 ft.
2017
Used
The Catalina 355 is an extremely popular model which gives the feel of a much larger boat.The high freeboard and wide beam create expansive interior volume for ...
$225,000
New Orleans, Loui... (United States of America)
43.08 ft.
2008
Used
Video Tour
Step aboard a vessel that truly stands apart: the 2008 Island Packet 41 PY Trawler, transformed into a one-of-a-kind motorsailer. Originally designed as a trawler, this rare model has been professionally enhanced with a mast and rigging installed by Mack Sails, adding stability and eff...
$199,000
Fort Lauderdale, (United States of America)
45.01 ft.
2024
New
Only Leopard 45 hybrid to be built!Electric Propulsion System with 2 x 25KWelectricmotors / 2 x 27KW lithium batteries / 1 range extending 24KW generator / 2KWFlexibl...
$999,000
Deltaville, (United States of America)
44.0 ft.
2015
Used
"Blissful Moments" Popular Leopard 44 model, ready to sail from Virginia, in perfect position forthesummer hurricane season!"Blissful Moments" is the newer version of...
$399,000
Anacortes, Washin... (United States of America)
35.01 ft.
1978
Used
Well-equipped 1978 Rafiki 35 Sailboat! Ready to sail, cruise, or live-aboard! 1978 Rafiki 35 full keel sailboat, well-equipped and ready for its next owner. On bo...
$27,800
Detaville, Virginia (United States of America)
40.32 ft.
2005
Used
Experience the perfect blend of performance and comfort aboard this meticulously maintained 2005 Hunter 41 AC monohull sailboat - BIG DOOR PRIZE. Equipped with a generator, solar power, and all-new electronics upgraded in 2016, including autopilot and radar, this vessel is ready for ex...
$129,000
Marathon, Florida (United States of America)
47.01 ft.
1981
Used
1981 TAI CHOI, CENTER COCKPIT CUTTER KETCH LOULYN In the water and the very definition of Walk on Sail Away. CTs are rugged, well-built boats capable of sail...
$135,000
Charleston, SC (United States of America)
39.01 ft.
1983
Used
"NImbus" is a meticulously maintained O'Day 39 designed by Phillip Briand and modeled after the Jeanneau Sun FIzz. This vessel is built to withstand heavy conditions while offering comfortable and spacious cabin layouts. Over the last 25 years, "NImbus" has sailed the Great Lakes, part...
$50,000
Dania Beach, (United States of America)
39.99 ft.
2020
Used
2020 ROBERTSON AND CAINE LEOPARD 40 - 3 Cabin - Mai Pen RaiBUILDERS REMARKS:The Leopard 40, a product of South African boat builders Robertson & Caine, features a...
$459,000
Kemah, Texas (United States of America)
49.02 ft.
1982
Used
General Description The Transpac 49 was built in Taiwan by the Transpacific Marine Company Ltd which was owned and run by two US owners. The boats were built for oce...
$189,900
Charleston, South... (United States of America)
37.01 ft.
2003
Used
The Jeanneau Sun Odyssey 37 is thoughtfully designed for effortless sailing, whether you have a full crew or are sailing shorthanded, with all lines leading aft to the enclosed cockpit. Equipped with a 2023 self-furling North Main Sail and a 2019 Quantum self-furling jib, handli...
$84,990
Saint Augustine, FL (United States of America)
41.01 ft.
2020
Used
"Kestrel" is a gorgeous example of the Seawind 1260 catamaran from the well regarded yard in Vietnam. The Seawind 1260 is a sporty cruising catamaran designed for comfortable liveaboard sailing. Known for its sleek modern lines and spacious layout, the 1260 offers a great balance of pe...
$585,000
St Thomas, Virgin... (United States of America)
31.0 ft.
2001
Used
The Catalina 310 is a well-regarded sailboat known for its combination of performance, comfort, and ease of handling, making it a popular choice among cruising enthus...
$65,000
Tampa, (United States of America)
39.44 ft.
2018
Used
Recent additions/upgrades (All added in December 2024):New 3/8 Anchor Chain - 150'Raymarine Quantum 2 DopplerRaymarine AIS 700Spectra Cape Horn Extreme 330 Watermaker...
$400,000
Pensacola, Florida (United States of America)
38.09 ft.
2023
Used
Video Tour
In the tradition of the latest 41.1, the Oceanis 38.1 cleverly combines practical features, performance, and elegance on a boat size where function generally outweighs personalization. The Oceanis range continues to stand by its desire to offer various options. Encore is well equipped ...
$325,000
Kemah, Texas (United States of America)
43.01 ft.
1995
Used
Introducing "Here Kitty Kitty," a distinctive 1995 Custom 43-foot Catamaran featuring daggerboards for enhanced sailing performance. With a generous 23-foot beam and a shallow 2-foot draft, this vessel is well-suited for navigating diverse waters. This is an excellent opportunity for t...
$75,000
Fort Pierce, Florida (United States of America)
41.99 ft.
2019
Used
Step aboard the stunning Lagoon 42, "2 Black Sheep," a well-equipped and meticulously maintained catamaran located in Fort Pierce, Florida. This truly turnkey loaded vessel will provide excellent comfort and style for your sailing adventures. Equipped with solar power for off-grid liv...
$569,000
Placida, Florida (United States of America)
41.99 ft.
1992
Used
1992 DNIEPER 1200!! GALVANIZED STEEL HULL! HYDRAULIC CENTERBOARD! A BEAUTY ON THE WATER! 1992 Dnieper Tropic 1200 This Dnieper is a professionally yard-built Trop...
$88,900
Stuart, Florida (United States of America)
33.33 ft.
1993
Used
33' Hunter 33.5 1993 with lots of Care and Upgrades Hunter Marine has combined contemporary styling, performance and a very roomy interior for the 33.5, fractional r...
$37,000
Stuart, Florida (United States of America)
44.26 ft.
1979
Used
44' CSY Center Cockpit 1979 We are pleased to offer this clean and ready-to-sail 44 CSY built for a private owner. The CSY 44 was a ruggedly built mid-cockpit cutte...
$72,500
Newport Beach, CA (United States of America)
52.0 ft.
2024
New
In Stock Boat | 52' Seawind 2024 CALL US FOR SPECIAL REBATE PROGRAM IN STOCK NOW - San Diego Don't miss out on this unique opportunity to take delivery of a S...
$1,200,000
Saint Augustine, FL (United States of America)
44.16 ft.
2023
Used
This is your opportunity to purchase a gorgeous example of the award-winning Balance 442 catamaran! "Kiwa" is fully equipped and ready to go sailing today.She was originally launched in Cape Town, South Africa in 2023 and is hull #8 of this coveted high-performance brand.Kiwa has recen...
$1,380,000
Bay Saint Louis, MS (United States of America)
43.01 ft.
2008
Used
Astraea was the goddess of innocence in Greek mythology, and her name means "star-maiden," evoking a sense of purity, grace, and celestial beauty. This Beneteau 43 is a stunning example of a high-performance cruiser, built to handle whatever the mighty Poseidon might throw her way. Kno...
$165,000
Fort Lauderdale, FL (United States of America)
50.0 ft.
2022
Used
Video Tour
St. Francis Catamarans are a quality-oriented company based out of South Africa. In business for over 25 years, they hone in on precise attention to detail by only producing four catamarans a year! With a small fleet of boats on the market, they maintain worldwide brand recognition amo...
$1,300,000
Fort Lauderdale, FL (United States of America)
45.01 ft.
2021
Used
Video Tour
Kymani is a 2021 Leopard 45 Owners Version. With a spacious sun lounge area on the coachroof in addition to all of the other great features Leopard catamarans have to offer, she is a beautifully equipped vessel designed for luxurious cruising. With just 780 hours on the Yanmar engines ...
$840,000
Branford, Connect... (United States of America)
27.99 ft.
1991
Used
Brilliant is a classic Morris Linda 28 that has undergone a complete refit in 2022 and 2023.As a practical matter she is as close to new without building her fr...
$129,999
* Price displayed is based on today's currency conversion rate of the listed sales price.
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.
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.
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.
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.
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.
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.
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.
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.
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
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.
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.