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
6,631 New and Used Sailboats
Beneteau Oceanis 55
Lighthouse Point,... (United States of America)
55.68 ft.
2015
Used
2015 Beneteau Oceanis 55' "Freedom" Freedom is by far the most well kept and appointed sailing vessel to hit the market!!! With 3 luxurious staterooms all with en...
$479,000
Bali 5.4
St Thomas, Virgin... (United States of America)
54.0 ft.
2019
Used
Galaxsea – A Bali 5.4 That Blends Luxury, Innovation, and Adventure Now based in the British Virgin Islands, Galaxsea is a stunning Bali 5.4 catamaran that offers t...
$929,999
Island Packet 465
Key West, Florida (United States of America)
46.0 ft.
2008
Used
Boat Overview Island Packet is world renown as a premier builder of blue water passage makers. The highest quality resins, triaxial fiberglass, and marine grade com...
$349,000
Cabo Rico NE400
Hampton, Virginia (United States of America)
41.99 ft.
1998
Used
Boat Overview "Bossa Nova" is a rare example of a Cabo Rico, Northeast 400 Pilot House model. She offers all the benefits of a secure and safe pilot house motor sai...
$215,000
Beneteau Oceanis 38 Weekender
Kemah, Texas (United States of America)
37.76 ft.
2017
Used
Boat Overview High-performing and as open to the sea as it is to life, the Oceanis 38 boasts new space organization options on board. The upgradeable sailing boat par excellence. It gives you a choice between two layouts (two or three cabins). It’s then up to you to customize your bo...
$237,500
Beneteau Oceanis 60
Newport, Rhode Is... (United States of America)
60.01 ft.
2016
Used
Boat Overview "Dolce Vita" is an exquisite example of the Beneteau Oceanis 60, featuring numerous upgrades typically found only on larger yachts. These enhancements...
$750,000
Jeanneau Sun Odyssey 419
Barrington, Rhode... (United States of America)
41.83 ft.
2018
Used
Price Adjustment Price adjustment down over 10% to a new low ask of $247,500. Seller still willing to consider offers. This is a very special boat - please read thr...
$247,500
Beneteau Oceanis 38.1
Falmouth, Massach... (United States of America)
37.76 ft.
2019
Used
Beneteau 38.1 Overview The Beneteau 38.1 features an exceptionally large cockpit, providing comfort while underway and an excellent space for entertaining at anchor...
$218,500
Beneteau Oceanis 37.1
South Dartmouth, ... (United States of America)
39.17 ft.
2025
New
Boat Overview 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 mod...
P.O.A.
Gemini 105 MC Catamaran.
Westport Point (United States of America)
34.0 ft.
2010
Used
Boat Overview Extremely desirable cruising multihull! Tony Smith built this one for himself and took to the Bahamas. (His pencil annotations are still inside the hu...
$119,900
Knierim Yachtbau Ker 52
Dana Point, Calif... (United States of America)
52.4 ft.
2012
Used
Boat Description Ker 52, FAST EXIT II is truly exceptional. Originally VARUNA and TONNERRE, she was designed as a turbocharged TP52 with a taller rig and lighter di...
P.O.A. *
Sweden Yachts C38-39
North Kingstown, ... (United States of America)
38.68 ft.
1984
Used
Boat Description A well prepared offshore cruising boat with the typical Swedish quality build. The single owner since new has added depth and weight to the keel fo...
$69,900
Beneteau Oceanis 331
Houston, Texas (United States of America)
32.91 ft.
2004
Used
Manufacturer's Description Designed by Groupe Finot, the Beneteau 331 offers a sophisticated hull with traditional lines. A spacious cockpit, top-of-the-line deck hardware and a roller furling main accent her ease of handling. The 331 features lots of extras such as standard refriger...
$67,500
Bali 4.8
St Thomas, Virgin... (United States of America)
48.75 ft.
2024
Used
Boat Overview Sea Fox is a beautiful example of a six stateroom, six head Bali 4.8. Sea Fox is fully loaded, including upgraded Yanmar 80 hp engines, Onan generator...
$900,000
Beneteau Oceanis 38.1
Falmouth, Massach... (United States of America)
37.76 ft.
2019
Used
Recent Price Reduction HIGHLY MOTIVATED SELLER! Overview The Oceanis 38.1 features a chined hull and twin canted rudder design that offers particularly surpris...
$218,500
Beneteau First 44
South Dartmouth, ... (United States of America)
48.1 ft.
2026
New
Boat Overview The BENETEAU First 44 is available in two main setups: a standard version and a performance option. It serves as a natural link between the First 36 a...
P.O.A.
Beneteau Oceanis 46.1
South Dartmouth, ... (United States of America)
47.93 ft.
2024
New
2024 BENETEAU Oceanis 46.1 The Oceanis 46.1 boasts all the features of a large cruising yacht, with a rare balance between elegance, usable space, and performance. ...
P.O.A.
Hallberg Rassy 31
Green Cove Spring... (United States of America)
31.5 ft.
2000
Used
Highlights Low engine hours - 2800 hours Standing rigging inspected and tuned in March 2023 In-mast furling mainsail High quality Elvstrom sail inventory ...
$99,000
Beneteau Oceanis 30.1
South Dartmouth, ... (United States of America)
31.27 ft.
2024
New
2024 BENETEAU Oceanis 30.1 Beautiful grey hull ~ teak cockpit ~ upgraded Raymarine electronics Overview The Oceanis 30.1 is easy to sail but lively to helm and...
P.O.A.
Beneteau First 36
South Dartmouth, ... (United States of America)
36.09 ft.
2026
New
Boat Overview The BENETEAU First 36 is designed to bridge the gap between high-tech racing developments and mainstream racer-cruisers. Even the standard version of ...
P.O.A.
Bristol 32
SALEM, Massachusetts (United States of America)
32.25 ft.
1979
Used
$26,000
J Boats J-109
Slidell, Louisiana (United States of America)
35.27 ft.
2004
Used
Video Tour
Overview Discover why hundreds of J/109 sailors simply "love" their boats. The J/109 is considered one of the best racer/cruisers ever built by J/Boats. Its performance record speaks for itself. Well-sailed, the J/109 is challenging to beat under any handicap system, including PHRF, ...
$135,000
O'day 32
Port Washington, ... (United States of America)
32.15 ft.
1987
Used
O'Day 322 Overview The O'Day 322 is a popular sailing yacht known for its versatility, comfort, and performance. Designed and manufactured by O'Day, a renowned Amer...
$21,900
Bavaria Vision 46
Gulfport, Mississ... (United States of America)
46.0 ft.
2016
Used
Video Tour
From Sail Magazine: "I’m not sure how the Farr Design Office did it—chalk it up to a nice big rudder and well balanced canoe body?—but the boat remained under control the entire time, even when we pushed the boat under too much canvas. As the wind started cranking up into the high te...
$230,000
Fountaine Pajot Mahe 36 Evolution - Owner's Ver...
Summerland Key, FL (United States of America)
39.01 ft.
2014
Used
Brake Aweigh is a remarkable 2014 Fountain Pajot Mahe 36 owner's version featuring the top Oceanique package. This vessel has had a single owner and has never been used for charter. The owner personally took delivery in La Rochelle, sailed down the coast, crossed the Atlantic, cruised ...
$249,900
Leopard 50
Port Canaveral, FL (United States of America)
50.59 ft.
2022
Used
Stock photos are shown (actual photos coming soon). Currently in Port Canaveral, FL soon to be in route to Hilton Head, SC. Get ready to experience the thrill of sa...
$1,249,000
Beneteau Oceanis 40.1
South Dartmouth, ... (United States of America)
42.26 ft.
2025
New
2025 BENETEAU Oceanis 40.1 Introducing the 2025 BENETEAU Oceanis 40.1—a 40-foot cruiser that masterfully combines performance, comfort, and versatility. Designed by...
P.O.A.
Beneteau Oceanis Yacht 54
South Dartmouth, ... (United States of America)
56.33 ft.
2025
New
Overview The two architects behind this free-flowing, wonderfully nimble 54-footer are Roberto Biscontini and Lorzenzo Argento. Their creation paves the way for a n...
P.O.A.
* 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.