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
6,524 New and Used Sailboats
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
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
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
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
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
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
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 46
Portsmouth, Rhode... (United States of America)
47.24 ft.
2008
Used
The 2008 Beneteau 46 Oceanis is a well-designed, performance-oriented cruising sailboat known for its spacious layout, modern amenities, and easy handling. Featuring ...
$205,000
Aalsmeer Yacht Custom 57 (Dutch Built)
Port Ludlow, Wash... (United States of America)
56.99 ft.
1962
Used
Boat Overview Aalsmeer Yacht Inc./G.J. Dekker Design. Mid-cockpit, ocean going, full keel, teak decks. Perkins 6-cylinder, 354 cu. generator 8KW Onan. General Description This Dutch built Dekker design was built by the Aalsmeer Yachts, and is considered by some to be the Rolls R...
$283,500
Bristol 32
SALEM, Massachusetts (United States of America)
32.25 ft.
1979
Used
$26,000
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
Lagoon 38
New Orleans, LA (United States of America)
43.08 ft.
2025
New
Video Tour
ALWAYS DREAM BIG! With the new Lagoon 38, each moment at sea is an escape from the everyday, a journey where dream destinations become realities and where memories are made in a comfortable, serene, inviting atmosphere. STEP ABOARD WITH FULL PEACE OF MIND The extended, specially adapte...
P.O.A. *
Prout 45S
Saint Augustine, FL (United States of America)
45.01 ft.
2009
Used
Rattlesnake is a fabulous example of why Prout catamarans are legendary in the boating world and includes several upgrades for off-grid, full-time living aboard. This Prout 45s is the perfect blend of seaworthiness, comfort, and ease of handling, making it an ideal choice for a full-ti...
$345,000
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
Catalina 38
North Monmouth, M... (United States of America)
37.99 ft.
1982
Used
1982 Catalina 38/SL Engine: 25HP Universal Diesel Engine Condition: Runs great and ready to hit the water!!! Pricing and Location This vessel is priced at $31,150 (offers encouraged). It is located in North Monmouth, Maine and is in good condition. Listing Information Thi...
$31,150
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
Catalina 28
Westbrook, Connec... (United States of America)
28.51 ft.
1991
Used
Interior Comfortable layout with 2 double berths and one aft under the cockpit. A large hatch and opening ports provide good interior ventilation and light. Maint...
$22,500
Freedom 35
Portsmouth , Rhod... (United States of America)
35.33 ft.
1996
Used
General Description Rising Star is a wonderful example of this David Pedrick designed performance cruiser from Freedom Yachts. Called the fastest freedom pound for ...
$74,900
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 54
Pensacola, Florida (United States of America)
54.0 ft.
2012
Used
Video Tour
54 Foot Beneteau Cruiser - Luxurious and Loaded! Ready for your next adventure! Overview The 2012 Beneteau Oceanis 54 Sailboat Cruiser -- where luxury meets performance, and every voyage becomes an unforgettable adventure. Set sail in style and comfort with this impressive vesse...
$275,000
Custom Boats 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
Lagoon 39
Palmetto, FL (United States of America)
38.48 ft.
2017
Used
Boat Overview 2017 Lagoon 39 Owner Version 'Sun Bums' - A Perfect Balance of Comfort & Performance. The 2017 Lagoon 39 Sun Bums is a sailing catamaran that blends comfort with performance, never chartered and only two owners. Designed by renowned naval architects Marc Van Peteghe...
$410,000
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...
$105,000
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...
$60,000
Lagoon 38
Kemah, TX (United States of America)
43.08 ft.
2025
New
Video Tour
ALWAYS DREAM BIG! With the new Lagoon 38, each moment at sea is an escape from the everyday, a journey where dream destinations become realities and where memories are made in a comfortable, serene, inviting atmosphere. STEP ABOARD WITH FULL PEACE OF MIND The extended, specially adapte...
P.O.A. *
Beneteau Oceanis 50
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...
$269,000
Bali 4.8
Fort Lauderdale, FL (United States of America)
48.0 ft.
2020
Used
48' Bali 2020 Kittiwake is a 2020 Bali 4.8 operating in the Bahamas and South Florida. She is well maintained with professional crew operating her year round and an...
$850,000
SLOCUM Pilothouse 43
Green Cove Spring... (United States of America)
42.49 ft.
1986
Used
Boat Overview "Madison Ann" is a versatile vessel that can be piloted from both inside and outside. Her living accommodations are notably spacious for a boat of thi...
$85,000
* 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.