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
4,402 New and Used Sailboats
Alerion 28 Express
$75,000
CONDITION:
Used
LENGTH:
27.99 ft.
|
YEAR:
2003
LOCATION:
New London, Connecticut (United States of America)
OFFERED BY:
Brewer Yacht Sales
The Alerion 28 Express is a descendent of Nathanial Herreshoff's 26 Alerion III lines with a modern touch that was designed as daysailer / racer that is easy to handle sail plan and a cockpit d...
Hinckley Sou'wester 59
$325,000
CONDITION:
Used
LENGTH:
59.25 ft.
|
YEAR:
1982
LOCATION:
Southwest Harbor, Maine (United States of America)
OFFERED BY:
Luke Brown Yachts
This McCurdy & Rhodes, center cockpit, ketch rigged Sou’wester 59’ offers a very spacious interior for her size, as well as a protected steering station. Easily managed for...
Alajuela 38
$148,400
CONDITION:
Used
LENGTH:
45.01 ft.
|
YEAR:
1974
LOCATION:
Topping, Virginia (United States of America)
OFFERED BY:
YaZu Yachting
Narnia is a unique blue-water cruising yacht whichwill appeal to traditionalists who enjoy simplicity coupled with modern materials and smart design ideas. Narnia will ap...
Sabre 452
$245,000
CONDITION:
Used
LENGTH:
45.18 ft.
|
YEAR:
2000
LOCATION:
Rock Hall, Maryland (United States of America)
OFFERED BY:
Yacht Sales International
"Alliance" is a very desirable Sabre 452 that has been diligently maintained by very competent owners who grew up sailing and maintaining quality yachts. It is the perfect yacht for those who w...
Bavaria 34
$55,000
CONDITION:
Used
LENGTH:
33.66 ft.
|
YEAR:
2004
LOCATION:
Solomons, Maryland (United States of America)
OFFERED BY:
Brewer Yacht Sales
"Cinque Terre" has been very well maintained. She looks like a much newer vessel. The owner took great pride in this boat and it shows. She is also very well equipped for a 32 foot vessel with ...
Dufour 36 Performance
$124,900
CONDITION:
Used
LENGTH:
35.99 ft.
|
YEAR:
2012
LOCATION:
Cranston, Rhode Island (United States of America)
OFFERED BY:
Latitude Yacht Brokerage
Serenity is a 2012 Dufour 36 Performance sailboat, 2012 Sailing World's Best Crossover Award Winner, 2013 Voile Magazine European Yacht of the Year Award Winner and a 2013 Sail Magazine Best Bo...
Moody 38-2 Sloop
$179,000
CONDITION:
Used
LENGTH:
38.42 ft.
|
YEAR:
2002
LOCATION:
Deep River, Connecticut (United States of America)
OFFERED BY:
Brewer Yacht Sales
Recent Upgrades NEW 5/2021 - House bank batteries Lifeline 31 XT 125 amp NEW 4/2021 - Belmar XT 170 alternator with serpentine belt NEW 5/2020 - Mercury 9.9 outboard NEW 2/2020 - ...
Moonen Departure
$35,000
CONDITION:
Used
LENGTH:
35.01 ft.
|
YEAR:
1982
LOCATION:
Stuart, Florida (United States of America)
OFFERED BY:
Manatee Pocket Yacht Sales
Penny - 1982 Departure 35 Sailboat Beautiful full keel, transom hung rudder, blue water sailboat. Spent most of her life on fresh water in Texas. Sailed to Florida and stored on the hard. Truc...
Catalina 350
$97,500
CONDITION:
Used
LENGTH:
35.43 ft.
|
YEAR:
2005
LOCATION:
Indiantown, Florida (United States of America)
OFFERED BY:
Manatee Pocket Yacht Sales
35' Catalina We are pleased to present this well maintained Catalina 350 for your consideration. The Catalina 350 was designed with creature comforts in mind according to Gerry Douglas. The bo...
Contest S
$48,000
CONDITION:
Used
LENGTH:
34.51 ft.
|
YEAR:
1990
LOCATION:
Indiantown, Florida (United States of America)
OFFERED BY:
Manatee Pocket Yacht Sales
1990 Contest 35S We are very pleased to present this Contest 35S for your sailing consideration! Conyplex, builder of the Contest 35S, is an established company that was a pioneer in fibergla...
Hallberg-Rassy 40
$230,000
CONDITION:
Used
LENGTH:
40.68 ft.
|
YEAR:
2009
LOCATION:
Holden Beach, North Carolina (United States of America)
OFFERED BY:
Integrity Yacht Sales
Welcome aboard C-Lion, a 2009 Hallberg-Rassy 40 SE sloop. Everywhere you look you will find superior craftsmanship combined with exceptional sailing performance. This boat will...
Hunter Deck Salon
$165,000
CONDITION:
Used
LENGTH:
40.32 ft.
|
YEAR:
2012
LOCATION:
Solomons, Maryland (United States of America)
OFFERED BY:
Brewer Yacht Sales
Kalypso has seen excellent care and maintenance from her original owner. He has continually upgraded her. She is in lovely condition and ready to cruise or sail south for the winter. ACCOMMOD...
C & C 44
$79,900
CONDITION:
Used
LENGTH:
44.0 ft.
|
YEAR:
1988
LOCATION:
Braintree, Massachusetts (United States of America)
OFFERED BY:
POP Sells
- Stock # Large C&C Cruiser for long-range voyages, weekend cruising, or living aboard! This 1988 C&C 44 sailboat is designed with a spacious two-stateroom layout. Thi...
Custom Whiting Yachts 40
$119,500
CONDITION:
Used
LENGTH:
39.5 ft.
|
YEAR:
1985
LOCATION:
Sequim, Washington (United States of America)
OFFERED BY:
United Yacht Sales
1985 Whiting Yachts 40 Cutter This is truly a Blue Water vessel capable of worldwide cruising in safety and comfort.Built in New Zealand by Whiting Yachts that have a reputation for qual...
Ta Shing Tashiba 40
$139,950
CONDITION:
Used
LENGTH:
44.0 ft.
|
YEAR:
1988
LOCATION:
Deale, Maryland (United States of America)
OFFERED BY:
Integrity Yacht Sales
HIGHLIGHTS Yanmar 4JH-TE Turbo replaced 2015 New fresh water pump 2019 Rebuilt raw water pump 2022 Installed electric fuel primer pump 2020 New fuel lift pump 2016 New f...
Mason 63
$195,000
CONDITION:
Used
LENGTH:
62.99 ft.
|
YEAR:
1984
LOCATION:
San Pedro (United States of America)
OFFERED BY:
Shoreline Yacht Group
ELECTRONICS DEPTHSOUNDER (RAYMARINE) RADAR/PLOTTER (RAYMARINE C80, C90w) AUTOPILOT (RAYMARINE ST70) LOG/KNOTMETER (RAYMARINE) WP/WS (RAYMARINE) COMPASS (RITCHEE) RADIO W/COCKPIT SPEAKERS...
ILIAD Catamarans 53F
$2,015,500
CONDITION:
Used
LENGTH:
52.99 ft.
|
YEAR:
2025
LOCATION:
Dania Beach, Florida (United States of America)
OFFERED BY:
Atlantic Yacht & Ship Inc
Featured Atlantic Yacht and Ship, specialists in Catamaran, is proud to offer this 53' 2025 ILIAD Catamarans Catamaran for sale in Dania Beach, Florida. Take a look at these images and videos,...
Nonsuch Auxiliary Sail
$75,000
CONDITION:
Used
LENGTH:
33.43 ft.
|
YEAR:
1988
LOCATION:
Mystic, Connecticut (United States of America)
OFFERED BY:
Brewer Yacht Sales
Accommodations Forward you have a queen sized bed to port with a large hanging locker to starboard with a vanity.. Aft to starboard is the enclosed head with separate stall shower. Aft to th...
Beneteau 42
$112,500
CONDITION:
Used
LENGTH:
41.67 ft.
|
YEAR:
2002
LOCATION:
Mystic, Connecticut (United States of America)
OFFERED BY:
Brewer Yacht Sales
Accommodations Forward you have the Master head with separate stall shower followed aft to starboard by a queen size bed and a settee to port. A ventilation Hatch and opening ports provide p...
Nautor Swan 391
$110,000
CONDITION:
Used
LENGTH:
39.9 ft.
|
YEAR:
1983
LOCATION:
Marion, Massachusetts (United States of America)
OFFERED BY:
Berthon International
This Swan 391 is one of the nicest we have seen. She has lived a pampered life in New England and has always been stored indoors during the winter months. Her decks have been replaced, she has ...
Island Packet 35 Packet Cat
$89,900
CONDITION:
Used
LENGTH:
35.01 ft.
|
YEAR:
1993
LOCATION:
Tampa, Florida (United States of America)
OFFERED BY:
POP Sells
- Stock # Rare find! Two Yanmar diesel motors. Spacious interior and cockpit. This rare 35 Packet Cat is being offered for sale by the second owner. It has two Yanmar diesel ...
Catalina 27
$15,750
CONDITION:
Used
LENGTH:
27.0 ft.
|
YEAR:
1983
LOCATION:
Freeport, Florida (United States of America)
OFFERED BY:
POP Sells
- Stock # Cruise the islands or finish the Great Loop in a super-clean Catalina! Experienced sailors know there is nothing like a Catalina. This Catalina 27 is nicely updated ...
Endeavour 42
$99,500
CONDITION:
Used
LENGTH:
42.26 ft.
|
YEAR:
1988
LOCATION:
St. Petersburg, Florida (United States of America)
OFFERED BY:
Fillingham Yacht Sales
This Endeavour is ready to GO! Great Liveaboard or Cruiser! Every used boat buyer looking for a comfortable affordable liveaboard cruiser must make compromises between condit...
Fountaine Pajot HELIA EVOLUTION 44
$449,000
CONDITION:
Used
LENGTH:
44.0 ft.
|
YEAR:
2017
LOCATION:
Fort Lauderdale, Florida (United States of America)
OFFERED BY:
YACHTS UNLIMITED
FULL MOON is 2017 FP Helia 44 with 4 cabin 4 head layout. This is the updated Evolution model and includes the raised lounge deck on the coach roof area. Perfect for lounging and sunning. Built ...
Lagoon 52
$775,000
CONDITION:
Used
LENGTH:
52.0 ft.
|
YEAR:
2015
LOCATION:
Charleston, SC, (United States of America)
OFFERED BY:
The Multihull Company
2015 Lagoon 52 Owners Version catamaran for sale listed exclusively with The Multihull Company. 5 cabin / 5 head Owner’s Version layout that sleeps 10 Laminate flooring Recently refinished teak ...
Lagoon 450F
$475,000
CONDITION:
Used
LENGTH:
45.01 ft.
|
YEAR:
2011
LOCATION:
Charleston, SC, (United States of America)
OFFERED BY:
The Multihull Company
The VPLP architects, together with Lagoon and the Nautadesign office, succeeded beautifully in developing a new 45 catamaran to replace the famous Lagoon 440. Of course, the irreplaceable qualit...
Antares PDQ 42
$425,000
CONDITION:
Used
LENGTH:
41.99 ft.
|
YEAR:
2002
LOCATION:
Saint Augustine, FL, (United States of America)
OFFERED BY:
The Multihull Company
Yeya is a beautiful example of the PDQ Antares 42, which was produced for a couple years prior to being officially rebranded as the Antares 44.The PDQ Antares 42 includes all the same design fea...
Cape Dory 36
$48,500
CONDITION:
Used
LENGTH:
35.99 ft.
|
YEAR:
1979
LOCATION:
League City, Texas (United States of America)
OFFERED BY:
POP Sells
- Stock # Very well maintained 1979 Cape Dory 36! Many replacements and upgrades. Ready to sail! 1979 Cape Dory 36 with Perkins 52 hp Diesel motor Many replacement parts and ...
* 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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