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
4,983 New and Used Sailboats
Newport, Rhode Is... (United States of America)
41.08 ft.
2025
New
Like her bigger sisters, the Moody DS41 displays all the attributes of the Moody DS45 and DS54: ease of handling, the option of twin powered headsails, excellent all-...
P.O.A. *
Tracys Landing, M... (United States of America)
36.42 ft.
2000
Used
The Beneteau 361 is a powerful and seafaring sailboat which will take you wherever you wish, with elegance and style. Innovative in terms of sailing pleasure and comf...
$55,000
Kilmarnock, Virginia (United States of America)
37.66 ft.
1988
Used
Bon Vivant is a classic example of Bruce King’s Ericson 38 design.This boat has been sailed, regularly maintained, and loved by her original owners since they t...
$49,900
Deep River, Conne... (United States of America)
46.16 ft.
2000
Used
“Reflection” 2000 Moody 46 Center Cockpit Cruiser. Call Hal Slater for a showing appointment today Accommodations The interior is spacious and bright with attract...
$199,000
St Petersburg, Fl... (United States of America)
39.99 ft.
1985
Used
Nice Cruiser! Two Staterooms & Two Heads, Newer A/C, Great to Liveaboard! 1985 Hunter 40-1 Cruiser This Hunter is a spacious and comfortable sloop with two sta...
$40,000
Deltaville, Virginia (United States of America)
41.99 ft.
2007
Used
The Beneteau 423 is a classic.It’s the last generation of Beneteau to sport the Cherry finish on the interior woodwork.The interior exudes warmth, thanks ...
$152,000
Deltaville, Virginia (United States of America)
45.73 ft.
2007
Used
Mitzie Lou has it all.She has a very comfortable and spacious 2-cabin, 2-head layout that offers two queen berths with private heads and separate showers....
$355,000
Oxford, Maryland (United States of America)
37.01 ft.
1984
Used
Accommodations The Tartan 37 is one of the best received Tartans ever built. Designed by Sparkman and Stephens. They are known for their excellent sailing abilit...
$59,000
Deltaville, Virginia (United States of America)
37.99 ft.
2018
Used
Watts Up Doc is a unique offering of a Maine Cat 38 with inboard OceanVolt electric propulsion.The previous owner undertook the conversion from outboard motors ...
$389,000
Stuart, Florida (United States of America)
35.76 ft.
2010
Used
2010 Jeanneau Sun Odyssey 36i We are very pleased to add this well kept 2010 Jeanneau Odyssey 36i to our sailing fleet of offerings. Designed by Marc Lombard, the 3...
$109,000
Bay Shore, New York (United States of America)
31.99 ft.
1996
Used
Beautiful Catalina 320 -- ready to create some great memories? This 1996 Catalina 320 is a well-maintained sailboat, perfect for those seeking both cruising comfort...
$35,600
Deltaville, VA (United States of America)
39.99 ft.
2019
Used
We are Proud to Present the Exceptional 2019 Leopard 40 Owners Version "Haven", Ready to Sail Away anywhere now!! 2019 ROBERTSON AND CAINE LEOPARD 40 – "Haven" BROK...
$499,000
Puerto Vallarta, ... (United States of America)
144.36 ft.
2014
Used
Bisou Boat | 44' Fountaine Pajot 2014 Fountaine Pajot Helia 44 - Owners Version Ready to Cruise - Located in Puerto Vallarta, Mexico Australian Registere...
$525,000
Daytona Beach, Fl... (United States of America)
42.49 ft.
1993
Used
Whether you dream of cruising around the world or simply spending weekends onboard in tranquility, the Hunter 42 might just be the perfect sailboat. The Hunter 42 of...
$109,900
Jacksonville, Flo... (United States of America)
39.07 ft.
1985
Used
Ideal size for long distance cruising, she can be handled by one experienced sailor, yet comfortably accommodate a family of four.Storage space is ample as well...
$44,500
Deltaville, Virginia (United States of America)
50.98 ft.
2003
Used
This Dettling 51, Blue Zone (#12 of 17 built), is a rare offering of a fine express cruising yacht with sleek lines, sea-kindly motion, extremely well appointed and c...
$629,000
Marina Del Rey, CA (United States of America)
137.8 ft.
2003
Used
Arlion Boat | 42' Catalina 2003 Second Owner after Catalina Yacht owner Inflatable Dinghy and 20hp Outboard Dinghy Davits New Strato Glass on Dodger ...
$175,000
Kemah, Texas (United States of America)
32.74 ft.
2007
Used
Accomodations The interior of the 309 feels much larger than her 31 feet. There is an easy descent (no steep ladder) into a very spacious main salon and galley are...
$74,900
Kemah, Texas (United States of America)
35.24 ft.
2005
Used
Updates Recent additions within theLast two years Jib Sunbrella Sun Cover replaced 33 lb Rocna self-righting anchor 140 ft chain rode and chain...
$83,900
Boston,MA, (United States of America)
37.14 ft.
2007
Used
Description The Bavaria 37 Cruiser is a well built, capable cruising yacht with a spacious modern cockpit and comfortable accommodations below in two private ...
$40,000
Bristol,RI, (United States of America)
42.39 ft.
2010
Used
Description This Jeanneau 42DS is in the water and ready to cruise right now. Designed by Marc Lombard, this comfortable cruiser comes equipped with many desi...
$174,000
New Bedford,MA, (United States of America)
33.92 ft.
2004
Used
Description This Beneteau 331 has been meticulously cared for since new by her owners. She is a comfortable and capable cruiser in a compact package She ...
$69,000
Punta Gorda, FL (United States of America)
37.99 ft.
2005
Used
*Rare Opportunity: 2005 Lagoon 380 S2 Catamaran Spacious 3-Cabin Owner's Version* This popular catamaran with extensive upgrades offers a perfect blend of performance and comfort for cruising enthusiasts. The owners suite occupies the starboard hull, providing a spacious private cabin ...
$245,000
Newport,RI, (United States of America)
34.12 ft.
2024
New
Description The newly launched Jeanneau Sun Fast 30 One Design is an affordable, innovative, powerful, and versatile 30-foot sailboat that aims to make offsho...
P.O.A.
Newport,RI, (United States of America)
33.17 ft.
2023
New
Description #1 DOUBLEHANDED RACE BOAT IN THE USA! A unique opportunity to own a "Performance Race Optimized" ex-demo, mint condition Sun Fast 3300 that has be...
$349,500
Green Cove Spring... (United States of America)
33.99 ft.
1987
Used
Beautiful Blue Water Sailer!! Wonderful Care!! Tiller Steering!! If you're searching for a sailboat that combines classic beauty with unmatched performance, look no...
$72,900
Westbrook, Connec... (United States of America)
29.99 ft.
1995
Used
Well maintained 1995 Beneteau Oceanis 300! Ready to sail! This 1995 Beneteau Oceanis 300 has been lovingly cared for in her travels from her home port in CT to Mart...
$44,450
* 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.