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
6,942 New and Used Sailboats
Westerly Oceanlord 41
Tracy's Landing, ... (United States of America)
40.49 ft.
1997
Used
Full Specifications Designed for Comfort and Performance Offshore. She points high and rides smooth... Recent Highlights Rigging Inspection: forestay rep...
$119,950
Bristol 45.5
Tracy's Landing, ... (United States of America)
45.24 ft.
1983
Used
Deck and Deck Hardware Astral features two-tone fiberglass decks with clean and open jack-lines, ensuring easy and safe movement around the boat. Notably, Astral ha...
$149,950
Dehler 47 Sq
Deltaville, Virginia (United States of America)
47.01 ft.
2005
Used
Boat Overview GAIA is a Jodel and Vrolijk designed Dehler 47 featuring a vinylester hull, teak decks, a deep draft of 7’9”, and a tall rig measuring 75’. Built for ...
P.O.A.
Sam L Morse Bristol Channel Cutter 28
Fort Pierce, Florida (United States of America)
37.66 ft.
1994
Used
Little Wing Little Wing may be the finest Bristol Channel Cutter 28 ever offered for sale—meticulously maintained, continuously upgraded, and ready to sail offshore...
$175,000
Bayfield 32c
Bradenton, Florida (United States of America)
31.99 ft.
1981
Used
Video Tour
1981 Bayfield 32C Cutter Rigged Full keel! Bluewater Sailor with tons of features and additions! Overview If you are in the market for a cruiser, look no further than this 1981 Bayfield 32C, priced right at $20,000 (offers encouraged). This vessel is located in Bradenton, Florid...
$20,000
J Boats J124
Annapolis, Maryland (United States of America)
39.99 ft.
2006
Used
"Airwaves" is in very nice condition, exceptionally well equipped and maintained to a discerning standard. Currently ready of the 2025 sailing season! Come take a l...
$189,000
Beneteau Oceanis Clipper 361
kemah, Texas (United States of America)
36.42 ft.
2003
Used
Preliminary Listing Preliminary listing subject to Seller's approval Key Features Roller Furling Main and Genoa New 110% Genoa 2022 New Mains...
$79,900
Lagoon Seventy 7
Miami, FL (United States of America)
76.35 ft.
2020
Used
ORB3 is the owner's 3rd Lagoon, full time captain and mate and strictly light, local family use. This unique Lagoon Seventy 7 catamaran for sale is professionally maintained, very well appointed and never chartered. She has a great layout for entertaining or future charter. Their next ...
$5,650,000
Beneteau Oceanis 60
Annapolis, Maryland (United States of America)
60.99 ft.
2016
Used
Oceanis 60 Cruising Yacht With power and elegance, this large cruising yacht will transport you beyond the realms of the joy of sailing. By embracing several innovative solutions, the Oceanis 60 has much to attract in its luxurious accommodation, excellent seakeeping and safety. S...
$665,000
Wauquiez Centurion 45s
Milford, Connecticut (United States of America)
45.93 ft.
2003
Used
Mechanical Disclaimer Engine and generator hours are as of the date of the original listing and are a representation of what the listing broker is told by the owner...
$169,900
Beneteau Oceanis 50
Austin, Texas (United States of America)
40.75 ft.
2018
Used
$269,000
Island Packet 31
Merritt Island, F... (United States of America)
31.0 ft.
1987
Used
1987 Island Packet IP31 - Off-Grid Cruiser Overview If you are in the market for a cruiser, look no further than this 1987 Island Packet IP31, priced right at $43,900 (offers encouraged). This sailboat is located in Merritt Island, Florida and is in good condition. She is also equi...
$43,900
Leopard 43
Saint Augustine, FL (United States of America)
43.01 ft.
2005
Used
A Classic Leopard 43 in Great Condition Spacious, Capable, and Built for Adventure. Espy Blue is a well-maintained 2005 Leopard 43, designed by the world-renowned Simonis & Voogd Design and built by Robertson & Caine in Cape Town, South Africa. Known for their strength, perform...
$279,000
Gemini 105 Mc
Marco Island, Flo... (United States of America)
33.99 ft.
2006
Used
Video Tour
2006 Gemini 105MC Catamaran Refurbished with many upgrades and repairs! Overview Experience sailing at its finest aboard a beautifully maintained 2006 Gemini 105MC Sailing Catamaran. Renowned for their exceptional combination of performance, comfort, stability, and reliability, ...
$84,500
Voyage Yachts 500
Saint Augustine, FL (United States of America)
50.0 ft.
2010
Used
Gods Grace is a stunning example of the esteemed Voyage brand. This vessel features the sought-after 3 cabin Owner's Version layout, complete with a spacious cockpit and salon. Gods Grace is the last of the 500 model ever constructed by the Voyage factory. Her original owner, an aerosp...
$519,000
Lagoon 42
Fort Lauderdale, FL (United States of America)
41.99 ft.
2018
Used
Video Tour
Overview Priced to Sell! Dockside and Available. Discover the perfect blend of luxury, performance, and comfort with this 4 Cabin 2018 Lagoon 42 catamaran for sale. Spring Tradition is meticulously maintained and upgraded, this vessel is ready to transform your sailing adventures. ...
$419,000
Fountaine Pajot Eleuthera 60
Fort Lauderdale, FL (United States of America)
60.01 ft.
2008
Used
Video Tour
Boat Overview JUST ARRIVED TO FORT LAUDERDALE! Stella Maris is a true blue-water cruiser built for circumnavigation, strength, and smooth handling in larger seas. Comfortably cruising at 10+ kt in the Caribbean trades, her record to date is 27.2 kt! Recent Works New rudder...
$484,000
Hunter 380
Clearwater, Florida (United States of America)
37.24 ft.
1999
Used
Specifications Accommodations • Galley to Starboard • Head with Shower to Port • Nav. Station forward of Head - Port • Settee forward of Nav. Station - Port • Dinette with Settee forward of Galley - Starboard • ALL CUSHIONS recovered 2025 • Forward V-berth cabin with Va...
$82,000
Hunter Deck Salon
Houston, Texas (United States of America)
43.18 ft.
2007
Used
Equipment List Manufacturer Provided Description The Hunter 44 Deck Salon features spacious accommodations generally seen only on much larger vessels. The hull sports a unique "bow hollow" forward, creating a longer waterline for increased lift and speed. The underbody aft also ha...
$144,500
Bali 4.4
Annapolis, Maryland (United States of America)
44.16 ft.
2026
New
Bali 4.4 Catamaran Overview Designed with long-term cruising comfort in mind, the Bali 4.4 is the ultimate catamaran for couples & families who dream of explori...
$835,981 *
Bali Catsmart
Annapolis, Maryland (United States of America)
38.58 ft.
2026
New
Discover the Bali Catsmart – Where Innovation Meets Comfort on the Water Step aboard the Bali Catsmart. Designed for sailors who crave comfort, performance, and int...
$546,130 *
Southerly 57 Rs
Charleston, South... (United States of America)
58.17 ft.
2010
Used
Video Tour
Boat Overview Soul Kitchen has been relaunched and recommissioned following a partial refit. She's back in the water and in better shape than ever! Innovative design, contemporary styling, powerful sailing performance, superior build quality, and luxurious accommodations are all ha...
$899,000
Fountaine Pajot Venezia 42
New Bern, North C... (United States of America)
41.99 ft.
1996
Used
"Loaded with Value – New Electronics, Spacious Layout & Smart Storage!" "SANDY K features brand-new Raymarine wind, depth, and speed instruments—reliable technology that enhances cruising confidence. The thoughtfully designed layout includes two queen cabins, a double cabin, du...
$169,000
C&C 35 MKIII
Milford, Connecticut (United States of America)
34.68 ft.
1984
Used
C&C 35 Mk III Overview The C&C 35 Mk III cruises and races well, providing an enjoyable experience for your crew. Style is the essence of the C&C 35 Mk ...
$14,900
Jeanneau 64
Annapoilis, Maryland (United States of America)
64.17 ft.
2016
Used
Overview Serenity is unquestionably the best equipped and most heavily optioned Jeanneau 64 on the water today. Her owner has spared no expenses to make her a yacht...
$1,145,000
Stuart Cutter Ketch
Deale, Maryland (United States of America)
64.01 ft.
1983
Used
62’ STUART BOATWORKS CRUISING CUTTER KETCH IF NOT NOW, WHEN? - WHILE YOU CAN ~~ PACIFIC HIGH is a one-of-a-kind, long-range cruising cutter ketch built by Stuart ...
$395,000
Grand Soleil 52 Long Cruise
Miami Beach, Florida (United States of America)
55.74 ft.
2017
Used
Boat Overview Estela is a highly customized version of the Grand Soleil 52 Long Cruise, designed to be the ultimate luxury performance cruiser. It has been outfitte...
$825,000
Cherubini 44 Ketch
Hoboken, New Jersey (United States of America)
44.0 ft.
1983
Used
Boat Overview This Cherubini 44 Ketch has undergone a significant refit in the past year, featuring a new engine, fuel tank, and all-new running gear. Her varnish s...
$324,500
* 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.