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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
6,961 New and Used Sailboats
Beneteau 40
Milford, Connecticut (United States of America)
39.83 ft.
2010
Used
This spacious Three (3) cabin layout has two large sleeping quarters: one forward and one aft and a nicely laid-out main salon. Starting forward you will find a priv...
$169,900
C&C 35 MKIII
Milford, Connecticut (United States of America)
34.68 ft.
1984
Used
The C&C 35 Mk III cruises and races well and your crew will have fun doing both. Style is the essence of the C&C35 MkIII. She has a very nice interior with go...
$14,900
C&C 41
Milford, Connecticut (United States of America)
40.75 ft.
1988
Used
One of C&C’s most successful designs the late model C&C 41 brings high-performance characteristics with her proven race-winning hull design and the luxury of ...
$49,900
Tartan 3500
Milford, Connecticut (United States of America)
35.24 ft.
2000
Used
PRICED FOR QUICK SALE !!! STILL TIME TO ENJOY SOME GREAT FALL SAILING!! You can't help but smile to yourself, feeling the warmth of the sun on your skin as your famil...
$96,000
Schock 34 PC
Milford, Connecticut (United States of America)
33.83 ft.
1987
Used
This is a 1987 WD Schock 34 pc (performance cruiser) is a Nelson Marek design, built by WD Schock on the west coast. She sails and handles wonderfully in any conditio...
$36,900
Bali Catspace
Annapolis, Maryland (United States of America)
40.32 ft.
2026
New
Explore the Seas in Style — Bali Catspace Step aboard the Bali Catspace, where innovative design meets unparalleled comfort. This modern 40-foot catamaran seamlessly...
$585,850 *
Sabre 425 Sloop
Wickford, Rhode I... (United States of America)
42.42 ft.
1996
Used
The Sabre 425 was designed to meet the demands of the sea while offering her crew handling characteristics that provide comfort and convenience. The deck plan was tho...
$159,000
Pacific Seacraft 34 Cutter
Milford, Connecticut (United States of America)
34.15 ft.
2000
Used
Understanding the heritage and the philosophy behind the Pacific Seacraft 34 is relatively easy. You need look only as far as the Pacific Seacraft 37. Clearly a sligh...
$89,900
Freedom 30
Milford, Connecticut (United States of America)
29.92 ft.
1987
Used
The Freedom 30 is a wonderful cruising yacht. She offers a very easy to handle rig, large, comfortable cockpit and easily traveled side decks. Below she offers room a...
$24,900
Beneteau First 345
Haddam, Connecticut (United States of America)
35.99 ft.
1985
Used
The world's leading line of racing/cruising yachts, FIRST series boats are designed for the most demanding racers, yet are fully equipped for the most comfortab...
$24,950
Freedom 38
Gloucester, Massa... (United States of America)
37.99 ft.
1990
Used
TRINITY is a well equipped Freedom 38 which offers spacious accommodations, and is very easy to handle due to its unique carbon unstayed mast and self tacking jib.&nb...
$75,000
LeComte Northeast 38
Milford, Connecticut (United States of America)
38.25 ft.
1968
Used
Designed by Bill Tripp and built by A. LeComte of Holland known for their quality construction, sold glass hull, Airex-cored decks and high quality yacht interiors. T...
$42,900
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 inte...
$548,688 *
Voyage Yachts 500
Saint Augustine, FL (United States of America)
50.0 ft.
2010
Used
Gods Grace is a beautiful example of the highly regarded Voyage brand. She has the desirable 3 cabin Owner's Version layout with a large cockpit and spacious salon. Gods Grace is the last of the 500 model to ever be built by the Voyage factory, her original owner was an aerospace engin...
$519,000
Nautitech 48 Open
Norfolk, VA (United States of America)
47.74 ft.
2025
New
Video Tour
2025 NAUTITECH 48 OPEN - OPEN A NEW HORIZON When ultimate comfort is combined with elegance and the pleasure of sailing, your travels become a true dream. For this new model, Nautitech raises the standards of comfort and sensations even higher. Perfect alchemy between architecture and ...
P.O.A. *
Catalina 380
Long Beach, (United States of America)
37.99 ft.
2001
Used
Fanfare is a fine example of the Catalina 380 which was first manufactured in 1997. Her layout is still known for comfort whether topsides or down below. Entering vi...
$99,000
Hunter 430
Kemah, Texas (United States of America)
42.49 ft.
1995
Used
The exterior design of the 430 includes a wraparound windshield with cover, integrated mainsheet arch with instrument pod, two-tone non-skid deck, walk-through transo...
$110,000
Nautitech 44 Open
Kemah, TX (United States of America)
43.67 ft.
2025
New
Video Tour
2025 NAUTITECH 44 OPEN - ALL YOUR DREAMS ONBOARD A LUXURY CATAMARAN BUILT FOR YOUR DREAM OF SAILING AROUND THE WORLD 2023 European Yacht of the Year 2023 Sail Magazine Top 10 Best Boats WINNER THE NAUTITECH STYLE AT ITS PEAK TO SEDUCE CRUISERS SEEKING PERFECTION The 44 Open is the natu...
P.O.A. *
Nautitech 40 Open
New Orleans, LA (United States of America)
39.24 ft.
2025
New
Video Tour
2025 NAUTITECH 40 OPEN - A PERFECT BALANCE BETWEEN PERFORMANCE AND LIFESTYLEThe 40 Open has been designed for lovers of sailing and good life. This luxury catamaran combines sailing sensations and absolute comfort on board, so that you never have to choose between the two. Whether you ...
P.O.A. *
Nautitech 40 Open
Kemah, TX (United States of America)
39.24 ft.
2025
New
Video Tour
2025 NAUTITECH 40 OPEN - A PERFECT BALANCE BETWEEN PERFORMANCE AND LIFESTYLE The 40 Open has been designed for lovers of sailing and good life. This luxury catamaran combines sailing sensations and absolute comfort on board, so that you never have to choose between the two. Whether you...
P.O.A. *
Lagoon 380 S2
Saint Augustine, FL (United States of America)
37.93 ft.
2014
Used
Finally Found embodies comfortable and effortless sailing. Finally Found is a wonderfully maintained 2014 Lagoon 380 S2, 4-cabin version. Designed by the renowned team at VPLP, this 380 S2 is celebrated globally for its ease of handling, comfortable living spaces, and outstanding build...
$290,000
Island Packet 349
Palmetto, Florida (United States of America)
38.25 ft.
2019
Used
Video Tour
The Island Packet 349 won Cruising World magazine's prestigeous "Best Midsize Cruiser" and the "Best Overall Domestic Boat" awards in 2019, using this boat as the test boat during the United States Sailboat Show in Annapolis, MD. Designer Comments The new Island Packet 34...
$398,000
Nautitech 48 Open
Norfolk, Virginia (United States of America)
48.0 ft.
2024
Used
New 2024 Nautitech 48 Open 2 Cabins / 2 Heads + "Flexibility Room" configurable up to 3 beds ( 7 beds total ) Two 75hp Diesel engines Volvo Penta with Saildrive ...
$1,250,000
Hunter 33-2
Groton, Connecticut (United States of America)
33.01 ft.
2004
Used
Details and Equipment Faux Castle-Details Raymarine Electronics (GPS, Wind, Depth, Speed) VHFB and G AIS Receiver (From VHF Radio to GPS) Raymarine Au...
$59,950
Nautitech 48 Open
Kemah, TX (United States of America)
47.74 ft.
2025
New
Video Tour
2025 NAUTITECH 48 OPEN - OPEN A NEW HORIZON When ultimate comfort is combined with elegance and the pleasure of sailing, your travels become a true dream. For this new model, Nautitech raises the standards of comfort and sensations even higher. Perfect alchemy between architecture and ...
P.O.A. *
Nautitech 40 Open
Annapolis, MD (United States of America)
39.24 ft.
2025
New
Video Tour
2025 NAUTITECH 40 OPEN - A PERFECT BALANCE BETWEEN PERFORMANCE AND LIFESTYLE The 40 Open has been designed for lovers of sailing and good life. This luxury catamaran combines sailing sensations and absolute comfort on board, so that you never have to choose between the two. Whether you...
P.O.A. *
Beneteau Oceanis 40
Saint Petersburg, FL (United States of America)
39.76 ft.
2011
Used
2011 Beneteau Oceanis 40 - 2 Cabin (Privately Owned / never chartered) The Oceanis 40 is an unequivocal invitation to delight in her design, comfort, and performance...
$157,500
Beneteau Oceanis 40
Saint Petersburg, FL (United States of America)
39.76 ft.
2011
Used
2011 Beneteau Oceanis 40 - 2 Cabin (Privately Owned / never chartered) The Oceanis 40 is an unequivocal invitation to delight in her design, comfort, and performance...
$157,500
* 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.