Oyster Sailboats

Explore Oyster sailboats and the details behind each model. If you are shopping for a Oyster sailboat, we keep an eye out for Used Oyster Sailboats.

Model Listings Year Built LOA (ft) Beam (ft) Draft (ft) Disp. (lbs) Hull Designer Rig Keel
Oyster 5656 for sale199657.33 ft16.17 ft7.83 ft57,320 lbsMonohullRob HumphreysCutterFin
Oyster 5322 for sale198553 ft15.75 ft7 ft40,800 lbsMonohullHolman & PyeMasthead SloopFin
Oyster 5420 for sale201353.92 ft15.58 ft7.87 ft46,942 lbsBulb
Oyster 57520 for sale201058.67 ft16.42 ft8.82 ft58,422 lbsMonohullRob HumphreysMasthead SloopFin
Oyster 8213 for sale200781.92 ft20.75 ft8.83 ft134,481 lbsMonohullRob HumphreysCutterFin
Oyster 3912 for sale197840.68 ft12.89 ft5.68 ft19,498 lbsMonohullDonald PyeKetchFin
Oyster 56511 for sale201759.35 ft16.83 ft8.2 ft56,372 lbsMonohullHumphreys Yacht DesignFractional SloopBulb
Oyster 5510 for sale198656.25 ft15.75 ft051,000 lbsMonohullHolman & PyleCutterFin
Oyster 7210 for sale74.7 ft19.19 ft9.51 ft0
Oyster 6559 for sale200965.48 ft18.44 ft9.68 ft85,979 lbsMonohullRob HumphreysCutterBulb
Oyster 5458 for sale201353.9 ft15.58 ft7.87 ft46,992 lbsBulb
Oyster 6258 for sale201563.55 ft17.85 ft9.19 ft73,854 lbsMonohullRob HumphreysMasthead SloopBulb
Oyster 467 for sale198246 ft14 ft6.5 ft31,980 lbsMonohullHolman & PyeKetchFin
Oyster 497 for sale51.83 ft15 ft7.25 ft0
Oyster 5957 for sale201762.5 ft17.59 ft8.79 ft67,918 lbsMonohullHumphreys Yacht DesignFractional SloopBulb
Oyster 627 for sale200063.32 ft17.72 ft8.53 ft70,547 lbsMonohullRob Humphreys & Oyster DesignCutterBulb
Oyster 4066 for sale198640.49 ft12.76 ft5.75 ft20,500 lbsMonohullHollman & PyleMasthead SloopFin
Oyster 426 for sale199741.83 ft12.83 ft6 ft26,600 lbsMonohullHolman & PyeMasthead SloopFin
Oyster 4356 for sale198343.42 ft13.71 ft6.33 ft29,000 lbsMonohullHolman & PyeCutterFin
Oyster 456 for sale199644.33 ft14 ft6.5 ft35,000 lbsMonohullHolman & PyeMasthead SloopFin
Oyster 4856 for sale199248.5 ft14 ft7 ft37,550 lbsMonohullHomann & PyleCutterFin
Oyster 4956 for sale202152.82 ft15.65 ft7.48 ft46,297 lbsMonohullHumphreys Yacht DesignFractional SloopBulb
Oyster 435 for sale198343.38 ft14.08 ft7.3 ft16,600 lbsMonohullStephen JonesFractional SloopFin
Oyster 8855 for sale201388.85 ft20.77 ft10.83 ft157,631 lbs
Oyster 374 for sale197837 ft12.08 ft6.16 ft16,530 lbsMonohullHolman & PyeMasthead SloopFin
Oyster 474 for sale47 ft14.01 ft6.5 ft0Fin
Oyster 48 Lightwave4 for sale198748 ft14.33 ft6 ft27,000 lbsMonohullCarl SchumacherMasthead SloopFin
Oyster 683 for sale199067.5 ft17.25 ft8.92 ft85,500 lbsMonohullHolman & PyeCutterFin
Oyster 8253 for sale201485.96 ft20.73 ft10.79 ft123,459 lbsBulb
Oyster 262 for sale197826.17 ft9.83 ft4.75 ft6,363 lbsMonohullHolman & PyeFractional SloopFin
Oyster UFO 342 for sale33.33 ft10.99 ft00
Oyster 37 Heritage2 for sale198437 ft12 ft5.33 ft14,534 lbsMonohullHolman & PyeMasthead SloopFin
Oyster 412 for sale198039.66 ft13.58 ft6.82 ft17,081 lbsMonohullStephen JonesMasthead SloopFin
Oyster 6752 for sale201569.13 ft18.54 ft9.68 ft82,672 lbsMonohullHumphreys Yacht DesignMasthead SloopBulb
Oyster SJ351 for sale198335 ft11.42 ft6.42 ft8,600 lbsMonohullStephen JonesFractional SloopFin
Oyster 395 Lightwave1 for sale198839.5 ft11.75 ft6.8 ft11,000 lbsMonohullCarl SchumacherMasthead SloopFin
Oyster 4611 for sale46 ft14.01 ft6.89 ft0Fin
Oyster 4751 for sale201548.59 ft14.47 ft7.09 ft35,274 lbsMonohullHolman & PyeMasthead SloopBulb
Oyster 661 for sale200566.83 ft17.98 ft8.83 ft87,633 lbsMonohullRob HumphreysMasthead SloopFin
Oyster 7451 for sale201474.61 ft19.39 ft10.17 ft118,955 lbsMonohullRob HumphreysFractional SloopBulb
Oyster 35 Extended1 for sale0000
Oyster 801 for sale0000
Oyster 49 Pilothouse1 for sale0000
Oyster SJ-27198126.9 ft10.17 ft4.59 ft4,600 lbsMonohullStephen JonesMasthead SloopFin
Oyster SJ-30197930.42 ft10.75 ft5.33 ft6,500 lbsMonohullStephen JonesFractional SloopFin
Oyster SJ-35198234.75 ft11.42 ft6.58 ft8,600 lbsMonohullStephen JonesFractional SloopFin
Oyster 61199461 ft16.83 ft8.25 ft62,000 lbsMonohullHolman & PyeCutterFin
Oyster 70199670 ft17.25 ft9.08 ft91,000 lbsMonohullHolman & PyeCutterFin
Oyster 7250000

Oyster sailboats: a deck-saloon signature carried through three changes of ownership

Oyster's history reads less like a straight line than a brand that survived repeated hand-offs: a founder who set out to build a racing boat and ended up building cruisers instead, a design partnership that has outlasted three different owners, and a construction identity — the light-filled deck saloon — that the company built its whole brand around. Few premium builders have gone through as much corporate turbulence and still kept a recognizable identity on the water.

Origins and ownership

Richard Matthews founded Oyster Yachts in 1973 while looking to build a racing boat. Matthews had already shown an entrepreneurial streak, starting a tea and coffee vending business at 19 using an inheritance left to him by an aunt. The boat that emerged from his racing ambitions was the UFO34, a Holman & Pye-designed 34-foot three-quarter tonner, which set Oyster on the design partnership that would define its first models. The pivot toward cruising came fast: at an early Southampton Boat Show, Oyster sold seven Oyster 37s between the Wednesday night and the show's final Sunday, after several days of no interest at all. Oyster Brokerage followed in 1984, built on the idea that no one was better placed to advise on a used Oyster than the people who built it, and Oyster Charter launched in 2005, putting the yard directly into the business of putting people aboard its own boats.

Ownership has changed hands three times since. Founder Richard Matthews sold Oyster Marine in 2008 to the UK private-equity firm Balmoral Capital, which also owned the Italian motor-yacht builder Canados; Matthews stayed on as chairman and the existing management team remained in place. Balmoral sold the company on to the Dutch private-equity firm HTP Investments in 2012. That ownership ended in February 2018, when HTP announced it would no longer support the company financially: Oyster stopped production, with the loss of some 380 employees at its Southampton and Wroxham, Norfolk sites, and administrators were appointed to the holding company, Oyster Marine Holdings Limited. The collapse came within months of Oyster calling 2017 a record year for its order book. Weeks later, gaming-software entrepreneur Richard Hadida bought Oyster and its subsidiaries, including Oyster Palma and Oyster Newport in the US, using his own personal fortune; his history with the brand went back five years, to a 2013 charter of the Oyster 885 Lush. Hadida installed a management team led by Oyster stalwart Paul Adamson, who had captained that same 885 in the 2014 Oyster World Rally, and within three months had yacht builders back at work in Wroxham on an Oyster 675, the first of two boats then under contract. By 2023, the company had grown from its 1973 standing start to 600 employees across six sites.

That rebuild followed a serious episode in the brand's history. In 2015, Oyster reviewed the design and construction of its Oyster 825 after the second hull off the line, Polina Star III, lost her keel and sank off the coast of Spain. Oyster said the 825's construction and design had taken Classification Society Rules and other standards into account, and its subsequent inspection of the rest of the 825 fleet — excluding Polina Star III itself — identified a possible weakness in how those boats' inner structures had been built. When Hadida took over in March 2018, he addressed the incident directly, calling it firmly in the firm's past and stressing that a repeat would never happen.

The designers

Holman & Pye drew Oyster's earliest boats, from the founding UFO34 through the Oyster 55, which became the range's early best-seller. The company's own history credits the Oyster 35, launched in 1978, as its first Oyster-branded yacht, and by the late 1970s the deck saloon had become Oyster's signature configuration, prized for flooding light into a part of the accommodation that had traditionally been dark and enclosed.

Oyster's partnership with naval architect Rob Humphreys and Humphreys Yacht Design began in the late 1990s: the Oyster 56, launched in 1998, was the first Oyster with lines drawn by the Lymington-based studio, and in 1999 Oyster formally commissioned Humphreys to design the Oyster 53. That relationship continued through the Oyster 565, whose plans were unveiled in 2016 after a long gestation, and into the boats built at the yard's newer Hythe facility. Separately, stylist and interior designer Andrew Winch reworked Oyster's exterior look, introducing the wrap-around-window, deck-saloon-eyebrow profile that remains a recognizable feature across the range.

Construction through the eras

The Oyster 56 also broke new ground below decks: designed in collaboration with Loughborough University's Ergonomics department, it was the first Oyster with an ergonomically engineered cockpit, and it went on to become the yard's most popular model, with 75 built over twelve years. Humphreys later carried that engineering focus into the range's largest boats, tank-testing twin-rudder configurations for the Oyster 82 and adopting twin rudders on the Oyster 885 after beam and draft constraints pushed him to draw fuller lines aft. That thinking culminated in 2012, when Humphreys drew the first Generation 6 (G6) hulls and decks: a sleeker profile with a wider beam aft, adding volume above and below decks while improving sailing performance. After the 2018 ownership change, production of the Oyster 495 began at a new facility in Hythe, near Southampton.

Who Oyster is for

Oyster has always paired cruising comfort with genuine sailing credentials: in 2007, Oyster yachts were class winners in both the Fastnet and Sydney Hobart races. That same competitive, community-minded culture carried into the Oyster World Rally, launched in 2013 to mark the company's 40th anniversary — 28 owners completed the inaugural edition, with a second rally following in 2017. Oyster suits buyers drawn to a deck-saloon cruiser built for serious offshore passages, backed by a brand that has weathered real corporate disruption without losing its design identity.

Frequently asked questions

01Who founded Oyster Yachts, and when?+
Richard Matthews founded Oyster in 1973 while looking to build a racing boat. The pivot toward cruising boats came quickly: early Oyster 37s sold out during a single Southampton Boat Show.
02What is Oyster's signature design feature?+
The deck saloon layout, which had become Oyster's signature configuration by the late 1970s, prized for flooding natural light into a part of the boat traditionally dark and enclosed. Stylist Andrew Winch later refined the look with the wrap-around windows and deck-saloon eyebrow that remain recognizable across the range.
03Who designed Oyster sailboats?+
Holman & Pye designed Oyster's early boats, including the founding UFO34 and the early best-selling Oyster 55. Naval architect Rob Humphreys and Humphreys Yacht Design have designed Oyster's boats since the late 1990s, including the Generation 6 (G6) range introduced in 2012.
04Has Oyster changed ownership?+
Yes. Founder Richard Matthews sold the company to Balmoral Capital in 2008; Balmoral sold it on to HTP Investments in 2012; Oyster entered administration in February 2018 after HTP withdrew financial support; and Richard Hadida bought the company weeks later, in March 2018, resuming production within three months.
05Who is an Oyster sailboat built for?+
Buyers seeking a deck-saloon bluewater cruiser from a yard with genuine racing pedigree — Oyster yachts won their class in both the 2007 Fastnet and Sydney Hobart races — and an active ownership community built around events like the Oyster World Rally.