Oyster 66 Sailboats for Sale & Market Overview

Rob Humphreys·2005·~12 hulls·Oyster Marine
Approximate drawing

Hover a measurement to read its value

Hull type
Monohull · fin
Rig
Masthead Sloop
LOA
66.83' · 20.37 m
Displ.
87,633 lbs · 39,750 kg
First year
2005

The Oyster 66, launched in 1996, represents a significant milestone in the evolution of the British builder's prestigious bluewater fleet. Designed by the renowned naval architect Rob Humphreys in collaboration with the Oyster design team, this model was conceived as a "thoroughbred" cruiser, bridging the gap between the highly successful Oyster 56 and the builder's larger superyachts. During its production run through roughly 2005, only 13 hulls were completed, making it a relatively rare and exclusive sight in the world's most remote anchorages. Built at the firm’s specialist yards in England, the 66 was among the first models to showcase the "Oyster 2000" styling—a refined aesthetic characterized by sophisticated joinery details and the iconic wraparound deck saloon windows that have since become the brand's global calling card. According to the Oyster Yachts Heritage archive, the model was engineered to offer the accommodation and luxury of a much larger vessel while remaining manageable for an experienced couple or a small crew.

Market snapshot

Median asking · 12 mo
Ask, not sold
Recent listings · 90 d
Listed for sale
3-month price trend
Insufficient data
Countries with listings
Global market

Recent Listings

3 for sale · sampled 10 newest

Comparable models

Similar length overall, displacement, and era. Click a row to jump to that model's market page.

Peer cross-shop

10 designs · same segment
ModelLOAMedian askListings · 12 moActive · 90 d
Oyster Yachts 5657.33'$ 592,2144428
Oyster Yachts 5353'$ 455,0002615
Oyster 5453.92'$ 639,839169
Oyster 48548.5'$ 295,000167
CNB 6667.61'$ 2,152,577147
Oyster Yachts 4951.83'$ 383,973135
Oyster 5556.25'$ 372,286134
Oyster Yachts 4646'$ 449,00094
Oyster 4544.33'$ 285,91085
Oyster 62563.55'$ 2,394,08284

Frequently asked questions

01What should I look at instead of a Oyster 66?+
Comparable models include Oyster Yachts 56, Oyster Yachts 53, Oyster 54. See the peer cross-shop table above for pricing and availability.