Islander 55 Sailboats for Sale & Market Overview

Bruce King·1968·Islander / Tradewind Yachts
Islander 55 drawingBuilder drawing
Hull Type
Monohull · centerboard
Rig
Masthead Sloop
LOA
54.67' · 16.66 m
Disp.
38,000 lbs · 17,237 kg
First year
1968

The Islander 55 represents the zenith of the Wayfarer Yacht Corporation's ambition during the 1970s. Designed by the acclaimed naval architect Bruce King, this flagship vessel was a radical departure from the smaller, coastaloriented cruisers that established the company’s reputation. While Islander Yachts was built on the success of Joseph McGlasson’s 24foot designs, the 55foot model was aimed squarely at the burgeoning market for luxury bluewater cruisers. The boat is characterized by its powerful ketch rig, a traditional clipperstyle bow (on some variants), and a heavydisplacement hull that prioritized stability and momentum over lightair agility. Because production was extremely limited—estimates suggest fewer than 15 hulls were completed—the Islander 55 is often regarded as a semicustom rarity in the secondary market. Its legacy is further complicated by the company's financial transitions; after Islander’s parent company, Radlon Inc., faced difficulties, the molds for the 55 were eventually acquired by Tradewinds Marine, which produced a small number of vessels known as the Tradewinds 55.

Market snapshot

Median asking · 12 mo
$ 89,000
Ask, not sold · 2 listings
Recent listings · 90 d
2
2 tracked · 12 mo
3-month price trend
0.0%
vs. 12-mo median
Countries with listings
Global market

Recent Listings

1 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

5 designs · same segment
ModelLOAMedian askListings · 12 moActive · 90 d
Oyster 5556.25'$ 370,192134
Discovery 5554.79'$ 649,995105
Hallberg-Rassy 5554.72'$ 1,217,018104
Nautor Swan Swan 55 CC54.98'$ 2,250,07476
Islander 55You are here$ 89,00022

Frequently asked questions

01How much does a used Islander 55 cost?+
The median asking price for a used Islander 55 over the past 12 months is $89,000. Prices vary by condition, year, equipment, and location.
02How many Islander 55 sailboats are for sale?+
2 Islander 55 listings have gone live in the last 90 days, and 2 have been tracked across the past 12 months.
03Are Islander 55 prices going up or down?+
The median asking price for the Islander 55 has remained stable over the last 3 months compared to the 12-month median.
04What should I look at instead of a Islander 55?+
Comparable models include Oyster 55, Discovery 55, Hallberg-Rassy 55. See the peer cross-shop table above for pricing and availability.