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, coastal-oriented cruisers that established the company’s reputation. While Islander Yachts was built on the success of Joseph McGlasson’s 24-foot designs, the 55-foot model was aimed squarely at the burgeoning market for luxury blue-water cruisers. The boat is characterized by its powerful ketch rig, a traditional clipper-style bow (on some variants), and a heavy-displacement hull that prioritized stability and momentum over light-air agility. Because production was extremely limited—estimates suggest fewer than 15 hulls were completed—the Islander 55 is often regarded as a semi-custom 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.
Islander 55 Sailboats for Sale & Market Overview
- Make
- Islander
- Model
- 55
- Builder
- Islander / Tradewind Yachts
- Designer
- Bruce King
- Number Built
- Production Year(s)
- 1968 - ??
Below are the most recent Islander 55 sailboat listings (up to 10).
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| Source | Year | Make | Model | Price | Cabins | Heads | City | Country | Listing Date | |
|---|---|---|---|---|---|---|---|---|---|---|
DISCLAIMER: We are not affiliated with any external listing websites in any way. We simply aggregate publicly available listings to make it easier for buyers to find sailboats for sale. We cannot guarantee the accuracy of the listings, so please verify all information with the seller before making any decisions.
Market Overview
Price & Volume Trends
Monthly breakdown
| Month | Listings | Median Asking Price (USD) |
|---|---|---|
| Apr 2026 | 2 | $89,000 |
| Model | LOA | Median Price (USD) | Listings | Recent |
|---|---|---|---|---|
| Tayana 55 | 55' | $204,950 | 26 | 12 |
| Islander 36 | 36.08' | $29,500 | 23 | 1 |
| Oyster 55 | 56.25' | $398,701 | 11 | 2 |
| Discovery 55 | 54.79' | $649,995 | 7 | 2 |
| Hallberg-Rassy 55 | 54.72' | $1,266,430 | 6 | 0 |
| Islander 40 MS | 44' | $30,000 | 5 | 2 |
| Nautor Swan Swan 55 CC | 54.98' | $2,179,437 | 5 | 4 |
| Pearson Vanguard 33 | 32.58' | $15,000 | 5 | 0 |
| Swan 55-S&S-1970 | 54.63' | $559,585 | 4 | 0 |
| Nautor Swan Swan 55 | 58.23' | $2,611,593 | 3 | 1 |
| Islander 55 | $89,000 | 2 | 2 |
| Country | Median Price (USD) | Listings (past 12 months) | Recent (90d) |
|---|---|---|---|
| Panama | $89,000 | 2 | 2 |
Frequently Asked Questions
- How 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.
- How many Islander 55 sailboats are for sale?
- We have tracked 2 Islander 55 listings over the past 12 months, with 2 listed within the last 90 days.
- Are 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 average.
- What are similar sailboats to the Islander 55?
- Comparable models include the Tayana 55, Islander 36, Oyster 55. See the comparison table above for pricing and availability.