The Whitby 55 represents the ultimate expression of the Whitby Boat Works' cruising ethos. Designed by the esteemed naval architect Ted Brewer and launched in the early 1980s, this flagship was a significant departure from the builder's high-volume production of the Alberg 30 or the Whitby 42. With only a handful of units produced—estimated at just two or three hulls—the Whitby 55 is an exceptionally rare blue-water cruiser that embodies the "go-anywhere" philosophy that Kurt and Doris Hansen championed before the yard's closure in 1988. It stands as a robust, overbuilt testament to the era of heavy-displacement Canadian yacht building, designed specifically for sailors who prioritize safety and volume over high-speed racing performance.
Whitby 55 Sailboats for Sale & Market Overview
- Make
- Whitby
- Model
- 55
- Builder
- Whitby Boat Works Ltd.
- Designer
- Ted Brewer
- Number Built
- Production Year(s)
- 1982 - ??
Below are the most recent Whitby 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) |
|---|---|---|
| Jan 2026 | 2 | $65,750 |
| Feb 2026 | 1 | $25,000 |
| Model | LOA | Median Price (USD) | Listings | Recent |
|---|---|---|---|---|
| Tayana 55 | 55' | $204,950 | 26 | 12 |
| Amel 55 | 56.76' | $933,624 | 18 | 3 |
| Whitby 42 | 42' | $62,783 | 16 | 5 |
| Oyster 55 | 56.25' | $398,701 | 11 | 2 |
| Cheoy Lee Offshore 47 | 46.75' | $124,975 | 8 | 3 |
| Moody 333 | 33' | $27,039 | 8 | 6 |
| Discovery 55 | 54.79' | $649,995 | 7 | 2 |
| Cape George 36 | 36' | $89,500 | 7 | 4 |
| Hallberg-Rassy 55 | 54.72' | $1,266,430 | 6 | 0 |
| Swan 55-S&S-1970 | 54.63' | $559,585 | 4 | 0 |
| Whitby 55 | $62,500 | 3 | 3 |
| Country | Median Price (USD) | Listings (past 12 months) | Recent (90d) |
|---|---|---|---|
| United States | $62,500 | 3 | 3 |
Frequently Asked Questions
- How much does a used Whitby 55 cost?
- The median asking price for a used Whitby 55 over the past 12 months is $62,500. Prices vary by condition, year, equipment, and location.
- How many Whitby 55 sailboats are for sale?
- We have tracked 3 Whitby 55 listings over the past 12 months, with 3 listed within the last 90 days.
- Are Whitby 55 prices going up or down?
- The median asking price for the Whitby 55 has remained stable over the last 3 months compared to the 12-month average.
- What are similar sailboats to the Whitby 55?
- Comparable models include the Tayana 55, Amel 55, Whitby 42. See the comparison table above for pricing and availability.