Whitby 55 Buyer's Guide
Shopping the brokerage market for a Whitby 55 means looking at Ted Brewer’s 55-foot ketch from Whitby Boat Works, a design offered in center-cockpit or pilothouse form with several interior layouts anchor. Built around a 43,500-pound hull with 18,000 pounds of ballast and a 15-foot 5-inch beam, it splits its 1,360 square feet of standard sail area across two masts to keep handling sane for a big boat. Examples on the market today reflect both the original charter-friendly intent and later owner priorities.
Layouts on the Used Market
The defining choice among surviving boats is deck style: center cockpit or pilothouse, both factory options from new. Interiors vary because Whitby offered multiple plans and would rework them—standard layouts run from an aft double berth with head and shower to two forward guest cabins sharing a second head. A low-rig version exists for inland-waterway bridge clearance, so a buyer’s intended cruising route should dictate whether that shorter mast matters.
Equipment and Common Upgrades
Energy and power systems are where modern refits show most: solar and lithium batteries are commonly fitted, while inverters and sometimes heating or hot water appear often. Navigation and safety gear frequently include radar, AIS, autopilot, chartplotter, and a life raft, with a hardtop often seen for helm protection. Sail-handling upgrades center on a furling main, commonly found, which suits the two-mast rig’s easy-handling brief.
What to Inspect
Inspection should follow normal large-yacht practice for the split rig’s mast step and standing rigging, the teak interior’s condition, and the specifics of whichever deck and interior configuration a given boat carries. Confirm whether a low-rig mast was original or modified if bridge clearance is a concern.
Availability and Buyer's Takeaway
These boats typically appear in the United States and Italy. For a buyer, the short list is: decide center-cockpit versus pilothouse; verify the rig height against your waterways; check that lithium and solar upgrades meet your autonomy needs; confirm the furling main and autopilot are serviceable; and inspect the teak interior for wear. The Whitby 55 remains a spacious, manageable two-master best matched to relaxed coastal cruising rather than barebones passage-making.
Price & volume trends
Monthly asking-price and listing-volume trends for the Whitby 55. The line shows the median ask each month; the bars show how many listings appeared.
Monthly breakdown · 2 rows
| Month | Listings | Median ask | Δ vs. last mo. |
|---|---|---|---|
| Jan 26 | 2 | $65,750 | — |
| Feb 26 | 1 | $25,000 | -62.0% |
Where they're listed
Whitby 55 listings appear across 1 country. United States has the most listings with 3.
Country view
3 listings · 1 country| Country | Median ask | Listings · 12 mo | Active · 90 d | Share |
|---|---|---|---|---|
| United States | $62,500 | 3 | 0 | 100.0% |
Comparable models
Similar length, displacement, and era. Open a row to compare that model's market page.
Similar boats to compare
7 similar designs| Model | LOA | Median ask | Listings · 12 mo | Active · 90 d |
|---|---|---|---|---|
| Tayana 55 | 55' | $ 189,900 | 37 | 5 |
| Amel 55 | 56.76' | $ 855,000 | 25 | 9 |
| Discovery Yachts 55 | 54.79' | $ 689,591 | 14 | 8 |
| Oyster 55 | 56.25' | $ 372,642 | 11 | 4 |
| Hallberg-Rassy 55 | 54.72' | $ 1,222,733 | 9 | 1 |
| Alden Boothbay Explorer | 58.58' | $ 222,500 | 6 | 3 |
| Whitby 55You are here | — | $ 62,500 | 3 | 0 |