Montgomery sailboats for sale

Buying a used Montgomery: a small lineup with a well-dated production record

A used Montgomery is a manageable search - the brand only ever built a handful of hull sizes - but it's not a uniform one. Jerry Montgomery designed some of these boats himself; Lyle Hess, who mentored Montgomery into yacht design in the first place, designed or substantially engineered the rest. That split matters less for a used buyer than the fact that the volume model, the 17, went through a series of specific, dated changes across its production run, so pinning down when a given hull was built tells you more than the model number alone.

Which era to target

The 17 sold fast out of the gate - the first two boats went to the Newport, Rhode Island and Annapolis boat shows in October, where Montgomery sold 36 of them - but those earliest examples were fixed-keeled. Dealers pushed immediately for something trailerable, and the boat was redesigned with a centerboard the following winter; that keel-centerboard version went on to dominate production, so a fixed-keel 17 is an early outlier rather than the norm.

From there the running changes come one per era. In 1978 the interior was reworked, with a full-length port quarter berth and settee replacing the galley. In 1981 a wet locker with improved cockpit drainage was added aft in the cockpit. Sometime in the mid-1980s, the casting company that made the 17's cast-iron centerboard mold went out of business and discarded it, forcing the keel-trunk mold to be modified to accept the smaller Montgomery 15's centerboard instead - a detail worth asking a seller about on any boat from that window. And in 1987 encapsulated lead ballast replaced iron, total ballast rose from 550 to 600 pounds, and the interior's quarter berth was shortened again to make room for a larger cockpit locker.

What to inspect across the range

The 1987 ballast switch marks a real inspection line on the 17. On earlier boats, the cast-iron centerboard is prone to rusting and binding inside the keel, and the encapsulated iron ballast can rust and expand enough to swell the keel and seize the centerboard entirely - serious enough that fixing it means cutting into the fiberglass to replace the ballast with lead. Owners dealing with the centerboard version of the problem generally describe removing the board, sandblasting and fairing it, then coating it in epoxy.

Navigating the lineup

The 17 is the best-documented entry point simply by volume - it ran for two decades and dominates what turns up used. The 15 sits below it as its own independent design rather than a downsized 17, so it's worth judging on its own terms rather than against its larger sibling. The 12 is rarer still, a small Hess-designed sloop built for yacht-club racing, and the 23 tops the range as the largest and most compromise-laden of the three, its hull mostly Hess's engineering. The marque's pedigree runs deeper still - Montgomery's own 10-footer took the only perfect quality score among 49 entries at Yacht Racing magazine's 1970 America's Teacup Trials, the trials that introduced the Laser and the Hobie 14 - though matching size and era to what you want to sail matters more than that history. The full model directory on this page breaks down each size in turn.