Chrysler 20 Sailboats for Sale & Market Overview

Halsey Herreshoff·1977·Chrysler Marine
Approximate drawing

Hover a measurement to read its value

Hull type
Monohull · wing
Rig
Masthead Sloop
LOA
20' · 6.1 m
Displ.
2,200 lbs · 998 kg
First year
1977

The Chrysler 20 was introduced in the mid1970s as a compact, trailerable response to the growing demand for "pocket cruisers" that could be easily managed by a small family or a solo sailor. Designed by the esteemed naval architect Halsey Herreshoff, the boat was intended to bridge the gap between Chrysler’s smaller daysailers, like the Mutineer 15, and the larger, more substantial Chrysler 22 and 26 models. Despite its shorter overall length, the Chrysler 20 retains the distinctive Herreshoff aesthetic—functional, sturdy, and surprisingly stiff under sail. It remains a popular choice for sailors who prioritize ease of launching and retrieving without sacrificing the security of a ballasted keel and a weathertight cabin.

Market snapshot

Median asking · 12 mo
Ask, not sold
Recent listings · 90 d
Listed for sale
3-month price trend
Insufficient data
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

10 designs · same segment
ModelLOAMedian askListings · 12 moActive · 90 d
Cape Dory 2524.83'$ 10,0002710
Cape Cutter 1923.62'$ 18,6792013
Rhodes 22 Continental22'$ 14,975163
Pacific Seacraft Flicka 2024'$ 27,650135
Friendship 2222'$ 9,250129
Com-Pac 2322.75'$ 6,950115
Dufour 2424.1'$ 9,947107
Schock Harbor 2020'$ 20,00075
Com-Pac 23 Mk IV23.92'$ 32,95074
Triton 2121.25'$ 83,44540

Frequently asked questions

01What should I look at instead of a Chrysler 20?+
Comparable models include Cape Dory 25, Cape Cutter 19, Rhodes 22 Continental. See the peer cross-shop table above for pricing and availability.