LISTINGSPORTOpen the app

Chesapeake Sailboats

Explore Chesapeake sailboats and the details behind each model. If you are shopping for a Chesapeake sailboat, we keep an eye out for Used Chesapeake Sailboats.

ImperialMetric

Model ↕	Listings ↓	Year Built ↕	LOA (ft) ↕	Beam (ft) ↕	Draft (ft) ↕	Disp. (lbs) ↕	Hull ↕	Designer ↕	Rig ↕	Keel ↕

Chesapeake 32	2 for sale	1960	32 ft	8.75 ft	4.75 ft	11,500 lbs	Monohull	Philip Rhodes	Masthead Sloop	Full
Chesapeake 20	—	1939	20 ft	6.58 ft	4.42 ft	950 lbs	Monohull	Ernest H. Hartge	Fractional Sloop	Centerboard
Chesapeake 30	—	1977	29.92 ft	11 ft	5.5 ft	8,000 lbs	Monohull	Bob Seidelmann	Masthead Sloop	Fin

Chesapeake Sailboats between 20 – 30 ft

Fractional Sloop1939

LOA: 20'
Beam: 6.58'
Draft: 4.42'
Disp.: 1k lb

Masthead Sloop1977

LOA: 29.92'
Beam: 11'
Draft: 5.5'
Disp.: 8k lb

Chesapeake Sailboats between 30 – 40 ft

Masthead Sloop1960–65

LOA: 32'
Beam: 8.75'
Draft: 4.75'
Disp.: 12k lb

Median ask$ 34k