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Chesapeake sailboats for sale

1 country
Market pulse · 12 mo
—
Median asking price · all Chesapeake
New listings · 90 d
—
Tracked · 12 mo
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Countries
1
Models
1
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Refreshed hourly

Chesapeake listings in the last 90 days across 1 country — compare prices, available boats, and specs across the used sailboat market. Filter by keel or rig even when the seller left it out, and get a heads-up when something new matches.

Browse listings →Create email alert
Example alert
Daily emails for “40-ft fin-keel fractional sloops under $ 200k”
Chesapeake38–42'Fin keelFractional sloop< $ 200k

Market snapshot

Median asking · 12 mo
—
Asking price
New listings · 90 d
—
Active now
Models
1
Production variants
Countries with listings
1
United States (100.0%)

Latest listings

showing 10 newest

View all Chesapeake listings →Aggregated from multiple (unaffiliated) sources · refreshed hourly.

Most shopped right now Top 12 by listings

Masthead Sloop1960–65
Chesapeake 32
LOA
32'
Beam
8.75'
Draft
4.75'
Disp.
12k lb
Median ask$ 34k
For sale2

Where they're listed

Chesapeake listings appear across 1 country. United States has the most listings with 11.

Listings by country
Count · past 12 months
Share of listings
Count · past 12 months

Country view

11 listings · 1 country
CountryMedian askListings · 12 moActive · 90 dShare
United States$ 6,495115100.0%

All Chesapeake models

1 model grouped by length overall. Open any model to see recent asking prices and active listings.

30–40 ft 1 model

Frequently asked questions

01Where are Chesapeake sailboats for sale?+
The busiest markets for used Chesapeake listings are United States (100.0%) of all listings over the past 12 months.
02Which Chesapeake models have the most listings?+
The most-listed Chesapeake models right now are Chesapeake 32. More listings usually make prices easier to read and give buyers more room to compare.