Freedom 39 Sailboats for Sale & Market Overview

Ron Holland/Garry Hoyt·1983·Freedom Yachts
Freedom 39 drawingBuilder drawing
Hull Type
Monohull · fin
Rig
Cat Ketch
LOA
39' · 11.89 m
Disp.
18,500 lbs · 8,391 kg
First year
1983

The Freedom 39 represents a pivotal moment in the evolution of Gary Hoyt’s "unstayed" design philosophy, blending his radical rigging concepts with a sophisticated hull form by the renowned naval architect Ron Holland. Produced by TillotsonPearson Inc. (TPI) in Rhode Island, the 39 was a significant departure from the more traditional, heavydisplacement Freedom 40 that preceded it. By commissioning Ron Holland—a designer synonymous with highperformance IOR racers—Freedom Yachts sought to prove that a rig without standing rigging could be paired with a modern, slippery hull to create a fast, capable offshore cruiser. This model was primarily delivered in two distinct rig configurations: the Cat Ketch and the Schooner, along with a specialized Pilothouse variant. Unlike the earlier models that utilized aluminum masts, the Freedom 39 leaned heavily into TPI’s expertise with carbon fiber, providing the strengthtoweight ratio necessary to support large sail areas without the need for shrouds or stays.

Market snapshot

Median asking · 12 mo
$ 22,125
Ask, not sold · 2 listings
Recent listings · 90 d
0
2 tracked · 12 mo
3-month price trend
Insufficient data
Countries with listings
Global market

Recent Listings

2 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

4 designs · same segment
ModelLOAMedian askListings · 12 moActive · 90 d
Freedom 3837.92'$ 71,501155
Freedom 3636.42'$ 47,95084
Freedom 3232.75'$ 18,75082
Freedom 39You are here$ 22,12520

Frequently asked questions

01How much does a used Freedom 39 cost?+
The median asking price for a used Freedom 39 over the past 12 months is $22,125. Prices vary by condition, year, equipment, and location.
02How many Freedom 39 sailboats are for sale?+
2 have been tracked across the past 12 months.
03Do Freedom 39 listings get price reductions?+
About 100% of Freedom 39 listings have had a price reduction, with an average discount of 14.8% off the original ask. A listing that has been on the market more than 90 days without a reduction usually signals the seller is not motivated.
04What should I look at instead of a Freedom 39?+
Comparable models include Freedom 38, Freedom 36, Freedom 32. See the peer cross-shop table above for pricing and availability.