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150data points analyzed by Sailpages.com to compile this FREEDOM 39 buyer’s report
FREEDOM 39

FREEDOM 39

Tillotson Pearson Inc,🇺🇸· Design: Ron Holland/Garry Hoyt
from 1983
$2.9K – $7.8K est. annual maintenance
Offshore CruisermonoCat Ketch (unstayed)Fin
FreedomYachts.org

Specifications

Hull

LOA39 ft
LWL31 ft
Beam12.83 ft
Draft5.5 ft/ 5 ft min
Displacement18,500 lb
Ballast5,300.2 lb
Hull speed1.34·√LWL7.5 kn

Rig & Sails

Pmainsail luff44.5 ft
Emainsail foot17.5 ft
PYmizzen luff39 ft
EYmizzen foot11.92 ft
Mainsail420.5 sq ft

About the FREEDOM 39

AKA FREEDOM 39 EXPRESS. A Pilot House version was also available. (See FREEDOM 39 PILOT HOUSE) The first boat was rigged as a schooner, with foremast considerably shorter than the main mast (both unstayed). How many boats were equipped with this rig is unknown. EY & PY = forward mast. Thanks to 'Lazy Jaques' for providing corrections.

Sailpages Buyer's Take

The Freedom 39 is a distinctive cat-ketch designed by Ron Holland and Garry Hoyt, built by Tillotson Pearson Inc in 1983 with an unknown total hull count. Its unique unstayed rig and heavy displacement of 18500.0 lb define its character as a robust, self-contained cruiser.

Best for:
This boat suits experienced coastal cruisers and offshore adventurers who value the simplicity of a cat-ketch rig and are prepared to manage the specific maintenance demands of its composite construction.
Bluewater capability:
With a displacement of 18500.0 lb and a low capsize ratio of 1.94, the Freedom 39 is well-suited for offshore passages, though its structural integrity depends heavily on addressing known hull and deck core vulnerabilities.
Comparables:
Comparable to other late-1980s heavy-displacement cruising yachts like the Cal 40 or Pearson 36, but distinguished by its unique cat-ketch rig and higher comfort ratio of 28.61.

Direct variant of the FREEDOM 39

Near-identical models — same hull, builder and designer, re-badged or lightly changed. Specs and owner-reported issues are typically shared across the group, so a sister model's page may carry detail this one doesn't.

Performance

Comfort28.6
Capsize1.94
SA/Disp18.8
Disp/Len277
Bal/Disp28.6

Pricing

We don't have market pricing data for the FREEDOM 39 yet. If you own one, help other buyers — what did you pay for it? Reports build a community price estimate over time.

Estimated Cost of Ownership

Based on 39ft LOA. Actual costs vary by condition, usage, and local rates.

$/ft/mo
Annual Maintenance
$2.9K – $7.8K
Hull, rigging, sails, engine service
Annual Docking
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Annual Insurance
N/A
No price data available

Known Issues & Pre-Purchase Inspection

17 reported issues across 6 systems for the FREEDOM 39, compiled from owner reports in sailing forums and owner-association material.

9 critical4 major4 minor
Structural6Rigging5Hull3Deck1Rudder1Keel1

Unlock the full inspection report

Thinking of buying a FREEDOM 39? This is an in-depth report on the faults this model is known for — so you know exactly what to check when you walk the boat. For the price of a coffee.

  • All 17 specific issues — severity, symptoms & fixes
  • Model-specific pre-purchase inspection checklist
  • Downloadable PDF to take to your surveyor — yours to keep

One-time $2.99 · secure checkout by Stripe · instant access · 30 days online, PDF yours to keep

Similar Sailboats

Which engine powers your FREEDOM 39?

We haven't confirmed the engine for this model yet. If you own or know one, tell us — as owners report in, we build an accurate picture over time.

Brands sometimes mentioned for this model: Yanmar, Perkins — is it one of these?

Already know your engine? Search all engines → to find its exact parts.

Used sails that fit the FREEDOM 39

Checking eBay for sails sized to this boat's rig…