โ† Browse all sailboats
78data points analyzed by Sailpages.com to compile this CONTESSA 39 buyerโ€™s report
CONTESSA 39

CONTESSA 39

Jeremy Rogers๐Ÿ‡ฌ๐Ÿ‡งยท Design: Doug Peterson
$52,490 avg$52,490 โ€“ $52,490 (1 listings)from 197912 built
$2.6K โ€“ $6.9K est. annual maintenance
Racer/CruisermonoMasthead SloopFin

Specifications

Hull

LOA38.67 ft
LWL33.16 ft
Beam12.25 ft
Draft7.25 ft
Displacement14,250 lb
Ballast6,975.4 lb
Hull speed1.34ยทโˆšLWL7.7 kn

Rig & Sails

Iforetriangle height52 ft
Jforetriangle base16.5 ft
Pmainsail luff51.5 ft
Emainsail foot12.5 ft

About the CONTESSA 39

Sloop rigged but designed and constructed to ocean sail as a cutter. There is an inner foredeck chain plate, inner headsail and staysail. Jeremy Rogers developed vacuum bag assisted resin transfer systems for building the Contessa 32 & 39 models. The CONTESSA 39 'Eclipse', owned by builder Jeremy Rogers, finished 2nd overall in the notorious Fastnet Race of 1979.

Sailpages Buyer's Take

The Contessa 39 is a rare, heavy-displacement cruising sloop designed by Doug Peterson and built by Jeremy Rogers in the UK, with only 12 hulls constructed in 1979. Its substantial build quality and classic design have earned it a dedicated following among owners who value seakindliness and traditional craftsmanship.

Best for:
This boat is ideally suited for experienced coastal and offshore cruisers who prioritize comfort and safety over speed, particularly those willing to invest significant time and resources into maintaining its complex wooden and composite structure.
Bluewater capability:
With a displacement of 14250.0 lb and a low capsize ratio of 2.02, the Contessa 39 is inherently stable and well-suited for bluewater passages, provided its critical structural components are meticulously maintained.
Comparables:
Comparable vessels include the Hallberg-Rassy 38 and the Tartan 38, as they share similar heavy displacement, fin keel configurations, and a reputation for robust offshore capability within the late-1970s production era.

Performance

Comfort22.5
Capsize2.02
SA/Disp19.4
Disp/Len174
Bal/Disp49.0

Market Price

Low
$52,490
Average
$52,490
High
$52,490
Based on 1 listings across 1 marketplace

Estimated Cost of Ownership

Based on 38.67ft LOA. Actual costs vary by condition, usage, and local rates.

$/ft/mo
Annual Maintenance
$2.6K โ€“ $6.9K
Hull, rigging, sails, engine service
Annual Docking
Enter zip code
Pick a country or enter a US zip for local rates
Annual Insurance
Enter zip code
For location-adjusted rates

Known Issues & Pre-Purchase Inspection

15 reported issues across 7 systems for the CONTESSA 39, compiled from owner reports in sailing forums and owner-association material.

5 critical5 major5 minor
Rigging4Engine4Deck2Rudder2Hull1Keel1Structural1

Unlock the full inspection report

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

  • โœ“ All 15 specific issues โ€” severity, symptoms & fixes
  • โœ“ Model-specific pre-purchase inspection checklist
  • โœ“ Downloadable PDF to take to your surveyor โ€” yours to keep

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

Similar Sailboats

Which engine powers your CONTESSA 39?

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

Already know your engine? Search all engines โ†’ to find its exact parts.

Used sails that fit the CONTESSA 39

Checking eBay for sails sized to this boat's rigโ€ฆ