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10data points analyzed by Sailpages.com to compile this GLOUCESTER 20 buyer’s report

GLOUCESTER 20

Gloucester Yachts Inc.🇺🇸· Design: Stuart Windley
$3,833 avg$2,500 – $5,500 (3 listings)from 1981165 built
$600 – $1.5K est. annual maintenance
DaysailermonoFractional SloopFinVariable

Specifications

Hull

LOA19.5 ft
LWL16.5 ft
Beam7.5 ft
Draft4.5 ft/ 1 ft min
Displacement1,650 lb
Ballast549.9 lb
Hull speed1.34·√LWL5.4 kn

Rig & Sails

Iforetriangle height21 ft
Jforetriangle base8 ft
Pmainsail luff22.5 ft
Emainsail foot8 ft
FLforestay8 ft
Mainsail181.2 sq ft
Jib (100%)84 sq ft
Spinnaker142.8 sq ft

About the GLOUCESTER 20

A fin keel version was also available, draft:3.0'.

Sailpages Buyer's Take

Designed by Stuart Windley and built by Gloucester Yachts Inc. (USA), the Gloucester 20 is a compact fractional sloop with a production run of 165 hulls completed in 1981. This data-driven synthesis highlights the boat's status as a specialized, low-volume build from a single year, emphasizing the importance of verifying specific build details given the limited production window.

Best for:
This vessel suits coastal cruisers and day-sailers seeking a lightweight, easily trailerable package with a fractional sloop rig, rather than serious offshore passagemakers.
Bluewater capability:
With a low displacement of 1650.0 lb and a comfort ratio of 10.0, the Gloucester 20 is not designed for bluewater cruising and is best restricted to protected coastal waters due to its light hull form.
Comparables:
Comparable boats include other 1980s trailerable fractional sloops like the O'Day 23 or Catalina 22, sharing similar beam and displacement characteristics that prioritize ease of handling and transport over heavy displacement cruising.

Direct variant of the GLOUCESTER 20

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.

GLOUCESTER 191983

Performance

Comfort10.0
Capsize2.54
SA/Disp20.2
Disp/Len164
Bal/Disp33.3

Estimated Value

Low Confidence
Based on 3 listings
Low
$2,331
Estimated Value
$2,719
High
$3,496
Inflation-adjusted to 2026 USD

Estimated Cost of Ownership

Based on 19.5ft LOA. Actual costs vary by condition, usage, and local rates.

$/ft/mo
Annual Maintenance
$600 – $1.5K
Hull, rigging, sails, engine service
Annual Docking
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Annual Insurance
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Known Issues & Pre-Purchase Inspection

4 reported issues across 3 systems for the GLOUCESTER 20, compiled from owner reports in sailing forums and owner-association material.

2 critical1 major1 minor
Rudder2Structural1Keel1

Unlock the full inspection report

Thinking of buying a GLOUCESTER 20? 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 4 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

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Which engine powers your GLOUCESTER 20?

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.

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

Used sails that fit the GLOUCESTER 20

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