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1data points analyzed by Sailpages.com to compile this GLOUCESTER 27 buyer’s report
GLOUCESTER 27

GLOUCESTER 27

Gloucester Yachts Inc.πŸ‡ΊπŸ‡ΈΒ· Design: Stuart Windley/Harry Sindle
from 1983
$1.1K – $2.9K est. annual maintenance
Offshore CruisermonoFractional SloopFin

Specifications

Hull

LOA26.67 ft
LWL21.5 ft
Beam8 ft
Draft3.5 ft
Displacement5,500 lb
Ballast2,499.8 lb
Hull speed1.34·√LWL6.2 kn

Rig & Sails

Iforetriangle height30 ft
Jforetriangle base11.25 ft
Pmainsail luff28.25 ft
Emainsail foot10.5 ft
FLforestay11.3 ft
Mainsail328.9 sq ft
Jib (100%)168.8 sq ft
Spinnaker286.9 sq ft

About the GLOUCESTER 27

Similar to the earlier LN-27.

Sailpages Buyer's Take

The Gloucester 27 is a compact coastal cruiser designed by Stuart Windley and Harry Sindle, built by Gloucester Yachts Inc. (USA) with production starting in 1983. While the exact total hull count is not definitively established in the available data, this model represents a specific era of American boatbuilding focused on manageable size and traditional aesthetics.

Best for:
This boat is best suited for coastal cruising and weekend sailing, appealing to owners who prioritize a manageable 26.67 ft LOA and a fractional sloop rig for ease of handling. Its 5500.0 lb displacement and 23.1 comfort ratio suggest it is ideal for those seeking a stable, dry ride in protected waters rather than high-performance racing.
Bluewater capability:
With a capsize ratio of 1.82 and a displacement of 5500.0 lb, the Gloucester 27 is generally considered suitable for coastal and nearshore cruising rather than extended bluewater passages. Its fin keel and 3.5 ft max draft provide adequate stability for bay and coastal sailing but lack the heavy displacement typically preferred for offshore endurance.
Comparables:
Comparable boats from this era include the Catalina 27 and O'Day 27, which share similar fractional sloop rigs and target the same market of entry-level cruisers. These models are comparable due to their similar beam widths (around 8.0 ft) and focus on interior volume within a sub-30-foot footprint.

Performance

Comfort23.1
Capsize1.82
SA/Disp16.1
Disp/Len247
Bal/Disp45.5

Pricing

We don't have market pricing data for the GLOUCESTER 27 yet. If you own one, help other buyers β€” what did you pay for it? Reports build a community price estimate over time.

Estimated Cost of Ownership

Based on 26.67ft LOA. Actual costs vary by condition, usage, and local rates.

$/ft/mo
Annual Maintenance
$1.1K – $2.9K
Hull, rigging, sails, engine service
Annual Docking
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Annual Insurance
N/A
No price data available

Known Issues & Pre-Purchase Inspection

We don't have enough data on the GLOUCESTER 27yet to publish model-specific findings we'd stand behind β€” but here's a free general inspection checklist, built from our research into what actually goes wrong on boats of this kind.

Drawn from 7,029 documented issues across 2,391 models, ordered so the areas that most often turn up problems come first.

1Structural & Bulkheads9732Standing Rigging6403Deck & Topsides6404Keel & Keel Bolts5535Rudder & Steering5086Hull & Bottom377
Free general pre-purchase checklist
25 survey areas β€” hull, keel, rig, engine, electrical and more. Take it aboard when you view any boat.

Own a GLOUCESTER 27? Reports from owners are what turn this into a model-specific checklist β€” and they're the reason the boats above it have one.

Similar Sailboats

Which engine powers your GLOUCESTER 27?

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

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

Used sails that fit the GLOUCESTER 27

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