• Slide: The Image of Sailboat on open water, Custom Lyle Hess Cutter, 1999, under clear blue sky. - 1The Image of Sailboat on open water, Custom Lyle Hess Cutter, 1999, under clear blue sky. - 1
  • Slide: The Image of Sailing on calm waters, a 1999 Custom Lyle Hess Cutter with American flag. - 2The Image of Sailing on calm waters, a 1999 Custom Lyle Hess Cutter with American flag. - 2
  • Slide: The Image of Sailboats on water with city skyline, featuring a 1999 Custom Lyle Hess Cutter. - 3The Image of Sailboats on water with city skyline, featuring a 1999 Custom Lyle Hess Cutter. - 3
  • Slide: The Image of Sailboats on a river near city buildings, featuring a 1999 Custom Lyle Hess Cutter. - 4The Image of Sailboats on a river near city buildings, featuring a 1999 Custom Lyle Hess Cutter. - 4
  • Slide: The Image of Sailboat on water with city skyline in background, Custom Lyle Hess Cutter, 1999. - 5The Image of Sailboat on water with city skyline in background, Custom Lyle Hess Cutter, 1999. - 5
  • Slide: The Image of Sailing on a 1999 Custom Lyle Hess Cutter near a city skyline at sunset. - 6The Image of Sailing on a 1999 Custom Lyle Hess Cutter near a city skyline at sunset. - 6
  • Slide: The Image of Sailboats anchored on calm water, featuring a 1999 Custom Lyle Hess Cutter named "Helen." - 7The Image of Sailboats anchored on calm water, featuring a 1999 Custom Lyle Hess Cutter named "Helen." - 7
  • Slide: The Image of Sailboats anchored on calm water at sunset, featuring a 1999 Custom Lyle Hess Cutter. - 8The Image of Sailboats anchored on calm water at sunset, featuring a 1999 Custom Lyle Hess Cutter. - 8
  • Slide: The Image of Sailboat "Helen" on calm water, Custom Lyle Hess Cutter, 1999, with scenic shoreline backdrop. - 9The Image of Sailboat "Helen" on calm water, Custom Lyle Hess Cutter, 1999, with scenic shoreline backdrop. - 9
  • Slide: The Image of Sailboat "Lyle Hess Cutter" 1999, anchored near coastal homes at sunset. - 10The Image of Sailboat "Lyle Hess Cutter" 1999, anchored near coastal homes at sunset. - 10
  • Slide: The Image of Interior of 1999 Custom Lyle Hess Cutter sailboat, featuring wooden cabinetry and compact kitchen area. - 11The Image of Interior of 1999 Custom Lyle Hess Cutter sailboat, featuring wooden cabinetry and compact kitchen area. - 11
  • Slide: The Image of Interior of a 1999 Custom Lyle Hess Cutter sailboat, featuring wood finishes and compact design. - 12The Image of Interior of a 1999 Custom Lyle Hess Cutter sailboat, featuring wood finishes and compact design. - 12
  • Slide: The Image of Interior of 1999 Custom Lyle Hess Cutter sailboat with wooden finishes and compact kitchen. - 13The Image of Interior of 1999 Custom Lyle Hess Cutter sailboat with wooden finishes and compact kitchen. - 13
  • Slide: The Image of Interior of 1999 Custom Lyle Hess Cutter sailboat with wood accents and cozy cabin space. - 14The Image of Interior of 1999 Custom Lyle Hess Cutter sailboat with wood accents and cozy cabin space. - 14
  • Slide: The Image of Interior of a 1999 Custom Lyle Hess Cutter sailboat with wooden cabinetry and control panels. - 15The Image of Interior of a 1999 Custom Lyle Hess Cutter sailboat with wooden cabinetry and control panels. - 15
  • Slide: The Image of Interior of a 1999 Custom Lyle Hess Cutter with wooden paneling and a cozy sleeping area. - 16The Image of Interior of a 1999 Custom Lyle Hess Cutter with wooden paneling and a cozy sleeping area. - 16
  • Slide: The Image of Cozy cabin interior of 1999 Custom Lyle Hess Cutter sailboat with wood accents and green bedding. - 17The Image of Cozy cabin interior of 1999 Custom Lyle Hess Cutter sailboat with wood accents and green bedding. - 17
  • Slide: The Image of Cockpit of 1999 Custom Lyle Hess Cutter with compass and navigation instruments. - 18The Image of Cockpit of 1999 Custom Lyle Hess Cutter with compass and navigation instruments. - 18
  • Slide: The Image of Electrical control panel on a 1999 Custom Lyle Hess Cutter sailboat. - 19The Image of Electrical control panel on a 1999 Custom Lyle Hess Cutter sailboat. - 19
  • Slide: The Image of Control panel of a 1999 Custom Lyle Hess Cutter with gauges and indicator lights. - 20The Image of Control panel of a 1999 Custom Lyle Hess Cutter with gauges and indicator lights. - 20
  • Slide: The Image of Red engine in a 1999 Custom Lyle Hess Cutter sailboat, surrounded by wiring and components. - 21The Image of Red engine in a 1999 Custom Lyle Hess Cutter sailboat, surrounded by wiring and components. - 21
  • Slide: The Image of Heavy-duty deep cycle battery with red and yellow cables in a 1999 Lyle Hess Cutter. - 22The Image of Heavy-duty deep cycle battery with red and yellow cables in a 1999 Lyle Hess Cutter. - 22
  • Slide: The Image of Battery setup in a 1999 Custom Lyle Hess Cutter boat with connected cables. - 23The Image of Battery setup in a 1999 Custom Lyle Hess Cutter boat with connected cables. - 23
  • Slide: The Image of 1999 Custom Lyle Hess Cutter boat interior with marine toilet and wooden storage shelves. - 24The Image of 1999 Custom Lyle Hess Cutter boat interior with marine toilet and wooden storage shelves. - 24
  • Slide: The Image of Sailboat on land near blue building, Custom Lyle Hess Cutter, 1999 model. - 25The Image of Sailboat on land near blue building, Custom Lyle Hess Cutter, 1999 model. - 25
  • Slide: The Image of Custom 1999 Lyle Hess Cutter sailboat named "HELEN" in Port Townsend, WA. - 26The Image of Custom 1999 Lyle Hess Cutter sailboat named "HELEN" in Port Townsend, WA. - 26
  • Slide: The Image of Sailboat in storage, Custom Lyle Hess Cutter, 1999, under wooden roof. - 27The Image of Sailboat in storage, Custom Lyle Hess Cutter, 1999, under wooden roof. - 27
  • Slide: The Image of Propeller of 1999 Custom Lyle Hess Cutter sailboat, viewed through turquoise hull opening. - 28The Image of Propeller of 1999 Custom Lyle Hess Cutter sailboat, viewed through turquoise hull opening. - 28
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1999 Custom Lyle Hess Cutter

$50,000

Used

Boat in Rockport, ME 04856 US

builtBuilt in 1999
Year the boat was built
model

Lyle Hess Cutter

Boat model
engine

1 Engine (Beta)

Engine type and count
length

32 feet

Overall boat length
fuel

Diesel

Fuel type
material

Wooden

Hull material

The Bluewater 32' Bristol Channel cutter "HELEN" was designed by Lyle Hess and superbly built in 1999 by Rockport Marine. Construction is traditional cedar planking on white oak frames and backbone with all bronze fasteners. Decks are solid teak and spars are Sitka spruce. The boat is outfitted with a new Beta diesel engine installed by Artisan Boatworks in 2022. Sails were new in 2016.

HELEN is a proven offshore cruiser of the highest possible standard, well outfitted and ready to head for the horizon. Recent survey is available upon request.

She was originally named SEQUEL, then IOLAIRE by the original owner, PHALAROPE by the second owner, and HELEN by the current Owners.

There are a tube of original plans which include the interior, sails, and rigging; as well as a large binder of photographs of her under construction at Rockport Marine - from laying the keel to launch.

There are two Dinghy's available: The original Iain Oughtred Acorn Tender - Cedar strip planked w/ Okume transom and trim; or a new 8' Fatty Knees with sailing rig and Shaw and Tenney oars.

Improvements made by current owners:

-Repower w/BETA 38 to include Bronze Engine Controls and Control Panel

-Clean Fuel Tanks

-New ABYC Compliant Holding Tank, head, and head plumbing.

-New Interior Cushions

-New Sail Covers

-New Bilge Pump and Thru-Hull

-New Batteries and charger

-New electrical system - major rewiring

-New Transducer / Depth Sounder

-Painted Transom

-New Anchor Rode 300' 5/16 Galvanized Chain

Nominal Length
32ft
Length Overall
33ft
Beam
12ft
Hull Material
wood
Engine 1
Engine Make
Beta
Fuel Type
diesel
Engine Year
2022
Disclaimer
The Company offers the details of this vessel in good faith but cannot guarantee or warrant the accuracy of this information nor warrant the condition of the vessel. A buyer should instruct his agents, or his surveyors, to investigate such details as the buyer desires validated. This vessel is offered subject to prior sale, price change, or withdrawal without notice.

Price History

DateEventPrice
1/29/26Initial price$50,000

Overview from around the web 1999 Custom Lyle Hess Cutter

Customers praise the 1999 Custom Lyle Hess Cutter for its classic design and exceptional craftsmanship

Many highlight its sturdy construction and seaworthy performance, making it ideal for both coastal cruising and extended offshore voyages. Owners appreciate the spacious and well-thought-out interior layout, which combines comfort with functionality. The cutter rig is noted for its ease of handling and versatility in various wind conditions. Overall, reviews commend this vessel for blending traditional aesthetics with reliable, practical sailing capabilities.

The Biggest Pros and Cons

The 1999 Custom Lyle Hess Cutter is a thoughtfully designed cruising sailboat known for its classic lines and robust construction. Here are some of the pros and cons to consider:

Pros

Classic Design: The hull and deck lines reflect traditional aesthetics, appealing to enthusiasts of timeless sailboat styling.

Solid Construction: Built with quality craftsmanship, ensuring durability and seaworthiness.

Cutter Rig: Offers versatile sail plan options, making it easier to balance the boat in varying wind conditions.

Good Offshore Capability: Designed to handle offshore passages with stability and safety.

Spacious Interior: Efficient layout providing comfortable accommodations for extended cruising.

Heavy Displacement: Contributes to a smooth ride in rough seas and good overall stability.

Cons

Heavier Weight: The solid build and heavy displacement may result in slower speeds compared to lighter, more modern designs.

Limited Modern Amenities: Being a classic design, it may lack some contemporary conveniences and systems found in newer vessels.

Maintenance Requirements: Traditional materials and construction can require more upkeep and specialized knowledge.

Maneuverability: The cutter rig and hull shape might demand more skill to handle, especially for less experienced sailors.

Made For

The 1999 Custom Lyle Hess Cutter is designed for sailors who appreciate traditional craftsmanship combined with reliable performance. Ideal for those seeking a sturdy and seaworthy vessel, it appeals to adventurers who value classic design and want a boat capable of handling long offshore passages with confidence and comfort. Whether you're an experienced cruiser or someone looking to embark on extended voyages, this cutter offers a timeless blend of durability and functionality.

Finance your dream boat!

Use our boat payment calculator to estimate monthly payments for 1999 Custom Lyle Hess Cutter. Enter your down payment, choose a loan term, and adjust the interest rate to see an instant payment estimate — ideal if you're calculating boat payments before you enquire. Wondering how much does a Sail Cruiser cost in today's market, or how much does a Custom cost for similar models? This boat financing calculator helps you compare scenarios in seconds, whether you're considering used boat financing or a new purchase.
Monthly payment
$567.49/mo
$
$
Loan amount$ 50,000
OR
%

Finance your dream boat!

Use our boat payment calculator to estimate monthly payments for 1999 Custom Lyle Hess Cutter. Enter your down payment, choose a loan term, and adjust the interest rate to see an instant payment estimate — ideal if you're calculating boat payments before you enquire. Wondering how much does a Sail Cruiser cost in today's market, or how much does a Custom cost for similar models? This boat financing calculator helps you compare scenarios in seconds, whether you're considering used boat financing or a new purchase.
Monthly payment
$567.49/mo
$
$
Loan amount$ 50,000
OR
%

Contact Artisan Boatworks Inc.

416 Main St, Rockport, ME, 04856

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Address

416 Main St
Rockport, ME 04856

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Contact Artisan Boatworks Inc. about 1999 Custom Lyle Hess Cutter

416 Main St, Rockport, ME, 04856

By checking this box, I consent to receive recurring marketing text messages, phone calls, and emails from Artisan Boatworks Inc. at the number and email provided, including messages sent using an autodialer or prerecorded voice. Message frequency varies. Message and data rates may apply. Reply STOP to opt out or HELP for assistance. Consent is not a condition of purchase. We'll also send helpful email updates about your boat search. You can unsubscribe whenever you like. See Terms of Use and Privacy Policy.

Contact Artisan Boatworks Inc.

416 Main St, Rockport, ME, 04856

By checking this box, I consent to receive recurring marketing text messages, phone calls, and emails from Artisan Boatworks Inc. at the number and email provided, including messages sent using an autodialer or prerecorded voice. Message frequency varies. Message and data rates may apply. Reply STOP to opt out or HELP for assistance. Consent is not a condition of purchase. We'll also send helpful email updates about your boat search. You can unsubscribe whenever you like. See Terms of Use and Privacy Policy.

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