Located in the historic western Massachusetts town of Chesterfield, the Classic Sailboat Shop specializes in the purchase, restoration and sale of small classic day sailers and weekenders in both fiberglass and wood. We specialize in fine used Marshall Cat Boats, Arey’s Pond Catboats and Daysailors, Rhodes 19 by Stuart Marine, Herreshoff designs from the Herreshoff 12 1/2 to the Fish Class and the magnificent Herreshoff Alerion, as well as Concordia Buzzards Bay 19, Point Jude 15, Arey’s Pond Catboats, Cape Dory Typhoon (one of our specialties), Melonseed Skifs, and of course a variety of Gannon & Benjamin Wooden Boats, as well as Joel White Designs such as the Bridges Point 24 and Rockport Marine and Brooklyn Boatyard small yachts. If you are considering selling or purchasing a fine sailboat, Feel free to contact us anytime at 413-335-6402 or e-mail Tim McElroy at: tim.classicsailboatshop@gmail.com

Updated November 17, 2025

Gannon & Benjamin 2005, 16″ Whitehall Rowing Boat Exceptional Condition

16’3″ Gannon & Benjamin Built Whitehall Rowing Boat in Excellent Condition. She glides wonderfully through the water and is admired wherever she goes. This beautiful boat was showcased in the Wooden Boat Magazine Calendar shortly after her build around 2005. She has been our personal rowing boat since 2010.

She can be rowed as a single or with two rowers. She comes with 2 pair of beautiful spruce Shaw and Tenney rowing oars and a galvanized trailer modified to properly support her hull.She has been professionally maintained yearly by Classic Sailboat Shop. Her seams have just been completely re-calked, her hull has been primed and painted with 3 coats of Interlux bright white, all of her brightwork has been stripped to wood and varnished with Epifanes Varnish, her bottom has been primed and painted with Sandusky Hard Bright Copper Bottom Paint. Her seats have been just painted with Epifanes (white with a slight tan tint), and her inboard cedar planking has 3 coats of Sutherland Wells Polymerized Tongue Oil.Asking $15,000/Best Offer

Call 413-335-6402 email Tim.classicsailboatshop@gmail.com

2004 Bridges Point 24 SOLD – This beautiful 2004 Joel White Designed Bridges Point 24 has been a fresh water boat since new. She is easily the finest BP 24 on the market and includes a 2022 Triad Trailer. For details, see below. Many additional photographs and be found on this site by clicking on “Boats” above.

This beautiful 2004 Joel White Designed Bridges Point 24 has been a fresh water boat since new. She is easily the finest BP 24 on the market and includes a 2022 Triad Trailer. Blue hull, red boot stripe, fresh smooth white bottom paint, and new professionally applied Epifanes Varnish.

She is fitted with Yanmar diesel, Mainsail, Harken Roller Furling Jib, depth finder, compass, stove, sink with cabinetry, fitted cushions, port-a-potty and a 2022 Custom Built Dual Axle, Float Off Triad Trailer with 4 wheel Hydraulic Disc Brakes, Tongue Extension, and Forward Ladder.
Very comfortable cabin for cruising or daysailing.
Located in western Massachusetts.

Inquire at 413-335-6402 or eMail – Tim.ClassicSailboatShop@Gmail.com

Melonseed Buy Crawford Boatworks – SOLD. Like New Condition! 413-335-6402 Tim.classicsailboatshop@gmail.com

This Crawford Melonseed Sailboat has been in heated indoor storage and unused since new from 2001 until August 2024. We have since sailed it twice with our grandchildren and placed back indoors. Everything is in like new condition.

Blue Hull, White Deck, Tanbark Sails and a nice boat cover made to fit from the manufacturer. The spars are beautifully varnished spruce.
The boat comes with a galvanized trailer that is in like new condition with almost no miles. The tires are now new as the trailer and boat have been in storage since new. Specifications LOA 13’ 8” Beam 4’ 3” Draft 6” to 2’ 6” . Sail area 62 sq. ft. 13’ 8” x 4’ 3” x 235 LBS.

1989 Point Jude Daysailer – SOLD. In storage and unused from 1989 until 2021. Now used only 3 seasons. This is as close to a new Point Jude 15 you will ever find. Torqueedo Travel 6003S Electric Outboard Available at additional cost. For details, click on Sailboats above. SOLD. Call 413-335-6402. or email Tim.classicsailboatshop@gmail.com

pj-2 pj-11 Summer 2021

Restoration Just Completed – Fiberglass reproduction of the Herreshoff Fish Class. SOLD

This is very much a sister ship to the Classic Boat Shop PISCES. All Sails, Spars and Rigging in Excellent Condition. This is a magnificent example of the Fish! The boat is available with or without the trailer.

Asking – Optional Trailer Availability. SOLD

Marconi rig with varnished wooden spars, Traditional club foot Jib
Powered by 15 HP Saildrive Unit (Not an outboard).

New Triad Trailer, New Topside Paint, New Boot Stripe Paint, New Varnish, Bottom heavily sanded to barrier coat with New Bottom Paint New Bronze Rudder Gudgeons and Pintles, New Wiring, New Fuel Line, New Fuel Tank, New Breaker Panel, New Buss Bar, New Bilge Pump Switch

The boat will be available with or without the trailer, pending the needs of the buyer.
The advertised price does not include the trailer

Buzzards Bay 15 Restoration Just Completed, July, 2020. SOLD

Herreshoff Buzzards Bay 15, (Similar to Watch Hill 15) Professionally built in 1993. Launched as “WHISPER” and Listed in the Herreshoff Registry as Build # 63.

Feel free to contact us at 413-335-6402or e-mail

Tim McElroy at: tim.classicsailboatshop@gmail.com

Herreshoff Buzzards Bay 15 SOLD

She is currently at Snediker Yacht Restoration located in Stonington Connecticut where in conjunction with Classic Sailboat Shop, her hull, deck finishes and bright finishes were completely removed as well as removal of seam compound above and below the waterline. She has now been re-calked, painted and varnished and looking gorgeous!

The price listed is for the boat, includes spars, sails, custom traditional rigging, boat covers and Custom lightweight aluminum trailer.

Professional Surveys may be conducted at Perspective Buyers expense. Reasonable Offers Will Be Considered.

SOLD 2012 Herreshoff Goldeneye Built by Cape Cod Shipbuilding. Stored Indoors, Unused for 5 Years. Shows Like a New Boat. See complete description below photos. (Listed Dec. 21, 2019)

SOLD

Feel free to contact us at 413-335-6402 or e-mail Tim McElroy at: tim.classicsailboatshop@gmail.com

Self Bailing Cockpit
Mainsail, Jib, Genoa, Storm Jib and Mooring Tent
Self Tailing Jib Sheet Winches with teak bases
Mainsail Halyard Winch
Bulkhead Mounted Ritchie Compass with Inclinometer
Custom Cockpit SoleTeak Grating
Custom Cabin Sole Teak Grating
Custom Cockpit Cabin Bulkhead Woodwork
Custom Cabin Interior Woodwork
Motor Mount
VHF Radio
Hand Held Sonar Depth Finder
Hand Held GPS

3.5 HP Mercury 4 Stroke Engine, or available for additional charge Almost New Electric Torquito 3000 Travel.
Triad Trailer with brakes, ladder, mast carrier and spare tire. Custom built to fit the Goldeneye Sailboat.
Anchor, Line and Rhode

SPECIFICATIONS

Length Overall	18’ 3”
Length Waterline	15’ 10”
Beam	6’ 4”
Sail Area	193 sq. ft.
Genoa	160 sq. ft.
Keel Lead	1320 lbs.
Displacement	2500 lbs

2005 Herreshoff Alerion Constructed By Gannon & Benjamin SOLD

Classic Sailboat Shop in conjunction with Snediker Yacht Restoration just completed refinishing all paint and varnish on this beautiful Alerion. Ready to go, she is outfitted with a 1GM10 Yanmar Diesel.

For details, Contact Tim McElroy at 413-335-6402 or email Tim.ClassicSailboatShop@gmail.com

HAVEN 12 1/2 By Eric Dow of Brooklin Maine (Sold)

Beautiful 2003 Haven 12 ½ built by the Eric Dow Boat Shop of Brooklin Maine. Joel White produced this design visually identical to the Herreshoff 12 ½ but with a centerboard and increased beam so that she can poke around in more shallow water than can the original Herreshoff, all the while maintaining many of the other attributes of the original Herreshoff design.

“DIANE” is in exceptional condition as she has only been sailed a handful of times and has spent most of her life indoors, unused.

“DIANE” is constructed of cold molded mahogany. She is a gaff rigged boat with a club footed, self tending jib. All blocks are of bronze.

She comes with a custom built 2003 Triad Trailer and a full storage cover. SOLD

Gannon & Benjamin Rowing Dingy

Coming from the drawing board of Nat Benjamin and built in Vineyard Haven by G&B in 2007, this beautiful rowing boat has spent most of it’s life, unused,and in covered storage at the Concordia Boat Yard. She was painted and varnished by the Concordia yard in 2015 and remains in superior like new condition. She is cedar planking on steam bent frames. Located in Western Massachusetts in the town of Williamsburg.
Call 413-335-6402 or email tim.classicsailboatshop@gmail.com

Cape Dory Typhoon Daysailer/Weekender Completely Refinished (Sold)

Professionally Restored Cape Dory Typhoon. Professional restoration in Rockport Maine Work completed January 2015.

1981 Cape Dory Typhoon
Hull professionally stripped and painted 2 part Awlgrip Blue
Botton professionally stripped, sanded and barrier coated with Interprotect
Decks and cockpit professionally painted 2 part Awlgrip
Nonskid professionally painted 2 part Awlgrip light beige
All Brightwork stripped and 7 coats of Epifanes Varnish
Professionally painted red boot stripe
New gold sheer pinstripe
New interior cockpit cushions 2014
Recent Mainsail with Stackpak and Harken Rollerfurling jib 2013
Depth and hull speed instruments, Hand Held VHF
Optional Triad Trailer
Anchor, Chain, Rode, life vests, flare gun safety package

Ready to sail.

SOLD… If you would like one just like it, we would be happy to restore another to your color specifications.

Located in Western Massachusetts, near Northampton.
Call 413-335-6402 or email tim.classicsailboatshop@gmail.com

Stuart Knockabout DRAMATIC PRICE REDUCTION Optional 2014 Triad Trailer available to buyer (SOLD)
DIAMOND LAKE DREAMER has just arrived on the east coast from Bambridge Island Washington, this 2000 Stuart Knockabout was maintained “Open Check Book.” This one owner Stuart has been impeccably maintained and very lightly used by her owner. She has Main, Jib, Genoa, Spinniker, full mooring cover and custom winter cover. Boat offered at without trailer. Trailer offered separately at a price negotiable with buyer of the boat. Call 413-335-6402 or email tim.classicsailboatshop@gmail.com

AREY’s POND DAYSAILER 2007 (SOLD)

Exceptional 2007 Arey’s Pond 18’10” Daysailer. Teak Decks, Roller Furling Genoa, Harken blocks and gear through out. Carbon Fiber Mast as well as a second custom built clear spruce mast and spar. 2007 galvanized trailer custom fit. This boat has been kept unused in indoor storage for the past three seasons.

Call Tim McElroy at 413-335-6402 or email tim.classicsailboatshop@gmail.com

2003 28′ Gannon & Benjamin “CELESTE” See below for details of this magnificent little yacht! SOLD

BRIDGES POINT 24 1998 Listed November 25, 2013 Bridges Point SOLD NAME: Bear TYPE: Bridges Point 24 YEAR: 1998 BUILDER: Wade Dow, Bridges Point Boat Yard DESIGNER: Joel White COMMENTS: The Bridges Point 24 design has been a very popular weekender/daysailer. She is a wonderful example of Joel White’s designs built by Maine Boat builder Wade Dow. New Awlgrip Finish 2006, Complete exterior varnish and wood finish August 2013, Toe rails removed, stripped, refinished & re-bedded August 2013. Diesel flushed & winterized, oil and filter changed, & fuel storage treated November 2013. For full details, please look under BOATS above on the page DASHBOARD. Feel free to call 413-335-6402 or email tim.classicsailboatshop@gmail.com

2003 GANNON & BENJAMIN 28′ “CELESTE” SOLDCELESTE has often been described as a magnificent piece of art from the drawing board of Nat Benjamin, built by the family of craftsmen and artists of Gannon & Benjamin Marine Railway company of Vineyard Haven.

Built true to Gannon & Benjamin form, she is built of steam bent frames on a backbone sawn from reaitivly massive timbers with carvel planking. Her backbone is angelique, while her frames are steam bent white oak. Planking is of white cedar, except for garboards and sheerstrakes where denser South American wana has been used from stem to stern. All deck joiner-work is silver bali (a mahogany-like wood). All spars are of spruce. Decks are of marine ply covered with Dynel and epoxy. Bronze fastenings are used throughout. All blocks and cleats are bronze.

At 9,489 lbs displacement and 394 sq. ft of sail, CELESTE is an absolute delight to sail. When the wind is unreliable, CELESTE is powered by a very well maintained Yanmar Diesel. The main sail has lazy jacks and two reef points. She is a keel /centerboard design drawing only 3′ with her board up, making it easy to bring her into the shallow harbors of the Vineyard and Buzzards Bay.

CELESTE sleeps two comfortably below in her lit cabin with berths port and starboard. Her two berths were just custom fitted with two new extra thick comfort foam cushions that provide an excellent nights sleep. The cabin is ventilated with four opening bronze ports and an adjustable bronze dorade. She has a sink with bronze hand pump port side and an extra large, well insulated ice box to starboard below the counter. She has ample stowage for several days out cruising. Her pottie set forward contains enough holding capacity for several days without need for pump out.

“CELESTE” can be seen on Martha’s Vineyard at her mooring in Vineyard Haven.

Should you wish to schedule a visit to CELESTE, or wish to discuss her particulars, please feel free to contact Tim McElroy at 413-335-6402

or e-mail tim.classicsailboatshop@gmail.com

NEW LISTING July 22, 2013

2003 Edey & Duff Doughdish Herreshoff 12 1/2. SOLD

CALAMITY is a comfortable, easy family daysailer, well suited for teaching someone to sail, or for an expert interested in class racing as she is equipped with numerous hardware and sail upgrades. Built by Edey and Duff in 2004, CALAMITY has been a well cared one owner boat since launching. She has been owned by a most meticulous owner and is in excellent condition. She has been always stored indoors for the winter. Dimensions LOA: 15 ft 10 in, Beam: 5 ft 10 in, LWL: 12 ft 6 in Draft: 2 ft 6 in Displacement: 1500 lbs. Ballast: 735 lbs Along with new Harkin blocks, non-stretch rigging, CALAMITY has 4 quality sets of sails, main and jib, from Harding, Sperry, and Quantum as well as 2 spinnakers with pole and gear. The varnish is in very good condition and her bottom has been painted with Interlux Baltoplate Anti-Fouling Paint, for a racing finish. CALAMITY will be sold at the advertised price with her standard cruising sails (main and jib) and without the Triad Trailer. She is available with the Triad Trailer and her full complement of sails at additional cost. All rigging, blocks cleats etc. come with the boat ready to sail. 4 sets of sails: Main and Jib from Harding, Sperry, and Quantum as well as 2 spinnakers Larger main and jib sheet blocks to accommodate larger diameter lines. Scheafer main sheet cam cleat, large mast mounted card compass “Quissett” spinnaker sheet blocks, Masthead wind indicator, Non-stretch halyards, Custom outhaul Aluminum spinnaker pole, Wooden spinnaker pole, Custom hand carved name boards “CALAMITY”, Varnish oar and bronze oar lock Should you wish to inspect CALAMITY she is currently stored at Ballentines Boat Shop Cataumet, Massachusetts Feel free to call 413-335-6402 or email tim.classicsailboatshop@gmail.com CALAMITY is a fabulous little yacht. The Doughdish is a fiberglass reproduction of the original Herreshoff 12 1/2 footer, constructed in foam sandwich fiberglass with teak trim. It is built to the exact hull dimensions and rig of the sloops designed by N. G. Herreshoff in 1914.

2008 Thomas Gilmer Blue Moon Yawl “TIME”

Blue Moon Yawl. $39,900. New to market September 3, 2013 Call Mark Scott 609-876-9507 SOLD2008 Blue Moon Yawl designed by Thomas Gilmer. Built in Rockport Maine, this little yawl “TIME” is a piece of art. Built of cedar plank on steam bent oak frames, she is 23′ on deck and 30′ overall. She displaces 8,000 lbs. Her Teak Decks and Bright Coachwork and Bronze Fittings are unparalleled in quality and beauty. Her tanbark sails are by the famous sailmakers of Gambell and Hunter of Camden Maine are in new condition, and include Gaff Rigged Main Sail, Club Footed Stay Sail, Roller Furling Jib, Top Sail and Mizzen. She has a Yanmar 2YM15 diesel engine with 25 hours of use. “TIME” has just been professionally painted and all bright work freshened with several new coats. Electronics include VHF, Garmin GPS, Depth and compass. Absolutely beautiful, “TIME” is the Prettiest Girl at the Dance, and in new, turn key condition. Cutts & Case, Maryland. Asking $39,900, Should you have questions or wish to arrange to see her, feel free to contact Mark Scott at 609-876-9507

OR 413-335-6402 or e-mail tim.classicsailboatshop@gmail.com

Classic Sailboat Shop

Specializing in the sale of small classic day sailers and weekenders

Welcome to Classic Sailboat Shop Updated November 17, 2025