Welcome to Classic Sailboat Shop Updated July 6, 2022

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, 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

News & Events September 3, 2022

 Melonseed Sailboat – $9,950.00


In like new condition as it has been in heated indoor storage with a classic automobile collection, and unused for 21 years.  Everything is in perfect condition.
The boat has an Ivory Hull, White Deck and Tanbark Sails and a perfect 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.
Asking $9,950/Best Offer.   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.

New Point Jude Daysailor with Tanbark Sails –     This 15’10” Point Jude Daysailor has never been sailed since being built in 1987.  In storage since built, this boat presents as like new.  This is the finest Point Jude Daysailer  I have ever come across.  It comes with it’s original 1987 Galvanized Trailer, also in like new condition.   Asking $9,900.00.  To Inquire, call 413-335-6402 or email Tim.classicsailboatshop@gmail.com


Summer 2021

Restoration Just Completed – Fiberglass reproduction of the Herreshoff Fish Class. 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 $49,000 – Optional Trailer Availability. SOLD

Pet 4

Pet 3

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

New Triad TrailerNew 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 WiringNew Fuel Line, New Fuel Tank,  New Breaker PanelNew Buss BarNew 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

Point Jude 15   15’10” Daysailor – Asking $9,300 – SOLD

Exceptional Point Jude 15 with Trailer.  It’s rare to come across a Point Jude Sailboat in such beautiful condition.  This boat has been trailer sailed, primarily in fresh water and kept under cover since new.  Sail Magazine has called the Point Jude Daysailor    ” The Finest Family Daysailor Ever Built.”
Highly  Recommended. Call 413-335-6402

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.   Asking $29,900.

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

Tim McElroy at:   tim.classicsailboatshop@gmail.com

BB15 1A

BB15 6A

BB15 D1

BB15 D1A

BB15 3A

Herreshoff Buzzards Bay 15 –  Asking $29,900

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.  Asking $37,900.         New Cost With Options Almost $80,000.  See complete description below photos.  (Listed Dec. 21, 2019)


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

Goldeneye 1



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


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  Asking $105,000.  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)

Diane Home Photo.JPG

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      Offered at $4,900 Sold

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

G&B Bow Length.jpg    unnamed-3.jpg

G&B Star Aft.jpg

Cape Dory Typhoon Daysailer/Weekender Completely Refinished  $19,900.00 (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. Asking $19,900/Offers Considered

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  $52,500   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 $52,500 without trailer. Trailer offered separately at a price negotiable with buyer of the boat. Call 413-335-6402 or email tim.classicsailboatshop@gmail.com
photo 2




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

POINT JUDE DAYSAILER 15″10″ REBUILT 2013 Asking $8,995.00 Sold

IMG_3626Beautiful Point Jude Daysailer rebuilt in 2013.  New cockpit coaming, New hull paint, New Centerboard, New rudder, New Centerboard Trunk Cap, New non-skid deck paint.  Mast, Boom sails and Rigging all in very good condition.  Ready to sail.  Trailer included.  Call 413-335-6402

2003  28′ Gannon & Benjamin “CELESTE”    Asking $69,000  See below for details of this magnificent little yacht!           SOLDCelestequarterview

BRIDGES POINT 24 1998  Listed November 25, 2013 Bridges Point SOLD Profile1 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” Asking $69,900. SOLDCelest ChristmasCELESTE 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
Asking $28,500  Offers Encouraged   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  SOLDThomas Gilmer Blue Moon Yawl2008 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