2012 18′ Herreshoff Goldeneye by Cape Cod Shipbuilding Exceptional Condition Asking $37,900. In Storage For Past 5 Years. Feel free to contact us at 413-335-6402 or e-mail Tim McElroy at: tim.classicsailboatshop@gmail.com

Unused and in storage (indoors) since 2015, This Cape Cod Shipbuilding Herreshoff Goldeneye Sailboat shows as new. Loaded with extras beyond the Builders listed options, a new boat such as this would cost almost $80,000.

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

Gannon & Benjamin built Herreshoff Alerion

Classic Sailboat Shop is excited to announce our acquisition of the Gannon & Benjamin built Herreshoff Alerion.  We are currently working on updating all of her paint and varnish for her exhibition at the 2017 Wooden Boat Show at Mystic Seaport.  We’re thrilled to have the opportunity to own and exhibit this magnificent reproduction of Capt. Nat’s favorite boat, built to the MIT Herreshoff plan specifications.



Gannon & Benjamin Rowing Dingy Asking $4,900.

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. She comes with a pair of custom Shaw & Tenney oars.                                                           Located in Western Massachusetts in the town of Williamsburg.
Call 413-335-6402 or email tim.classicsailboatshop@gmail.com

G&B Bow Length.jpg

Cape Dory Typhoon Daysailer/Weekender Completely Refinished $19,900.00

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 $24,000/Offers Considered

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

Stuart Knockabout with 2014 Triad Trailer


photo 2 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 $64,500 without trailer. Trailer offered separately at a price negotiable with buyer of the boat. Call 413-335-6402 or email tim.classicsailboatshop@gmail.com

Arey’s Pond Daysailer 18’10” Built 2007



This Exceptional Arey’s Pond Daysailer has been keept indoors, unused for the past three seasons.  In the past three seasons, she has only been taken out to bring to the Maine Boat Builders Show or The Wooden Boat Show at Mystic Seaport as she has all possible options and is a magnificent example of what can be built.  This one owner boat is now on the market for less than half the price as the cost of having one built today.

She is a cold molded wooden boat and includes Teak Decks, All Harken Hardware, Roller Furling, Custom Fitted Galvanized Trailer, Lazy Jacks, Reef Points in the Main Sail, two separare masts and booms (one pair is spruce, the second carbon fiber).

For details, call Tim at 413-335-6402 or email tim.classicsailboatshop@gmail.com

Bridges Point 24 – 1998 Joel White Design, Wade Dow Built

Bridges Point 24    (See Photos Below)

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.

DISPLACEMENT: 3,944 lbs   BALLAST: 2,100 lbs

LOA: 24’ 0”                                      BEAM: 7’ 9”

LWL:18’ 8”                                       DRAFT: 3’ 5”

SAIL AREA : 278 SQ. FT           JIB: 130% Genoa

ENGINE: Yanmar GM 10 Diesel, 9HP FUEL: 6 Gallons

CONSTRUCTION:  Hand laid molded fiberglass deck and cabin, green hull, internal lead ballast, solid fiberglass rudder and structural girders.  ‘Metalmast’  spars are painted Oyster white aluminum with internal rope halyards, Mast is keel stepped, aluminum boom painted Oyster white, forward cabin V Berth  with cushions (Beige) and shelves,  Lewmar opening hatch and screen  forward for ventilation, Companion-way screen for additional ventilation.  Four bronze port lights, Awlgrip white boot top, varnished teak exterior trim, all bronze deck hardware includes 8” bronze bow cleat, two bronze bow chocks, two bronze stern cleats and chocks.   Cockpit has fiberglass contoured seats. Small galley to port has stainless steel sink and cooler. Marine portable toilet at foot of V-berth. Teak varnished drop boards. Located in Northampton, Massachusetts.  Should you wish to visit and look over this exceptional boat, feel free to call 413-335-6402or e-mail tim.classicsailboatshop@gmail.com


mainsail  (178 sq ft)  Mainsail cover

jib 130% furling with UV Cover

roller furling

Two bronze  #16 self-tailing  sheet winches

Two bronze # 6 winches – one for Jib halyard and one for main halyard

Internal rope halyards, Stainless steel stays and chromed turnbuckles

Harken blocks and traveler Back stay adjuster, Boom vang

STEERING:  Varnished tiller steering


Standard Horizon Explorer VHF with mic,  1- 12 V Battery, Navigation lights

EQUIPMENT:     Wind vane, Bulkhead mount compass, Porta-potti, Whale bilge pump, V-Berth cushions, mainsail cover, Braided dock lines, Anchor, Chain and Rhode

Boat can be sold with or without the trailer shown.Profile1 Bright Coaming BEAR 1 Cockpit 3 Tiller Bright Coaming & Winch Cockpit 1 Diesel 1 Cabin Port Cabin Starboard Port Profile From Bow

Located in Northampton, Massachusetts.  Should you wish to inspect the boat see “BEAR” feel free to call 413-335-6402 or e-mail tazmanian_tigger@msn.com

Bulls Eye Sailboat Rebuilt in 2005 Built by Cape Cod Ship Building


Completely Rebuilt in 2005, this Cape Cod Shipbuilding Bullseye is in outstanding condition.
New sails in 2005 – Main Sail, Jib and Spinniker as well as New Harken Roller Furling 2005
New Mast, Boom, standing and running rigging 2005, New Bilge Pump and Solar Pannel 2005
New Triad Trailer 2005
New Mainsail Stack-Pak 2005
Hull and decks stripped and awlgripped 2005, 
New Cockpit Seats 2005
Bottom stripped, barrier coated 2005
New Bottom Paint 2013
New Torqueedo Electric Motor with remote throttle control 2005

As some buyers do not require a trailer or motor, the trailer and Torqueedo electric motor are available separately.

Located in Northampton, Massachusetts

Should you wish to see this boat feel free to contact me at 413-335-6402 or email tim.classicsailboatshop@gmail.com

Gannon and Benjamin 28′ Gaff Rigg “CELESTE” 2003 Built 2003



Celest 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