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Sail Boats

From classic wooden sloops to modern offshore cruisers — each boat hand-selected for quality, condition, and provenance.

39 boats currently listed · 7 sold

Featured

1997 31'2" Joel White

Pudding — Center Harbor 31 Sloop

Hull #3 of Joel White's Center Harbor 31, built at Brooklin Boat Yard in 1997. A cold-molded wood/epoxy fractional sloop with carbon spars, all-Harken gear, and a beautifully simple varnished-teak cockpit and interior. A pure, elegant daysailer and weekender.

$125,000 Details →

Attitude — Sabre 34 Targa Aft-Cabin Sloop

Featured

1989 34' Roger Hewson

Attitude — Sabre 34 Targa Aft-Cabin Sloop

A 1989 Sabre 34 Targa / Aft-Cabin — the pinnacle of Sabre's 34 evolution, with a private aft cabin, sit-down nav station, and a well-lit two-cabin interior. Two owners from new, meticulously maintained and always stored indoors. Westerbeke diesel, full electronics, and extensive canvas.

$55,000 Details →

Featured

1987 34' Frank Loud

Cady — Frank Loud Cutter

The last of the Frank Loud Cutters — built by the designer as his own family yacht. Traditionally constructed of mahogany carvel over white oak, recently strip-refastened and refinished from the waterline to the rabbet, with all-new standing rigging. A wholesome, uncomplicated wooden family cruiser.

$27,000 Details →

Christina — Pacific Seacraft Dana 24 Cutter

Featured

1987 27' W.I.B. Crealock

Christina — Pacific Seacraft Dana 24 Cutter

A 1987 Pacific Seacraft Dana 24 — Bill Crealock's classic pocket cruiser, solidly built with bronze hardware, teak joinery, and a walk-in head. Equally at home crossing oceans or gunk-holing in quiet coves. Yanmar diesel, roller-furling headsail, and Camber-Spar staysail.

$54,000 Details →

Featured

2019 26' N.G. Herreshoff

Nonoro — Herreshoff Alerion 26 Sloop

A 2019 Herreshoff Alerion 26 daysailer, cold-molded in wood/epoxy by Brion Rieff Boatbuilders, with quiet Bellmarine electric propulsion, in-boom furling main, and a self-tacking, roller-furling jib. Impeccably finished bronze and varnished teak, and dry-sailed just a handful of days each year since new.

$175,000 Details →

Price Reduced

1989 50'4" Niels Helleberg

Amelie — Alden 50 Sloop

A classic Niels Helleberg-designed Alden 50 sloop that, under current ownership, has seen a major multi-year (2020–2025) refit by Brooklin Boat Yard with significant upgrades to equipment, design, sail plan and rig. Back on the market at a significantly reduced price.

$320,000 $245,000 Details →

Featured

1930 21' Nathanael G. Herreshoff

Fluke — Herreshoff Fish Class

One of the beloved Herreshoff Fish Class one-designs — an enlarged 12½ with a short cabin top — built by Herreshoff Manufacturing Co. and lovingly maintained by the same marine professional for over 30 years.

$31,000 Details →

Madrigal — Sparkman & Stephens / Paul Luke Yawl

Featured

1958 46' Sparkman & Stephens (Design #1330)

Madrigal — Sparkman & Stephens / Paul Luke Yawl

A 1958 Sparkman & Stephens design built by Paul E. Luke and in the same family since launch — a fast racer/cruiser with a celebrated racing career, well maintained with timely upgrades by Brooklin Boat Yard.

$130,000 Details →

Nasket — Joel White / Brooklin Boat Yard Ketch

Featured

1971 37'5" Joel White (after Sam Crocker)

Nasket — Joel White / Brooklin Boat Yard Ketch

A handsome 1971 ketch custom built by Brooklin Boat Yard to a Sam Crocker design tweaked by Joel White. Easy to handle with an excellent turn of speed, a spacious traditional interior, and an extensive list of recent upgrades.

$65,000 Details →

Under Contract

1971 34'6" Frank MacLear & Bob Harris

Hara — Allied Seabreeze 35 Sloop

A classic American fiberglass cruiser by MacLear & Harris, built by Allied — a direct production evolution of the famous S&S yawl Finisterre. Rugged, overbuilt construction and a keel/centerboard configuration make her a proven, seaworthy blue-water cruiser.

$24,000 Details →

Featured

1978 27'1" Carl Alberg

Rocketman — Cape Dory 27 Sloop

An uncomplicated, rugged Cape Dory 27 — a Carl Alberg design universally admired by knowledgeable sailors. Owned and maintained by a Brooklin Boat Yard employee for the past decade, repowered with an 8 HP Mercury outboard, with new cushions throughout.

$4,000 Details →

Featured

1936 27'3" Knud Reimers

Svek — Reimers Tumlaren Sloop

A beloved 1936 Tumlaren — Knud Reimers's 20 Square Metre one-design — given a professional structural rebuild and Best in Show at the 2022 WoodenBoat Show. Copper-riveted Oregon pine over oak, fresh rig and brightwork, and a full sail inventory. Conveys on a custom trailer, ready for her next 90 years.

$34,000 Details →

Price Reduced

2013 47'6" Brooklin Boat Yard

Sparrow — Eggemoggin47 Sloop

A wolf in sheep's clothing combining classic elegance with modern sailing performance. Carbon fiber composite hull, fractional carbon fiber mast, fin/bulb keel, and carbon fiber rudder. Designed and built by Brooklin Boat Yard.

$575,000 $525,000 Details →

Price Reduced

2000 46'9" Bob Stephens

Zebra — W-Class W-46 Sloop

A stunning Spirit of Tradition yacht with long, sweeping overhangs fore and aft. Traditional aesthetics paired with modern performance including carbon-fiber spars and modern foil shapes. Built by Rockport Marine.

$325,000 $285,000 Details →

Nimble — Norton 30 Spirit of Tradition Sloop

Price Reduced

1989 34' Tom Norton

Nimble — Norton 30 Spirit of Tradition Sloop

A responsive day sailor and racer with modern aesthetics and classic appeal. Cold-molded Bruynzeel mahogany with carbon fiber reinforcement, Hall Spars mast, and a comprehensive recent refit history.

$59,000 $49,000 Details →

Price Reduced

1985 31' Ted Hood & Dieter Empacher

Potpourri — Bristol 31.1 Sloop

An excellent example of the mid-1980s cruiser-racer from a collaboration between sailing icon Ted Hood and designer Dieter Empacher. Suited for both distant cruising and handicapped racing.

$32,000 $30,000 Details →

Price Reduced

1973 42'2" John G. Alden (Design #925D)

Shanti — Alden K/CB Yawl

A John G. Alden-designed wooden yawl that has educated multiple classes of owners through Atlantic crossings and Mediterranean cruising. Completely refastened in 2018 by Rockport Marine.

$135,000 $95,000 Details →

Night Heron — 1961 Geerd Hendel / Bigelow Brothers Marconi Cutter

Price Reduced

1961 32'0" Geerd Hendel

Night Heron — 1961 Geerd Hendel / Bigelow Brothers Marconi Cutter

A 1961 Geerd Hendel-designed Marconi Cutter, built by Bigelow Brothers of Monument Beach. Mahogany over oak, bronze fastened, with current 2026 service complete. Sail-away condition.

$33,000 $28,000 Details →

Price Reduced

1952 50' Frederick Parker

Bellina — Parker Staysail Ketch

A 1952 English-built staysail ketch with copper-riveted mahogany hull over English oak frames. Walk-in engine room, pilot house, and comprehensive cruising systems. Thoughtfully upgraded and ready for departure.

$66,000 $55,000 Details →

2000 44' Eric Sponberg

Bagatelle — Sponberg/Waters Fast Sloop

A custom lightweight performance sloop designed to plane in under 20 knots of wind. Cold-molded wood-epoxy hull with carbon fiber mast, stainless steel fin keel with lead bulb, and water ballast system. Nine sails included.

$50,000 Details →

1937 33' Knud Reimers

Vixen — 15 Square Meter Sloop

A rare 1937 Swedish-built 15 Square Meter racing yacht designed by Knud Reimers. Fully restored by Brooklin Boat Yard in 2013. Rich racing history including association with legendary designer Uffa Fox.

$90,000 Details →

1970 62' David C. McIntosh

Audacity — Bud MacIntosh Schooner

Built in 1970 by legendary wooden boat builder Bud McIntosh, this 62-foot schooner is a rare opportunity to own a piece of living maritime history. Copper rivet-fastened mahogany hull, varnished spruce spars.

$49,900 Details →

1974 31'3" Howard Chapelle / William Menger

Shellback — Menger Oysterman 23 Ketch

A sliding-gunter, ketch-rigged Menger Oysterman 23 based on Howard Chapelle's 'Blue Crab' skipjack design. Used almost exclusively as a daysailer in Maine, and her Magic-Tilt trailer makes launching effortless.

$2,000 Details →

1970 48'1" William Tripp, Jr.

Katrinka — Tripp 48 Sloop

Designed by Bill Tripp Sr. as a racing and cruising yacht. Won her class in the 1980 Newport Bermuda Race. Complete 2008 restoration by Brooklin Boat Yard with carbon fiber mast and modern systems.

$450,000 Details →

1961 42' Sam Crocker

Ms. Reilly — Sam Crocker Schooner

Originally commissioned for Roger Duncan, author of 'The Cruising Guide to the New England Coast.' Built by Reed's Shipyard in 1961 with a 2023 engine replacement and extensive recent systems overhaul.

$39,000 Details →

1965 39' David C. (Bud) MacIntosh

Cedar — Bud MacIntosh Sloop

Originally launched in 1965 as 'Go Go Girl,' restored by Paul Rollins and documented in WoodenBoat magazine. Relaunched in 2023 after comprehensive restoration from a Vermont field discovery.

$80,000 Details →

Under Contract

1984 33'2" Klass T. Kremer

Thistle — Waarschip Fin Keel Sloop

A recently modernized Dutch-built racer with new aluminum mast, carbon fiber boom, updated rigging, fresh paint, and new sails. Competitive in the Eggemoggin Reach Regatta Spirit of Tradition class.

$45,000 Details →

2023 33'9" Brion Rieff

Susan — Brion Rieff 34 Sloop

A beautifully crafted cold-molded wooden sloop inspired by the classic Alerion design. Vacuum-bagged construction with epoxy-coated Douglas fir frames and a teak interior. Under the care of Brooklin Boat Yard since first launched.

$350,000 Details →

1973 28' L. Francis Herreshoff

Petrel — Herreshoff Rozinante

A classic L. Francis Herreshoff Rozinante double-ender built in Portland, Oregon. Electric outboard auxiliary. Includes 8' fiberglass dinghy with oars.

$24,900 Details →

1979 37'9" Lyle Hess

Paragon — Bristol Channel Cutter

A Lyle Hess-designed bluewater cruiser built to withstand years of punishment from blue water cruising. Remarkable sailing performance, exceptional seaworthiness, and extensive accommodations.

$60,000 Details →

2001 46'9" Robert Stephens

Mustang — W-Class W-46 Sloop

A visually stunning Spirit of Tradition W-Class yacht optimized for racing while maintaining classic aesthetics. Cold-molded wood-epoxy construction by Rockport Marine. Comprehensive racing refit.

$500,000 Details →

1958 35'6" Einar Ohlson

Ellida — 1958 Ohlson 35 Yawl

Hull #12 of 48 Ohlson 35 yawls built in Gothenburg, Sweden. Recently restored with Silver award at the International Antique and Classic Boat Society show in 2022.

$30,000 Details →

1934 41' W. Starling Burgess

Little Dipper — Starling Burgess Cutter

A 1934 Starling Burgess-designed cutter originally commissioned by Buckminster Fuller. Extensively restored 2009-2010 with new deck, planking, cockpit, and spars. New Gamble & Hunter sails (2018).

$109,000 Details →

1997 45' John G. Alden

Renaissance — Alden Off Soundings Yawl

A 1997 construction of a classic John G. Alden design, cedar planked with copper rivet fastening on white oak frames. Lovingly maintained with extensive recent upgrades including new sails, electronics, and keel bolts.

$110,000 Details →

1973 41' Ted Brewer / Robert Walstrom

Integrity — Quoddy Pilot Ketch

A meticulously maintained Quoddy Pilot Ketch presenting close to new condition for her 50+ years. Brand new Beta 38 diesel with under 50 hours, rig redesigned by Nat Benjamin, and comprehensive recent upgrades.

$79,000 Details →

1960 38'6" John G. Alden

Muskrat — Alden Challenger K/CB Yawl

A John G. Alden-designed Challenger Yawl built by Halmatic Ltd. in fiberglass with mahogany superstructure. Elegant and sea-kindly, with a keel-and-centerboard design that draws just 4' for access to gunkholing waters.

$45,000 Details →

1997 48'6" L. Francis Herreshoff

Walrus — Herreshoff Motorsailer Ketch

Judges Choice For Best In Show 2025 at WoodenBoat Show, Mystic CT. A Herreshoff-designed motorsailer with twin diesels, 680 watts of solar, and comprehensive 2021-2023 upgrades including new electronics, rigging, and LFP batteries.

$285,000 Details →

1956 30' E.G. Van de Stadt

Lyceum — Van de Stadt 30 Sloop

A Dutch-built Van de Stadt design with a thorough and pro-active restoration history keeping her in good working order. Brand new 2023 Nanni diesel engine.

$49,500 Details →

1963 32' Robert G. Henry, Jr.

Drift — International 500 Yawl

A German-built International 500 Yawl designed by Robert G. Henry, consistently maintained in exceptional condition since 1963. Westerbeke diesel with 1,529 hours.

$38,900 Details →

Pleione — 2004 Jim Taylor / Bruce Dyson Custom 8-Metre Sloop

Sold

2004 48'0" Jim Taylor

Pleione — 2004 Jim Taylor / Bruce Dyson Custom 8-Metre Sloop

A custom 8-Metre Class sloop designed by Jim Taylor and built by Bruce Dyson — balancing classic 1930s aesthetics with modern performance technology. Cold-molded Spanish cedar and Honduras mahogany over wood-epoxy. Sold through Brooklin Boat Yard Brokerage.

Sold Details →

Sold

1997 31'1" Joel White

Windward — Center Harbor 31

A Joel White-designed, Brooklin Boat Yard-built Center Harbor 31. Previously raced competitively, with a 2015 major refit including shallow-draft keel replacement. Includes custom float-on/float-off trailer.

Sold Details →

Sold

1995 17'0" Traditional Whitehall design

Whitehall — 1995 Rowing/Sailing Gig

A traditional carvel-planked rowing and sailing gig in the classic 19th-century Whitehall style — three rowing stations, lug sail, varnished mahogany trim, and a Karavan trailer. Sold through Brooklin Boat Yard Brokerage.

Sold Details →

Sold

1989 24' Joel White

Clover — Bridges Point 24

A Joel White-designed Bridges Point 24 with a unique interior layout, varnished mahogany interior with bronze hardware, and 2022 Gambell & Hunter sails. Includes double-axle trailer.

Sold Details →

Jabberwocky — 1981 Jarvis Newman Dictator Friendship Sloop

Sold

1981 31'0" Wallstrom, Watkins & Associates

Jabberwocky — 1981 Jarvis Newman Dictator Friendship Sloop

Custom-built Dictator-model fiberglass Friendship Sloop (Sail No. 189), built by Jarvis Newman and completed by master carpenter Roger Nehrbass. Owned for a time by Newman himself. A beautiful example of an updated classic Maine boat. Sold through Brooklin Boat Yard Brokerage.

Sold Details →

Sold

1977 30'3" Carl Alberg

Emma — 1977 Cape Dory Cutter 30

A well-equipped Carl Alberg-designed Cape Dory Cutter — proven coastal Maine cruiser. Recent updates include a Beta Marine 16 engine (2024), Furuno wireless radar, Standard Horizon VHF, Jabsco head, and Spade primary anchor with Lewmar electric windlass.

Sold Details →

Sold

1960 12'4" John Beetle (Beetle Cat one-design)

Fiona Too — Beetle Cat

A classic Beetle Cat — the iconic gaff-rigged catboat one-design that's been delighting sailors of all ages on New England waters since 1921. Sold through Brooklin Boat Yard Brokerage.

Sold Details →

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