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Description

TBD

Condition

Condition Consistent with Age and wear, Highwaymen Work often created with inexpensive materials, Small Craquelure and Upson Shine through is par for course on many pieces, always inspect all pictures thoroughly, Florida Highwaymen Auction LLC only guarantees Authenticity! That being said no particular major issues with this piece.

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20% aboveUS$100,000.00

TBD

Lot 0014

Estimate $50-$50,000May 30, 2026, 3:00 PM EDT

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$50

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Florida Highwaymen Short but Sweeeet!

May 30, 2026 3:00 PM EDT

Davie, FL, United States

Sam Newton, Florida Highwaymen Painting, 16 x 20 — This Old Road: Sam Newton, Florida Highwaymen Painting, 16 x 20?Framed: 26 x 30?Masonite?This Old Road One of the standout Sam Newton paintings in the auction, this unusually detailed masonite street scene shows

May 30, 2026Sam Newton, Florida Highwaymen Painting, 16 x 20 — This Old Road

Curtis Arnett, Florida Highwaymen Painting, 24 x 36 — Too Tall Pines: Curtis Arnett, Florida Highwaymen Painting, 24 x 36?Framed: 27 x 39?Canvas?Too Tall Pines An unusually refined and highly important early Curtis Arnett canvas dated 1979, this painting captures the

May 30, 2026Curtis Arnett, Florida Highwaymen Painting, 24 x 36 — Too Tall Pines

US$3,100(2 bids)

Willie Reagan, Florida Highwaymen Painting, 16 x 20 — The Water Around the Knees: Willie Reagan, Florida Highwaymen Painting, 16 x 20?Framed: 20 x 24?Canvas?The Water Around the Knees A particularly sharp and highly detailed Willie Reagan swamp scene, this striking canvas

May 30, 2026Willie Reagan, Florida Highwaymen Painting, 16 x 20 — The Water Around the Knees

Chico Wheeler, Florida Highwaymen Painting, 16 x 20 — Dream Logic and Atmospheric Sleep Science: Chico Wheeler, Florida Highwaymen Painting, 16 x 20?Framed: 18 x 22?Canvas?Dream Logic and Atmospheric Sleep Science A mesmerizing Chico Wheeler nocturne built almost entirely through layered

May 30, 2026Chico Wheeler, Florida Highwaymen Painting, 16 x 20 — Dream Logic and Atmospheric Sleep Science

Mary Ann Carroll, Florida Highwaymen Painting, 24 x 36 — Moonlight Breaking: Mary Ann Carroll, Florida Highwaymen Painting, 24 x 36 — Moonlight Breaking Mary Ann Carroll, Florida Highwaymen Painting, 24 x 36?Framed: 28 x 40?Upson Board?Moonlight Breaking A deeply

May 30, 2026Mary Ann Carroll, Florida Highwaymen Painting, 24 x 36 — Moonlight Breaking

Sam Newton, Florida Highwaymen Painting, 24 x 36 — Orange Breaking Into Purple: Sam Newton, Florida Highwaymen Painting, 24 x 36?Framed: 28 x 40?Upson Board?Orange Breaking Into Purple One of the leading Sam Newton paintings in the auction, this dramatic Upson board crosswater

May 30, 2026Sam Newton, Florida Highwaymen Painting, 24 x 36 — Orange Breaking Into Purple

Sylvester Wells, Florida Highwaymen Painting, 12 x 16 — Nocturnal Luminescence: Sylvester Wells, Florida Highwaymen Painting, 12 x 16?Framed: 16 x 20?Upson Board?Nocturnal Luminescence A particularly strong and quietly memorable early Sylvester Wells nocturne, this desirable

May 30, 2026Sylvester Wells, Florida Highwaymen Painting, 12 x 16 — Nocturnal Luminescence

Al Black, Florida Highwaymen Painting, 30 x 40 — Nothing but Time Beneath the Red Canopy: Al Black, Florida Highwaymen Painting, 30 x 40?Framed: 33 x 43?Canvas?Nothing but Time Beneath the Red Canopy A striking large-scale Al Black prison-era poinciana painting, this vividly colored

May 30, 2026Al Black, Florida Highwaymen Painting, 30 x 40 — Nothing but Time Beneath the Red Canopy

Larry Hillpot, Florida Landscape Painting, 20 x 23 — Intercoastal Drift: Larry Hillpot, Florida Landscape Painting, 20 x 23?Canvas Board?Intercoastal Drift A relaxed and highly atmospheric Florida waterway scene by Larry Hillpot, this softly rendered coastal composition

May 30, 2026Larry Hillpot, Florida Landscape Painting, 20 x 23 — Intercoastal Drift

Roderick Hair, Florida Highwaymen Legacy Paintings, 5 x 10 and 8 x 10 — Two Hair Apparitions in: Roderick Hair, Florida Highwaymen Legacy Paintings, approximately 5 x 10 and 8 x 10?Masonite?Two Hair Apparitions in Miniature A highly entertaining and unusually vibrant pair of small-format

May 30, 2026Roderick Hair, Florida Highwaymen Legacy Paintings, 5 x 10 and 8 x 10 — Two Hair Apparitions in

TBD: TBD

May 30, 2026TBD

Al Black, Florida Highwaymen Painting, 12 x 20 — Screeching Tires Through the Dream State: Al Black, Florida Highwaymen Painting, 12 x 20?Framed: 17 x 25?Canvas Board?Screeching Tires Through the Dream State A colorful and very appealing earlier Al Black roadside river scene, this canvas

May 30, 2026Al Black, Florida Highwaymen Painting, 12 x 20 — Screeching Tires Through the Dream State

TBD: TBD

May 30, 2026TBD

Al Black, Florida Highwaymen Painting, 16 x 20 — Scarlet Canopy and Mild Avian Confusion: Al Black, Florida Highwaymen Painting, 16 x 20?Framed: 19 x 23?Canvas Board?Scarlet Canopy and Mild Avian Confusion A wonderfully playful later Al Black poinciana scene, this colorful canvas board

May 30, 2026Al Black, Florida Highwaymen Painting, 16 x 20 — Scarlet Canopy and Mild Avian Confusion

R.L. Lewis, Florida Highwaymen Painting, 12 x 9 — Moss and Neon Along the Shoreline: R.L. Lewis, Florida Highwaymen Painting, 12 x 9?Framed: 15 x 12?Canvas Board?Moss and Neon Along the Shoreline A highly recognizable later-period R.L. Lewis river scene executed in the artist’s

May 30, 2026R.L. Lewis, Florida Highwaymen Painting, 12 x 9 — Moss and Neon Along the Shoreline

Al Black, Florida Highwaymen Painting, 24 x 36 — Eddie’s Place, Midday Drift: Al Black, Florida Highwaymen Painting, 24 x 36?Framed: 29 x 41?Masonite?Eddie’s Midday Drift A vivid and highly characteristic Al Black rendering of Eddie’s Place, one of the most culturally

May 30, 2026Al Black, Florida Highwaymen Painting, 24 x 36 — Eddie’s Place, Midday Drift

TBD: TBD

May 30, 2026TBD

Sam Newton, Florida Highwaymen Painting, 24 x 36 — Sable Palm and Sail, Moss and Glow: Sam Newton, Florida Highwaymen Painting, 24 x 36?Framed: 30 x 42?Canvas?Sable Palm and Sail, Moss and Glow An exceptionally uncommon early Sam Newton canvas painting signed and dated 1971, this

May 30, 2026Sam Newton, Florida Highwaymen Painting, 24 x 36 — Sable Palm and Sail, Moss and Glow

Harold Newton, Florida Highwaymen Painting, 12 x 24 — Orange Sky, Evening Breeze: Harold Newton, Florida Highwaymen Painting, 12 x 24?Framed: 14 x 26?Upson Board?Orange Sky, Evening Breeze A straightforward and very appealing Harold Newton coastal scene on desirable Upson board,

May 30, 2026Harold Newton, Florida Highwaymen Painting, 12 x 24 — Orange Sky, Evening Breeze

US$3,500(1 bid)

Hezekiah Baker,Signrd A Black, Florida Highwaymen Painting, 24 x 36 — St. Lucie Backyard Under: Hezekiah Baker, Florida Highwaymen Painting, 24 x 36?Framed: 28 x 40?Upson Board?St. Lucie Backyard Under Moss A particularly atmospheric St. Lucie River scene, this work is signed “Al Black”

May 30, 2026Hezekiah Baker,Signrd A Black, Florida Highwaymen Painting, 24 x 36 — St. Lucie Backyard Under

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