Highwaymen Paintings

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Florida Highwaymen Style Painting: Florida Highwaymen Painting

Apr 26, 2026

Florida Highwaymen Style Painting

Miami Treasure Auctions

AL BLACK FLORIDA HIGHWAYMEN 2 OF 2 RIVER SCENE: Black, Albert “Blood” (1947-2025) Florida Highwaymen Painting. Oil on Masonite - signed lower right. Executed in brush. the second work in the river pair, this painting deepens the dialogu

Apr 25, 2026

AL BLACK FLORIDA HIGHWAYMEN 2 OF 2 RIVER SCENE

AL BLACK FLORIDA HIGHWAYMEN THREE PALMS: Black, Albert “Blood” (1947-2025) Florida Highwaymen Painting. Oil on Masonite - signed lower right. Painted on the textured side of the board. Executed in brush. Evening descends over the

Apr 25, 2026

AL BLACK FLORIDA HIGHWAYMEN THREE PALMS

JAMES GIBSON FLORIDA HIGHWAYMEN BLUE MONOCHROME: Gibson, James (1938 - 2017) Florida Highwaymen Painting. Oil on Upson - signed lower right. Executed in pallet knife. In this monochromatic Gibson composition, deep blues dissolve into velvety blacks,

Apr 25, 2026

JAMES GIBSON FLORIDA HIGHWAYMEN BLUE MONOCHROME

WILLIE DANIELS FLORIDA HIGHWAYMEN PINK SUNSET: Daniels, Willie (1950-2021) Florida Highwaymen Painting. Oil on canvas - signed lower right. Executed in brush. In this luminous Florida river scene, the artist captures the quiet drama of dusk. A lon

Apr 25, 2026

WILLIE DANIELS FLORIDA HIGHWAYMEN PINK SUNSET

ISAAC KNIGHT FLORIDA HIGHWAYMEN POINCIANA BLOOM: Knight, "Issac" Isaac (1942-2022) Florida Highwaymen Painting. Oil on Canvas Board - signed lower right and verso. Executed in brush and palette knife. Knight’s circa-2002wetland scene centers o

Apr 25, 2026

ISAAC KNIGHT FLORIDA HIGHWAYMEN POINCIANA BLOOM

SAM NEWTON FLORIDA HIGHWAYMEN STORMY HORIZON: Newton, Samuel (B.1948) Florida Highwaymen Painting. Oil on Masonite - signed lower right. Executed with brush and palette knife. Waves detonate against the rocky shoreline, their force softened by sh

Apr 25, 2026

SAM NEWTON FLORIDA HIGHWAYMEN STORMY HORIZON

SAM NEWTON FLORIDA HIGHWAYMEN RIVER'S EDGE: Newton, Samuel (B.1948) Florida Highwaymen Painting. Oil on Masonite - signed lower middle 1982. Executed with brush and palette knife. Life along the river’s edge unfolds through the artistR

Apr 25, 2026

SAM NEWTON FLORIDA HIGHWAYMEN RIVER'S EDGE

SAM NEWTON FLORIDA HIGHWAYMEN PASSAGE OF TIME: Newton, Samuel (B.1948) Florida Highwaymen Painting. Oil on Orange Peel Upson - signed lower right. Executed in brush and palette knife. Three palm trees rise majestically, their forms sculpted in thi

Apr 25, 2026

SAM NEWTON FLORIDA HIGHWAYMEN PASSAGE OF TIME

GEORGE BUCKNER FLORIDA HIGHWAYMEN COOL MOONLIGHT: Buckner, George (1942-2002) Florida Highwaymen Painting. Oil on orange peel Upson - signed lower right. Executed in knife and brush. Buckner’s early study on Upson reveals the nascent language o

Apr 25, 2026

GEORGE BUCKNER FLORIDA HIGHWAYMEN COOL MOONLIGHT

AL BLACK FLORIDA HIGHWAYMEN BLUE RIVER: Black, Albert “Blood” (1947-2025) Florida Highwaymen Painting. Oil on Masonite - signed lower right. Executed in brush. In this evocative canvas, Florida Highwaymen painter and salesman Al

Apr 25, 2026

AL BLACK FLORIDA HIGHWAYMEN BLUE RIVER

ISAAC KNIGHT FLORIDA HIGHWAYMEN JACARANDA: Knight, "Issac" Isaac (1942-2022) Florida Highwaymen painting. Oil on Masonite - signed lower right. Executed with brush and palette knife. A radiant jacaranda is in full yellow bloom, its canopy anch

Apr 25, 2026

ISAAC KNIGHT FLORIDA HIGHWAYMEN JACARANDA

WILLIE DANIELS FLORIDA HIGHWAYMEN NOCTURNAL CALM: Daniels, Willie (1950-2021) Florida Highwaymen Painting. Oil on Canvas Board - signed lower right. Executed with brush and palette knife. A deep blue sky meets the river's surface in a seamless glow a

Apr 25, 2026

WILLIE DANIELS FLORIDA HIGHWAYMEN NOCTURNAL CALM

LIVINGSTON ROBERTS FLORIDA HIGHWAYMEN TRANQUILITY: Roberts, Livingston “Castro” (1942-2004) Florida Highwaymen Painting. Oil on Upson - signed lower right. Exhibited at Highwaymen Heritage African American Forum Pratt &Whitney 2020. Execut

Apr 25, 2026

LIVINGSTON ROBERTS FLORIDA HIGHWAYMEN TRANQUILITY

JAMES GIBSON FLORIDA HIGHWAYMEN VIVID WETLAND: Gibson, James (1938-2017) Florida Highwaymen Painting. Oil on Canvas - signed lower right and card on verso. Executed in pallet knife. This luminous wetland study reveals a masterful command of atmosp

Apr 25, 2026

JAMES GIBSON FLORIDA HIGHWAYMEN VIVID WETLAND

ISAAC KNIGHT FLORIDA HIGHWAYMEN ROYAL POINCIANA: Knight, Isaac (1941-2022) Florida Highwaymen Painting. Oil on Upson - signed lower right. Executed in brush and knife. This painting presents a vintage Poinciana tree at the height of its bloom, its l

Apr 25, 2026

ISAAC KNIGHT FLORIDA HIGHWAYMEN ROYAL POINCIANA

WILLIE DANIELS FLORIDA HIGHWAYMEN SPOIL ISLAND: Daniels, Willie (1950-2021) Florida Highwaymen Painting. Oil on Upson - signed lower right. Executed with brush and palette knife. Moonlight casts shades of yellow and tangerine across the river, bath

Apr 25, 2026

WILLIE DANIELS FLORIDA HIGHWAYMEN SPOIL ISLAND

R.A. MCLENDON FLORIDA HIGHWAYMEN SUBTLE SHORE: McLendon, R.A. “Roy” (1932-2024) Florida Highwaymen Painting. Oil on Canvas - signed lower right. Executed in brush. This Rio Mar painting beautifully captures the essence of coastal tranq

Apr 25, 2026

R.A. MCLENDON FLORIDA HIGHWAYMEN SUBTLE SHORE

ALFRED HAIR FLORIDA HIGHWAYMEN SUMMERLIN SUMMER: Hair, Alfred (1941-1970) Florida Highwaymen Painting. Oil on Linen Upson - signed lower right. Painted verso over a preliminary sketch. Executed in palette knife on a field of brushwork. Summerlin Doc

Apr 25, 2026

ALFRED HAIR FLORIDA HIGHWAYMEN SUMMERLIN SUMMER

John Maynor, Florida Highwaymen Painting, 12 x 14 — The Line of Fire: Florida Highwaymen Painting John Maynor Oil on Masonite Frame Dimensions: 14 x 16 inches Painting Dimensions: 12 x 14 inches A compact, high-impact example of John Maynor’s signature color work—bu

May 02, 2026

John Maynor, Florida Highwaymen Painting, 12 x 14 — The Line of Fire

Florida Highwaymen Auctions LLC

(1 bid)

Al Black, Florida Highwaymen Painting, 12 x 24 — Blue Running Through: Florida Highwaymen Painting Al Black Oil on Canvas Frame Dimensions 30 x 18 inches Painting Dimensions 12 x 24 inches This one keeps it narrow and direct. A single palm leans out over the waterline, w

May 02, 2026

Al Black, Florida Highwaymen Painting, 12 x 24 — Blue Running Through

Florida Highwaymen Auctions LLC

Johnny Daniels, Florida Highwaymen Painting, 20 x 24 — Blue Night, Tall Palms: Florida Highwaymen Painting Johnny Daniels Oil on Canvas Frame Dimensions: 28 x 32 inches Painting Dimensions: 20 x 24 inches A wide, open river scene built around two tall sable palms rising clean th

May 02, 2026

Johnny Daniels, Florida Highwaymen Painting, 20 x 24 — Blue Night, Tall Palms

Florida Highwaymen Auctions LLC

James Gibson, Florida Highwaymen Painting, 18 x 24 — The Water Glows Back: Florida Highwaymen Painting James Gibson Oil on Upson Board Frame Dimensions 27 x 21 inches Painting Dimensions 18 x 24 inches This one holds the light and sends it back. A classic Gibson night scene

May 02, 2026

James Gibson, Florida Highwaymen Painting, 18 x 24 — The Water Glows Back

Florida Highwaymen Auctions LLC

SAM NEWTON FLORIDA HIGHWAYMEN TRIPLE PALM: Newton, Samuel (B.1948) Florida Highwaymen Painting. Oil on orange peel Upson- signed lower right. Executed in palette knife. Under a cool lunar glow, three palms rise as rhythmic verticals against th

Apr 25, 2026

SAM NEWTON FLORIDA HIGHWAYMEN TRIPLE PALM

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