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Jun 30, 2024 Auction
by Florida Highwaymen Auctions LLC

Florida Highwaymen painting featuring a lone palm tree swaying in the ocean breeze against a twilight sky. The artwork’s deep blues and soft golden hues create a serene coastal atmosphere, while gentle waves shimmer under the fading sunlight. This collectible artwork embodies the Highwaymen’s signature style, capturing the tranquil beauty of Florida’s shoreline with expressive brushwork and bold color contrasts.
LOT 1001
Tracy Newton, 'Windy Day', 2nd Gen. Highway Men - Oil Painting, 16"x20"

‘Windy Day’ by Tracy Newton captures a breezy Florida scene, with windblown palms swaying under a dynamic sky. As the son of Sam Newton, Tracy honors the Highwaymen legacy while showcasing his unique style. This vibrant 16”x20” oil painting beautifully reflects Florida’s natural charm and energy.


Florida Highwaymen painting featuring a lone palm tree swaying in the ocean breeze against a twilight sky. The artwork’s deep blues and soft golden hues create a serene coastal atmosphere, while gentle waves shimmer under the fading sunlight. This collectible artwork embodies the Highwaymen’s signature style, capturing the tranquil beauty of Florida’s shoreline with expressive brushwork and bold color contrasts.
LOOT 1002
James Gibson, ‘Moonlight’, Oil Painting on Canvas, 20x12, C. 1970

‘Moonlight’ by James Gibson is a serene depiction of Florida’s landscape bathed in soft, silvery moonlight. The painting captures the tranquil glow of the moon reflecting on calm waters, framed by lush foliage and iconic palms. This 20”x12” oil on canvas showcases Gibson’s mastery of light and shadow, creating an atmosphere of peace and quiet beauty. A timeless piece from the 1970s that embodies the spirit of the Florida Highwaymen.

Florida Highwaymen painting depicting a windswept palm tree leaning over a tranquil waterfront at dusk. The sky is filled with soft blues and grays as clouds reflect the fading sunlight, casting a glow over the calm waters. A rustic wooden dock extends into the distance, adding to the serene beauty of this Old Florida coastal scene. This collectible artwork exemplifies the Highwaymen’s signature style, blending movement, light, and nature in a timeless composition.
LOT 1003
Livingston Roberts, 'Night Palm', Highway Men - Oil Painting on Upson, 24"x18"

‘Night Palm’ by Livingston Roberts captures the quiet elegance of a solitary palm under the moonlit sky. This 24”x18” oil painting on Upson board reflects the artist’s signature style, blending deep blues and silvers to evoke a serene nighttime atmosphere. Roberts’ work exemplifies the timeless beauty and tranquility of Florida’s landscapes, a hallmark of the Highwaymen legacy.

Florida Highwaymen triptych painting set featuring three coastal scenes framed in gold. The central artwork showcases a windswept palm tree on a serene beach, with turquoise waves rolling under a bright blue sky. The two side panels complement the scene with additional palm trees and ocean views, creating a stunning panoramic effect. This collectible set exemplifies the Highwaymen’s signature style, capturing the timeless beauty of Florida’s shoreline.
LOT 1004
Al Black, 'Beach Themed Tryptich', Highway Men Oil Painting on Masonite, 19"x7.5"

‘Beach Themed Triptych’ by Al Black is a stunning three-panel composition celebrating Florida’s coastal beauty. Each panel showcases a vibrant beach scene, from swaying palms to shimmering waters under a radiant sky. Painted on Masonite, this 19”x7.5” work highlights Black’s vivid color palette and mastery of coastal landscapes, making it a unique piece within the Highwaymen tradition.

Florida Highwaymen painting featuring a tranquil river landscape at sunset. The sky is illuminated with soft golden and pink hues, reflecting beautifully on the calm water below. A lone pine tree stands tall in the foreground, framed by lush greenery and distant palm trees. Birds glide across the sky, adding movement to the serene composition. This collectible artwork exemplifies the Highwaymen’s signature style, capturing the timeless beauty of Florida’s natural landscapes.
LOT 1005
James Gibson, 'Fire Sky Reflection', Highway Men Oil Painting, 24"x18"

‘Fire Sky Reflection’ by James Gibson captures the dramatic beauty of a Florida sunset, with fiery red and orange tones illuminating the sky and reflecting on tranquil waters. This 24”x18” oil painting exemplifies Gibson’s ability to blend bold colors and serene landscapes, showcasing the timeless charm of the Highwaymen’s iconic style.

Florida Highwaymen painting by R. Demps featuring a vibrant Royal Poinciana tree in full bloom, its fiery red-orange canopy contrasting against a deep blue sky. Framed by swaying palm trees, the scene overlooks a calm waterfront, evoking the tropical beauty of Old Florida. This collectible artwork showcases the Highwaymen’s signature style, capturing the essence of Florida’s lush landscapes with bold colors and expressive brushwork.
LOT 1006
Rodney Demps, 'Dreamy Poinciana', Highway Men Oil Painting, 24"x18"

‘Dreamy Poinciana’ by Rodney Demps features a vibrant Royal Poinciana tree in full bloom, its fiery red flowers contrasted against a serene Florida landscape. This 24”x18” oil painting captures the essence of the Highwaymen’s style, blending bold colors and soft, dreamlike brushstrokes to celebrate the beauty of Florida’s tropical flora.

Florida Highwaymen painting depicting a breathtaking coastal sunset with windswept palm trees along a rocky shoreline. The sky blends warm orange and deep purple hues, reflecting beautifully on the gentle waves and wet sand. This collectible artwork captures the tranquil beauty of Old Florida’s beaches, exemplifying the bold colors and expressive brushwork characteristic of the Highwaymen style.
LOT 1007
Ahmed Eltemtamy, 'Six Palm Sunset', Oil Painting on Masonite, 20"x16"

‘Six Palm Sunset’ by Ahmed Eltemtamy captures the serene beauty of a tropical evening, with six palms silhouetted against a vibrant sunset. The rich oranges, purples, and soft pinks of the sky reflect on tranquil waters below, creating a harmonious and calming scene. This 20”x16” oil painting on Masonite showcases Eltemtamy’s mastery of light and composition, making it a stunning celebration of Florida’s coastal charm.

Florida Highwaymen painting featuring a majestic Royal Poinciana tree in full bloom, framed in a distressed white wooden frame. The tree’s vibrant red canopy stands against a stunning waterfront view, with a sailboat drifting in the distance under a colorful sky. This collectible artwork captures the essence of Old Florida’s natural beauty, showcasing the Highwaymen’s signature style with bold colors and expressive brushwork.
LOT 1008
Norman Wright, Cotton Candy Poinciana 20X30 Masonite

‘Cotton Candy Poinciana’ by Norman Wright showcases a vibrant Royal Poinciana tree with delicate, pastel-toned blooms resembling cotton candy. Set against a tranquil Florida landscape, the tree’s radiant colors contrast beautifully with the soft hues of the sky and lush greenery. This 20”x30” oil painting on Masonite reflects Wright’s skill in capturing the subtleties of nature’s beauty, offering a serene and visually striking scene.

Florida Highwaymen painting depicting a peaceful marshland scene with a lone egret standing by a reflective pond. Surrounded by golden grass and towering pine trees, the artwork captures the untouched beauty of Florida’s natural landscapes. Billowing clouds in the background enhance the tranquil atmosphere, making this collectible artwork a timeless representation of the Highwaymen’s signature style.
LOT 1009
Roy Mclendon, 'Back Country Log', Highway Men - Oil Painting on Upson, 24"x18"

‘Back Country Log’ by Roy McLendon depicts a serene rural Florida landscape, featuring a fallen log amidst lush greenery and a peaceful backdrop of marshes or wetlands. Painted on Upson board, this 24”x18” piece showcases McLendon’s ability to capture the quiet beauty of Florida’s untamed wilderness, emphasizing natural textures and earthy tones. A classic example of the Highwaymen’s dedication to Florida’s landscapes.

Florida Highwaymen painting featuring a dramatic sunset sky with fiery red and orange hues reflecting over a calm river. Two white egrets stand gracefully in the shallows, while lush greenery frames the vibrant horizon. The intense colors and dynamic brushwork capture the breathtaking beauty of Florida’s wetlands, exemplifying the bold and expressive style of the Highwaymen artists.
LOT 1010
Johnny Daniels, 'Sky of Flame', Highway Men Oil Painting on Upson, 36"x24"

‘Sky of Flame’ by Johnny Daniels is a striking depiction of a fiery Florida sunset, with intense red and orange hues dominating the sky. The glowing horizon transitions into softer reflections on the surrounding landscape, framed by shadowed silhouettes of trees and marshlands. This 36”x24” oil painting on Upson board exemplifies Daniels’ dynamic brushwork and vibrant color palette, capturing the raw beauty and intensity of Florida’s natural scenes.

Florida Highwaymen painting featuring a stunning Royal Poinciana tree in full bloom, its vibrant red canopy stretching wide under a bright blue sky. Towering palm trees and lush greenery frame the tranquil waterfront in the background, while billowing clouds add depth to the composition. This collectible artwork exemplifies the Highwaymen’s signature style, capturing the vivid beauty of Old Florida’s landscapes.
LOT 1011
Majestic Royal Poinciana by the Lake

This captivating painting features a vibrant Royal Poinciana tree in full bloom, its fiery red canopy spreading wide across a serene lakeside setting. Framed by towering palms and a dynamic sky with soft clouds, the scene captures the lush beauty of Florida’s tropical landscapes. The intricate detailing of the tree’s branches and blossoms, paired with the tranquil backdrop, creates a striking composition that celebrates the harmony of nature. A stunning example of vibrant Floridian artistry.

Florida Highwaymen painting showcasing a magnificent Royal Poinciana tree in full bloom, its fiery red-orange blossoms reflected in a peaceful pond. The lush green landscape and soft pastel sky create a tranquil atmosphere, highlighting the beauty of Old Florida’s scenery. This collectible artwork embodies the Highwaymen’s signature style, featuring bold colors and expressive brushstrokes that capture the essence of Florida’s natural landscapes.
LOT 1012
Isaac Knight, 'Red Tree on the Lake', Highway Men - Oil Painting on Upson, 36"x24"

‘Red Tree on the Lake’ by Isaac Knight showcases a vibrant red tree standing prominently by a serene lake. The bold crimson hues of the tree contrast beautifully with the calm blues and greens of the surrounding water and landscape. Painted on Upson board, this 36”x24” piece reflects Knight’s ability to combine dramatic color with tranquil scenery, exemplifying the timeless appeal of Florida’s natural beauty through the Highwaymen’s iconic style.

Florida Highwaymen painting depicting a serene wetland scene with two elegant egrets standing in shallow water. A tall, windswept palm tree leans over the reflective river, framed by lush greenery. Billowing golden clouds fill the sky, casting a warm glow over the tranquil landscape. This collectible artwork embodies the Highwaymen’s signature style, capturing the timeless beauty of Old Florida’s untouched wilderness.
LOT 1013
Harold Newton, 'Water Birds', Highway Men Oil Painting on Masonite, 18"x12"

‘Water Birds’ by Harold Newton portrays a serene Florida wetland scene, featuring graceful water birds wading amidst calm, reflective waters. The delicate interplay of soft blues and greens highlights Newton’s mastery of light and natural textures. Painted on Masonite, this 18”x12” piece captures the tranquility and elegance of Florida’s wildlife, exemplifying the timeless charm of the Highwaymen’s iconic landscapes.


Florida Highwaymen painting featuring a charming Old Florida coastal village with a dirt path leading to a small wooden cottage. A vibrant Royal Poinciana tree in full bloom adds a splash of red against the lush green landscape. Tall palm trees sway in the breeze, and a sailboat drifts on the tranquil waters, capturing the essence of Florida’s coastal beauty. This collectible artwork exemplifies the Highwaymen’s signature style, blending nostalgia and vivid landscapes.
LOT 1014
Sam Newton, 'Poinciana House on the Water', Highway Men - Oil Painting on Masonite, 18"x14"

‘Poinciana House on the Water’ by Sam Newton depicts a serene Florida landscape featuring a radiant Royal Poinciana tree in full bloom beside a tranquil waterfront home. The vibrant red foliage contrasts against the soft blues of the water and sky, creating a harmonious balance of color and composition. This 18”x14” oil painting on Masonite reflects Newton’s ability to blend vibrant natural elements with the quiet charm of Florida’s rural beauty, embodying the timeless appeal of the Highwaymen’s work.

Florida Highwaymen painting showcasing a breathtaking wetland scene at sunrise, with towering cypress trees draped in Spanish moss. The calm waters reflect the vibrant hues of the sky, while two elegant white egrets take flight above floating lily pads. This collectible artwork captures the untouched beauty of Florida’s swamps and wetlands, exemplifying the Highwaymen’s signature style with its rich colors and serene atmosphere.
LOT 1015
Charles Walker, 'Cypress Sanctuary', Highway Man - Oil Painting on Canvas, 30"x40"

‘Cypress Sanctuary’ by Charles Walker captures the tranquil beauty of a Florida wetland, featuring towering cypress trees draped with moss and reflected in still, glassy waters. The earthy tones of the trees contrast with the soft blues and greens of the serene backdrop, creating a peaceful and immersive composition. This 30”x40” oil painting on canvas highlights Walker’s meticulous attention to detail and his ability to convey the quiet majesty of Florida’s natural landscapes, showcasing his unique approach within the Highwaymen tradition.

Florida Highwaymen painting featuring a lush tropical river scene with tall palm trees on a small island, reflecting in the calm waters. The vibrant greenery and dramatic cloudscape create a serene and picturesque composition. Spanish moss drapes from overhanging branches, adding to the untouched beauty of Old Florida’s wetlands. This collectible artwork showcases the Highwaymen’s signature style, capturing the natural elegance of Florida’s landscapes.
LOT 1016
James Gibson, 'Still Dreaming', Highway Men - Oil Painting on Canvas, 30"x24"

‘Still Dreaming’ by James Gibson portrays a serene Florida waterway surrounded by lush greenery and softly glowing light. The tranquil reflections on the water mirror the vibrant landscape, creating a dreamlike atmosphere. This 30”x24” oil painting on canvas exemplifies Gibson’s mastery of light and color, capturing the quiet beauty and timeless allure of Florida’s natural scenery, a hallmark of the Highwaymen legacy.

Florida Highwaymen painting depicting a rural Florida highway stretching into the horizon, flanked by towering pine and palm trees. The vast sky, filled with billowing clouds, casts soft light over the open landscape, evoking the peacefulness of Old Florida’s countryside. This collectible artwork exemplifies the Highwaymen’s signature style, capturing the scenic beauty of Florida’s backroads and natural surroundings.
LOT 1017
Willie Daniels, 'Country Road', Highway Men Oil Painting on Wood, 36"x28"

‘Country Road’ by Willie Daniels captures the rustic charm of a winding path through Florida’s countryside. Framed by lush greenery and scattered wildflowers, the road leads into a serene horizon under a softly lit sky. Painted on wood, this 36”x28” piece showcases Daniels’ skill in creating depth and atmosphere, evoking the peaceful beauty of rural Florida landscapes. A classic representation of the Highwaymen’s artistic vision.

Florida Highwaymen painting depicting a dramatic coastal storm scene with a towering lighthouse standing resilient against crashing ocean waves. A windswept palm tree bends under the force of strong winds, while dark storm clouds gather in the sky. This collectible artwork captures the raw power and beauty of Florida’s coastline, exemplifying the Highwaymen’s signature style with expressive brushstrokes and bold contrasts.
LOT 1018
Harold Newton, 'Guiding Light', Highway Men - Oil Painting on Masonite, 22.5"x17.5"

‘Guiding Light’ by Harold Newton beautifully depicts a serene Florida seascape illuminated by the soft glow of a lighthouse. The radiant light guides the viewer’s eye across calm waters, framed by lush greenery and a tranquil sky. This 22.5”x17.5” oil painting on Masonite exemplifies Newton’s mastery of light and composition, capturing the timeless charm and tranquility of Florida’s coastal beauty. A stunning testament to the enduring legacy of the Highwaymen.

Florida Highwaymen painting featuring a serene tropical beach scene with two swaying palm trees overlooking the ocean. Gentle waves roll onto the sandy shore under a vast sky filled with billowing clouds, while seagulls soar above the turquoise waters. This collectible artwork captures the timeless beauty of Florida’s coastline, exemplifying the Highwaymen’s signature style with vibrant colors and expressive brushwork.
LOT 1019
Roy Mclendon, 'Sharp Palms', Oil Painting on Canvas, 36"x24"

‘Sharp Palms’ by Roy McLendon captures the striking elegance of towering palm trees against a serene Florida backdrop. The intricate detailing of the palms contrasts beautifully with the soft blues of the sky and subtle tones of the surrounding landscape. This 36”x24” oil painting on canvas highlights McLendon’s ability to blend bold natural elements with a peaceful composition, celebrating the timeless beauty of Florida’s tropical scenery.

Florida Highwaymen painting depicting a moody coastal scene with windswept palm trees bending under the force of an approaching storm. The dark ocean stretches toward the horizon, with crashing waves reflecting the stormy sky filled with dramatic clouds. This collectible artwork captures the raw power of Florida’s shoreline, showcasing the Highwaymen’s signature style with expressive brushstrokes and atmospheric depth.
LOT 1020
Florida Highwaymen by Harold Newton (1934-1994) "Rio Mar Storm". 24" x 48" w/o frame

‘Rio Mar Storm’ by Harold Newton is a dramatic depiction of a storm rolling over Florida’s coastline. The painting features dark, turbulent skies meeting the restless waters of Rio Mar, with windblown palms bending under the force of nature. This 24”x48” oil painting captures Newton’s mastery of light and shadow, bringing intensity and emotion to the scene. A testament to the raw beauty of Florida’s landscapes, this piece exemplifies the power and elegance of the Highwaymen’s iconic style.

Florida Highwaymen painting featuring a peaceful river landscape with gently leaning trees reflecting on the calm blue waters. The bright sky is filled with soft clouds, casting warm light over the lush greenery lining the shore. This collectible artwork captures the tranquil beauty of Florida’s natural scenery, exemplifying the Highwaymen’s signature style with vibrant colors and expressive brushwork.
LOT 1021
Alfred Hair, 'Clear Day on the River', Highway Men - Oil Painting, 36"x24"

‘Clear Day on the River’ by Alfred Hair captures the peaceful beauty of a sunny Florida river scene. The painting showcases calm, reflective waters framed by lush greenery and scattered palms, all bathed in warm sunlight. Hair’s dynamic brushstrokes and vibrant color palette bring the composition to life, creating a sense of movement and energy. This 36”x24” oil painting exemplifies Hair’s signature style and the enduring charm of the Highwaymen’s celebrated landscapes.

Florida Highwaymen painting featuring a lush tropical river scene with tall palm trees reflecting in the calm, green waters. Dense foliage and vibrant greenery frame the landscape, while a bright blue sky with fluffy clouds adds depth and warmth to the composition. This collectible artwork captures the serene beauty of Florida’s untouched wetlands, exemplifying the Highwaymen’s signature style with rich colors and natural elegance.
LOT 1022
Curtis Arnett, 'Green Paradise', Highway Men - Oil Painting, 20"x16"

‘Green Paradise’ by Curtis Arnett depicts a serene Florida scene brimming with lush greenery and swaying palms. The tranquil waters and vibrant vegetation create a harmonious composition, inviting viewers into a peaceful tropical escape. This 20”x16” oil painting exemplifies Arnett’s mastery of detail and his dedication to showcasing Florida’s natural splendor, making it a standout piece in the Highwaymen legacy.

Florida Highwaymen painting showcasing a serene river landscape with towering palm trees reflecting in the still blue waters. The lush green foliage and misty horizon create a dreamlike atmosphere, while a lone egret wades near the shoreline. This collectible artwork captures the untouched beauty of Florida’s natural landscapes, exemplifying the Highwaymen’s signature style with vivid colors and tranquil composition.
LOT 1023
Johnny Daniels, "Two Palms on the Water", Florida Highwaymen Masonite Oil Painting, 20"x16"

‘Two Palms on the Water’ by Johnny Daniels depicts a serene Florida scene featuring two elegant palm trees reflected in calm waters under a soft, radiant sky. This 20”x16” oil painting on Masonite captures Daniels’ mastery of light and composition, showcasing the peaceful beauty of Florida’s natural landscapes. A classic example of the Highwaymen’s celebrated style.

Florida Highwaymen painting featuring a striking sunset with a fiery red and orange sky reflecting over a tranquil river. A lone palm tree leans dramatically on a small island, surrounded by lush marsh grasses and silhouetted cypress trees. A flock of birds soars across the glowing horizon, enhancing the scene’s dynamic energy. This collectible artwork captures the essence of Florida’s wild beauty, exemplifying the Highwaymen’s signature style with bold colors and expressive brushwork.
LOT 1024
James Gibson, 'Tequila Sunrise', Highway Men - Oil Painting on Upson, 30"x24"

‘Tequila Sunrise’ by James Gibson is a vivid portrayal of a glowing Florida sunrise, with fiery red, orange, and golden hues radiating across the sky. The vibrant colors reflect on the tranquil waters below, framed by swaying palms that add depth and movement to the scene. This 30”x24” oil painting on Upson board exemplifies Gibson’s skill in capturing the dynamic beauty of Florida’s landscapes, making it a striking addition to the Highwaymen’s iconic collection.

Florida Highwaymen painting depicting a misty river scene framed by lush, overhanging greenery. A lone palm tree stands tall amid the fog, while three elegant egrets wade in the still waters below. The soft, ethereal light enhances the serene and untouched beauty of Florida’s wetlands, making this collectible artwork a perfect representation of the Highwaymen’s signature style.
LOT 1025
Harold Newton, 'Three Birds', Highway Men - Oil Painting on Upson, 18"x14"

‘Three Birds’ by Harold Newton captures a peaceful Florida wetland scene, with three elegant birds wading in calm, reflective waters. The soft hues of the sky and delicate greenery frame the composition, highlighting Newton’s ability to convey both tranquility and detail. This 18”x14” oil painting on Upson board showcases Newton’s mastery of light and natural elements, a hallmark of the Highwaymen’s celebrated work.

Florida Highwaymen painting featuring a majestic Royal Poinciana tree with vibrant red-orange blossoms, its twisted branches reaching over a sunlit dirt path. Two figures walk beneath the tree, carrying baskets, while rolling hills and a bright blue sky with soft clouds complete the tranquil scene. This collectible artwork exemplifies the Highwaymen’s signature style, celebrating the beauty of Florida’s landscapes with vivid colors and expressive brushstrokes.
LOT 1026
Livingston Roberts, 'Jamaica Scene', Highway Men - Oil Painting on Upson, 36"x24"

‘Jamaica Scene’ by Livingston Roberts transports viewers to a tropical paradise, capturing the lush vibrancy of a Jamaican landscape. This 36”x24” oil painting on Upson board features swaying palm trees, serene waters, and a radiant sky, evoking the warmth and tranquility of the tropics. Roberts’ use of bold colors and dynamic brushstrokes brings the scene to life, making it a standout piece in the Highwaymen’s legacy.

Florida Highwaymen painting of a tranquil river at dusk, with a moss-draped cypress tree standing in the foreground. The deep blue water reflects the fading light, while elegant white birds glide above the surface. Towering pines line the horizon, creating a sense of depth and natural serenity. This collectible artwork captures the timeless beauty of Florida’s wetlands, exemplifying the Highwaymen’s signature style with rich colors and atmospheric detail.
LOT 1027
R.L. Lewis, 'Blue Dream', Highway Men - Oil Painting on Canvas, 20"x16"

‘Blue Dream’ by R.L. Lewis is a serene depiction of Florida’s waterways under a tranquil blue sky. The soft gradients of blue dominate the canvas, reflecting on calm waters surrounded by lush greenery and distant palms. This 20”x16” oil painting on canvas highlights Lewis’s ability to blend light and color, creating a dreamlike atmosphere that embodies the peaceful beauty of Florida’s natural landscapes. A classic example of the Highwaymen’s artistry.

Florida Highwaymen painting of a breathtaking sunset over a tranquil river, with the sky glowing in rich hues of tangerine and gold. Tall palm trees and dense foliage frame the scene, casting striking reflections in the still water. A group of white birds wades near the shore, adding to the peaceful ambiance. This collectible artwork captures the essence of Florida’s natural beauty, exemplifying the Highwaymen’s signature style with vivid colors and bold contrasts.
LOT 1028
Mary Ann Carroll, 'Tangerine Sky', Highway Men - Oil Painting on Upson, 36"x24"

‘Tangerine Sky’ by Mary Ann Carroll captures the vibrant beauty of a Florida sunset, with warm tangerine and orange hues dominating the sky. The glowing horizon reflects on calm waters, framed by silhouettes of swaying palm trees and lush foliage. This 36”x24” oil painting on Upson board showcases Carroll’s mastery of color and her unique ability to convey the tranquility and energy of Florida’s landscapes, solidifying her place as the “First Lady” of the Highwaymen.

Florida Highwaymen painting of a dramatic sunset over a vast marshland, with deep orange and red hues reflecting on the water’s surface. A Florida panther lounges on a fallen tree trunk, blending into the wild, untouched landscape. The darkening sky and dense foliage add to the painting’s mysterious and untamed atmosphere. This collectible artwork embodies the Highwaymen’s signature style, showcasing the beauty and raw power of Florida’s wilderness.
LOT 1029
Charles 'Chico' Wheeler, 'Florida Panther', Highway Men - Oil Painting on Masonite, 36"x24"

‘Florida Panther’ by Charles ‘Chico’ Wheeler is a striking depiction of one of Florida’s most iconic and endangered animals. Set against a lush, natural backdrop, the painting captures the majestic panther in its serene yet powerful essence, blending bold details with rich, earthy tones. This 36”x24” oil painting on Masonite exemplifies Wheeler’s ability to combine wildlife artistry with the Highwaymen’s celebrated style, highlighting the beauty and mystique of Florida’s wilderness.

Florida Highwaymen painting depicting a nostalgic street scene featuring ‘Eddie’s Place,’ a vibrant green roadside building with people gathered outside. A vintage car is parked nearby, and a red fire hydrant adds a pop of color to the foreground. Towering palm trees, birds in flight, and a brilliant blue sky contrast against the earthy tones of the rustic structures. This collectible artwork captures the charm of Old Florida, showcasing the Highwaymen’s signature style with bold colors and expressive brushwork.
LOT 1030
Michael Love, 'Eddie's Place', 2nd Generation Highway Men - Oil on Canvas, 24"x18"

‘Eddie’s Place’ by Michael Love offers a nostalgic glimpse into a serene Florida homestead surrounded by lush greenery and tranquil waters. This 24”x18” oil on canvas captures the warmth and charm of rural Florida, with soft brushstrokes and a vibrant color palette. As part of the 2nd Generation Highwaymen, Love continues the legacy of celebrating Florida’s natural beauty and historic landscapes through his art.


Florida Highwaymen painting of a moonlit coastal scene, framed by lush palm trees and dense tropical foliage. A sailboat glides across the shimmering turquoise waters under a deep blue sky, with seagulls soaring above. An old wooden dock sits in the foreground, adding to the tranquil, nostalgic atmosphere. This collectible artwork captures the essence of Old Florida’s unspoiled beauty, showcasing the Highwaymen’s signature style with luminous colors and striking contrasts.
LOT 1031
Johnny Daniels, 'Night Boat', Highway Men - Oil Painting on Masonite, 30"x24"

‘Night Boat’ by Johnny Daniels captures the quiet mystery of a Florida waterway under a moonlit sky. A lone boat rests peacefully on the reflective water, surrounded by silhouettes of trees and subtle highlights of light. This 30”x24”



Florida Highwaymen painting of a striking royal poinciana tree in full bloom, with vibrant red flowers contrasting against a bright blue sky and turquoise waters in the background. The tree’s sprawling branches and lush foliage create a dramatic focal point, embodying the beauty of Old Florida’s tropical landscape. This collectible artwork showcases the Highwaymen’s masterful use of bold colors and expressive brushstrokes, capturing the essence of Florida’s natural splendor.
LOT 1032
Nathan Clements, 'Poinciana', Oil on Masonite, 12"x9"

‘Poinciana’ by Nathan Clements is a vibrant depiction of a blooming Royal Poinciana tree, its fiery red flowers radiating against a tranquil Florida landscape. Painted on a compact 12”x9” Masonite board, the piece captures the essence of tropical beauty with its bold colors and detailed brushwork. This artwork reflects Clements’ ability to celebrate Florida’s iconic flora in a vivid and captivating style.

Florida Highwaymen painting of a windswept palm tree on a sandy coastal dune, overlooking the vibrant blue ocean with rolling waves and a dramatic sunset sky. The artwork captures the essence of Old Florida’s untouched tropical beauty, with rich, bold colors and expressive brushstrokes. A stunning depiction of the Sunshine State’s serene shoreline, this collectible piece embodies the signature style of the legendary Highwaymen artists.
LOT 1033
Nathan Clements, 'Beach Color', Oil Painting on Masonite, 12"x9"

‘Beach Color’ by Nathan Clements portrays a serene coastal scene, with soft waves lapping against the shore under a radiant sky. Vibrant hues of the beach and surrounding tropical elements bring the composition to life, showcasing Clements’ skill in capturing the natural beauty of Florida’s beaches. This 12”x9” oil painting on Masonite delivers a compact yet impactful representation of the coast’s tranquility and charm.

Florida Highwaymen painting of a moonlit ocean wave crashing onto the shore, with a luminous reflection shimmering on the wet sand. The dramatic seascape captures the beauty of a nighttime coastal scene, featuring deep blues, glowing turquoise waters, and soft, misty highlights. A classic representation of the Highwaymen’s signature style, showcasing the untouched allure of Florida’s beaches.
LOT 1034
Willie Daniels, (Al Black Signed), 'Wave Break', Highway Men - Oil Painting on Upson, 36"x24"

‘Wave Break’ by Willie Daniels, with Al Black’s signature, captures the dynamic energy of waves crashing against the shore under a vibrant Florida sky. The bold brushstrokes and rich blue tones convey the motion and power of the ocean, while the soft gradient of the horizon adds balance and serenity. This 36”x24” oil painting on Upson board is a testament to the collaborative spirit of the Highwaymen and their dedication to depicting Florida’s natural splendor.

Florida Highwaymen painting of a stormy beach scene with towering ocean waves crashing under a dramatic cloudy sky. Windblown palm trees sway in the foreground, adding movement to the coastal landscape. This classic seascape captures the raw power of nature, painted in the distinctive style of the Highwaymen artists.
LOT 1035
Johnny Daniels, 'Old Rio Mar', Highway Men - Oil Painting on Upson, 36"x24"

‘Old Rio Mar’ by Johnny Daniels showcases a tranquil Florida coastal scene with serene waters and bending palms under a softly glowing sky. The painting captures the timeless beauty of the Rio Mar area, blending vibrant hues with delicate brushwork to evoke a sense of peace and nostalgia. This 36”x24” oil painting on Upson board reflects Daniels’ ability to celebrate Florida’s natural landscapes with a signature style that defines the Highwaymen legacy.

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