Highwaymen Art For Sale

Very early (1950's)Harold Newton reverse Rio Mar scene. The light and motion in this painting are simply spectacular, showcasing Mr. Newton's talent at a very early age. Ready to hang.

This painting appears to be an original work by Hezekiah Baker (1940–2007), a notable member of the Florida Highwaymen. Based on recent auction data and market trends as of 2026, its estimated value is likely between $3,000 and $7,000, Medium: Larger works on Upson board or Masonite from the artist's prime decades (1950s–70s) typically hold the most value. This specific piece appears to be part of his "Rare Firesky" series, characterized by vibrant sunset colors over Florida's wetlands, typically featuring iconic loblolly pines and wading birds like egrets. Sale (Summerlin Dock) sold for $12,500 2025

NOTE: IN BEAUTIFUL PRE-OWNED CONDTION.

The motion captured in this painting is incredible! Ready to hang.

ORIGINAL OWNERS STICKER ON BACK - "MR DAVID P FOLDS OF PALM BEACH GARDENS, FLORIDA". BACK OF PAINTING HAS A WATER STAIN AT TOP BUT DOES NOT EFFECT ART. MOONLIGHT OVER THE WATER - AMAZING IMAGE.

R. A. McLendon Original Florida Highwaymen Painting 24" x 30" Oil on Canvas. This painting is from a local estate. It measures 24" x 30" excluding the frame. Including the frame, it measures 28" x 34". The frame shows minor wear. Please see all photos and email with any questions. Please see my other listings for more Original Florida Artist Paintings. Shipping charges are based on the actual weight and box size. Thanks!!!

CANVAS BOARD 16 X 20.

MASONITE 8X20.

CANVAS 8X10.

MASONITE 18 X 24.

NOTE: THERE IS A DEAD ANT INSIDE AT THE BOTTOM LEFT OF THE PRINT.

Willie Daniels (1950-2019) Highwaymen painting of a Florida moonlit night river landscape with tall heavy palette palm trees, birds, green vegetation, and dock extending into the water. Signed lower right. Measures 20" x 16" on canvas & 23.5" x 19.5" w/ frame. $3,500 or make an offer

Oil on Board - signed lower right. Very Large Hazy Afternoon on the St Lucie River.

MASONITE 6 X 28.

SYLVESTER WELLS HOF HIGHWAYMEN SIGNED ACRYLIC PAINTING ON CANVAS COA

This is a beautiful Al Black (Original Florida Highwaymen) signed oil on Masonite board of tree and birds on the Glades. This measures 16 by 20 inches the painting only and framed 21 by 25 inches and is in excellent condition. A rare estate find that will add Florida History and elegance to any decor.

CANVAS 36 X 18.

PANEL 16X20.

MASONITE 20X11.

The landscape piece reflects the natural beauty of Florida, making it a unique and authentic addition to any art collection. Signed on lower right.

CANVAS 12 X 24.

Oil on Masonite signed lower right •COA. Signed oil on Canvas Panel by Al Black.

It is a large, one-of-a-kind piece that depicts a beautiful landscape on the way to the river. The painting features unbelievable detail and is a perfect example of realism style. It is a contemporary piece, and is handmade with great care.

Original Florida Highwaymen painting by Charles "Chico" Wheeler (1946 - 2019). Non-smoking home. Read my feedback and buy with confidence. Please ask all questions prior to purchase.

Don't miss the chance to own this original piece from the 1980s. Al Black (B.1947/D. Oil on Masonite signed lower right • Dated 1980. ).

The light in this painting and blended sky is simply spectacular! Mr. Newton is considered by many to be Florida's best living landscape artist, paintings like this is the reason why. The painting is an unusual 26" by 30" painted on Masonite.

The title of this exceptional historic Robert Butler (1943-2014) print is "Cane Grinding Season". Robert Butler, originally from small town Baxley, GA, grew up in Okeechobee, Florida in the storied Everglades region.

Oil on Masonite signed lower right •. Signed oil on Masonite by John Maynor.

ORIGINAL PAINTING ON LINEN PANEL. PAINTING 20 X 16.

In like new condition.

The product is a large painting by Al Black, a Florida Highwayman artist, on Masonite.

Original Florida Highwaymen painting by John Maynor (1948 - 2016). 100% of proceeds to charity. Local pick up from Sun City Center, Florida only. Please ask all questions prior to purchase. Non-smoking home.

As pictured condition Please see all photos Measures approximately 17.5” x 22” framed 13.25” x 18” scene

Up for sale is a lovely painting of a boathouse and beautiful orange flamboyan tree under a sunny blue sky, with palms trees and birds above and below. Photo of Al Black with painting on verso. Great color and texture on this painting.

MASONITE 6 X 27-1/2.

CANVAS 12 X 24.

Great bargain price for HAZEKIAH HUDSON BAKER and collectors great piece for Offices, Restaurants and for you Living room. • Provenance: M.KNOEDLER & Co., Gallery label verso. Strong collector liquidity in the Florida art market.

The product is an original highwaymen painting by artist RL Lewis, purchased directly from the artist. This medium-sized painting depicts a nature-themed landscape in a realist style, created using oil painting techniques on canvas. Produced in the United States during the 1980s, this one-of-a-kind piece captures the essence of the artist's unique vision and skill.

MASONITE 11X20.

AL BLACK (D.)HOF HIGHWAYMEN SIGNED PAIR OF TWO OIL PAINTINGS MASONITE COA

Handmade in the United States, this unique painting is a stunning addition to any art collection.

CHARLES "CHICO" WHEELER (Dec'd 2019) HOF FL. Oil on Masonite - signed on back only •COA. Signed oil on Masonite by Chico Wheeler. NOTE: Painting not signed on front because it is an unfinished work.

Painting is in excellent condition.

People worldwide are collecting art works by Mazz. a few years later he lived in Jupiter FL and sold paintings at the Marina in Singer island. He fished at the Jupiter inlet daily and painted at night. Looking for unspoiled nature and quieter fishing spots, he moved to St Lucie in the late 80's and still fishes on a regular basis.

Highwaymen Painting Authentic. Painted By Curtis Arnett. 9x11 This is a one of a kind painting by Highwayman Curtis Arnett. This was personalized to my father.

This limited edition print titled "Piney Woods" by A.E. "Beanie" Backus is a must-have for any art collector. PRINT 799/1000 COA. This is a HAND SIGNED PRINT and is labeled as such. (Hand signed as well as showing the original painting signature with date of 1976).

R.A. McLendon Jr. Second Generation Highwaymen Florida Oil Painting. Scene of a boat on the river with an oncoming storm. Painting is 14x11. 18 3/4 x 15 3/4 with frame.

ORIGINAL PAINTING ON MASONITE. PAINTING 18 X 24.

Oil on Masonite - signed lower right•COA.

CANVAS PANEL 24 X 20.

CANVAS 11 X 14.

CHICO WHEELER (D.) SIGNED OIL PAINTING X 2 UPSON BOARD HOF HIGHWAYMEN COA

#36 - ASK JOE.

• COA Tranquil moonlit water.

Hand signed.

This is a original oil painting by. T.S Driskell from 1965 . Signed & has his thumb print. One of a kind its in great shape for being 60 yrs old. Own a piece of history. The product is an original painting by T.S Driskell, featuring the theme of highwaymen. This artwork falls under the category of paintings and is considered an original piece, meaning it is not a licensed reproduction. It showcases the unique style and creativity of the artist, making it a valuable addition to any art collection or display.

The is an original oil painting by artist Sam Newton, a member of the Highwaymen. This large painting features the riverside scene of Florida, signed by the artist and framed. It is a contemporary art piece with a realistic style, showcasing the unique beauty of the Florida landscape. The painting is one of a kind and handmade, showcasing the artist's talent in oil painting techniques from the 1970s-1979 time period. It is a stunning original piece that captures the essence of the Florida landscape. Notice the heart made by the tree branches. Measures 34" high an 28" wide. With a decorative molding frame. Scratched signature on the lower right corner. would make a valuable addition to any art collection and a great investment.

LEMUEL NEWTON (d) HOF FL HIGHWAYMEN SIGNED OIL PAINTING ON UPSON FRAMED COA. Condition is New. Shipped with USPS Priority Mail.

LINEN 18X12.

MASONITE 16X20.

Butler, Robert (1943-2014) Florida Artist Painting. Giclee on canvas - signed lower left in print and hand signed. A small church and covered bridge in the distance. We were recently told a story about this particular image.

MASONITE 14 X 11.

Hand signed.

Hand signed.

Original Florida HIGHWAYMEN R.L. LEWIS Moonlit FLORIDA EVERGLADES. Condition is New. Shipped with USPS Ground Advantage.

Gorgeous painting, is in excellent condition.

The detailed painting captures the essence of a serene marsh ecosystem at sunset, making it a charming and unique addition to any art collection.

We are delighted to offering for your consideration a Superb!! Vintage authentic *Al Black (1947-2025)* Florida Highwaymen artist oil painting on board depicting a gorgeous Beach Scene and Palms. Please scroll below for *Al Black* brief Biography. Indeed a very attractive painting that will make a Collector very very happy!. Condition Report: We do our very best to describe the condition to the best of our knowledge. The Piece is in Excellent condition for it's age and presents well. Wear commensurate by age and use. Please check all the pictures they are part of the description. PLEASE ask all questions and concern that you have about this piece before bidding or buying. Please read all of the description and terms of sale. Measurements: The Painting measures approx. 30" (76cm) Long x approx. 24" (46cm) Tall (Framed).

Never before seen portrait painting. This painting was well looked after.

A nice Lemuel Newton attr., younger brother of Harold and Sam and an original member of the Florida highwaymen, oil on canvas. Signed "L. Newton" in lower right corner. No scratches or damage to painting area (see photos). Canvas frame size is 12"×16"; image size is 11 1/2"×15 1/2"; frame size is 22"×18". A beautiful painting but could use a light cleaning. Photos are part of the description, from a smoke free Utah home. Ships UPS Ground w/insurance and req'd signature receipt. Note: I CAN NOT SHIP THIS TO A USPS PO BOX, sorry.

NEW HEZEKIAH BAKER JR. ORIGINAL PAINTING ON LINEN PANEL.

Al Black oil on upson signed lower right hand corner dated 83’ item is unique in a way that swans where used instead of birds 36 x 24 Framed

HEZEKIAH BAKER, JR. Lush greenery surrounding a New England stream.

HEZEKIAH BAKER (Dec'd) HOF FL.

HEZEKIAH BAKER, JR.

MASONITE 24X18.

MASONITE 12.5 X 24.

The product is an original oil painting by artist Willie Daniels, created in Florida during the 1960s. This medium-sized piece features a landscape of Florida, signed by the artist, making it a one-of-a-kind (OOAK) artwork. The canvas material and unique production technique add to the authenticity and value of this piece, making it a special addition to any art collection.

TUTTI JENKINS SIGNED X 2 PAINTING MASONITE LEGACY HIGHWAYMEN COA

Oils on Masonite Signed.

Illegibly signed low left the painting depicts a tall cypress tree reaching out from the water dripping with Spanish moss while orange, yellow and green trees line the river.

Chico started his painting in the mid to late 1960’s, occasionally these early works unsigned. Beautiful painting by Charles "Chico" Wheeler, his style like no other looks 3d. CHICO WHEELER.

Including a certificate of authenticity.

My goal is for you to be 100% satisfied. Communication can solve so much. I do not have great photography skills but I try to get the most accurate photos I can.

Avid collectors of these early works by the artists were happy to own the art and the artists enjoy the newly gained notoriety. Robert Butler’s art career began in Okeechobee Fl in 1963. All nine of his adult children carry on the art legacy.

CANVAS PANEL 24X12.

A few years later he lived in Jupiter FL and sold paintings at the Marina in Singer island. He fished at the Jupiter inlet daily and painted at night. Looking for unspoiled nature and quieter fishing spots, he moved to St Lucie in the late 80's and still fishes on a regular basis.

CHARLES "CHICO" WHEELER (Dec'd 2019) HOF FL. This painting was done by Wheeler in the mid to late 1960's.

Nice painting by Johnny Daniels.

Tracy is a second generation Highwayman. These are Tracy Newton originals.

CANVAS 24 X 18.

HEZEKIAH BAKER, JR. Created with oil on canvas, it features a beautiful scene of sailboats off the coast of Florida. Produced in 2024, this original work is sure to impress.

Official number is 26 artists. this painting on canvas showcases the artists’ creativity. Whether you are an art collector or simply looking for a beautiful piece to adorn your walls, this painting is an excellent choice.

Wow - What a Chico ! One of the best out there !

Jupiter Lighthouse Oil on canvas 24in X 12in canvas and Frame 29 1/2in X 15 1/2 This stunning painting of the Jupiter Lighthouse, created by artist Vtynes and nephew of the renowned James Gibson, is a true masterpiece. The attention to detail and use of vibrant colors truly bring this Florida Highwaymen original to life. The painting features the iconic Jupiter Lighthouse, which stands tall against a backdrop of lush greenery and a serene blue sky. This piece is perfect for any art lover who appreciates the beauty of nature and wants to add a touch of elegance to their collection. Don't miss out on this one-of-a-kind piece of art!

Certificate of authenticity written and signed by 'Charles "Chico" Wheeler.

Career span 1963-2014. A One of a kind unique piece. Original painting by Robert Butler (Sr) 2002.

Creating over 200,000 paintings in the 20th century. Provenance: Acquired directly from Al Black in 2024.

Al Balck signature on lower right. Provenance: Al Balck collection.

Creating over 200,000 paintings in the 20th century. Provenance: Acquired directly from Al Black in 2025.

Creating over 200,000 paintings in the 20th century. Provenance: Acquired directly from Al Black in 2024.

With : Certificate of authenticity from Al Black.

Materials: Oil on Masonite.

Creating over 200,000 paintings in the 20th century. Provenance: Acquired directly from Al Black in 2025.

Creating over 200,000 paintings in the 20th century. And a small red car. Provenance: Acquired directly from Al Black in 2025. Origin: Florida.

Creating over 200,000 paintings in the 20th century. Provenance: Acquired directly from Al Black in 2024. With the certificate of Authenticity from Al Black. Origin: Florida.

Creating over 200,000 paintings in the 20th century. Provenance: Acquired directly from Al Black in 2024.

Charles "Chico" Wheeler was born around 1946. He was a master of the pallet knife. It has been said that Chico Wheeler would paint a painting and give it to his girlfriends.His landscapes and seascapes are dreamy and very colorful.

Bold strokes of fiery orange and golden yellow, across the sky, creating a dramatic backdrop to the tall, moss-draped cypress trees that dominate the scene. The reflection of the sky's warm hues dances across the water below, where two elegant white birds stand at the edge of a quiet pond, adding a serene focal point to the composition.

Material: Acrylic on canvas.

This Al Black Florida Highwaymen Oil on Masonite Painting is a large, framed, original oil painting , signed by the artist. Measuring 40" x 33.5", this piece is a unique and handmade artwork from the Florida, USA region. The painting features a realistic style and is a part of the Florida Highwaymen culture, making it a valuable addition to any art collection. COA included by Al Black

Creating over 200,000 paintings in the 20th century. A small sailboat is visisble in the distance, adding a sense of scale to the vastness of the scene. On the right side, lush green vegetation, including palm trees, lines the shore,, providing a contrast to the warm hues of the sky and water.

Material: Oil on Masonite board.

The Blue Scene. Al Balck signature on lower right. A white egret stands gracefully near the water's edge, and a small bridge or dock is visble in the distance, adding a touch of human presence to the natural scene.

At the center stand three iconic palm trees, their reflections mirrored in the still blue waters, surrounded by lush greenery and graceful wading birds. The work exemplifies Black’s skillful brushwork, rich use of color, and ability to convey Florida’s natural splendor.

Creating over 200,000 paintings in the 20th century. Provenance: Acquired directly from Al Black in 2025. Several white birds are flying in the sky and wading in the water, adding a sense of life to the scene.

Florida Landscape. Al Balck signature on lower right. Provenance: Al Balck collection.

Florida Landscape. Al Balck signature on lower right. Provenance: Al Balck collection.

Creating over 200,000 paintings in the 20th century. the symbolic three birds that represent the Holy Trinity are present in the painting. Provenance: Acquired directly from Al Black in 2025.

The inclusion of the ocean adds a sense of depth and tranquility to the painting, while the moon casts a gentle light over the water, creating a serene and atmospheric effect.

Al Balck signature on lower right. Provenance: Al Balck collection.

Creating over 200,000 paintings in the 20th century. Provenance: Acquired directly from Al Black in 2024.

Calm waters. The painting features lush green foliage, including trees draped with Spanish moss and prominent tall palm tree on the right. A calm body of water reflects the surrounding greenery and a light blue sky with scattered clouds.

Creating over 200,000 paintings in the 20th century. Two palm trees, leaning slightly towards the ocean, stand prominently on the right side, adding a tropical feel to the scene. The sky is a mix of blue an white clouds.

I have found information on a Harold H High (b. 1936,) who once resided in Lithia, Florida, about an hour and a half drive from Brooksville. I believe this is likely the artist of this painting. The artistic style, color palette, and materials used in this piece have striking similarities with Sam Newton, Harold Newton, and Lem Newton, who may have worked closely with the artist of this piece.

Signature: Signed by the artist, R. Edwards. Condition report: The painting is in pristine condition with no visible flaws or signs of wear. The colors are vibrant, and the paint layers are well-preserved.

Signed lower left. Palette knife and brush were used to create this scene of an inlet.

Oil on Masonite type hardboard.

Very Big Very Old. Very Rare.

Highwaymen Painting Michael Sears Everglades Florida. Original, modern-day Florida Highwayman painting by contemporary artist, Micheal Sears. Large Oil on Masonite. Worn framed. Artist Signed. Measures 21-1/2" tall x 27-1/2" wide. Condition is very good. Michael Sears (1962- present) is 2nd generation trained by George Buckner Jr. Original member, and personally influenced by the several other members of this art movement with whom he interacted. He remains true to Highwaymen subject, style, materials and outdoor selling methods.

Ellis Buckner (1943 - 1991) oil on canvas. Behold in silent wonderment an awe inspiring Ellis moonlit masterpiece. There is a small speck on missing paint in the top right hand corner. Canvas measures 16 x 20 framed to an overall size of 21 x 25. Non-smoking home. Read my feedback and buy with confidence. Please ask all questions prior to purchase.

Please see all the pictures as they are the most important part of the description. All original, Al Black, Florida Highwaymen, oil on Masonite painting. The painting is in excellent condition. The painting features a royal Poinciana with a colorful sky. The Masonite measures 16 inches by 38 inches. Overall, with the frame, the painting measures 19.5 inches by 41.5 inches. The painting requires does not require any attention. The painting is ready to hang and enjoy. The painting is for local pickup only. You are welcome to preview the painting prior to purchasing if you are so inclined. Thank you for viewing and good luck!

Original Florida Highwaymen painting by Sylvester Wells (1938 - 2023) Oil painting. Signed. 16 x 20 unframed. Read my feedback and buy with confidence. Please ask all questions prior to purchase.

Original Florida Highwaymen painting by Charles "Chico" Wheeler (1946 - 2019). Non-smoking home. Read my feedback and buy with confidence. Please ask all questions prior to purchase.

Original Florida Highwaymen painting by Issac Knight (1941 - 2022) Oil painting. Signed. 16 x 20 unframed. Read my feedback and buy with confidence. Please ask all questions prior to purchase.

Original Florida Highwaymen painting by Harold Newton (1934 - 1994). Oil painting with lovely water hyacinths. Signed. 24 x 30 unframed. Read my feedback and buy with confidence. Please ask all questions prior to purchase.

Original Florida Highwaymen painting by Lemuel Newton (1950 - 2014). Oil painting. Signed. 18 x 24 unframed. Read my feedback and buy with confidence. Please ask all questions prior to purchase.

Original Florida Highwaymen painting by James Gibson (1938 - 2017). 100% of proceeds to charity. Please ask all questions prior to purchase. Non-smoking home. Pick up from Sun City Center, Florida only.

Original Florida Highwaymen painting by Mary Ann Carroll (1940 - 2019). Oil painting on Upson board. Stormy ocean scene with waves crashing on the rocks. Original frame. Signed lower right 24 x 32 (27 x 35 inch with frame) Non-smoking home. Read my feedback and buy with confidence. Please ask all questions prior to purchase.

Please see all the pictures as they are the most important part of the description. All original, vintage, Isaac Knight, Florida Highwaymen, oil on artist board painting. The painting measures 24 inches by 36 inches. Overall, with the frame, the painting measures 28 inches by 40 inches. It is a very well-done painting with a vibrant blue color. The painting comes with the original frame. The painting is signed and dated. The painting needs nothing. The painting is ready to hang and enjoy! The painting is local pickup only. The painting is available for preview before purchasing if so desired. Thank you for viewing, and good luck!