Highwaymen Art For Sale

Doretha was married to Alfred hair. Exquisite details and colors. Doretha Hair signed her painting on the front and identifies herself in writing on the back as the widow of Alfred Hair. Certificate of Authenticity from Collectors Depot adds to its value and authenticity.

NOTE: IN BEAUTIFUL PRE-OWNED CONDTION.

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

Al Black original highwaymen painting 30”x34”

Everyone needs a fire sky for your collection. The great Willie Daniels - Oil on canvas board, brush and palette knife. 16x20 framed to overall size of 20x23. Local Pickup Tampa/Sarasota

Perfect for art collectors and enthusiasts looking for a unique and original piece to add to their collection.

MASONITE 20X11.

CANVAS BOARD 16 X 20.

Painting 8 x 10.

This remarkable painting is thickly textured with layers of paint swirled together in an impressionistic fashion. It looks as if there’s a single undercoat of either yellow or purplish grey with the other used on top for the background and as the basis for the luminous morning effect.

Item: We have an original Willie Daniels (W. Daniels)-Signed Oil Painting! The scene is a calm Florida waterfront with palm trees and seagulls. A nice, rare piece to collect! Markings: Front: Signed: W. Daniels.

HEZEKIAH BAKER JR SON OF HIGHWAYMEN SIGNED BOARD COA

The Highwaymen Al Black 12 x 16 Royal Poinciana Painting is a beautiful and unique artwork created by the Highwaymen, a group of African American artists from the mid-20th century. This painting captures the essence of nature with vibrant colors and intricate details, making it a stunning addition to any art collection. The 12 x 16 size adds a sense of immediacy and intimacy to the piece, inviting viewers to connect with the artist's vision and technique.

This large oil painting tribute by artist Anne Langley captures the beauty of the Florida Cypress Swamp in the 1960s. The realist style painting, framed and signed by the artist, showcases the intricate details and natural theme of the landscape. This one-of-a-kind piece, produced with oil painting technique, is a unique tribute to the American culture and a must-have for art collectors interested in nature-inspired works from the 1960s.

Original Al Black highwayman painting

She specializes in vibrant, historical landscapes of Florida, frequently featuring Red Royal Poincianas, purple jacarandas, and natural backcountry, and her work was notably acquired by President Barack Obama and the First Lady in 2014.

• COA Tranquil moonlit water.

CHICO WHEELER (D.) SIGNED MASONITE PAINTING HOF HIGHWAYMEN COA

The painting is in excellent condition. The purple hyacinths add beautiful, lush color and create a beautiful backdrop for the birds in this back country water scene. The painting is ready to hang and enjoy!

CANVAS 36 X 18.

SAM NEWTON HOF HIGHWAYMEN SIGNED UPSON PAINTING COA

AL BLACK (D) SIGNED MASONITE PAINTING HOF HIGHWAYMEN COA

A fantastic classic James Gibson palm tree painting. James Gibson is one of the original 26 Florida HOF Highwaymen Artists. Oil on stretched canvas 14”x18” unframed dimension. Framed dimensions are approximately 17 1/2”x21 1/2”. Free pickup or local delivery available. Highwayman highway man men

WILLIE DANIELS (1950-2021). CANVAS SIZE 18 X 24. SIGNED LOWER RIGHT. EXCELLENT CONDITION.

A. Black Florida landscape Highwaymen painter 30x24 w/frame 34x28

MASONITE 11X20.

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

AL BLACK HOF HIGHWAYMEN SIGNED CANVAS PANEL PAINTING COA

CANVAS 12 X 24.

Wow, what an amazing Al Black Prison Painting in excellent original condition 24x36 on canvas. This is by far the nicest poinciana tree he did while he was in prison! You won't find a better example! Thank you for looking and buying!! This painting comes with free shipping!!

CANVAS 8X10.

JOHN MAYNOR (D) HOF HIGHWAYMEN SIGNED CANVAS PAINTING COA

Gibson Signed Framed Landscape Painting Palm Trees Florida Highwaymen

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

DARRIN REAGAN SON OF HOF HIGHWAYMEN WILLIE REAGAN SIGNED PANEL PAINTING COA

The product is a 12 x 16 painting of a scene featuring highwaymen, possibly in a stylized or abstract representation. This artwork falls under the category of paintings in the art genre, showcasing a unique and detailed depiction of a specific subject. It may be created using various techniques and materials, such as oil, acrylic, watercolor, or digital media, giving it a distinct aesthetic appeal. Perfect for art enthusiasts or collectors looking to add a unique piece to their collection.

MARK STANFORD HOF HIGHWAYMEN SIGNED CANVAS PANEL COA

This is a rare A. E. "Beanie" Backus "Florida Highwaymen HOF" hand signed and numbered 356/1000 "Piney Woods" Lithograph. This measures 20 by 30 inches just the lithograph and framed and matted 30 by 40 inches and is in very good condition. Put out by Hutchington House in 1977. Frame has a couple of small nicks and lithograph in excellent condition with a light scratch in clouds as pictured and comes with no glass. Comes in as is condition. A rare estate find that will add elegance and Florida History to any decor.

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.

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

SMALL ORIGINAL HIGHWAYMAN PAINTING SIGNED BY ISAAC KNIGHT. Signed with paint knife in the lower right foreground. This is a double signed piece by Isaac Knight. On the painting and on verso with a dedication signature by Knight.

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. ).

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.

20x30 Original Alfred Hair Moonlight river scene. Excellent condition.

TUTTI JENKINS SIGNED X 2 PAINTING MASONITE LEGACY HIGHWAYMEN COA

Signature: "Robert Butler" Lower right side. Canvas is in good shape. Up for sale is a lovely painting of a catamaran sailing in a tropical sea under a sunny blue sky, with cumulus clouds and a beach in the background.

There are slight imperfections which are consistent with age as noted in the photos.

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

original art paintings. Condition is New. Shipped with USPS Ground Advantage.

Material: Acrylic on canvas.

MASONITE 24X18.

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

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.

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.

MASONITE 12.5 X 24.

NEW HEZEKIAH BAKER JR. ORIGINAL PAINTING ON LINEN PANEL.

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

MASONITE 8X20.

His recent works show a more polished technique, while maintaining the vibrancy and energy that define his legacy. He signs his works as ?. R.L. Lewis?.

HEZEKIAH BAKER (Dec'd) HOF FL.

Hezekiah Hudson Baker (1940-2007). depicts a landscape of a Florida beach and is signed by A. Black. in lower right side corner as shown.

Please see all the pictures as they are the most important part of the description. All original, Tracy Newton, son of Florida Highwaymen Sam Newton, oil on Masonite painting. The painting is in excellent condition. The painting displays old Florida home with a clothesline, a couple people, and a royal Poinciana. The painting has the original Highwaymen style frame. The Masonite measures 24 inches by 30 inches. Overall, with the frame the painting measures 28.5 inches by 34.5 inches. The painting does not require any attention. The painting is ready to hang and enjoy! The painting may be picked up or shipped. I only ship within the continental United States. The painting may be previewed prior to purchasing. Please message me for any questions. Thank you for viewing, and good luck!

ISSAC KNIGHT (D) HOF HIGHWAYMEN SIGNED CANVAS PAINTING COA

ORIGINAL PAINTING ON MASONITE. PAINTING 18 X 24.

SYLVESTER WELLS HOF HIGHWAYMEN SIGNED ACRYLIC PAINTING ON CANVAS COA

ORIGINAL PAINTING ON LINEN PANEL. PAINTING 20 X 16.

CANVAS 12 X 24.

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

Hand signed.

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.

SYLVESTER WELLS (D) HOF HIGHWAYMEN SIGNED UPSON BOARD PAINTING COA

Painting is in excellent condition.

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.

TRACY NEWTON SON OF SAM NEWTON HOF HIGHWAYMEN SIGNED MASONITE PAINTING COA

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

CANVAS PANEL 24 X 20.

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.

MASONITE 6 X 27-1/2.

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

CANVAS PANEL 24X12.

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

Hand signed.

Oil on canvas. Vibrantly colored and highly detailed nature scene with a large prominent poinciana tree in bloom with a dusk sky background and Florida swamp style background. Painting is signed in the lower left corner by artist AJ Brown, and is signed and titled on the back of the canvas.

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

CANVAS 11 X 14.

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

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

Oils on Masonite Signed.

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

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.

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

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.

#36 - ASK JOE.

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.

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

LINEN 18X12.

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

HEZEKIAH BAKER, JR.

Hand signed.

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

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).

With : Certificate of authenticity from Al Black.

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.

Materials: Oil on Masonite.

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

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

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.

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.

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.

CANVAS 24 X 18.

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

In like new condition.

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.

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

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. the symbolic three birds that represent the Holy Trinity are present in the painting. Provenance: Acquired directly from Al Black in 2025.

Material: Oil on Masonite board.

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

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.

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.

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

Very Big Very Old. Very Rare.

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

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.

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!

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.

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!

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

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. Local pickup 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.

Oil on Masonite type hardboard.

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

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 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 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.

Alfred Hair at night, in full regalia. A full night scene with Alfred Hair doing exactly what you want to see him do. Everything is working at once, from the lighting to the structure to the surface.

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.

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.

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.

J. Daniels Signed Framed Realism Deer Landscape Canvas Painting

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 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.

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.

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.

Executed in brush and palette knife. Impressively mature blend of color in peach coloration, both sky and water.

Oil on Masonite, full palette knife. Everglade Oasis radiates vitality, with a live oak in the foreground adorned by impasto palette knife strokes and dripping Spanish moss. Newton’s textured approach amplifies the lush beauty, turning nature’s tranquility into an electrifying visual experience.

Brush and palette. Local pickup Tampa/Sarasota.

Oil on Masonite - signed. Palette knife on a field of brushwork. The moon attempts to pierce through cloud cover, casting a gentle glow. Placid river waters reflect the delicate light, creating a serene ambiance.