Highwaymen Art For Sale

Oil on Masonite - signed lower right. Created with brush and palette knife. Calm waters of the tributary flow into the choppy waters in the background. Condition: Very Fine.

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

NOTE: IN BEAUTIFUL PRE-OWNED CONDTION.

It is an original, one-of-a-kind piece that was handmade using acrylic and oil painting techniques. This unique piece of art is perfect for collectors and enthusiasts of Florida landscapes and realism style paintings.

🔹 About the Artist –R.A. McLendon. Artist: R.A. McLendon (signed). 🔹 About This Painting.

(Refer to Photos) Still a beautiful early painting. " INDIAN RIVER ". This painting was professionally touched up in a few spots due to spots of paint loss. The professional that touched it up was Mr. Al Black himself.

MASONITE 12 X 24.

CANVAS 24 X 18.

MASONITE 18 X 12.

MASONITE 12 X 9.

Estate Fresh! Large Sam Newton original Highwaymen painting. Signed in bottom right-hand corner. Beautiful, evening Florida landscape. Painting measures 24" x 36". Frame measures 31" x 43". The back is marked the original price of the painting, which was $18.00. Very rare piece of Florida art history! Guaranteed accurate as described! Condition: Please refer to photos. I've recently purchased two large collections, so please keep checking back for more!

This is a beautiful Al Black signed (Original Florida Highwaymen) oil on board painting of a palm tree over canal with boat and birds flying. This measures 14 by 20 inches just the painting and framed 19 by 23 inches and is in excellent condition. a rare estate find that will add Florida history and elegance to any decor. Sorry to say Al Black passes away on Monday 05-12-2025.

The artwork is signed by A.E. Backus and is an original lithography print produced in 1976. This rare find is a must-have for any art enthusiast and would make a great gift as well.

CANVAS PANEL 11 X 14.

This is an original landscape painting by Willie Daniels, a member of the renowned Highwaymen group of artists from southern Florida. The painting is done on canvas using oil painting techniques and is signed by the artist. It comes with a Certificate of Authenticity issued by Treasure Coast Collectibles. The artwork measures 18 inches in length and 24 inches in height, and it is framed. This handmade piece showcases a beautiful landscape theme, making it a valuable addition to any art collection. Frame measures 21.5’’ x 27.5’’

The AL Black Highwaymen Painting is an original, medium-sized oil painting created by artist Al Black. This piece features a beautiful Florida scene as its subject, measuring 17 inches in height and 21 inches in width. The painting is framed and signed by the artist, making it a unique and handmade work of art that would make a beautiful addition to any art collection or living space. From an estate sale. Lovingly displayed for about 8 years.

Oil on Canvas signed lower right •.

MASONITE 24 X 18.

SYLVESTER WELLS HOF HIGHWAYMEN SIGNED ACRYLIC PAINTING ON CANVAS COA

~~Creaky Weathervane Collectibles and Wares~~.

This is a beautiful Al Black signed (Original Florida Highwaymen) oil on board painting of bird and trees over body of water with red sky. This measures just the painting 15 by 19 inches and framed 18 by 23 inches and is in excellent condition. A rare estate find that will add Florida History and elegance to any decor. Sorry to say Al Black had passed away on Monday 05-12-2025.

18" x 25-7/8".

This is aa rare Johnny Daniels (Original Florida Highwaymen 1954-2009) signed Golen Sunset with Egrets & Palms oil on upson. This measures 24 by 30 inches just the painting and framed 27 by 33 inches and is in excellent condition. A rare eseate find that will add elegance and Floride History to any decor.

Signed oil on canvas by Issac Knight.

Florida Sketch - Signed in print lower right. EARLY MORNING FLORIDA. Whether in the glades, the beaches, the rivers, the savannas, or the back country, his paintings capture a unique sense of place that is instantly recognizable and beloved.

Sketch - Signed lower right. LAKE YALE FLORIDA. Whether in the glades, the beaches, the rivers, the savannas, or the back country, his paintings capture a unique sense of place that is instantly recognizable and beloved.

CANVAS PANEL 7 X 5.

Original Florida HIGHWAYMEN R.L. LEWIS Seaside With Sailboat Small 7” By 5”

MASONITE 16 X 24.

Oil on Masonite. Signed lower right.

MASONITE 25 X 21.

This exquisite, large format impressionist oil painting depicts a wide Florida landscape at sunset. The marshland shows tall grass in the foreground being swayed by a gentle breeze, a wide river in the middle while distant groupings of trees sit on the horizon and island to the right.

Estate Palm Beach Florida Close to Mar al largo Signed Overall good condition Framed See images

MASONITE 24 X 18.

Original piece in impeccable condition. Shipped carefully with FedEx. Currently hanging in a large room exposed to cigar smoke.

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

This "Rare Original Florida Highwaymen R.A. McLendon Sr." is a medium-sized oil painting on canvas board created by artist Roy McLendon Sr. in 1962. This impressionistic painting depicts a landscape scene and is an original piece produced during the 1960-1969 time period in Florida, USA. The artwork showcases the unique style and technique of the renowned Florida Highwaymen group, known for their vibrant and dynamic landscape paintings. I believe this to be a commissioned painting. 16'' x 20'' Framed size 18'' x 22''

Original artwork. Impeccable condition. Item will be carefully shipped with Fedex. Currently hanging in a large room with cigar smoke exposure.

ORIGINAL PAINTING ON LINEN PANEL. PAINTING 20 X 16.

This is one of my favorites selling pieces of my collection ,as I go.

CANVAS PANEL 24 X 18. VERY HEAVY ITEM ORNATE.

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

Artist signed lower right as shown.

C H ALDERMAN O/M Florida Highwaymen Art Painting Oil On Masonite 17 X 27 See images some wear see images frame size not included in measurements Being sold in as is found condition No refunds no returns no exchanges

The painting is signed by Lillie Knight on behalf of Issac Knight, adding to its unique history and value. Don't miss your chance to own a piece of Florida history with this stunning artwork. Signed Masonite by Lillie Knight, proxy for Issac Knight.

This is a beautiful Al Black (Original Florida Highwaymen) signed oil on board of a water scene with egret and palm tree. This measures 12 by 24 inches just the painting and framed 17 by 29 inches and is in excellent condition. A Rare estate find that will add elegance and Florida history to any decor. Sorry to say Al Black had passed away Monday 05-12-2025.

Oil on Masonite signed lower right •.

MASONITE 12.5 X 24.

This is a beautiful Al Black signed (Original Florida Highwaymen) oil on board of Birds and palm tree over canal. This measures 14 by 18 inches just the painting and framed 18 by 22 inches and is in excellent condition. A rare estate find that will add Florida History and elegance to any decor. Sorry to say Al Black had passed away on Monday 05-12-2025.

Oil on Masonite signed lower right (x2) and lower left (x1) •COA. Created using oil on Masonite, they feature stunning blue skies over a serene Saint Lucie River. Don't miss the chance to own this one-of-a-kind piece (x3).

Painted on stretched canvas, 24"x20".

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.

CANVAS 24 X 20.

This painting is an original artwork by Tracy Newton, who is the son of the renowned Highwaymen artist Sam Newton. The landscape painting is done on vintage canvas using oil painting technique and measures 20 inches in length and 16 inches in height. It is framed and comes with a Certificate of Authenticity issued by Treasure Coast Collectibles. This handmade piece showcases the traditional Florida Highwaymen style and is signed by Tracy Newton, making it a valuable addition to any art collection. Frame measures 20x24 inches

In like new condition.

This is a beautiful rare Willie Daniels (Original Florida Highwaymen 1950 - 2021) Signed oil on upson board painting of a Florida Backwood river scene. This measures 24 by 36 inches just the painting and framed 28 by 41 inches and is in excellent condition. A rare estate find that will add elegance and Florida history to any decor.

Painted on old canvas board with a thick brushed and thick pallet knife technique. This painting has been professionally cleaned and preserved.

Painting offered here is a rare oil on Masonite by St. Augustine artist Emmett Fritz . Mr. Fritz was a member of The Lost Colony Artist of St. Augustine. He was active thru the 50's 60's and 70's. This painting is not the typical street scene he was know for painting but a very nice beach scene . It is in excellent condition. 8'' x 12'' and ready to hang.

HEZEKIAH BAKER (Dec'd) HOF FL.

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

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.

This limited edition print titled "Piney Woods" by A.E. "Beanie" Backus is a must-have for any art collector. Don't miss out on the opportunity to own this rare piece of art! PRINT 965/1000 COA. This is a signed print and is labeled as such.

#36 - ASK JOE.

Hand signed.

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

Under a radiant sky brushed with dramatic white clouds and a quiet beach. The turquoise to deep blue gradient of the sky gives a sense of early morning or late afternoon light.

This painting was newly painted by our friend Rodney.

Painting is in excellent condition.

Nice painting by Johnny Daniels.

Oil on Masonite - signed lower right•COA.

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

Oil on Masonite - signed lower left •COA.

With : Certificate of authenticity from Al Black.

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.

Oil on Masonite signed lower right •COA.

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

Don't miss out on the opportunity to own this exceptional artwork.

Oil on Masonite signed lower right •.

Don't miss the chance to own this original piece from the 1980s. Oil on Masonite signed lower right • Dated 1980.

This original painting titled "Pre-Highwaymen Florida artist Emmett Fritz St. Augustine" is a medium-sized landscape piece created by the artist Emmett Fritz in the style of Impressionism. The painting, produced using oil on canvas, depicts a scene from St. Augustine and is signed by the artist. It measures 16 inches in length and 20 inches in height, framed and ready to display as a one-of-a-kind piece from the 1960s.

Original artwork. Impeccable condition. Item will be carefully shipped with Fedex. Currently hanging in a large room with cigar smoke exposure.

• COA Tranquil moonlit water.

Nice painting by Johnny Daniels.

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.

CANVAS 24 X 18.

CANVAS 36 X 18.

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.

NEW HEZEKIAH BAKER JR. ORIGINAL PAINTING ON LINEN PANEL.

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

Gorgeous paintings by Al Black.

Hand signed.

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

MASONITE 12 X 16 X 1. MASONITE 12 X 19 X 2.

Oil on Masonite - signed lower light. Executed in brush and palette knife. Includes COA.

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.

Painting. By James Gibson 1938-2017) Florida Highwaymen Painting. Oil on Canvas - signed lower right by James Gibson . Canvas measures 24x36 in. Framed to overall size of 28x40 in.

Rodney has not painted for over 1 year. Rodney had just begun painting again.

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

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.

This is a beautiful vintage Sam Newton (Original Florida Highwaymen) oil on board painting of a beach scene with palm trees over looking the ocean waves. This measures just the painting 23 by 27 inches and framed 27 by 31 inches and is in excellent condition. A rare estate find that will add elegance and Florida history to any decor.

Hand signed.

MASONITE 8 X 20.

This is a RARE R.A. (ROY) McLendon (1932-2024) (Original Florida Highwaymen) signed oil on board painting "1960's Northern fall Scene". This measures 23 by 35 inches just the painting and framed 27 by 38 inches and in excellent condition. On back is a photo of his son holding his dad's painting signed by his son also on paper. R. A. Mclendon signature is etched in right hand lower corner of the painting and is hard to see without flashlight. A rare estate find that will act elegance and Florida history to any decor.

Signed and dated ('78) bottom right •COA. Gorgeous painting, is in excellent condition.

Oil on Masonite - signed lower left •COA.

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

Refer to photos for more details. The contrast between the lush red foliage and the serene water creates a striking visual effect. Signature: Signed by artist "K Hair".

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.

Florida waterway and landscape.

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

A.E. "BEANIE" BACKUS (d.). WITH ORIGINAL LITHO SKETCH PRINT •.

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.

Including a certificate of authenticity.

Hand signed.

This is a very unusual Sylvester wells painting.

Rare painting of a boat house.

Florida Highwayman R.L. Lewis. Lewis is known for hisbold use of color in his work, a constant throughout his six decades of painting. “I use the color to display the mood I am experiencing. Often, I am focused on there being so many people who are spiritually or emotionally dead and not even aware of it.

Florida landscape.

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.

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

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.

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.

Gorgeous painting, is in excellent condition.

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.

Oils on Masonite Signed.

None of the band had formal art training, but shared techniques and styles as they each developed in their craft. Faintly in the back ground one sees just the hint of rain in the distance, drawing one's eyes into the heart of the painting.

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

Old Village town people. Vtg Oil Painting 22.5x24.5" Canvas.

“I have owned the painting for 20 years and believed until 2022 that it was done as a collaboration between Al Hair and Backus. I showed them this painting. Both of them were certain that it was a Backus.

Chico usually sketched his work prior to painting and this is one that was found by his estate after Chico's passing on 7/11/2019.

This is a Doretha Hair original.

Please see all the pictures as they are the most important part of the description. All original, vintage, Emmett Fritz, oil on Masonite painting. The painting is in excellent, original condition as you can see by the pictures. The painting comes nicely framed and ready to hang and enjoy. The Masonite measures 11 X 14 inches. With the frame the painting measures 14 X 17 inches overall. The painting also comes with an original St. Augustine carriage license plate! The carriages had to have one of these small license plates on it in order to operate in St. Augustine. The mini license plate measures 3 inches by 6 inches and is made of steel. The license plate is 100% original and authentic as well. I only ship within the continental United States. Thank you for viewing and good luck!

Tracy is a second generation Highwayman. TRACY NEWTON - SON OF FLORIDA HIGHWAYMAN SAM NEWTON - OIL PAINTING ON CANVAS PANEL- SIGNED - COA. This is a Tracy Newton original.

Oil on masonite artist board depicting curved palm trees with long fronds overlooking an estuary in the background.

DARRIN REAGAN SON OF HOF HIGHWATMEN WILLIE REAGAN SIGNED CANVAS PAINTING COA

This beautiful landscape is signed on the back by his widow Doretha Hair to prove was done by Al Hair. I think this is one of the largest paintings ever done by Al Hair. I also think this artwork should be professionally cleaned as it is over 50 years old.

LOCAL PICKUP ONLY so condition can be accepted. The painting is very nice and in descent condition, but not perfect.

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 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.

Alfred Hair (1941-1970) Florida Highwaymen Painting. Oil on pebble Upson - signed lower right. Executed in Palette knife upon a field of brushwork. Lone palm along the moonlit river. Board measures 11x24 framed to overall size of 16X28. Provenance: Palm Beach Shriners Club 4/30/1966 Read my feedback and buy with confidence. Please ask questions prior to purchase.

ART MASONITE 36 X 24. #94 - ASK JOE.

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.

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

Oil on Masonite type hardboard.

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.

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

Very Big Very Old. Very Rare.

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.

36 x 26.5 on artist conservation board. Wood frame with UV acrylic shatter guard. S.M. "Sylvester" Wells (1938 - 2023). This quintessential Wells painting was a self portrait of him with his sister as he visualized it in a church he once visited in Georgia. Wells recounted the story among others in a 2019 interview at his home in Alabama. Called to the ministry as a young boy, Wells referred to his art as a way to "put food on the table." Non-smoking home. Read my feedback and buy with confidence. Please ask all questions prior to purchase.

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.