Highwaymen Art For Sale

Highwaymen Paintings for Sale

Below are listings of Florida Highwaymen paintings for sale on eBay. While eBay is generally a safe and secure outlet for obtaining authentic Florida Highwaymen art, there are fakes and misrepresentations out there. We have done our best to filter out misrepresentations, but research is important to ensure you are purchasing an authentic painting by an original Florida Highwaymen artist. We are an eBay partner and may earn compensation through these listings.

Florida Highwaymen *original* Livingston "Castro" Roberts Painting 18 X 24

$8,000.00
Signed lower left. Palette knife and brush were used to create this scene of an inlet.
Seller: yorkies_r_cute (100.0% positive feedback)

Florida Highwaymen *original* Mary Ann Carroll Painting 24 X 32

$10,500.00
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. Will be professionally packaged by UPS, insured, and shipped signature required. Please ask all questions prior to purchase.
Seller: yorkies_r_cute (100.0% positive feedback)

Florida Highwaymen *original* Sam Newton Painting 16 X 20

$6,000.00
Oil on Masonite type hardboard.
Seller: yorkies_r_cute (100.0% positive feedback)

1994 Highwaymen Robert Butler Signed Print "A Homestead Remembered" Le 542/1000

$1,299.99
NOTE: THERE IS A DEAD ANT INSIDE AT THE BOTTOM LEFT OF THE PRINT.
Seller: collecting-the-past (100.0% positive feedback)

Sylvester S.m Wells HOF Fla Highwaymen Painting Signed Oil On Upson

$4,500.00
S .M Wells oil on upson 36x24 Great painting by him Original Frame
Seller: just_bradys (100.0% positive feedback)

Al Black Original Highwaymen Signed Oil On Upson 36 X 24

$3,299.00
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
Seller: just_bradys (100.0% positive feedback)

Florida Highwaymen HOF Al Black Prison Painting 2002 #1

$1,000.00
This was done while he was in prison.
Seller: thelounginglizards (100.0% positive feedback)

Oil Painting Oil On Board By Sam Newton "Florida Highwaymen Pastoral Waterway"

$9,900.00
This painting depicts a serene Florida scene, featuring a tranquil waterway bordered by lush vegetation and under a vibrant sky.
Seller: auctionwallstreet (100.0% positive feedback)

C H Alderman O/m Florida Highwaymen Art Painting Oil On Masonite 17 X 27

$999.99
C H ALDERMAN O/M Florida Highwaymen Art Painting Oil On Masonite 17 X 27See images some wear see images frame size not included in measurements Being sold in as is found condition No refunds no returns no exchanges
Seller: tacomoney (100.0% positive feedback)

Original James Gibson Florida Highwaymen Painting - 16x20" Masonite

$2,775.00
Seller: floridahighwaymenartworkco (100.0% positive feedback)

Florida Highwaymen *original* James Gibson Painting 29 X 21

$3,000.00
Seller: yorkies_r_cute (100.0% positive feedback)

Chico Wheeler D. HOF FL Highwaymen Painting Signed 2x Oil On Masonite Framed COA

$1,694.00
CHARLES "CHICO" WHEELER (Dec'd 2019) HOF FL. Oil on Masonite - signed lower right •COA. Signed 2x oil on Masonite by Chico Wheeler.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

James Gibson *original* Florida Highwaymen Painting 100% Goes To Charity 11 X 21

$2,000.00
Original Florida Highwaymen painting by James Gibson (1938 - 2017). 100% of proceeds to charity. Will be professionally packaged and shipped by UPS signature required. Please ask all questions prior to purchase. Non-smoking home.
Seller: friends-of-manatees (100.0% positive feedback)

1989 Highwaymen Robert Butler Signed Ap Framed Print Of COAchman Mcmullen Cabin

$1,999.00
NOTE: IN BEAUTIFUL PRE-OWNED CONDTION.
Seller: collecting-the-past (100.0% positive feedback)

Ellis Buckner *original* Florida Highwaymen Painting (1943 - 1991)

$8,000.00
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. Will be professionally packaged and shipped by UPS signature required. Please ask all questions prior to purchase.
Seller: yorkies_r_cute (100.0% positive feedback)

Florida Highwaymen *original* Rodney Demps Painting 16 X 20

$1,500.00
Original Florida Highwaymen painting by Rodney Demps. Non-smoking home. Read my feedback and buy with confidence. Will be professionally packaged by UPS and shipped signature required. Please ask all questions prior to purchase.
Seller: yorkies_r_cute (100.0% positive feedback)

Pair Of Oversized Framed Highwaymen Prints By Livingston Roberts 34”x46” Htf

$800.00
This listing is for a pair (2) lithograph prints from Florida Highwaymen , Livingston Roberts . Both items are framed and matted under glass and measure out to a large format at 34.5”x46” . They are both in very fine condition and ready to be hanged and enjoyed . Due to their size and weight they can not be shipped but if you live reasonably close to St Lucie County I will deliver them to you or you can pick up as well . These are wicked hard to find. The first one is a dirt road along a full bloom Royal Poinciana . The second is a classic St Lucie River scene both by Roberts . If you would like any additional photos please let me know .
Seller: boudazuffa (100.0% positive feedback)

Al Black Florida Highwaymen Signed Oil On Masonite Painting Of Canal Scene 24x30

$900.00
This is a beautiful Al Black Original Florida Highwaymen signed oil on masonite of a canal scene with palm trees and cranes. This measures 24 by 30 inches just the painting and framed 29 by 36 inches and is in very good condition but has a scratch on upper left corner as pictured. Also signed on back as pictured. A rare estate find that will add elegance and Florida history to any decor.
Seller: beachantiques (99.6% positive feedback)

Chico Wheeler D. HOF FL Highwaymen Painting Signed 2x Oil On Masonite Framed COA

$1,294.00
CHARLES "CHICO" WHEELER (Dec'd 2019) HOF FL. Oil on Masonite - signed lower right •COA. Signed 2x oil on Masonite by Chico Wheeler.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

James Hutchinson (D.) HOF Florida Highwaymen Hand Signed Litho Ltd Ed. Print COA

$1,144.00
The print depicts a serene scene of a deer drinking along a Florida waterway. Ideal for art enthusiasts and collectors alike, this print is a must-have for those who appreciate the beauty of Florida's wildlife and landscape.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Masonite Framed COA

$694.00
Oil on Masonite signed lower right •COA.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

John Maynor D. HOF Florida Highwaymen Oil Painting Signed Oil Framed COA

$1,894.00
Oil on Masonite signed lower right •. Signed oil on Masonite by John Maynor.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black Original Florida Highwaymen Signed Oil On Board Inlet Scene (15 By 21")

$875.00
This is a beautiful Original Florida Highwaymen Al Black signed oil on board of a Florida Inlet Scene. This measures 15 by 21 just the painting and framed 19 by 25 inches and is in excellent condition. A rare estate find that will add elegance and Florida history to any decor.
Seller: beachantiques (99.6% positive feedback)

Al Black Original Florida Highway Highwaymen Signed "Jacarada Tree Oil On Board

$1,050.00
This is a beautiful Al Black Original Florida Highwaymen signed oil on board "Jacaranda Tree Path". This measures21 by 27 inches just the painting and framed 27 by 32 inches and is in excellent condition. A rare estate find that will add elegance to any decor. Own a piece of Florida history.
Seller: beachantiques (99.6% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Canvas Panel Framed COA

$975.00
Oil on Canvas panel signed lower right •COA. Signed oil on Canvas Panel by Al Black.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Original Al Black Signed Highwaymen Painting 18x24 Old Florida Sunset

$950.00
Fantastic original Highwaymen, Al Black, oil on masonite framed painting. Painting is 1`8 x 24" and overall measures 19 3/8 x 25 1/2" with frame. Absolutely original and signed by the artist at lower right - see photos. Very good condition and comes from a smoke-free home.
Seller: toyzarous (100.0% positive feedback)

Al Black Signed (Florida Highwaymen) Landscape Oil On Canvas Painting 16 By 20"

$875.00
This is a beautiful Original Florida highwaymen Al black signed oil on canvas of a landscape painting. This measures 16 by 20 inches just the painting and framed 21 by 25 inches and is in excellent condition. A rare estate find that will add elegance and Florida history to any decor.
Seller: beachantiques (99.6% positive feedback)

Willie Daniels (D) HOF FL Highwaymen Painting Signed Oil On Art Board Framed COA

$2,695.00
Oil on Canvas panel. Signed lower right.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Sylvester Wells *original* Florida Highwaymen Painting

$6,000.00
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. Will be professionally packaged by UPS and shipped by UPS signature required. Please ask all questions prior to purchase.
Seller: yorkies_r_cute (100.0% positive feedback)

Florida Highwaymen *original* Charles "Chico" Wheeler Painting 16 X 20

$5,000.00
Original Florida Highwaymen painting by Charles "Chico" Wheeler (1946 - 2019). Non-smoking home. Read my feedback and buy with confidence. Will be professionally packaged by UPS and shipped signature required. Please ask all questions prior to purchase.
Seller: yorkies_r_cute (100.0% positive feedback)

Chico Wheeler Florida Highwaymen River Sunrise

$2,999.00
Full palette knife. The sky awakens as the sun rises over the river. Chico is known for his detailed landscapes.
Seller: angela_adessa_estate_sales (100.0% positive feedback)

Rare A.e. Backus Florida Sketch On Paper "Anhingas-everglades" Framed Highwaymen

$1,599.00
It features the work of renowned artist A.E. Backus (1906-1990) and is part of the original production from 1976. The piece is signed by Backus himself, adding to its rarity and value. The piece captures the essence of Florida's natural beauty, with a focus on the cypress swamp region.
Seller: angela_adessa_estate_sales (100.0% positive feedback)

Sam Newton HOF Florida Highwaymen Painting Signed Oil On Upson Board Framed COA

$5,929.00
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Rodney Demps (D.) HOF Fl. Highwaymen Painting Signed Oil On Masonite Framed COA

$2,295.00
Oil on Masonite - signed lower right•COA.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black (Florida Highwaymen) Signed Inlet Scene Oil On Masonite (18 By 24")

$850.00
This is a beautiful Al Black (Original Florida Highwaymen) signed oil on Masonite board painting of an inlet scene. This measures 18 by 24 inches just the painting and framed 23 by 29 inches and is in excellent condition but frame has a couple of small nicks. A rare estate find that will add elegance and Florida history to any decor.
Seller: beachantiques (99.6% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Canvas Panel Framed COA

$944.00
Oil on Canvas panel signed lower right •COA. Signed oil on Canvas Panel by Al Black.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Alfred Hair (D.) HOF Florida Highwaymen Painting Signed Oil On Upson Board COA

$4,429.00
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Sam Newton HOF Florida Highwaymen Painting Signed Oil On Upson Board Framed COA

$4,254.00
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Rare A.e. Backus Florida Sketch On Paper"Windy Day Everglades" Framed Highwaymen

$1,599.00
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.
Seller: angela_adessa_estate_sales (100.0% positive feedback)

Carnell Smith (D) HOF FL Highwaymen Painting Signed Oil On Canvas Panel Framed

$2,394.00
Carnell Smith signed the back of the painting as well. Hand signed. CARNELL SMITH (Dec'd 2015) HOF FL.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black Signed & Dated 1985 Florida Highwaymen Oil N Board Painting Inlet Scene

$1,500.00
This is a vintage rare Al Black signed & Dated 1985 oil on board painting of an inlet scene with birds and palm trees. This measures 24 by 36 inches just the painting and framed 28 by 39 inches and is in excellent condition but frame has some minor wear. A rare estate find that will add elegance and Florida history to any decor.
Seller: beachantiques (99.6% positive feedback)

Rodney Demps (D.) HOF Fl. Highwaymen Painting Signed Oil On Masonite Framed COA

$1,994.00
Oil on Masonite - signed lower left •COA.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Original Highwaymen Painter Rodney Demps 14in X 18in R Demps Art On Canvas

$799.99
“I painted a lot of Florida scenes. I used to watch him paint. The more you do it, it gets cleaner and cleaner.”. He died on June 17, 2020. In a 2013video interview with. ART FOR SALE.
Seller: marketingholders (99.3% positive feedback)

Willie Daniels (D) HOF FL Highwaymen Painting Signed Oil On Masonite Framed COA

$2,495.00
Oil on Masonite. Signed lower right.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Original Highwaymen Painter Rodney Demps 24” X 36” R Demps Wall Art Painting

$999.00
“I painted a lot of Florida scenes. I used to watch him paint. The more you do it, it gets cleaner and cleaner.”. He died on June 17, 2020. ART FOR SALE.
Seller: marketingholders (99.3% positive feedback)

Hezekiah Baker (Dec'd) HOF FL Highwaymen Painting Oil On Upson Board Framed COA

$4,594.00
HEZEKIAH BAKER (Dec'd) HOF FL.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Original Highwaymen Painter Rodney Demps 24” X 36” R Demps Wall Painting

$999.00
“I painted a lot of Florida scenes. I used to watch him paint. The more you do it, it gets cleaner and cleaner.”. He died on June 17, 2020. ART FOR SALE.
Seller: marketingholders (99.3% positive feedback)

Al Black Original Highwaymen Signed Oil On Board 36 X 24

$1,499.99
Born in 1947 near Jackson, Miss., stories of Black’s life until his early 20s are devoid of any hint that life as an artist awaited him. In his teens he labored as a fieldworker picking vegetables and fruit, later graduating to various roles as a driver.
Seller: marketingholders (99.3% positive feedback)

Al Black Original Highwaymen Signed Oil On Board 36 X 24

$1,499.99
Born in 1947 near Jackson, Miss., stories of Black’s life until his early 20s are devoid of any hint that life as an artist awaited him. In his teens he labored as a fieldworker picking vegetables and fruit, later graduating to various roles as a driver.
Seller: marketingholders (99.3% positive feedback)

Rare Authenic James Gibson Florida Highwaymen Oil On Board "Lemon Sepia"

$3,695.00
This handcrafted painting features a stunning Florida landscape with intricate details that capture the essence of its beauty. This original oil painting was produced in the 1970s in the United States and is a perfect addition to any art collection or for those who appreciate realism and the beauty of landscapes.
Seller: marblemike (99.3% positive feedback)

Al Black HOF Florida Highwaymen Paintings (2) Signed Oil On Masonite Framed COA

$1,864.00
Oil on Masonite signed lower right •COA.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

A.e. "Beanie" Backus Painting (Highwaymen) 1960s

$18,500.00
“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.
Seller: midbeachmaven (100.0% positive feedback)

Willie Daniel’s Florida Highwaymen Painting Everglade Cranes Birds

$3,199.99
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.
Seller: tdk_collectibles (99.7% positive feedback)

Highwaymen Painting By Al Black - Tabebuia Tree

$1,550.00
Tabebuia Tree on the pond with tangerine sky.
Seller: rnbwrdr (100.0% positive feedback)

Al Black Signed Florida Highwaymen Cove Scene Oil On Masonite (24 By 36")

$1,100.00
This is a beautiful Al Black signed original Florida Highwaymen oil on masonite painting of a cove scene with fisherman and birds. This measures 24 by 36 inches just the painting and frames 32 by 44 inches and is in very good condition but has a couple of nicks as pictured. Comes in as is condition. a rare estate find that with add elegance and Florida history to any decor.
Seller: beachantiques (99.6% positive feedback)

Al Black Original Highwaymen Signed Oil On Board 36 X 24

$1,499.99
Born in 1947 near Jackson, Miss., stories of Black’s life until his early 20s are devoid of any hint that life as an artist awaited him. In his teens he labored as a fieldworker picking vegetables and fruit, later graduating to various roles as a driver.
Seller: marketingholders (99.3% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Canvas Panel Framed COA

$774.00
Oil on Canvas panel signed lower right •COA. Signed oil on Canvas Panel by Al Black.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Rodney Demps HOF Fl. Highwaymen Painting Signed Oil On Upson Board Framed COA

$2,474.00
• COA Tranquil moonlit water.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Original Rare Issac Knight Florida Highwaymen Hall Of Fame Artist, Framed

$1,395.00
He was born on a large farm outside Tallahassee, at 17 he moved to Ft Pierce Florida, developed a cooperative style through Alfred Hain and his brother in law Al Black.
Seller: angela_adessa_estate_sales (100.0% positive feedback)

Al Black HOF Florida Highwaymen Oil Painting On Guitar (Rare) COA

$1,800.00
An Al Black original. Oil painting on a guitar. Signed lower right.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Rare Authenic James Gibson Florida Highwaymen Oil Painting, Upson Board

$7,000.00
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.
Seller: northwoodacres (100.0% positive feedback)

James Gibson (D) HOF FL Highwaymen Painting Signed Oil On Upson Board Framed COA

$2,193.00
Painting is in excellent condition.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Canvas Panel Framed COA

$974.00
Oil on Masonite signed lower right •COA. Signed oil on Canvas Panel by Al Black.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Issac Knight D. HOF FL Highwaymen Painting Signed Oil On Canvas Panel Framed COA

$624.00
Signed 2x oil on canvas panel by Issac Knight.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Masonite Framed COA

$724.00
Oil on Masonite signed lower right •COA.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

R.l. Lewis HOF Florida Highwaymen Painting Signed Oil On Canvas Framed COA

$2,294.95
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Sam Newton HOF Florida Highwaymen Painting Signed Oil On Upson Board Framed COA

$5,279.00
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black Original Florida Highwaymen Signed Oil On Board Palm Tree Over Inlet

$875.00
This is a beautiful Original Florida Highwaymen Al Black signed oil on board of Palm Tree over Inlet with birds. This measures 15 by 21 inches just the painting and 19 by 25 inches framed and in excellent condition. A rare estate find that will add elegance and Florida history to any decor.
Seller: beachantiques (99.6% positive feedback)

Al Black Original Highwaymen Signed Oil On Board 36 X 24

$1,499.99
Born in 1947 near Jackson, Miss., stories of Black’s life until his early 20s are devoid of any hint that life as an artist awaited him. In his teens he labored as a fieldworker picking vegetables and fruit, later graduating to various roles as a driver.
Seller: marketingholders (99.3% positive feedback)

Johnny Daniels Florida Highwaymen Golden Sunrise Oil On Board Large Stunning COA

$5,990.00
Including a certificate of authenticity.
Seller: angela_adessa_estate_sales (100.0% positive feedback)

Florida Highwaymen *original* Johnny Daniels Painting 24 X 36

$6,000.00
Vibrant backwater scene with birds in flight, a rare Kingfisher bird on branch, palm and oak trees with Spanish moss.
Seller: yorkies_r_cute (100.0% positive feedback)

Rodney Demps (Dec'd) HOF Fl. Highwaymen Painting Signed X2 Painting Framed COA

$944.00
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Rodney Demps HOF Highwaymen Painting Oil On Canvas Panel Florida Waterway Road

$1,100.00
3 birds take flight to the left of the scene as a stiff breeze moves in. Painting is in good condition, nice shine to oils.
Seller: mleighcannon-4 (100.0% positive feedback)

Carnell Smith (D) HOF FL Highwaymen Painting Signed Oil On Canvas Framed COA

$1,894.00
Palm tree leaning into the warmth of the evening sun. Hand signed. CARNELL SMITH (Dec'd 2015) HOF FL.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Chico Wheeler (D) HOF FL Highwaymen Painting Signed Oil On Masonite Framed COA

$1,394.00
CHARLES "CHICO" WHEELER (Dec'd 2019) HOF FL. Oil on Masonite - signed lower right •COA. Signed oil on Masonite by Chico Wheeler.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Issac Knight D HOF Fla Highwaymen Painting Signed Oil On Canvas Panel Framed COA

$1,399.00
Signed oil on canvas panel by Issac Knight. Painting is n excellent condition.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Canvas Panel Framed COA

$9,144.00
Oil on Canvas panel signed lower right •COA. Signed oil on Canvas Panel by Al Black.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

James Gibson (D) HOF FL Highwaymen Painting Signed Oil On Upson Board Framed COA

$2,419.00
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Rare Jonny Damiels Florida Highwaymen Legend, Mixed Media ,oil On Canvas Signed

$2,990.00
Seller: angela_adessa_estate_sales (100.0% positive feedback)

James Gibson (D) HOF FL Highwaymen Painting Signed Oil On Upson Board Framed COA

$2,679.00
Hand signed.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Rodney Demps (D.) HOF Fl. Highwaymen Painting Signed Oil On Masonite Framed COA

$974.00
Oil on Masonite - signed 2x lower left and on the back•COA.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Masonite Framed COA

$1,295.00
Oil on Masonite signed lower right •.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Masonite Framed COA

$874.00
Don't miss out on the opportunity to own a piece of history! Oil on Masonite signed lower right •COA.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Masonite Framed COA

$1,494.00
Oil on Masonite signed lower right •.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Masonite Framed COA

$1,274.00
Oil on Masonite signed lower right •COA.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Tracy Newton 2nd Generation Florida Highwaymen Painting

$950.00
Tracy Newton is the son of Sam Newton, one of the 26 original highwaymen. While he is not an original Highwayman, he is a highly skilled artist who paints in that style. Pastel mid-day polychromatic depiction of the South Fork of the St Lucie River. Artist board 20x16, framed to an overall 23x19 with rustic gray frame. Check my other Florida Highwaymen paintings that are being put up for sale. I had intended to keep these for a number of years yet, but I got a terminal cancer diagnosis so I’m trying to sell them now before my sons put them in a yard sale with a $10 price tag or some crazy thing.
Seller: hosta1 (100.0% positive feedback)

James Gibson (D) HOF FL Highwaymen Painting Signed Oil On Upson Board Framed COA

$3,849.00
Signed and dated ('67) lower right.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black Original Highwaymen Signed Oil On Board 36 X 24

$1,499.99
Born in 1947 near Jackson, Miss., stories of Black’s life until his early 20s are devoid of any hint that life as an artist awaited him. In his teens he labored as a fieldworker picking vegetables and fruit, later graduating to various roles as a driver.
Seller: marketingholders (99.3% positive feedback)

Highwaymen Painting Collectible Items Highwaymen Memorabilia Vhs Signed Calendar

$1,500.00
Having 2 of these pamphlets would let you display both the outside and inside together for a nice display.
Seller: treasureoaks22 (100.0% positive feedback)

Highwaymen Painting - Al Black

$1,200.00
Oil on Board - signed lower right.
Seller: flholliday (0.0% positive feedback)

Lemuel Newton (Dec'd) HOF FL Highwaymen Vintage Painting Signed Oil On Upson COA

$4,620.00
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Rodney Demps D. HOF Fl. Highwaymen Oil Painting Signed X2 On Panel Framed COA

$794.00
Rodney has not painted for over 1 year. This painting was newly painted, after Rodney decided to paint, once again.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Masonite Framed COA

$844.00
Oil on Masonite signed lower right •COA.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Highwaymen Paintings - Charles Walker

$12,000.00
Highwaymen Charles Walker. One of his early paintings on board 11” x 14” Frame measures 19” x 22”HighwaymenHighwaymanHighway menHighway manFlorida landscape
Seller: walterfletcher (100.0% positive feedback)

Carnell Smith (D) HOF FL Highwaymen Painting Signed Oil On Masonite Framed COA

$2,144.00
CARNELL SMITH (Dec'd 2015) HOF FL. Oil on Masonite - signed lower right •COA. Signed oil on Masonite by Carnell Smtih.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Canvas Panel Framed COA

$1,474.00
Oil on Masonite signed lower right •COA. Signed oil on Canvas Panel by Al Black.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Johnny Daniels (D) HOF FL Highwaymen Painting Signed Oil On Masonite Framed COA

$1,950.00
Oil on Masonite. Signed lower right.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Indian River School Florida Highwaymen Johnny Stovall

$3,195.95
Up for sale is this commissioned oil on canvas board by artist Johnny Stovall. Johnny is a friend of my family and I had him paint this painting along with another commissioned painting. This painting and the other work is one of his best works.
Seller: mikespike66 (100.0% positive feedback)

Rare A.e. Backus Florida Sketch On Paper Everglades Framed Highwaymen

$1,599.00
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.
Seller: angela_adessa_estate_sales (100.0% positive feedback)

Serena Williams (Tennis) By Chico Wheeler (D) Highwaymen Painting Signed COA

$5,695.00
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

John Maynor *original* Florida Highwaymen Painting 100% Goes To Charity 10 X 16

$2,000.00
Original Florida Highwaymen painting by John Maynor (1948 - 2016). 100% of proceeds to charity. Will be professionally packaged, insured and shipped by UPS signature required. Please ask all questions prior to purchase. Non-smoking home.
Seller: friends-of-manatees (100.0% positive feedback)

Rodney Demps D. HOF Fl. Highwaymen Signed Upson Painting Of His Wife Framed COA

$2,174.00
Never before seen portrait painting. This painting was well looked after.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Florida Highwaymen *original* Charles "Chico" Wheeler Painting 17 X 22.5

$5,000.00
Original Florida Highwaymen painting by Charles "Chico" Wheeler (1946 - 2019). Non-smoking home. Read my feedback and buy with confidence. Will be professionally packaged by UPS and shipped signature required. Please ask all questions prior to purchase.
Seller: yorkies_r_cute (100.0% positive feedback)

Al Black Original Florida Highwaymen Signed Oil Board Florida Pines Reflections

$975.00
This is a beautiful Original Florida Highwaymen Al Black signed oil on board "Florida Pines Reflections". This measures 18 by 24 inches just the painting and framed 22 by 28 inches and is in excellent condition. A rare estate find that will add elegance to any decor especially in Florida.
Seller: beachantiques (99.6% positive feedback)

A.e. "Beanie" Backus (D.) HOF Highwaymen Original Signed Check Framed COA

$1,794.00
A.E. "BEANIE" BACKUS (d.). WITH ORIGINAL LITHO SKETCH PRINT •.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Chico Wheeler Florida Highwaymen Sunset With COA, From Street Corners To Museums

$3,999.00
Oil on Masonite - signed lower light. Executed in brush and palette knife. Includes COA.
Seller: angela_adessa_estate_sales (100.0% positive feedback)

James Gibson (D) HOF FL Highwaymen Painting Signed Oil On Upson Board Framed COA

$3,778.00
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Masonite Framed COA

$1,194.00
Oil on Masonite signed lower right •.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Rodney Demps (D.) HOF Fl. Highwaymen Painting Signed Oil On Masonite Framed COA

$2,194.00
Oil on Masonite - signed lower left •COA.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Masonite Framed COA

$894.00
Oil on Masonite signed lower right •.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Rodney Demps D. HOF Fl. Highwaymen Painting Signed X2 Oil On Upson Framed COA

$744.00
This painting was newly painted by our friend Rodney.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black Highwaymen Painting 'river Palm Colors' On Canvas Al Black

$3,489.00
This stunning painting by Al Black captures the essence of the Florida landscape with vibrant colors and intricate brushstrokes.
Seller: ijusthadtolet..itgo (100.0% positive feedback)

Original Florida Everglades Watercolor Painting, Highwaymen Painting? Signed

$1,200.00
Artist signed lower right as shown. Beautiful original work of art. No exceptions!
Seller: jack_blue (100.0% positive feedback)

Freddie Gibson Brother Of Florida Highwaymen James Gibson - Oil On Canvas 24x36

$1,580.00
This one-of-a-kind painting features a stunning palm tree and ocean landscape created by renowned Florida artist Freddie Gibson the brother of Florida Highwaymen James Gibson. Measuring 24 inches in height and 36 inches in length, this large piece is an original oil painting on masonite material and is framed to perfection. The painting depicts a natural scene with the utmost attention to detail, showcasing Freddie Gibson's impressive impressionism style.
Seller: akashicwreckage (100.0% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Masonite Framed COA

$944.00
Oil on Masonite signed lower right •.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Masonite Framed COA

$949.00
Oil on Masonite signed lower right •.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Chico Wheeler (D) HOF FL Highwaymen Painting Signed 2x Oil - Masonite Framed COA

$1,644.00
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.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Masonite Framed COA

$944.00
Oil on Masonite signed lower right •.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

James Gibson (D) HOF FL Highwaymen Painting Signed Oil On Upson Board Framed COA

$2,679.00
Hand signed.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Rare Antique Florida River Landscape Folk Art Oil Painting Pre Highwaymen Signed

$635.00
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.
Seller: henningfineart (99.6% positive feedback)

Florida Highwaymen *original* Charles "Chico" Wheeler Painting 18.5 X 14.5

$5,000.00
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. Will be professionally packaged by UPS and shipped signature required. Please ask all questions prior to purchase.
Seller: yorkies_r_cute (100.0% positive feedback)

Florida Highwaymen Art Fine Art Oil Painting On Board-robert Butler

$8,500.00
Artist in Residence to the Imperial Solomon Court of the Crown-Prince of Ethiopia Prince Ermias Selassie Haile-Selassie Representative artist 50th Anniversary of the Nature Conservancy Gov. Jeb Bush Coin appointee Etc.
Seller: butlers_art (100.0% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Masonite Framed COA

$974.00
Oil on Masonite signed lower right •COA.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Rodney Demps D. HOF Fl. Highwaymen Painting Signed X2 Oil On Upson Framed COA

$644.00
This painting was newly painted by our friend Rodney.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Canvas Panel Framed COA

$1,244.00
Oil on Masonite signed lower right •COA. Signed oil on Canvas Panel by Al Black.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Florida Highwaymen 2nd Generation Tracy Newton Painting Oil On Canvas 16x20

$955.00
This painting by Tracy Newton is a stunning example of 2nd Generation Florida Highwaymen art. The landscape subject is presented in a realistic and impressionistic style, with beautiful use of color and brush strokes. The canvas measures 16 inches in height and 20 inches in length, and is framed for display. The painting is an original, one of a kind piece, signed by the artist and produced using oil painting techniques. It represents a unique cultural heritage from the Florida region, specifically the Highwaymen tradition. This oil painting is sure to bring a touch of nature and artistry to any collection.
Seller: akashicwreckage (100.0% positive feedback)

Rodney Demps D.hof Fl. Highwaymen Painting Signed X2 Oil On Canvas Framed COA

$1,294.00
Rodney has not painted for over 1 year. Rodney had just begun painting again.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black HOF Florida Highwaymen Painting Signed Oil On Masonite Framed COA

$999.00
Oil on Masonite signed lower right •COA.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Vintage Oil Painting 22x24 Canvas Sgn Newton ? Highwaymen Old Village People

$850.00
Old Village town people. Vtg Oil Painting 22.5x24.5" Canvas.
Seller: ioccog (99.7% positive feedback)

Rare Authenic Tracy Newton 2nd Generation Florida Highwaymen Oil On Board "

$2,499.00
Oil on Board - signed lower right.
Seller: angela_adessa_estate_sales (100.0% positive feedback)

Rodney Demps D. HOF Fl. Highwaymen Painting Signed X2 Oil On Upson Framed COA

$649.00
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Rare A.e. Backus Florida Sketch On Paper "Mangroves Florida" Framed Highwaymen

$1,599.00
The piece, created in 1976 by renowned artist A.E. Backus, features a breathtaking view of Florida's mangroves in a landscape orientation. The item also includes details such as the subject matter of the piece, the framing and matting, and the production technique used.
Seller: angela_adessa_estate_sales (100.0% positive feedback)

Oil Painting On Upson Board Highwaymen James Gibson 'green River Palm'

$3,999.00
This painting, with its focus on a "Green River Palm," captures the lush beauty and tranquil atmosphere of the Florida landscape.
Seller: auctionwallstreet (100.0% positive feedback)

Chico Wheeler (D) HOF FL Highwaymen Painting Signed Oil - Upson Board Framed COA

$2,749.00
CHARLES "CHICO" WHEELER (Dec'd 2019) HOF FL. This painting was done by Wheeler in the mid to late 1960's.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Johnny Daniels (D.) HOF FL Highwaymen Signed Oil On Vintage Masonite Framed COA

$1,994.00
Nice painting by Johnny Daniels.
Seller: cdifl (100.0% positive feedback)

Johnny Daniels (D.) HOF FL Highwaymen Signed Oil On Vintage Masonite Framed COA

$2,994.00
Nice painting by Johnny Daniels.
Seller: cdifl (100.0% positive feedback)

Highwaymen Painting, Al Black, 29 X 25

$1,395.00
Beautiful sunset painting, no scratches. Rare find.
Seller: ugotit305 (100.0% positive feedback)

Hezekiah Baker (D.)hof FL Highwaymen X2 Signed Oil Painting On Upson Framed COA

$3,694.00
Florida waterway and landscape.
Seller: cdifl (100.0% positive feedback)

Original Florida Highwayman Paintings By J. Gibson

$3,600.00
The trooper wanted to take a look in his trunk. “I opened the trunk and he saw the paintings. Then, he saw his color. He asked, ‘Are those for sale?. What about that blue one?'”. It was raw, primitive, and real.”.
Seller: sjtreasures (100.0% positive feedback)

Lemuel Newton (D) HOF FL Highwaymen Signed Oil Painting On Masonite Framed COA

$2,744.00
Signed and dated ('78) bottom right •COA. Gorgeous painting, is in excellent condition.
Seller: cdifl (100.0% positive feedback)

Indian River School Florida Highwaymen Johnny Stovall

$3,195.95
Up for sale is this commissioned oil on canvas board by artist Johnny Stovall. Johnny is a friend of my family and I had him paint this painting along with another commissioned painting. This painting and the other work is one of his best works.
Seller: mikespike66 (100.0% positive feedback)

Hezekiah Baker (D) HOF FL Highwaymen Signed Oil Painting On Upson Framed COA

$5,400.00
Painting is in fine condition.
Seller: cdifl (100.0% positive feedback)

Charles "Chico" Wheeler (D.2019) HOF Highwaymen Sketch "Boat" Signed Framed COA

$779.00
Certificate of authenticity written and signed by 'Charles "Chico" Wheeler.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Alfred Hair 24x36 'moonlit River Palms' Stunning Details Circa 1960s

$7,999.00
Moonlit river scene with two tall palms, a cabbage palm, spanish moss, heavy palette knife work.
Seller: angela_adessa_estate_sales (100.0% positive feedback)

Johnny Daniels (D.) HOF FL Highwaymen Signed Upson Board Painting Framed COA

$3,600.00
Nice painting by Johnny Daniels.
Seller: cdifl (100.0% positive feedback)

Johnny Daniels (D.) HOF FL Highwaymen Signed Upson Board Painting Framed COA

$3,994.00
Signed lower right corner •COA.
Seller: cdifl (100.0% positive feedback)

🔥smitty - Florida Landscape Artist, Oil Painting, Florida Highwaymen Student,

$1,295.00
Oils on Masonite Signed.
Seller: luckyfindbrokers (99.5% positive feedback)

Highwaymen Florida Painting - Al Black - 30.5 X 36.5 - Framed

$1,800.00
Beautiful RARE PAINTING BY AL BLACK Very detailed picture of the Florida Everglades with Palm trees and birds. Signature located on the back and bottom right hand corner.
Seller: ugotit305 (100.0% positive feedback)

Highwaymen Painting - Al Black - 25 X 29 - Framed - Rare Find

$1,295.00
Rare painting of a boat house.
Seller: ugotit305 (100.0% positive feedback)

Oil Painting On Masonite Board Florida Highwaymen Sunset By Al Black

$1,900.00
Signed by the artist adds.
Seller: auctionwallstreet (100.0% positive feedback)

Doretha Hair (Widow Of Highwayman Alfred Hair) Signed Oil On Masonite Framed COA

$543.00
This is a Doretha Hair original.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Al Black HOF Florida Highwaymen Paintings (2) Oil On Masonite Framed COA

$1,874.00
Gorgeous paintings by Al Black.
Seller: cdifl (100.0% positive feedback)

Rare A.e. Backus Florida Sketch On Paper "Lake Yale Florida " Framed Highwaymen

$1,599.00
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.
Seller: angela_adessa_estate_sales (100.0% positive feedback)

Lemuel Newton (D) HOF FL Highwaymen Signed Oil Painting On Masonite Framed COA

$3,694.00
Gorgeous painting, is in excellent condition.
Seller: cdifl (100.0% positive feedback)

Very Rare Oil Painting On Masonite Board By Mary Ann Carroll "Harvest Moon"

$5,499.00
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.
Seller: auctionwallstreet (100.0% positive feedback)

Hezekiah Baker (D) HOF FL Highwaymen Signed Oil Painting On Upson Framed COA

$4,494.00
Florida landscape.
Seller: cdifl (100.0% positive feedback)

Rodney Demps (1953-2017) Original Florida Highman Palm Trees Overlooking Estuary

$1,499.00
Oil on masonite artist board depicting curved palm trees with long fronds overlooking an estuary in the background.
Seller: angela_adessa_estate_sales (100.0% positive feedback)

Tracy Newton (Son Of Highwayman Sam Newton) Signed Oil On Canvas Panel Framed

$759.00
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.
Seller: treasurecoastcollectibles1 (100.0% positive feedback)

Oil On Masonite Board Painting ''river House'' By Al Black

$1,600.00
Seller: auctionwallstreet (100.0% positive feedback)

Emmett Fritz, Oil On Masonite Painting

$1,499.99
This painting is a harbor scene from Gloucester, Massachusetts, depicting the boats and docks. It is beautifully done. I am not sure how many paintings he did of Gloucester. The artist's card is on the back of the painting and is titled Gloucester 1953.
Seller: floridaartonline (100.0% positive feedback)

Lg. Vintage James Gibson Signed (Florida Highwaymen) "Green River" Oil On Upton

$3,350.00
This is a beautiful large vintage James Gibson signed (Original Florida highwaymen) oil on upton board painting of Green River Scene. This measures just the painting 24 by 48 inches and framed 28 by 51 inches and is in very good condition and done with palette knife.. A rare estate find that will add elegance and Florida history to your decor. This is for local pick up only in Pompano Beach Florida 33062 or i have a local UPS store that will pick up wrap insure and ship to you.
Seller: beachantiques (99.6% positive feedback)

Rare Very Large Highwaymen James Gibson Antique Painting Upson Board 40 X 24.5

$4,249.99
Very Big Very Old. Very Rare.
Seller: cryp (98.8% positive feedback)

Isaac Knight, Florida Highwaymen, Oil On Artist Board

$2,799.99
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! 
Seller: floridaartonline (100.0% positive feedback)
Scroll to Top