CONTACT
Feel free to reach out with any questions, comments, or concerns. We are happy to assist you in both the buying and selling of any artwork by the Highwaymen, as well as provide free information on the artists and the group.
We know it how hard it can be to find out whether your painting is a trinket,
a treasure, or a trip to the thrift store.
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So we are here to help.
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RECEIVE INFO OR A FREE ESTIMATE
Even if you are not interested in selling, we are happy to provide as much info as we can on your painting. If you have a piece that you are interested in receiving information, a free general market value appraisal, or insurance appraisal on, you can submit an inquiry below. If you have images, please email them to info@floridahighwaymenartwork.com or text them to 863-899-9356.
If you are wondering "How Much Does a Highwaymen Painting Cost?" or "What are Highwaymen Paintings Worth?", the simple answer is anywhere from $500-$50,000. But in order to pinpoint exactly what a painting is worth, you will need to look at a few different factors. If you are interested in knowing about a specific painting and what it's worth, you can always submit a free inquiry for a market evaluation above. If you are trying to understand more about the reasoning behind values or how sellers price a painting, there are several factors that should be considered. Similar to the 4 "C's" of buying diamonds (Cut, Color, Clarity, Carat), you should evaluate Highwaymen paintings on 5 factors: Artist, Scene, Age, Size, and Execution. While the rules all have exceptions, pricing typically follows these standards:​
WHAT ARE HIGHWAYMEN PAINTINGS WORTH?
ARTIST
Artist is certainly the most important factor when assessing the value of any Highwaymen Painting. The artist will determine the base desirability for a painting, as certain artists are much more sought after than others. For example, Harold Newton, who was a premier founder of the group, has a consistently higher starting price than most of the other artists (minimum price for Harold Newton is roughly $2,500). An artist like Al Black, who is still alive and painting hundreds of paintings each year, has a much lower starting price than other artists because of his style and the availability of his paintings in the marketplace (Al Blacks work starts out around $500). For the full list of artists, click here. You can determine the artist by locating the signature in the bottom right or left of your painting. If your painting is unsigned, check out the "unsigned works" section below.
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SCENE
The scene or landscape depicted in the painting is the second most important factor to determine price. Paintings of some favorites such as Fire Sky Sunsets, Poinciana Trees, or Rio Mar Beach will often command higher prices than the more generic scenes. In addition to this, paintings that capture extra elements such as people, buildings, boats, wildlife, or specific landmark locations can add tremendous value to the right painting. For example, a Sam Newton painting of a poinciana tree will on average have a higher value than that of a St. Lucie River scene (much more common).
However, that same St Lucie River painting with an added element of a person, boat, or cattle, could drastically increase the value above the poinciana painting. Addressing the rarity of the scene will help determine the value very quickly.
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AGE
As with most collectibles, the older original pieces will often be worth more than the newer ones that were produced at a much higher rate. The
"Golden Era" of Highwaymen Artwork would be those paintings produced in the 1950s-1970s, as these are some of the earliest examples of paintings by artists when they were still selling door to door. While there are of course exceptions to that rule (especially regarding execution), higher prices are often associated with original older Upson Board paintings. For example, a painting by Mary Ann Carroll on Upson from the 1960s, will on average sell for significantly more than a painting of the same scene, size, and execution done in the early 2000s. It's important to address in this section that the medium which the painting is painted on will help determine age and value.
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EXECUTION
Execution refers to the quality with which the painting was painted. Because the Highwaymen were painting fast paced and the same scenes constantly, their work sometimes lacked purpose or detail (they were going for quantity over quality). This means that there can be drastic differences in quality between paintings by the same artist painting the same scene. For example, an Alfred Hair painting done in the "Fast Grass" style (paintings he typically finished in less than an hour), are worth far less than his more methodical and detailed works. A well detailed, higher quality "backwoods hammock" scene by Hair could sell for twice or even three times that of the same "backwoods hammock" with a lesser execution.
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SIZE
Size would be the final element that contributes to the value of a Highwaymen Painting. While not always true, Often a painting that features all the same elements as another but is larger, will command a higher price. Again, this assumption is under "ceteris paribus", all other things between the two compared paintings being equal. For example, a 1980s Upson 16x20" Livingston Roberts painting of "Rio Mar", will typically be worth less than the same 1980s Livingston Roberts "Rio Mar" if it was 24x36".