The Highwaymen: African American Visions of the Florida Landscape by Circle Auction

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The Highwaymen: African American Visions of the Florida Landscape

Start: Aug 30, 2025 10:00AM EDT

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A single-owner collection of works by the Florida Highwaymen, a collective of 26 African American landscape painters formed in the 1950s. Denied the opportunity to show their work in the art galleries of the Jim Crow South, these artists, led by Harold Newton and Alfred Hair, drove up and down the roads of Southeast Florida selling their paintings out of the trunks of their cars. Their vibrant scenery and enterprising spirit stand as an inspiring example of Black art overcoming adverse circumstances, and today each member of the Highwaymen are inductees of the Florida Artists Hall of Fame.

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Harold Newton "Windy Morning, Indian River [Jumbo]" Oil on Upson Board

Lot 1

Harold Newton "Windy Morning, Indian River [Jumbo]" Oil on Upson Board

Estimate

$4,000 - $8,000

19 Bids

Sold for

$9,250

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Livingston Roberts "Everglades Sunset" Oil on Upson Board

Lot 2

Livingston Roberts "Everglades Sunset" Oil on Upson Board

Estimate

$2,000 - $4,000

6 Bids

Sold for

$7,250

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Harold Newton "Storm Clouds over the Everglades" Oil on Upson Board

Lot 3

Harold Newton "Storm Clouds over the Everglades" Oil on Upson Board

Estimate

$4,000 - $6,000

9 Bids

Sold for

$7,500

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Alfred Hair "Ocean Palms [Jumbo]" Oil on Upson Board

Lot 4

Alfred Hair "Ocean Palms [Jumbo]" Oil on Upson Board

Estimate

$2,000 - $4,000

9 Bids

Sold for

$4,000

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Harold Newton "Royal Poinciana" Oil on Board

Lot 5

Harold Newton "Royal Poinciana" Oil on Board

Estimate

$5,000 - $10,000

34 Bids

Sold for

$13,500

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Roy McLendon "Sunset" Oil on Upson Board

Lot 6

Roy McLendon "Sunset" Oil on Upson Board

Estimate

$2,000 - $4,000

8 Bids

Sold for

$5,750

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Harold Newton "Upshore Sunset [Jumbo]" Oil on Upson Board

Lot 7

Harold Newton "Upshore Sunset [Jumbo]" Oil on Upson Board

Estimate

$10,000 - $15,000

44 Bids

Sold for

$45,000

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Sam Newton "South Fork at Twilight" Oil on Upson Board

Lot 8

Sam Newton "South Fork at Twilight" Oil on Upson Board

Estimate

$2,000 - $3,000

11 Bids

Sold for

$4,100

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Harold Newton "Hibiscus on the River Road" Oil on Canvas Board

Lot 9

Harold Newton "Hibiscus on the River Road" Oil on Canvas Board

Estimate

$4,000 - $6,000

12 Bids

Sold for

$7,000

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George Buckner "Clouds over Florida Waters" Oil on Board

Lot 10

George Buckner "Clouds over Florida Waters" Oil on Board

Estimate

$2,000 - $4,000

11 Bids

Sold for

$4,000

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Harold Newton "Approaching Storm [Jumbo]" Oil on Upson Board

Lot 11

Harold Newton "Approaching Storm [Jumbo]" Oil on Upson Board

Estimate

$5,000 - $10,000

11 Bids

Sold for

$13,500

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Mary Ann Carroll "Royal Poinciana" Oil on Upson Board

Lot 12

Mary Ann Carroll "Royal Poinciana" Oil on Upson Board

Estimate

$1,500 - $2,500

23 Bids

Sold for

$7,750

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Harold Newton "Summerlin Dock, Evening" Oil on Board

Lot 13

Harold Newton "Summerlin Dock, Evening" Oil on Board

Estimate

$4,000 - $8,000

17 Bids

Sold for

$7,000

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Livingston Roberts "Riverbend" Oil on Upson Board

Lot 14

Livingston Roberts "Riverbend" Oil on Upson Board

Estimate

$2,000 - $4,000

6 Bids

Sold for

$3,800

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Harold Newton "Rio Mar, Vero Beach [Jumbo]" Oil on Masonite

Lot 15

Harold Newton "Rio Mar, Vero Beach [Jumbo]" Oil on Masonite

Estimate

$4,000 - $8,000

21 Bids

Sold for

$7,000

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Roy McLendon "Heron in the Glades" Oil on Upson Board

Lot 16

Roy McLendon "Heron in the Glades" Oil on Upson Board

Estimate

$2,000 - $4,000

12 Bids

Sold for

$3,800

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Harold Newton "Grazing Cattle" Oil on Canvas Board

Lot 17

Harold Newton "Grazing Cattle" Oil on Canvas Board

Estimate

$4,000 - $6,000

23 Bids

Sold for

$21,000

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Sam Newton "Moonlit Palm, St. Lucie River" Oil on Upson Board

Lot 18

Sam Newton "Moonlit Palm, St. Lucie River" Oil on Upson Board

Estimate

$1,500 - $2,500

8 Bids

Sold for

$3,200

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Sam Newton "Moonlight, St. Lucie" Oil on Upson Board

Lot 19

Sam Newton "Moonlight, St. Lucie" Oil on Upson Board

Estimate

$1,500 - $2,500

22 Bids

Sold for

$3,000

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Harold Newton "Evening at Vero Beach" Oil on Board

Lot 20

Harold Newton "Evening at Vero Beach" Oil on Board

Estimate

$3,000 - $5,000

18 Bids

Sold for

$6,750

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Willie Reagan "Village Poinciana" Oil on Canvas

Lot 21

Willie Reagan "Village Poinciana" Oil on Canvas

Estimate

$2,000 - $4,000

23 Bids

Sold for

$6,250

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Harold Newton "South Fork, St. Lucie" Oil on Masonite

Lot 22

Harold Newton "South Fork, St. Lucie" Oil on Masonite

Estimate

$2,000 - $4,000

10 Bids

Sold for

$4,100

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Alfred Hair "Breaking Waves [Jumbo]" Oil on Upson Board

Lot 23

Alfred Hair "Breaking Waves [Jumbo]" Oil on Upson Board

Estimate

$2,000 - $4,000

13 Bids

Sold for

$4,300

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Harold Newton "Riverbend" Oil on Board

Lot 24

Harold Newton "Riverbend" Oil on Board

Estimate

$2,000 - $4,000

24 Bids

Sold for

$4,800

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Livingston Roberts "Moonlit Dock" Oil on Upson Board

Lot 25

Livingston Roberts "Moonlit Dock" Oil on Upson Board

Estimate

$1,500 - $2,500

8 Bids

Sold for

$6,750

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Harold Newton "Waves Crashing on Rocks [Jumbo]" Oil on Upson Board

Lot 26

Harold Newton "Waves Crashing on Rocks [Jumbo]" Oil on Upson Board

Estimate

$2,000 - $3,000

10 Bids

Sold for

$3,900

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Lemuel Newton "Trees in the Everglades" Oil on Upson Board

Lot 27

Lemuel Newton "Trees in the Everglades" Oil on Upson Board

Estimate

$1,000 - $1,500

4 Bids

Sold for

$5,750

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Harold Newton "Night Palms" Oil on Upson Board

Lot 28

Harold Newton "Night Palms" Oil on Upson Board

Estimate

$3,000 - $5,000

22 Bids

Sold for

$5,000

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Sam Newton "Indian River Drive" Oil on Masonite

Lot 29

Sam Newton "Indian River Drive" Oil on Masonite

Estimate

$2,000 - $4,000

5 Bids

Sold for

$3,300

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Harold Newton "Backwater" Oil on Board

Lot 30

Harold Newton "Backwater" Oil on Board

Estimate

$2,000 - $4,000

12 Bids

Sold for

$7,500

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Johnny Daniels "Sailboat on Rough Seas" Oil on Board

Lot 31

Johnny Daniels "Sailboat on Rough Seas" Oil on Board

Estimate

$1,000 - $2,000

5 Bids

Sold for

$2,500

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Harold Newton "Sailing on the Indian River" Oil on Board

Lot 32

Harold Newton "Sailing on the Indian River" Oil on Board

Estimate

$2,000 - $3,000

25 Bids

Sold for

$6,250

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Roy McLendon "Backcountry Shack with Poinciana" Oil on Canvas

Lot 33

Roy McLendon "Backcountry Shack with Poinciana" Oil on Canvas

Estimate

$1,500 - $2,500

21 Bids

Sold for

$4,800

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Harold Newton "Indian River" Oil on Canvas

Lot 34

Harold Newton "Indian River" Oil on Canvas

Estimate

$2,000 - $4,000

40 Bids

Sold for

$13,500

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Al Black "River at Dusk" Oil on Upson Board

Lot 35

Al Black "River at Dusk" Oil on Upson Board

Estimate

$800 - $1,200

11 Bids

Sold for

$2,600

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George & Ellis Buckner "Royal Poinciana, Evening" Oil on Upson Board

Lot 36

George & Ellis Buckner "Royal Poinciana, Evening" Oil on Upson Board

Estimate

$1,000 - $2,000

39 Bids

Sold for

$6,000

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Books on A.E. Backus, Harold Newton, and Florida Art

Lot 37

Books on A.E. Backus, Harold Newton, and Florida Art

Estimate

$50 - $100

5 Bids

Sold for

$450

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Don D. Brown "Tranquility" Oil on Canvas

Lot 38

Don D. Brown "Tranquility" Oil on Canvas

Estimate

$500 - $1,000

17 Bids

Sold for

$2,000

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Don D. Brown "Rio Mar" Oil on Canvas

Lot 39

Don D. Brown "Rio Mar" Oil on Canvas

Estimate

$400 - $800

30 Bids

Sold for

$4,300

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John Durham "Lake Okeechobee" Oil on Canvas (2001)

Lot 40

John Durham "Lake Okeechobee" Oil on Canvas (2001)

Estimate

$200 - $400

4 Bids

Sold for

$300

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Florida School Oil on Canvas, Everglades Sunset with Sheep

Lot 41

Florida School Oil on Canvas, Everglades Sunset with Sheep

Estimate

$200 - $400

24 Bids

Sold for

$1,900

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Alice W.I. Loomis "Chester's Tin Roof" Oil on Canvas (1997)

Lot 42

Alice W.I. Loomis "Chester's Tin Roof" Oil on Canvas (1997)

Estimate

$200 - $300

19 Bids

Sold for

$750

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Alice W.I. Loomis "Beyond the Garden Gate" Oil on Canvas (1998)

Lot 43

Alice W.I. Loomis "Beyond the Garden Gate" Oil on Canvas (1998)

Estimate

$200 - $300

4 Bids

Sold for

$275

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Reynolds Beal "Cottage by the Ocean" Watercolor/ Gouache (1941)

Lot 44

Reynolds Beal "Cottage by the Ocean" Watercolor/ Gouache (1941)

Estimate

$400 - $800

4 Bids

Sold for

$800

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Hildegarde Hamilton Oil on Canvas, Poinciana and Palms

Lot 45

Hildegarde Hamilton Oil on Canvas, Poinciana and Palms

Estimate

$200 - $400

3 Bids

Sold for

$950

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J. Noecker "Florida Palms" Watercolor

Lot 46

J. Noecker "Florida Palms" Watercolor

Estimate

$50 - $150

4 Bids

Sold for

$125

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John Townsend Monumental Bronze of Dolphins

Lot 47

John Townsend Monumental Bronze of Dolphins

Estimate

$3,000 - $5,000

52 Bids

Sold for

$11,500

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Michael Scott "Drowned Trees with Blue Sky" Oil (1993)

Lot 48

Michael Scott "Drowned Trees with Blue Sky" Oil (1993)

Estimate

$200 - $300

Unsold

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