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304 used pickup trucks, SUVs and trailers for sale in Madison, NC & South Boston, VA

White 2023 Ford F-150 XLT for sale in South Boston, VAPhotos of 2023 Ford F-150 XLT for sale in South Boston, VA at Smart FordAnother view of 2023 Ford F-150 XLT for sale in South Boston, VA at Smart FordMore photos of 2023 Ford F-150 XLT at Smart Ford, VAMore photos of 2023 Ford F-150 XLT at Smart Ford, VA
Stock # D93648
XLT
109,301 miles
Condition:
Pre-owned
Smart Buy Price
$32,999
$487 / mo. est.
Black 2021 Porsche Cayenne for sale in South Boston, VAPhotos of 2021 Porsche Cayenne for sale in South Boston, VA at Smart FordAnother view of 2021 Porsche Cayenne for sale in South Boston, VA at Smart FordMore photos of 2021 Porsche Cayenne at Smart Ford, VAMore photos of 2021 Porsche Cayenne at Smart Ford, VA
Stock # A02410
Base
24,108 miles
Condition:
Pre-owned
Smart Buy Price
$49,999
$738 / mo. est.
Silver 2024 Toyota Highlander LE for sale in Madison, NCPhotos of 2024 Toyota Highlander LE for sale in Madison, NC at Smart ChevroletAnother view of 2024 Toyota Highlander LE for sale in Madison, NC at Smart ChevroletMore photos of 2024 Toyota Highlander LE at Smart Chevrolet, NCMore photos of 2024 Toyota Highlander LE at Smart Chevrolet, NC
Stock # 539865
LE
38,777 miles
Condition:
Pre-owned
Smart Buy Price
$31,776
$469 / mo. est.
Gray 2025 Genesis GV80 2.5T for sale in Madison, NCPhotos of 2025 Genesis GV80 2.5T for sale in Madison, NC at Smart ChevroletAnother view of 2025 Genesis GV80 2.5T for sale in Madison, NC at Smart ChevroletMore photos of 2025 Genesis GV80 2.5T at Smart Chevrolet, NCMore photos of 2025 Genesis GV80 2.5T at Smart Chevrolet, NC
Stock # 249146
2.5T
15,478 miles
Condition:
Pre-owned
Smart Buy Price
$47,998
$708 / mo. est.
Unknown 2025 Texas Pride Gooseneck Dump Trailer for sale in Madison, NCPhotos of 2025 Texas Pride Gooseneck Dump Trailer for sale in Madison, NC at Smart ChevroletAnother view of 2025 Texas Pride Gooseneck Dump Trailer for sale in Madison, NC at Smart ChevroletMore photos of 2025 Texas Pride Gooseneck Dump Trailer at Smart Chevrolet, NCMore photos of 2025 Texas Pride Gooseneck Dump Trailer at Smart Chevrolet, NC
Stock # 065562
Dump Trailer
1 miles
Condition:
Pre-owned
Smart Buy Price
$17,998
$266 / mo. est.
White 2024 Chevrolet Silverado 1500 WT for sale in Madison, NCPhotos of 2024 Chevrolet Silverado 1500 WT for sale in Madison, NC at Smart ChevroletAnother view of 2024 Chevrolet Silverado 1500 WT for sale in Madison, NC at Smart ChevroletMore photos of 2024 Chevrolet Silverado 1500 WT at Smart Chevrolet, NCMore photos of 2024 Chevrolet Silverado 1500 WT at Smart Chevrolet, NC
Stock # 323388
Condition:
Pre-owned
Smart Buy Price
$30,481
$450 / mo. est.
Unknown 2026 Jeep Gladiator Mojave for sale in South Boston, VAPhotos of 2026 Jeep Gladiator Mojave for sale in South Boston, VA at Smart FordAnother view of 2026 Jeep Gladiator Mojave for sale in South Boston, VA at Smart FordMore photos of 2026 Jeep Gladiator Mojave at Smart Ford, VAMore photos of 2026 Jeep Gladiator Mojave at Smart Ford, VA
Stock # 153569
Mojave
7,016 miles
Condition:
Pre-owned
Smart Buy Price
$54,999
$812 / mo. est.

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Beige 2023 Nissan Titan PRO-4X for sale in Madison, NCPhotos of 2023 Nissan Titan PRO-4X for sale in Madison, NC at Smart ChevroletAnother view of 2023 Nissan Titan PRO-4X for sale in Madison, NC at Smart ChevroletMore photos of 2023 Nissan Titan PRO-4X at Smart Chevrolet, NCMore photos of 2023 Nissan Titan PRO-4X at Smart Chevrolet, NC
Stock # 109903
PRO-4X
68,794 miles
Condition:
Pre-owned
Smart Buy Price
$36,526
$539 / mo. est.
Gray 2024 Ford F-250SD XLT for sale in South Boston, VAPhotos of 2024 Ford F-250SD XLT for sale in South Boston, VA at Smart FordAnother view of 2024 Ford F-250SD XLT for sale in South Boston, VA at Smart FordMore photos of 2024 Ford F-250SD XLT at Smart Ford, VAMore photos of 2024 Ford F-250SD XLT at Smart Ford, VA
Stock # E00852
XLT
71,168 miles
Condition:
Pre-owned
Smart Buy Price
$46,899
$692 / mo. est.
Red 2024 Jeep Wrangler Sahara 4xe for sale in South Boston, VAPhotos of 2024 Jeep Wrangler Sahara 4xe for sale in South Boston, VA at Smart FordAnother view of 2024 Jeep Wrangler Sahara 4xe for sale in South Boston, VA at Smart FordMore photos of 2024 Jeep Wrangler Sahara 4xe at Smart Ford, VAMore photos of 2024 Jeep Wrangler Sahara 4xe at Smart Ford, VA
Stock # 231972
Sahara 4xe
24,613 miles
Condition:
Pre-owned
Smart Buy Price
$32,999
$487 / mo. est.
White 2022 Ford F-250SD XLT for sale in Madison, NCPhotos of 2022 Ford F-250SD XLT for sale in Madison, NC at Smart ChevroletAnother view of 2022 Ford F-250SD XLT for sale in Madison, NC at Smart ChevroletMore photos of 2022 Ford F-250SD XLT at Smart Chevrolet, NCMore photos of 2022 Ford F-250SD XLT at Smart Chevrolet, NC
Stock # G35194
XLT
72,317 miles
Condition:
Pre-owned
Smart Buy Price
$46,912
$692 / mo. est.
White 2016 Mercedes-Benz Sprinter 3500 Cargo 170 WB for sale in South Boston, VAPhotos of 2016 Mercedes-Benz Sprinter 3500 Cargo 170 WB for sale in South Boston, VA at Smart FordAnother view of 2016 Mercedes-Benz Sprinter 3500 Cargo 170 WB for sale in South Boston, VA at Smart FordMore photos of 2016 Mercedes-Benz Sprinter 3500 Cargo 170 WB at Smart Ford, VAMore photos of 2016 Mercedes-Benz Sprinter 3500 Cargo 170 WB at Smart Ford, VA
Stock # 197499
Cargo 170 WB
82,904 miles
Condition:
Pre-owned
Smart Buy Price
$35,499
$524 / mo. est.
Silver 2017 Ford F-150 Raptor for sale in Madison, NCPhotos of 2017 Ford F-150 Raptor for sale in Madison, NC at Smart ChevroletAnother view of 2017 Ford F-150 Raptor for sale in Madison, NC at Smart ChevroletMore photos of 2017 Ford F-150 Raptor at Smart Chevrolet, NCMore photos of 2017 Ford F-150 Raptor at Smart Chevrolet, NC
Stock # A39926
Raptor
76,783 miles
Condition:
Pre-owned
Smart Buy Price
$39,998
$590 / mo. est.

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White 2022 Ram ProMaster City Cargo Van for sale in Madison, NCPhotos of 2022 Ram ProMaster City Cargo Van for sale in Madison, NC at Smart ChevroletAnother view of 2022 Ram ProMaster City Cargo Van for sale in Madison, NC at Smart ChevroletMore photos of 2022 Ram ProMaster City Cargo Van at Smart Chevrolet, NCMore photos of 2022 Ram ProMaster City Cargo Van at Smart Chevrolet, NC
Stock # Y60976
Cargo Van
80,175 miles
Condition:
Pre-owned
Smart Buy Price
$18,998
$280 / mo. est.
Unknown 2021 GMC Yukon Denali for sale in South Boston, VAPhotos of 2021 GMC Yukon Denali for sale in South Boston, VA at Smart FordAnother view of 2021 GMC Yukon Denali for sale in South Boston, VA at Smart FordMore photos of 2021 GMC Yukon Denali at Smart Ford, VAMore photos of 2021 GMC Yukon Denali at Smart Ford, VA
Stock # 237108
Denali
55,441 miles
Condition:
Pre-owned
Smart Buy Price
$50,499
$745 / mo. est.
Red 2024 Ford F-350SD XL for sale in South Boston, VAPhotos of 2024 Ford F-350SD XL for sale in South Boston, VA at Smart FordAnother view of 2024 Ford F-350SD XL for sale in South Boston, VA at Smart FordMore photos of 2024 Ford F-350SD XL at Smart Ford, VAMore photos of 2024 Ford F-350SD XL at Smart Ford, VA
Stock # F75725
XL
40,629 miles
Condition:
Pre-owned
Smart Buy Price
$57,999
$856 / mo. est.
Blue 2026 Tesla Model Y Premium for sale in South Boston, VAPhotos of 2026 Tesla Model Y Premium for sale in South Boston, VA at Smart FordAnother view of 2026 Tesla Model Y Premium for sale in South Boston, VA at Smart FordMore photos of 2026 Tesla Model Y Premium at Smart Ford, VAMore photos of 2026 Tesla Model Y Premium at Smart Ford, VA
Stock # 458702
Premium
4,358 miles
Condition:
Pre-owned
Smart Buy Price
$47,499
$701 / mo. est.
Black 2024 Genesis GV70 2.5T Select for sale in South Boston, VAPhotos of 2024 Genesis GV70 2.5T Select for sale in South Boston, VA at Smart FordAnother view of 2024 Genesis GV70 2.5T Select for sale in South Boston, VA at Smart FordMore photos of 2024 Genesis GV70 2.5T Select at Smart Ford, VAMore photos of 2024 Genesis GV70 2.5T Select at Smart Ford, VA
Stock # 006745
2.5T Select
70,582 miles
Condition:
Pre-owned
Smart Buy Price
$33,499
$494 / mo. est.
White 2023 Ram ProMaster 2500 High Roof for sale in Madison, NCPhotos of 2023 Ram ProMaster 2500 High Roof for sale in Madison, NC at Smart ChevroletAnother view of 2023 Ram ProMaster 2500 High Roof for sale in Madison, NC at Smart ChevroletMore photos of 2023 Ram ProMaster 2500 High Roof at Smart Chevrolet, NCMore photos of 2023 Ram ProMaster 2500 High Roof at Smart Chevrolet, NC
Stock # 579030
High Roof
1,810 miles
Condition:
Pre-owned
Smart Buy Price
$38,998
$576 / mo. est.

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Black 2024 Kia Sportage X-Pro Prestige for sale in Madison, NCPhotos of 2024 Kia Sportage X-Pro Prestige for sale in Madison, NC at Smart ChevroletAnother view of 2024 Kia Sportage X-Pro Prestige for sale in Madison, NC at Smart ChevroletMore photos of 2024 Kia Sportage X-Pro Prestige at Smart Chevrolet, NCMore photos of 2024 Kia Sportage X-Pro Prestige at Smart Chevrolet, NC
Stock # 147977
X-Pro Prestige
9,382 miles
Condition:
Pre-owned
Smart Buy Price
$31,998
$472 / mo. est.
White 2017 Audi A4 2.0T ultra Premium for sale in Madison, NCPhotos of 2017 Audi A4 2.0T ultra Premium for sale in Madison, NC at Smart ChevroletAnother view of 2017 Audi A4 2.0T ultra Premium for sale in Madison, NC at Smart ChevroletMore photos of 2017 Audi A4 2.0T ultra Premium at Smart Chevrolet, NCMore photos of 2017 Audi A4 2.0T ultra Premium at Smart Chevrolet, NC
Stock # 045013A
2.0T ultra Premium
102,416 miles
Condition:
Pre-owned
Smart Buy Price
$10,298
$152 / mo. est.
Black 2013 Mercedes-Benz M-Class ML 350 for sale in Madison, NCPhotos of 2013 Mercedes-Benz M-Class ML 350 for sale in Madison, NC at Smart ChevroletAnother view of 2013 Mercedes-Benz M-Class ML 350 for sale in Madison, NC at Smart ChevroletMore photos of 2013 Mercedes-Benz M-Class ML 350 at Smart Chevrolet, NCMore photos of 2013 Mercedes-Benz M-Class ML 350 at Smart Chevrolet, NC
Stock # 163108
ML 350
103,530 miles
Condition:
Pre-owned
Smart Buy Price
$11,699
$173 / mo. est.
White 2024 Jeep Wrangler Willys for sale in South Boston, VAPhotos of 2024 Jeep Wrangler Willys for sale in South Boston, VA at Smart FordAnother view of 2024 Jeep Wrangler Willys for sale in South Boston, VA at Smart FordMore photos of 2024 Jeep Wrangler Willys at Smart Ford, VAMore photos of 2024 Jeep Wrangler Willys at Smart Ford, VA
Stock # 236797
Willys
57,401 miles
Condition:
Pre-owned
Smart Buy Price
$34,999
$517 / mo. est.
Black 2025 GMC Sierra 1500 AT4 for sale in South Boston, VAPhotos of 2025 GMC Sierra 1500 AT4 for sale in South Boston, VA at Smart FordAnother view of 2025 GMC Sierra 1500 AT4 for sale in South Boston, VA at Smart FordMore photos of 2025 GMC Sierra 1500 AT4 at Smart Ford, VAMore photos of 2025 GMC Sierra 1500 AT4 at Smart Ford, VA
Stock # 238602
AT4
10,508 miles
Condition:
Pre-owned
Smart Buy Price
$60,999
$900 / mo. est.
Gray 2023 GMC Sierra 1500 Denali for sale in South Boston, VAPhotos of 2023 GMC Sierra 1500 Denali for sale in South Boston, VA at Smart FordAnother view of 2023 GMC Sierra 1500 Denali for sale in South Boston, VA at Smart FordMore photos of 2023 GMC Sierra 1500 Denali at Smart Ford, VAMore photos of 2023 GMC Sierra 1500 Denali at Smart Ford, VA
Stock # 196181
Denali
38,892 miles
Condition:
Pre-owned
Smart Buy Price
$49,499
$731 / mo. est.
Showing 201-225 of 304 results

Information deemed reliable, but not guaranteed. Interested parties should confirm all data before relying on it to make a purchase decision. All prices and specifications are subject to change without notice. Prices may not include additional fees such as government fees and taxes, title and registration fees, finance charges, dealer document preparation fees, processing fees, and emission testing and compliance charges.