Indian Chieftain motorcycles for sale in Sanford, Florida

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2025 Indian Motorcycle Chieftain PowerPlus Dark Horse w/PowerBand Audio Blue Dusk

2025 Indian Motorcycle Chieftain PowerPlus Dark Horse w/PowerBand Audio Blue Dusk

$30,499

Sanford, Florida

Year 2025

Make Indian Motorcycle

Model Chieftain PowerPlus Dark Horse W/PowerBand Audio Blue Dusk

Category Cruiser

Engine -

Posted Over 1 Month

Call us today to set up an appointment for a demo ride and ask about our finance options! 321-926-1050

2025 Indian Motorcycle Chieftain PowerPlus Dark Horse 112 w/PowerBand Black Smoke

2025 Indian Motorcycle Chieftain PowerPlus Dark Horse 112 w/PowerBand Black Smoke

$32,749

Sanford, Florida

Year 2025

Make Indian Motorcycle

Model Chieftain PowerPlus Dark Horse 112 W/PowerBand Black Smoke

Category Cruiser

Engine -

Posted Over 1 Month

Call us today to set up an appointment for a demo ride and ask about our finance options! 321-926-1050

2025 Indian Motorcycle Chieftain PowerPlus Dark Horse 112 w/PowerBand Ghost White Metallic Smoke

2025 Indian Motorcycle Chieftain PowerPlus Dark Horse 112 w/PowerBand Ghost White Metallic Smoke

$33,499

Sanford, Florida

Year 2025

Make Indian Motorcycle

Model Chieftain PowerPlus Dark Horse 112 W/PowerBand Ghost White Metallic Smoke

Category Cruiser

Engine -

Posted Over 1 Month

This listing was published on 03/29/2025 . The location is Sanford and sold by Sky Powersports Sanford.

2025 Indian Motorcycle Chieftain PowerPlus Limited 112 Black Metallic

2025 Indian Motorcycle Chieftain PowerPlus Limited 112 Black Metallic

$30,499

Sanford, Florida

Year 2025

Make Indian Motorcycle

Model Chieftain PowerPlus Limited 112 Black Metallic

Category Cruiser

Engine -

Posted Over 1 Month

Call us today to set up an appointment for a demo ride and ask about our finance options! 321-926-1050

2025 Indian Motorcycle Chieftain Limited w/PowerBand Audio Sunset Red Metallic

2025 Indian Motorcycle Chieftain Limited w/PowerBand Audio Sunset Red Metallic

$30,999

Sanford, Florida

Year 2025

Make Indian Motorcycle

Model Chieftain Limited W/PowerBand Audio Sunset Red Metallic

Category Cruiser

Engine -

Posted Over 1 Month

Call us today to set up an appointment for a demo ride and ask about our finance options! 321-926-1050

2025 Indian Motorcycle Chieftain Black Metallic

2025 Indian Motorcycle Chieftain Black Metallic

$23,999

Sanford, Florida

Year 2025

Make Indian Motorcycle

Model Chieftain Black Metallic

Category Cruiser

Engine -

Posted Over 1 Month

Call us today to set up an appointment for a demo ride and ask about our finance options! 321-926-1050

2024 Indian Motorcycle Chieftain Limited with Powerband Audio Package Spirit Blue Metallic

2024 Indian Motorcycle Chieftain Limited with Powerband Audio Package Spirit Blue Metallic

$26,509

Sanford, Florida

Year 2024

Make Indian Motorcycle

Model Chieftain Limited With Powerband Audio Package Spirit Blue Metallic

Category Cruiser

Engine -

Posted Over 1 Month

Call us today to set up an appointment for a demo ride and ask about our finance options! 321-926-1050

2024 Indian Motorcycle Chieftain Dark Horse Ghost White Metallic Smoke

2024 Indian Motorcycle Chieftain Dark Horse Ghost White Metallic Smoke

$26,294

Sanford, Florida

Year 2024

Make Indian Motorcycle

Model Chieftain Dark Horse Ghost White Metallic Smoke

Category Cruiser

Engine -

Posted Over 1 Month

$1,000 Trade credit, As low as 4.99% for 36 months. Call us today to set up an appointment for a demo ride and ask about our finance options! 321-926-1050

2019 Indian Motorcycle Chieftain Limited Thunder Black Pearl

2019 Indian Motorcycle Chieftain Limited Thunder Black Pearl

$15,999

Sanford, Florida

Year 2019

Make Indian Motorcycle

Model Chieftain Limited Thunder Black Pearl

Category Cruiser

Engine -

Posted Over 1 Month

Call us today to set up an appointment for a demo ride and ask about our finance options! 321-926-1050

2019 Indian Motorcycle Chieftain Limited Ruby Metallic

2019 Indian Motorcycle Chieftain Limited Ruby Metallic

$14,999

Sanford, Florida

Year 2019

Make Indian Motorcycle

Model Chieftain Limited Ruby Metallic

Category Cruiser

Engine -

Posted Over 1 Month

Call us today to set up an appointment for a demo ride and ask about our finance options! 321-926-1050

2021 Indian Motorcycle Chieftain Dark Horse Icon Crimson Metallic

2021 Indian Motorcycle Chieftain Dark Horse Icon Crimson Metallic

$20,999

Sanford, Florida

Year 2021

Make Indian Motorcycle

Model Chieftain Dark Horse Icon Crimson Metallic

Category Cruiser

Engine -

Posted Over 1 Month

Call us today to set up an appointment for a demo ride and ask about our finance options! 321-926-1050

2016 Indian Chieftain Star Silver and Thunder Black

2016 Indian Chieftain Star Silver and Thunder Black

$19,988

Sanford, Florida

Year 2016

Make Indian

Model Chieftain Star Silver And Thunder Black

Category Cruiser Motorcycles

Engine -

Posted Over 1 Month

2016 Indian Chieftain Star Silver and Thunder Black, WARRANTY, TRADES WELCOME, FINANCING 1-800-838-4055 2016 Indian® Chieftain® Star Silver and Thunder Black HOPE YOU LIKE BEING THE CENTER OF ATTENTION Followers need not apply. Built to go your own way, this hard-bagger rides a lane apart. A rolling testament to American ingenuity. The first faired, hard bagger Indian motorcycle is a stunning bike. Cruise around town. Roar down the freeway with the music blasting. Take a long trip across state lines. Then put down the side stand, take a step back and look at one of the most striking motorcycles ever made.

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1941 BMW R75 WITH SIDECAR

1941 BMW R75 WITH SIDECAR

Olive Branch, MS

$40,750

2022 Harley-Davidson XL883N

2022 Harley-Davidson XL883N

Phoenix, AZ

$6,995

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2012 Harley-Davidson FLHXSE

Phoenix, AZ

$14,777