Updated November 12, 2026. Figures below are read live from the MotoGossip index and change as listings do.
As of November 12, 2026, the MotoGossip index holds 292 priced Harley-Davidson FREEWHEELER listings at 140 dealers. Median asking prices by model year run from $16,460 for the 2016 to $33,763 for the 2025. The cheapest state right now is CA, with a median of $16,997 across 4 listings.
The median asking price for a 2025 Harley-Davidson FREEWHEELER is $33,763, across 28 listings in the MotoGossip index as of November 12, 2026.
The median asking price for a 2024 Harley-Davidson FREEWHEELER is $27,965, across 76 listings in the MotoGossip index as of November 12, 2026.
The median asking price for a 2023 Harley-Davidson FREEWHEELER is $24,999, across 35 listings in the MotoGossip index as of November 12, 2026.
The median asking price for a 2022 Harley-Davidson FREEWHEELER is $23,988, across 27 listings in the MotoGossip index as of November 12, 2026.
The median asking price for a 2021 Harley-Davidson FREEWHEELER is $22,999, across 21 listings in the MotoGossip index as of November 12, 2026.
The median asking price for a 2020 Harley-Davidson FREEWHEELER is $22,097, across 14 listings in the MotoGossip index as of November 12, 2026.
The median asking price for a 2019 Harley-Davidson FREEWHEELER is $22,990, across 21 listings in the MotoGossip index as of November 12, 2026.
The median asking price for a 2018 Harley-Davidson FREEWHEELER is $19,999, across 24 listings in the MotoGossip index as of November 12, 2026.
The median asking price for a 2017 Harley-Davidson FREEWHEELER is $17,999, across 17 listings in the MotoGossip index as of November 12, 2026.
The median asking price for a 2016 Harley-Davidson FREEWHEELER is $16,460, across 11 listings in the MotoGossip index as of November 12, 2026.
The median asking price for a 2015 Harley-Davidson FREEWHEELER is $17,229, across 18 listings in the MotoGossip index as of November 12, 2026.
The cheapest typical asking price right now is at Caswell Cycle in Mora, MN, at a median of $13,650. The priciest is at Towerslegendaryhd in Carroll, IA, at a median of $33,763. Both are medians of that dealer’s own current listings for this model, not a single asking price.
Across 15 weeks of data, from week 2026-W31 to week 2026-W46, the median ask among newly indexed FREEWHEELER listings has run from $20,450 to $29,995. Our index only goes back to late July 2026, so this is a short window and not a multi-year price history; treat it as a read on recent weeks, not a long-term trend.
| Listing | Year | Price | Mileage | Seller | Location |
|---|---|---|---|---|---|
| 2020 Harley-Davidson® Freewheeler® | 2020 | $13,650 | Mileage unlisted | Caswell Cycle | Mora, MN |
| 2015 Harley-Davidson® Freewheeler™ Vivid Black | 2015 | $14,000 | Mileage unlisted | Victoria Harley-Davidson | Victoria, TX |
| 2016 Harley-Davidson® FLRT Freewheeler® | 2016 | $14,995 | Mileage unlisted | Cycles Skis & ATVS | Tucson, AZ |
| 2016 Harley-Davidson® FLRT - Freewheeler® | 2016 | $14,999 | 14,256 mi | iMotorsports | Elmhurst, IL |
| 2015 Harley-Davidson® FLRT - Freewheeler™ | 2015 | $15,199 | 6,596 mi | Neal Ketner Motors | Winston Salem, NC |
| 2017 Harley-Davidson Freewheeler | 2017 | $15,648 | 8,747 mi | Sooner Indian Motorcycles | Norman, OK |
| 2015 Harley-Davidson® Freewheeler® (FLRT) | 2015 | $15,888 | 2,649 mi | State 8 Motorcycles | Cuyahoga Falls, OH |
| 2015 Harley-Davidson® FLRT - Freewheeler™ | 2015 | $15,950 | 2,487 mi | Dream Machines of Kansas, Home of Indian Motorcycle of Wichita | Wichita, KS |
| 2016 Harley-Davidson® FLRT - Freewheeler® | 2016 | $15,950 | 12,461 mi | Dream Machines of Kansas, Home of Indian Motorcycle of Wichita | Wichita, KS |
| 2015 Harley-Davidson Freewheeler™ | 2015 | $15,990 | 10,310 mi | J & J Motors Inc. | Massillon, OH |