$10,980
Used 2001 Harley-Davidson Cruiser
Softail Deuce DEUCE
Stock # 056838
<p></p>
Conrad's Harley-Davidson*
Shorewood, IL
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Harley-Davidson Softail Motorcycles for sale Near South Haven, MI
42 
117 Harley-Davidson SOFTAIL Motorcycles For Sale
$6,999
Used 2001 Harley-Davidson Cruiser
FXST/FXSTI Softail® Standard STANDARD
Stock # H040927
<p>FXST/FXSTI Softail® Standard</p>Harley-Davidson's Softail Standard is classically and conservatively styled so that owners can customize from mild
Indian Motorcycle of Racine
Racine, WI
$6,500
Used 2007 Harley-Davidson Cruiser
SOFTAIL DELUXE DELUXE
This 2007 Harley-Davidson Softail Deluxe is a classic cruiser motorcycle known for its timeless design and impressive performance. With low mileage of
Private Seller
Frankfort, IL
$7,999
Used 2021 Harley-Davidson Cruiser
SOFTAIL STANDARD STANDARD
<p> 2021 Harley-Davidson Softail </p><p>Only 2,452 miles — barely broken in and ready to ride!</p><p>Equipped with:</p><p>- Detachable windshield</p><
Dead End Cycles
Defiance, OH
$9,995
Used 2023 Harley-Davidson Standard
FXST STANDARD
Stock # M-9540
<p>2023 Harley-Davidson FXST, </p><p><strong>MILWAUKEE 8 SOFTAIL STANDARD</strong></p><p><strong>Displacement:</strong> 107 cu. in. (1745 cc)<br><stro
Randy's Cycles
Marengo, IL
$8,780
Used 2015 Harley-Davidson Cruiser
FLSTC103 Heritage Softail HERITAGE
Stock # 2551M
2015 Harley-Davidson FLSTC103 Heritage Softail, Check out this beautiful Harley Heritage Softail! Bike is in excellent condition. Apes, pipes and air
Stevenson Auto Sales
Kankakee, IL
$26,998
Used 2022 Harley-Davidson Cruiser
Softail FXRST - Low Rider El Diablo LOW RIDER EL DIABLO
Stock # 057243C
2022 Harley-Davidson Softail FXRST - Low Rider El Diablo, 2022 Harley-Davidson® Low Rider® El Diablo ++<strong>Unmatched Selection We Stand Behind</st
Arsenal Harley-Davidson
Waterford Twp, MI
$5,822
Used 2006 Harley-Davidson Standard
FXSTD - Softail Deuce DEUCE
Stock # 33140
2006 Harley-Davidson FXSTD - Softail Deuce , 2006 Harley-Davidson® Softail® Deuce™ <p>Take a good long look at the lean, narrow design of the Softail®
Planet Powersports
Coldwater, MI
$9,899
Used 2018 Harley-Davidson® Cruiser
FXFB - Softail® Fat Bob® FAT BOB
Stock # 031056
2018 Harley-Davidson® FXFB - Softail® Fat Bob®, WOW FACTOR! ONLY 2241 MILES, 21" AND 18" ARLEN NESS WHEELS, COBRA EXHAUST, S&S HIGH FLOW INTAKE, MUSTA
Road Track And Trail
Big Bend, WI
$9,977
Used 2018 Harley-Davidson® Cruiser
FLDE - Softail® Deluxe DELUXE
Stock # 27005A
2018 Harley-Davidson® FLDE - Softail® Deluxe, Fresh key fob batteries and fresh fluids! Wedge fairing, ape hanger handlebars, wide white walls, 2 into
Suburban Motors Harley-Davidson
Thiensville, WI
$12,999
Used 2015 Harley-Davidson Cruiser
Softail Slim® SLIM
Stock # HAR030029
<p>Softail Slim®</p>The perfect blend of classic, raw bobber style and contemporary power creates a modern ride with unmistakable old-iron attitude.
Van Der Zee Motorplex
South Haven, MI
$14,901
Used 2018 Harley-Davidson Cruiser
Softail® Deluxe 107 DELUXE
Stock # EIM069080
<p>BEAUTIFUL TO THE BONE</p><p style="margin-bottom: 1em;">Show-stopping, old-school glam, Deluxe is a nostalgic boulevard custom that turns heads.</p
Elkhart Indian Motorcycle
Elkhart, IN
$15,313
Used 2023 Harley-Davidson Cruiser
FXFBS Softail Fat Bob 114 FAT BOB 114
Stock # H22972U
<p>Experience the raw power of the 2023 Harley-Davidson FXFBS Softail Fat Bob 114.</p><p>This used motorcycle is a stunning blend of style and perform
Motoworks Chicago
Chicago, IL
$8,499
Used 2008 Harley-Davidson Sportbike
FXCW - Rocker ROCKER
Stock # A11455
<p>Experience the open road with the 2008 Harley-Davidson FXCW - Rocker. This used motorcycle blends classic style with modern performance. Perfect fo
iMotorsports
Elmhurst, IL
$6,900
Used 2020 Harley-Davidson Cruiser
FXST Softail Standard STANDARD
Stock # H53099U
2020 Harley-Davidson FXST Softail Standard, <p>2020 Harley Davidson FXST Softail Standard. Rinehart performance exhaust, sissy bar, solo seat, engine
Motor Cycle Center Inc
Villa Park, IL
$12,995
Used 2020 Harley-Davidson Cruiser
Softail Standard STANDARD
Stock # U2946
2020 Harley-Davidson Softail Standard, <p>The new Softail® Standard motorcycle offers the essential Harley-Davidson® cruiser experience - a lean Bobbe
House Of Harley-Davidson Milwaukee
Milwaukee, WI
$7,999
Used 2008 Harley-Davidson Cruiser
Softail® Rocker™ ROCKER
Stock # 066656
<p>This used 2008 Softail® Rocker™ is in excellent condition with low 4k miles! Comes equipped with a Stage 1 Heavy Breather Air Intake, New Tires, Se
Monster Powersports
Wauconda, IL
$14,743
New 2024 Harley-Davidson Cruiser
Softail® Standard STANDARD
Stock # 52924
<p>ONLY THE ESSENTIALS.</p><p style="margin-bottom: 1em;">A raw, stripped-down, bobber-style bike, the Harley-Davidson Softail Standard is an ideal bl
Town & Country Sports Center
Cement City, MI
$9,488
Used 2019 Harley-Davidson Cruiser
Softail FXLR - Low Rider LOW RIDER
Stock # P2738A
2019 Harley-Davidson Softail FXLR - Low Rider, 2019 Harley-Davidson® Softail® Low Rider® <strong>RUGGED INDIVIDUALISM TURNED TO METAL</strong><p>With
Chi-Town Harley-Davidson
Tinley Parl, IL
$5,525
Used 1997 Harley-Davidson® Cruiser
FXSTC - Softail® Custom CUSTOM
Stock # 27448A
<p>Experience the classic charm of a 1997 Harley-Davidson® FXSTC - Softail® Custom. This used motorcycle combines timeless design with the thrill of t
Suburban Motors Harley-Davidson
Thiensville, WI
$6,199
Used 2005 Harley-Davidson® Cruiser
FLSTN - Softail® Deluxe DELUXE
Stock # 383P
<p>Experience the classic charm of the 2005 Harley-Davidson® FLSTN - Softail® Deluxe.</p> <p>Used 2005 Harley-Davidson® FLSTN - Softail® Deluxe moto
Gina's Motorsports
Monee, IL
$5,999
Used 2003 Harley-Davidson® Cruiser
FXSTDI - Softail® Deuce Injection DEUCE
Stock # 117118
2003 Harley-Davidson® FXSTDI - Softail® Deuce Injection, ONLY 4325 MILES, 1-OWNER, VANCE AND HINES EXHAUST, HIGH FLOW INTAKE, CHROME FORKS, HANDLEBAR
Road Track And Trail
Big Bend, WI
$10,995
Used 2024 Harley-Davidson Cruiser
Softail® Standard STANDARD
Stock # 5132
<p>ONLY THE ESSENTIALS. LOW 844 MILES @ A GREAT VALUE</p><p style="margin-bottom: 1em;"> Jamie's Customs is family owned and operated, we have been ar
Jamie's Customs
Big Bend, WI
$13,495
Used 2009 Harley-Davidson® Cruiser
FLSTSB - Cross Bones CROSS BONES
Stock # 10176
2009 Harley-Davidson FLSTSB - Cross Bones , 2009 Harley Davidson CrossBones FLSTSB with 4050 miles only, excellent condition for its year so review pi
HnH Cycles
Romeoville, IL
$12,898
Used 2022 Harley-Davidson Touring
Softail FXBBS - Street Bob 114 STREET BOB 114
Stock # N071A
<p>Experience the open road with the 2022 Harley-Davidson Softail FXBBS - Street Bob 114. This used motorcycle is built for cruising and adventure. Fe
Phantom Harley-Davidson
Manteno, IL
$12,999
Used 2018 Harley-Davidson® Cruiser
FLDE - Softail® Deluxe DELUXE
Stock # u40438
2018 Harley-Davidson® FLDE - Softail® Deluxe, <p><strong>13,383 MILES | 107 MILWAUKEE-EIGHT | HANGER BARS | EXHAUST | INTAKE & TUNE</strong></p> <p><s
C&C Sports
Brighton, MI
$12,997
Used 2019 Harley-Davidson Cruiser
Softail Slim® SLIM
Stock # 066319
<p>THE CLASSIC BOBBER HAS BEEN REBORN</p><p style="margin-bottom: 1em;">A stripped-down, souped-up, bobber with a post WWII era look. You get the powe
Hankster's Motorsports
Janesville, WI
$7,976
Used 2010 Harley-Davidson Standard
FLSTN DELUXE
Stock # HD024465
<p>Experience the classic allure of this Harley-Davidson. This Used 2010 Harley-Davidson FLSTN Deluxe Standard is ready for the open road. It’s ideal
Monroe Motorsports
Monroe, MI
$20,498
Used 2024 Harley-Davidson Cruiser
Softail FLHCS - Heritage Classic HERITAGE SOFTAIL CLASSIC
Stock # 042291
2024 Harley-Davidson Softail FLHCS - Heritage Classic, 2024 Harley-Davidson® Heritage Classic ++<strong>Unmatched Selection We Stand Behind</strong> <
Arsenal Harley-Davidson
Waterford Twp, MI
$6,500
Used 1994 Harley-Davidson Cruiser
SOFTAIL FXST FXST
1994 Harley-Davidson FXSTS Springer Softail with iconic classic Springer front end. Classic cruiser known for nostalgic old-school front suspension, v
Private Seller
Skokie, IL
$0
New 2026 Harley-Davidson Cruiser
Deadwood™ DEADWOOD
Stock # 045135
<p>The Black Sheep of the Black Hills</p>The 2026 Deadwood™ channels the same wandering spirit that’s pulled riders toward Sturgis and the Black Hills
Conrad's Harley-Davidson*
Shorewood, IL
$0
New 2026 Harley-Davidson Cruiser
Deadwood™ DEADWOOD
Stock # 046138
<p>The Black Sheep of the Black Hills</p>The 2026 Deadwood™ channels the same wandering spirit that’s pulled riders toward Sturgis and the Black Hills
Conrad's Harley-Davidson*
Shorewood, IL
$7,500
Used 2003 Harley-Davidson Cruiser
SOFTAIL DEUCE DEUCE
The Harley-Davidson Softail Deuce 100 Anniversary Edition. Low mileage. Ridden smoothly. maintenance records.<br><br><br>
Private Seller
Grand Rapids, MI
$0
New 2026 Harley-Davidson Cruiser
Softail FXBB - Street Bob STREET BOB
Stock # 038108
2026 Harley-Davidson Softail FXBB - Street Bob, 2026 Harley-Davidson® Street Bob® <strong>The New Definition of “Less Is More”</strong><p>The 2026 Str
Arsenal Harley-Davidson
Waterford Twp, MI
$5,250
Used 2006 Harley-Davidson Cruiser
SOFTAIL DEUCE DEUCE
Custom everything - Lots - n Lots of Chrome Fresh paint and airbrushing - Corbin Seat - good tires meticulously maintained. Moving on to a Touring mod
Private Seller
Skokie, IL
$7,313
Used 2020 Harley-Davidson Cruiser
FXST Softail Standard STANDARD
Stock # H53099U
2020 Harley-Davidson FXST Softail Standard, <p>2020 Harley Davidson FXST Softail Standard. Rinehart performance exhaust, sissy bar, solo seat, engine
Motoworks Chicago
Chicago, IL
$16,349
Used 2019 Harley-Davidson Cruiser
Softail Slim® SLIM
Stock # H012192
<p>THE CLASSIC BOBBER HAS BEEN REBORN</p>A stripped-down, souped-up, bobber with a post WWII era look. You get the power and soul-satisfying sound of
Indian Motorcycle of Racine
Racine, WI
$4,850
Used 1997 Harley-Davidson Classic / Vintage
SOFTAIL CUSTOM CUSTOM
<p>Contact AJ 312-933-0113 The 1997 HARLEY-DAVIDSON SOFTAIL CUSTOM is a classic and vintage motorcycle with a rich history and timeless design. With 4
Private Seller
Oak Lawn, IL
$8,999
Used 2017 Harley-Davidson Cruiser
FLS - Softail Slim SLIM
Stock # A11574
<p>Experience the classic charm of the 2017 Harley-Davidson FLS - Softail Slim.</p> <p>Used 2017 Harley-Davidson FLS - Softail Slim motorcycle. This
iMotorsports
Elmhurst, IL
$15,999
Used 2007 Harley-Davidson Cruiser
FXSTSSE - Softail Screamin' Eagle Springer SPRINGER SOFTAIL
Stock # A11370
<p>Experience the classic allure of the open road with this 2007 Harley-Davidson FXSTSSE - Softail Screamin' Eagle Springer. This used motorcycle is p
iMotorsports
Elmhurst, IL
$11,999
Used 2016 Harley-Davidson Cruiser
FLSTN - Softail Deluxe DELUXE
Stock # A11427
<p>Experience the classic blend of style and performance with the 2016 Harley-Davidson FLSTN - Softail Deluxe.</p> <p>This used Harley-Davidson FLST
iMotorsports
Elmhurst, IL
$0
Used 2003 Harley-Davidson Standard
FXSTI STANDARD
Stock # A11670
<p>Experience the open road with the 2003 Harley-Davidson FXSTI. This used motorcycle is perfect for cruising and enjoying the ride. With its classic
iMotorsports
Elmhurst, IL
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