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Gray Used Harley-Davidson Motorcycles for Sale in Massachusetts

Looking to buy a Harley-Davidson motorcycle in Massachusetts? Browse our extensive inventory of new and used Harley-Davidson motorcycles from local Harley-Davidson dealers and private sellers in Massachusetts. Compare prices, models, trims, options and specifications between different Harley-Davidson motorcycles on Cycle Trader.
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50 Used Harley-Davidson Motorcycles For Sale

2016 Harley-Davidson STREET BOB DYNA in Great Barrington, MA
$9,200

Used 2016 Harley-Davidson Cruiser

STREET BOB DYNA
Bought the bike with only 1,000 miles so basically since new, runs and drives awesome. Few bolts have some surface rust due to getting wet. Replaced both tires at the beginning of the year as well as breaks. Parts list attached in the picture, a few have been change or taken off the bike. Priced to sell, feel free to reach out with any questions. Parts list: Arlen Ness mirrorsSpeed King shorty levers Thrashing Supply militant pegs and shifterProgressive 490 13 & APR hardwareDuralast Gold BatteryUpgraded CVO speedometer, WG gloss black console, housing and CVO battery cover, ARP bolts and red washersCVO digital gauge and in-dash digital gas gauge LAC 14 KageFighter Tbars Memphis Shade Road Warriors Dynojet Power vision tunerCobra RPT 2:1Performance Machine Max air cleanerKahuna Cover trim set and HD gripsDominion front and rear, fork nuts trimLeather synthetic H-D bagsH-D screaming eagle spark plug Moons MC LED head
Private Seller
Great Barrington, MA
2022 Harley-Davidson Iron 883™ IRON in Pittsfield, MA
$8,799

Used 2022 Harley-Davidson Standard

Iron 883™ IRON
Stock # 409188
<p style="margin-bottom: 1em;">Blacked-out and stripped-down with a legendary profile.  The Sportster Iron 883 is nothing to sneeze at.  No matter if it's a un through the corners or a quick trip across town you'll go with a smile on your face.  Not broke in yet but you aren't paying for a new machine.  This makes it extremely desirable because you can still make it your own.  </p><p></p>
Ronnie's Pittsfield
Pittsfield, MA
2020 Harley-Davidson Street Glide® Special SPECIAL in Pittsfield, MA
$22,199

Used 2020 Harley-Davidson Touring

Street Glide® Special SPECIAL
Stock # 672845
<p>KICKS HOT ROD BAGGER STYLE INTO A HIGHER GEAR</p><p style="margin-bottom: 1em;">The custom hot rod bagger look stops people in their tracks. Now powered up with the Milwaukee-Eight® 114 engine, you’ll leave them in your dust.  Pretty much a Dark Theme with the only addition is the extra Road Pegs for your feet.  If this bike doesn't get you to where you want to go, none of them will.</p><p></p>
Ronnie's Pittsfield
Pittsfield, MA
2014 Harley-Davidson Softail Slim® SLIM in Pittsfield, MA
$10,499

Used 2014 Harley-Davidson Cruiser

Softail Slim® SLIM
Stock # 014560
<p>Softail Slim®</p><p style="margin-bottom: 1em;"> The perfect blend of classic, raw bobber style and contemporary power creates a modern ride with unmistakable old-iron attitude. • 23.8 in. seat height - lowest of all Harley® motorcycles • Chopped rear fender over 144 mm rear tire • Air-cooled, Twin Cam 103B™ engine • Gloss black, round air-cleaner cover • Hollywood handlebar with cross-brace • Jiffy stand with easy liftoff.  Custom Bars.</p><p></p>
Ronnie's Pittsfield
Pittsfield, MA
2008 Harley-Davidson Street Glide® in Pittsfield, MA
$9,299

Used 2008 Harley-Davidson Touring

Street Glide®
Stock # 703015
<p>Street Glide®</p><p style="margin-bottom: 1em;">FROM THE STRIPPED FRONT FENDER ON BACK, THE WORLD HAS NEVER SEEN A PRODUCTION TOURING MACHINE LIKE IT. An immaculately clean fairing with solo headlamp and integrated mirrors. Slammed suspension and a new lowered antenna. Added comfort in the seat, for longer viewings over the low smoked wind deflector.  Raised Custom Bars, Custom Air Cleaner, 2 into 1 Pipes, 3-D smoked chrome emblems on the tank. A ground effects rear fender with LED lightshow. Cruise control available as a factory-installed option. And should you want to stop and check it all out, new Brembo® brakes with optional ABS.</p><p></p>
Ronnie's Pittsfield
Pittsfield, MA
2014 Harley-Davidson Ultra Limited ULTRA LIMITED in Springfield, MA
$9,990

Used 2014 Harley-Davidson Touring

Ultra Limited ULTRA LIMITED
<p>GRAY AND BLACK, 49190 MILES, PYTHON EXHAUST, HEATED GRIPS, GPS, RUNS GREAT, SUPER CLEAN, AND ONLY $9990</p><p style="margin-bottom: 1em;">Starting at $25,899 The farther you go on a motorcycle, the better it gets. Whether riding one or building a new one from LED headlamp to taillight. Welcome to the top-of-the-line bagger. • NEW - Twin-Cooled™ high output Twin Cam 103™ engine • NEW - Reflex™ linked brakes with ABS, standard • NEW - Jukebox media compartment with one-touch push-to-open door, and USB connection • NEW - Heated hand grips and redesigned shotgun seat • NEW - Redesigned saddlebags with one-touch latch</p><p></p>
Mutual Enterprises Inc.
Springfield, MA
2009 Harley-Davidson ELECTRA GLIDE ULTRA CLASSIC ULTRA CLASSIC in Ludlow, MA
$5,999

Used 2009 Harley-Davidson Touring

ELECTRA GLIDE ULTRA CLASSIC ULTRA CLASSIC
<p>THIS HARLEY DAVIDSON ULTRA IS IN EXCELLENT CONDITION, VERY CLEAN, 96 CUBIC INCH ENGINE 6 SPEED TRANSMISSION, LOTS OF NICE EXTRAS. Discount Motor Sales Inc. PLEASE CALL OR TEXT 413-279-4379 ALL TYPES OF TRADES CONSIDERED https://www.discount-motorsales.com 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 of $299, processing fees, and emission testing and compliance charges.</p>
Discount Motor Sales Inc.
Ludlow, MA
2020 Harley-Davidson Sportster XL883N - Iron 883 XL883N in Auburn, MA
$9,933

Used 2020 Harley-Davidson Cruiser

Sportster XL883N - Iron 883 XL883N
Stock # 413572
2020 Harley-Davidson Sportster XL883N - Iron 883, 4,800 Miles Fully Serviced by H-D Master Techs 110-point H-D Inspection Genuine H-D Parts Extensive list of Quality Checks and Function Verifications Fluids, Filters and Parts Replaced Hand Detailed (Polished and Waxed) all done to ensure Sheldons H-Ds mechanical, functional and cosmetic standards are met. You can feel safe and confident with the knowledge that every single bike Sheldons sells is an excellent, premium quality bike. LOCATED at Sheldons in Auburn Ma - TEXT Now: (508) 721-9876<br> <br> This Immaculate > #1 Priced > Low Miles (4,800 miles) > Fully Serviced > XL883N - Sportster Iron 883 is a legit exact same as Brand New with 4,800 miles and it is a drop dead gorgeous in River Rock Gray - 2020 Harley-Davidson XL883N - Sportster Iron 883 came in as new bike trade-in and Only has 8,000 Miles. Look at the pictures. You will be amazed. This bike is perfect and is mint, mint, mint! The previous owner bought a brand new bike and took fantastic care of this bike. You will be impressed with the condition of this bike. The bike looks Brand New! The previous owner loved this bike and it shows the minute you see it. It was always stored inside and babied. He regularly hand washed and waxed the bike and kept it mint! He is super meticulous with his bikes.It always serviced properly and is a great bike for someone looking for that mint bike for not a lot of money! We just reduced it so hurry these low mile, super clean bikes in this price range always go super quick! Take advantage and save some $$$. <br> <br><br>Every single Pre-Owned Motorcycle that comes from Sheldon H-D is fully serviced and inspected from top to bottom. We perform a thorough deep dive via Harley-Davidson Certified 110-point Quality Inspection Checklist and the work is performed by Factory Trained Harley-Davidson Certified Master technicians. We use Genuine H-D parts and the bikes go through an extensive list of checks and function verifications to ensure Sheldon’s H-D mechanical, functional and cosmetic standards are met. Every bike that goes out the door is a mint bike and all our pre-owned bikes have the option of getting an extended Warranty giving you the confidence to know you’re buying a premium quality used bike.<br>
NF Sheldon Harley-Davidson
Auburn, MA
2018 Harley-Davidson® FLHRXS - Road King® Special SPECIAL in Bellingham, MA
$17,900

Used 2018 Harley-Davidson® Touring

FLHRXS - Road King® Special SPECIAL
2018 Harley-Davidson® FLHRXS - Road King® Special, 1746cc<br>2,452 Miles<br>Industrial Gray Denim<br>Fuel Injection<br>Rinehart Exhaust<br>Screamin Eagle Air Cleaner<br>Custom Grips<br>Custom Highway Pegs<br>Custom Shifter Pegs<br>Custom Derby Cover<br>LED Turn Signals<br>Flush Mount Fuel Cap<br>Flush Mount LED Fuel Gauge<br>ABS Brakes<br>Cruise Control<br>Factory Security<br>107ci<br>6 Speed
Todd's Motorcycles
Bellingham, MA
2023 Harley-Davidson Pan America 1250 Special 1250 SPECIAL in North Billerica, MA
$21,977

Used 2023 Harley-Davidson Standard

Pan America 1250 Special 1250 SPECIAL
Stock # U302884
2023 Harley-Davidson Pan America 1250 Special, IMMACULATE CONDITION! Used 2023 Gray Haze Harley-Davidson Pan America Special RA1250S For Sale! The Pan America motorcycle is Harley-Davidson s explore-it-all machine for riders who see touring as detouring on road and off. This rugged, powerful, technologically advanced multi-purpose vehicle is designed from the ground up to be?capable, confidence inspiring, and fun wherever the road may take you. The Pan America 1250 Special model is a premium adventure touring motorcycle loaded with exclusive features.Come in and let one of our expert Fit specialists give you more details! While you're at it give it a test ride!
High Octane Harley-Davidson
North Billerica, MA
2023 Harley-Davidson Breakout in North Billerica, MA
$20,977

Used 2023 Harley-Davidson Cruiser

Breakout
Stock # U072094
2023 Harley-Davidson Breakout, Experience Thrilling Freedom with this 2023 Harley-Davidson Breakout!With a mere 209 miles on the clock, this Black Denim beauty is practically brand new, offering you the excitement of a fresh ride with the value of a used bike.Crafted to Harley-Davidson's exacting standards, the Breakout promises an exhilarating ride with its powerful engine and iconic style. Whether you're tearing up the asphalt or cruising through town, this bike commands attention at every turn.Don't let this opportunity slip away. Schedule your test ride today and discover the unmatched thrill of owning a Harley-Davidson Breakout!
High Octane Harley-Davidson
North Billerica, MA
2021 Harley-Davidson® Street Glide® Special SPECIAL in North Billerica, MA
$22,088

Used 2021 Harley-Davidson® Touring

Street Glide® Special SPECIAL
Stock # U610261
2021 Harley-Davidson® Street Glide® Special, <p>A factory-custom bagger with highway-shredding power offered with new two-tone paint options, and with a choice of a blacked-out or bright chrome styling treatments, giving the customer a choice of a look that’s dark and sinister, or brilliant and more traditional. All Special models are now equipped with the high-performance Ventilator air cleaner with a washable filter element, and a new low-profile engine guard, the Milwaukee-Eight 114 V-Twin engine and Prodigy wheels. The original hot rod bagger rolls behind the classic Harley-Davidson batwing fairing. Authoritative power meets long-haul comfort and custom style. Bright white Daymaker LED headlamp pushes out an impressive punch that lights up the road and makes the motorcycle more conspicuous in daytime. Put down your smartphone and come in and give it a test ride already!</p>
High Octane Harley-Davidson
North Billerica, MA
2021 Harley-Davidson® Pan America 1250 Special 1250 SPECIAL in North Billerica, MA
$18,577

Used 2021 Harley-Davidson® Standard

Pan America 1250 Special 1250 SPECIAL
Stock # U307987
2021 Harley-Davidson® Pan America 1250 Special, <p>PERFECT CONDITION! Used 2021 Gauntlet Gray Metallic Harley-Davidson Pan America Special RA1250S For Sale!</p><p>Exploring the world from a motorcycle engages the senses as the landscapes, sights and sounds create a deep, visceral adventure.<br>The all-new Pan America 1250 adventure motorcycle is Harley-Davidson’s explore-it-all machine for those who are driven to push boundaries and don’t want to be confined by the limits of roads.<br>Adventure touring riders seek out new experiences in any direction, on any terrain, to explore the undiscovered, sleep under the stars and immerse themselves in the journey. </p><p>The Pan America was built for these explorers, to go further, until they find themselves in places few have traveled.<br>Come give it a test ride and imagine the possibilities!</p>
High Octane Harley-Davidson
North Billerica, MA
2021 Harley-Davidson® Road Glide® Limited LIMITED in North Billerica, MA
$22,688

Used 2021 Harley-Davidson® Touring

Road Glide® Limited LIMITED
Stock # U617541
2021 Harley-Davidson® Road Glide® Limited, <p>A long-haul, two-up touring specialist featuring the distinctive aerodynamic Road Glide shark-nose fairing with triple split stream vents that limit rider head buffeting. The standard Milwaukee-Eight 114 engine delivers smooth, powerful touring performance while dual Daymaker LED headlamps offer outstanding night visibility. Premium Touring suspension includes an easy-adjust rear shock pre-load for a smooth, confident ride. Reflex Electronic Linked Brakes with ABS deliver confident braking performance. The Boom! Box GTS infotainment system with color touch screen offers navigation, communication and entertainment options.</p>
High Octane Harley-Davidson
North Billerica, MA
2018 Harley-Davidson Street Bob FXBB in Westport, MA
$11,995

Used 2018 Harley-Davidson Cruiser

Street Bob FXBB
Stock # HDC902D
<p>Rev up your adrenaline and hit the open road with this stunning 2018 Harley Davidson Street Bob!  Equipped with a thundering Milwaukee-Eight® 107 engine, it delivers smooth rides and heart-pounding acceleration. </p><p>This Street Bob is in great condition and has been meticulously maintained by Harley dealers only.  Enjoy the comfortable ergonomics and precise handling for a thrilling ride.  Customize it to express your individuality and take advantage of the advanced technology.</p><p>Feel free to message/call us with any questions, or simply stop by the shop and check it out!</p><ul><li>No Dealer or Hidden fees</li><li>Price is 100% Out-the-Door</li><li>No Cost Warranty included</li><li>Nationwide Financing available</li><li>0% Interest Layaway Plan available</li><li>All Trades and Offers considered</li><li>Door-to-Door Delivery available</li></ul>
Windmill Cycles
Westport, MA
2018 Harley-Davidson CVO Street Glide FLHXSE CVO in Plymouth, MA
$23,999

Used 2018 Harley-Davidson Touring

CVO Street Glide FLHXSE CVO
Stock # AV3387
2018 Harley-Davidson CVO Street Glide FLHXSE, Introducing the 2018 Harley Davidson CVO Street Glide we just received! This bike is insanely clean and only has just over 10,000 miles on it! Dare I say this bike is in perfect condition. With the CVO's 117ci motor this bike pulls like a fighter jet and has the Boom Audio sound system to really knock your socks off with whatever music you deicide to listen to when out on the open road! Come check it out today!Motorcycles508 54 Holman Rd Plymouth MA 02360508-857-3777www.mc508.comWe stock over 150 Pre Owned Motorcycles at the lowest prices around! All Bikes are fully serviced and ready to go.Visit Motorcycles 508 online at mc508.com to see more pictures of this vehicle or call us at508-857-3777today to schedule a time to come see it!.
Motorcycles 508
Plymouth, MA
2022 Harley-Davidson Iron 883 IRON in North Billerica, MA
$0

Used 2022 Harley-Davidson Cruiser

Iron 883 IRON
Stock # U405461
2022 Harley-Davidson Iron 883, PERFECT CONDITION! Used 2022 Gunship Gray Harley-Davidson Sportster Iron 883 XL883N For Sale! Authentic Harley-Davidson style through and through. The rubber-mounted 883cc Evolution engine runs hard and rides smooth for thousands of miles so you can just ride.This model is perfect for Urban riders seeking iconic style and V-Twin rumble and riders who want Middleweight power paired with precision handling. Come in and give it a test ride!
High Octane Harley-Davidson
North Billerica, MA
2022 Harley-Davidson® Low Rider® S S in North Billerica, MA
$0

Used 2022 Harley-Davidson® Cruiser

Low Rider® S S
Stock # U051305
2022 Harley-Davidson® Low Rider® S, <p>AMAZING CONDITION! Used 2022 Gunship Gray Harley-Davidson Softail Low Rider S FXLRS For Sale! An aggressive performance kingpin designed for the unapologetic power-hungry rider. An everything-black overload, paired with a deep solo seat for lone-wolf attitude. Top it off with a high-performance Milwaukee-Eight 117 V-Twin engine with precision oil/air cooling is the new pinnacle of torque and displacement in a factory-installed Harley-Davidson powertrain. Come in and give it a test ride and feel the M8 177ci for yourself!</p>
High Octane Harley-Davidson
North Billerica, MA
2022 Harley-Davidson® Street Bob® 114 114 in North Billerica, MA
$0

Used 2022 Harley-Davidson® Cruiser

Street Bob® 114 114
Stock # U014678
2022 Harley-Davidson® Street Bob® 114, <p>AMAZING CONDITION! Used 2022 Gauntlet Gray Harley-Davidson Softail Street Bob 114 FXBBS For Sale! No nonsense, raw bobber attitude packed into the lightest weight Softail, equipped with a Milwaukee-Eight 114 engine. A perfect performance base for customization. Milwaukee-Eight 114 engine, the most powerful option for a Softail. Two-up seating, black steel laced wheels, dark finishes. Available in four unique paint schemes, with the classic “Number One” graphic on the fuel tank. Come in and give it a test ride!</p>
High Octane Harley-Davidson
North Billerica, MA
2022 Harley-Davidson® Iron 883 IRON in North Billerica, MA
$0

Used 2022 Harley-Davidson® Cruiser

Iron 883 IRON
Stock # U405212
2022 Harley-Davidson® Iron 883 , <p>It was one of the early Dark Custom motorcycles. A dark pioneer of raw, blacked-out, stripped-down custom aggression. So the question was: how do you make something that good better? Here’s the answer. You build on it. All new suspension. A new rolled leather seat. Jaw dropping new pipes and wheels. All the details dialed in tight. The all-new Iron 883 motorcycle. Welcome to the state of the Dark Custom motorcycle art.Aggressive throwback styling taken to a place altogether new. No need to shine this machine. Just get on and tear up the nearest street.</p>
High Octane Harley-Davidson
North Billerica, MA
2021 Harley-Davidson Pan America 1250 Special 1250 SPECIAL in North Billerica, MA
$0

Used 2021 Harley-Davidson Dual Sport

Pan America 1250 Special 1250 SPECIAL
Stock # U307987
2021 Harley-Davidson Pan America 1250 Special, PERFECT CONDITION! Used 2021 Gauntlet Gray Metallic Harley-Davidson Pan America Special RA1250S For Sale!Exploring the world from a motorcycle engages the senses as the landscapes, sights and sounds create a deep, visceral adventure.The all-new Pan America 1250 adventure motorcycle is Harley-Davidson s explore-it-all machine for those who are driven to push boundaries and don t want to be confined by the limits of roads.Adventure touring riders seek out new experiences in any direction, on any terrain, to explore the undiscovered, sleep under the stars and immerse themselves in the journey. The Pan America was built for these explorers, to go further, until they find themselves in places few have traveled.Come give it a test ride and imagine the possibilities!
High Octane Harley-Davidson
North Billerica, MA
2021 Harley-Davidson® Road Glide® Limited LIMITED in North Billerica, MA
$0

Used 2021 Harley-Davidson® Touring

Road Glide® Limited LIMITED
Stock # U672900
2021 Harley-Davidson® Road Glide® Limited, <p>AMAZING CONDITION! Used 2021 Gauntlet Gray Metallic Harley-Davidson Road Glide Limited FLTRK For Sale! A long-haul, two-up touring specialist featuring the distinctive aerodynamic Road Glide shark-nose fairing with triple split stream vents that limit rider head buffeting. The standard Milwaukee-Eight 114 engine delivers smooth, powerful touring performance while dual Daymaker LED headlamps offer outstanding night visibility. Premium Touring suspension includes an easy-adjust rear shock pre-load for a smooth, confident ride. Reflex Electronic Linked Brakes with ABS deliver confident braking performance. The Boom! Box GTS infotainment system with color touch screen offers navigation, communication and entertainment options. Come in and give it a Test ride!</p>
High Octane Harley-Davidson
North Billerica, MA
2021 Harley-Davidson® Street Glide® in North Billerica, MA
$0

Used 2021 Harley-Davidson® Touring

Street Glide®
Stock # U606749
2021 Harley-Davidson® Street Glide®, <p>EXQUISITE CONDITION! Used 2021 River Rock Gray Harley-Davidson Street Glide FLHX For Sale! The look is backed up by the refined power of a Milwaukee-Eight 107 engine and high-performance suspension for an unmatched ride. THIS IS THE RIGHT BIKE FOR Riders seeking a slammed custom look, High-style in town and traveling the long road with a Milwaukee-Eight® 107 V-Twin engine and batwing fairing. It's got an upright riding position, Floorboards, a Passenger seat, spacious Saddlebags, and a Fork mounted fairing with Infotainment to help you navigate while blasting your favorite riding tunes! - This Street Glide even comes with Speakers installed into the Lids of the saddlebags! Come in and give it a Test ride</p>
High Octane Harley-Davidson
North Billerica, MA
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