- Seller: Mark S (Contact)
- Location: Willowbrook, Illinois
- Mileage: 19,554 Shown
- Chassis #: 1HD4CJM18XK146676
- Title Status: Clean
- Engine: 883cc w/Screaming Eagle Kit
- Transmission: 5-Speed Manual
Harley-Davidson’s Sportster has long been one of the most approachable ways into the brand, offering classic styling, manageable size, and plenty of aftermarket support. This 1999 Harley-Davidson Sportster 883 appears to be a clean rider with tasteful upgrades, extra accessories, and a very reasonable reserve. Located in Willowbrook, Illinois, it is now offered at auction with a clean Wisconsin title.
The bike shows 19,554 miles and is powered by Harley’s Evolution V-twin paired with a 5-speed manual transmission. The seller states that a previous owner claimed the engine was bored to 1200cc using a Screamin’ Eagle kit, though no paperwork is available to document the conversion. Because of that, prospective bidders should treat the claim as just that, a claim, but it would be worth taking a closer look.
Finished in black, this Sportster has a traditional, no-nonsense Harley look. The photos show a clean bike with orange Scott high-performance ignition wires, straight pipes, drag bars, highway bars/case savers, forward controls, and a trimmed black fuel tank. The overall presentation is simple, purposeful, and more cruiser than showpiece. The only noticeable flaw is a small dent on the top of the fuel tank, which the seller has provided a photo of.
The seller notes that the sale will include several extras, including a two-up seat, backrest, and removable windshield. Those additions give the next owner some flexibility depending on whether they want a stripped-down solo look or a more comfortable setup for longer rides.
Sportsters are popular because they are easy to ride, easy to modify, and easy to maintain compared with many larger motorcycles. This example looks like a good candidate for someone who wants an affordable Harley to ride as-is, personalize further, or use as a weekend cruiser. With a clean title, under 20k miles, useful accessories, and a low reserve, this 1999 Harley-Davidson Sportster should appeal to riders looking for a simple, classic American V-twin without spending big money.
The Screaming Eagle kit on HD’s site shows jugs, pistons and heads. The jugs and heads are matte black not bare aluminum.
Nice looking bike.
Write up says they bored the 883 jugs for the 1200 slugs, which would have been possible in ’99.
I bought a 99 883 in 2000 and put over 80,000 miles on it and never had a problem with it. Gave it to my brother when I found a 99 1200 with only 14,000 miles on it for 2500 bucks. Have had it for 3 years so far and no problems either. Both have been great bikes!
A good ol’ Sportie! It seems to me they came out with this version in the mid 80s. A friend of mine got one and rode the wheels off it. My brother bought one in the 90s and put well over 100K miles on it. I remember the oil pump being the most worn out pump I ever saw and I am truly amazed that the engine hung together as long as it did.
I’m not sure if he’s still got it or not. Since his boys rode it, I wouldn’t be surprised if one of them still rides it…
I always thought Harley missed the boat BIG TIME, by not offering a dual sport Sportster. And,,,,you know what’s coming, uhp, uhp, uhp,,,several( many) years ago( 2014?), before I moved to Colorado, I was living at my parents in Milwaukee getting the house ready to sell, when I get a call from George, saying he was in town and has 2 tickets to the Harley Museum, and since his lovely wife wasn’t going, would I like to go? We had a wonderful afternoon, even though I walked right past him in the parking lot, but we never met before. I’ll never forget that, my friend. I strongly advise anyone in the Milwaukee area to check it out. Like the Studebaker museum, you shan’t be disappointed. Thanks again, pal :)
Always looked like fun bikes to me. 👍
This is a good bike if you’re a woman who wants to start riding. A few years ago my friend asked if I would ride his wife’s sporty around the block to make sure it was performing ok. It was fine but I do remember that the CG was quite high up which made it handle way different than my Dyna.
Thank GOD a Harley finally graces the screen. All these ring dings has me a bit twitterpated. Now, I happen to notice, not 1 tums up( I did all those) and no bids and less interest than a show shovel on the 4th of July. I am upset about that, instead of twin HD pipes in the night, all we hear are the stories now,,in the night. For most of us responding to this, we have fond memories of biking. Today, when was the last time you even SAW a group of bikes? ANY KIND OF BIKE? Well, just the way the cookie crumbled, I suppose, and so far 2026 is shaping up to be the most deadly of all time in Colorado for motorcycles.
Yeah, well, shows what distracted driving can do, and I won’t ride a motorcycle in traffic today.
Not the case 25 years ago( eep). After my divorce in ’99, we sold our farmhouse and I had a wad of cash, but no family or house. In desperation to fill that void, I went to the local HD dealer, and overpaid $10grand for a rebuilt 1985 FXRT, the “GoldWing” of Harleys. Oh, but t’was no GW, and I loved that bike, except for the belt drive that me or my GF never had an issue with,,,still. I removed the fairing, and made it into a low-rider bagger. All my friends had Harleys, and we’d go on rides, I only hope are duplicated in Heaven. I met my girl friend about that time, I lived with for 12 years, and she had a 1999 HD XL Sporty 1200S, that was her brothers, and at the time, was the top of the line Sporty. She was kind of a bigger gal, and would have been more at home on my bike, but it was her 1st ( and only) bike and I tell you what, that was a really nice bike. It wasn’t my “Big Twin”, but I’ve been around older Sportsters, and not impressed, but the 1200 was the perfect sport bike. Always started( electric) PLENTY of power, and just rode nice. No Asian bike can compare, even my GWs. Sorry, motorcycling ka-put, and that’s a shame. We sure had fun with these, hey? I don’t know what is fun today. Thank you, BFs, someone, if any, will get a really nice bike here.
I still have my 1981 FLHS that I bought new in 81. Love that shovelhead.
Three things I learned after buying my wife an 883 sportster:
1. It’s a great starter bike, especially for women – actually no. It’s a terrible starter bike. A 125cc enduro on the trails or around the ‘hood is a great way to learn to ride. At nearly 600 lb., sportys are very heavy for a new rider or anyone under 175 lbs. for that matter. They also handle poorly and have terrible brakes…not for the inexperienced rider, especially one you care about. It’s the cheapest HD for a reason.
2. Riding an 883 is pretty much like riding any other HD – no again. Thinking of the 883 as the worst sport bike ever made helps here. The motor wants to rev but doesn’t make much power and almost no low end grunt. If you try to lug it around like a big twin, you’re going to get run over. You have to rev it to the limiter to get anything out of it, and that won’t be much. I could outrun it on my son’s Ninja 250.
3. The 3.3 gallon peanut tank is cool – nope. It’s a pain in the butt…get the big tank.
On the bright side, an unbaffled set of sideshots will make it sound awesome, and for about $4K, you can get a Brembo front brake kit and some good Ohlins rear shocks, which make any sporty much safer and easier to live with. And you can always convert it to a 1250 when you’re ready.