Most unsold listings aren't bad — they're just priced like new instead of priced like used.
A good starting rule: look up what the item costs brand new today, then price used furniture at 30-50% of that if it's in good condition, and electronics at 40-60% depending on age and whether the original box/charger is included. Buyers on classifieds expect a real discount versus retail — that's the whole appeal.
Condition matters more than brand for furniture. A well-kept IKEA couch will often outsell a stained designer one. Be upfront about scratches, stains, or missing parts in the listing itself — it saves you from awkward in-person negotiations and builds trust before anyone shows up.
For electronics, mention the age, battery health if relevant, and whether it's unlocked (for phones). "iPhone 12, unlocked, battery at 87%, no cracks" tells a buyer everything they need in one line.
If an item doesn't get interest in the first week, drop the price 10-15% rather than waiting — Chicago's classifieds market moves fast, and stale listings tend to get skipped over even after a price cut, so it's better to adjust early.
Bundle small items. "Desk + chair + lamp, $60 for all three" often moves faster than three separate $25 listings, because it saves the buyer a second trip.