Craigslist, as a popular free online classified advertisement site that still maintains a broad user base, needs a redesign to meet the needs of modern users. According to interviews with its current users, the redesign will focus on buyers and sellers. The necessary improvements include (1) New UI and UX design. (2) Increase credibility and reliability by establishing and measuring trust, primarily of the buyer towards the seller. (3) A suggestion sale price based on various possible factors of previous sales when posting an item for sale. With the new Craigslist, the buyers can find trustworthy sellers more efficiently through seller rating (rating and review based on previous sales) and social network accounts. The sellers could sell their items faster while making an acceptable profit if they choose to use the system’s suggested sale price.