When looking for used sailboats for sale for the first time, the buyer might face a bunch of daunting decisions. You are talking tens of thousands of dollars for a boat that might be 20 years old or older. For example, a 35 foot Pearson made in 1986 could go for $50,000. It all depends on what type of sailboat you want as well as where you are going to sail it. If you want a big sailboat with a fully enclosed saloon, a large galley, two heads, an engine with low hours and berths for the entire family, it is going to cost more than a vessel made for day trips on a lake. Also, that big boat rated for offshore sailing is going to cost more. Oceangoing sailboats have to survive rougher seas than sailboats used on coastal waterways or the Great Lakes.
The navigation electronics on an offshore vessel are going to look more like what you see on a cruise ship. You are likely to have radar and electronics to sail in bad weather and total darkness. Larger sailboats are going to have at least one diesel engine to get you to shore in an emergency. You might be interested in a sloop with an open saloon. The saloon is the “living room” or social area where people gather. They can be open to the weather or fully enclosed or any mix in between.
Every added feature on a sailboat increases its value. Also, there are some top manufacturers that have a proud history of producing quality sailboats. Some of their older models might be a better investment than buying a bargain new model of a similar style of sailboat. You do need to do a lot of research on the the particular boat you find yourself interested in, but the rewards of sailing cannot be beat.