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Length
How long a sailboat is will have a huge bearing on the price. However, this isn't the only thing you need to consider when looking at length. The actual length of a boat also determines things like how much mooring will be.
You see, you'll be paying per foot of the dock that you occupy, so the longer the boat, the more you'll pay on a monthly basis to keep your boat tied up at a dock. Some people, because of this, prefer to anchor out in the bay and keep only a small rowboat so they can get out to their boat and not have to pay huge moorage fees. However, if you plan to travel around with your boat, this is something to consider.
Price isn't the only thing in play here. How much room do you actually need? A very small sailboat can be nice for short outings or playing around. They are also quite popular for regattas, if you are interested in that sort of thing. However, the smaller boats also tend to capsize easily and are not stable enough for anything apart from slightly choppy water, which renders them quite limited.
A longer sailboat, 25-35 feet can actually include space for a home inside. If you plan to spend a lot of time on your boat, this is something to consider. It can be nice to have a spot to get out of the wind and make a cup of tea or lay down and relax while anchored. Having a living space means you can also take longer trips up and down the coast or out to islands . . . some people even travel continuously this way, living on their boat. Obviously, the more people that will be on the boat and the longer the time spent living there will affect how long you want it.
Keep in mind that the bigger the sailboat, the more difficult it will be to sail with just one person. Larger sailboats are either automatic or require two or three people to run it, something to remember when you are purchasing. How many people will you have to sail the boat with? Don't exceed the number unless you plan to hire extra hands.
Material
There are many different materials to build a sailboat from. You will likely have a preference based on looks already, but it's good to know a bit more about each sailboat material before you choose a used sailboat.
Concrete: This is not a very common boat material, but it does exist and should be avoided. Used concrete sailboats are usually a recipe for disaster and are too heavy and difficult to work with for a beginner.
Wood: Older sailboats are probably going to be made out of wood. This can be very beautiful, particularly when properly maintained. With the right woods, a sailboat can be lovely to look at. However, there are plenty of problems associated with wood.
Even treated wood will tend to rot away over time and it is something that also attracts insects and pests, both air and waterborne, which will destroy the wood. If you do opt to look at buying a wooden used sailboat, make sure you have a complete inspection done of the entire boat, above and below. Keep in mind that wood will require a LOT of maintenance and must be frequently painted or treated to keep it intact. This is not a great material for beginners or anyone who wants a boat they can use when they need it and leave it between times. Investing in a wooden sailboat is a bigger investment than the initial cost.
Fiberglass: This is by far the most common material for boats in general, including sailboats. Nearly all newer used sailboats will be built from fiberglass. It's resistant to corrosion and tends to be very durable. Make sure that there is no major damage to the finish, which could require some hefty repairs later. This includes gashes or gouges below the waterline, cracked finish or a very dull gelcoat that will require repainting, a costly endeavor.
Steel: While very hardy in construction, steel tends to be prone to rust which can render a great boat useless. Be sure to have a professional inspection if you are looking at a steel used sailboat.
Price
Buying a used sailboat is going to be your best bet for sticking to a budget. Brand new boats tend to be very expensive and while they do come in pristine condition, they don't come with sails, rigging, and all the gear that you'll need in order to actually sail your boat.
Usually, used sailboats will come with extras that you would otherwise have to buy separately. The sails and rigging will be used, as well, but if you take the time to look them over and make sure that they are in decent condition, this could be a very good deal. It saves a lot of money since you don't need to go out and find a set of sails and other extras, which can really add up.
Having your own sailboat, whether you just want a small one to have fun with close to shore or a larger boat that you can entertain on, is a great experience. You'll need to make sure that the maintenance is something that is kept up, or your beautiful boat can quickly turn into a money gobbling monster. Likewise, it's a good idea to have a used sailboat thoroughly inspected, no matter what material it's built from. You'll want to know just what you're getting and make sure that it is what you've paid for.

