What about for $30,000 or less
There are a lot of good boast out there under $30K. The key is to figure out where you are going to sail, what your abilities are and what your real needs and wants will be. Different sailing venues favor different types of boats. Boats below mostly leab toward good performance, reasonable accomodations and construction suitable for coastal cruising: (These should all be under $30K, most have inboards which I think is preferable for cruising.)
-Albin Ballad (30 feet (1973-1978) $12-20K)
These are reasonably fast and very well built and finished boats. They are not especially roomy but are good boats for short handing. They are beautiful looking boats. Most have a Volvo 10 hp diesel.
Albin Cumulus (28 feet-(early 1980''s) $15-18K)
These fractional rigged sloops would be a ideal first boat. They are reasonably fast (although 60 sec''s a mile slower than my Laser 28) and easy to handle. They are nicely finished and typically have diesels. The interiors on these boats are not exactly plush but is reasonable for the kind of stuff we do on the Chesapeake.
Beneteau First 30 or 30E (30 feet (early 1980''s) $18-22K)
Fairly modern design that should sail reasonably well. Not the most solid boats but fine for around the Chesapeake or Long Island Sound. They had diesels and pretty good hardware. The 30E might be a fractional rig, I don''t recall.
-C&C Corvette (31 feet (1967- 1970) $15-22K) and -C&C Redwing (30 footer ( 1965-1970) $12K- 20K)
Attractive and reasonably venerable designs; they are not especially fast but OK for the era. The Corvettes are moderately long keel/ centerboard boats and so are great for poking around the shallower areas of the Bay. The Redwings are fin keel/space rudder boats. They are really not competitive racers any longer.
Cal 2-30 and Cal 2-29''s (just under 30 feet (mid 1960-early 1970''s) $10-18K)
These are reasonably built racer cruisers that have reasonable accommodations and pretty fair sailing ability. Like the Cal 25, the design is a dated and if the gear has not been updated will be less convenient than a more modern design.
Dehler 31 (31 feet (Mid to late 1980''s) under $20K to mid-20K range)
These are really neat little boats. They are not as fast as my Laser 28, for example, but are quite fast and look easy to sail and single-hand. They are fractional rigged and have a very nice interior plan. They would one of my favorites on this list for a first boat that can be both cruised and raced.
Dufour 2800 (28 feet (mid 1980''s) mid $20K)
These are OK boats with a big following. They are not my favorite but they would not be a bad boat if the price were right.
Irwin Competition 30 (30 feet(mid 1970''s) $12-16K)
These were well rounded little boats that sailed well and had reasonably nice interiors. There was one that dominated its class in PHRF for years. Irwin''s were not the most solidly built boats and so you are looking for a well maintained example in reasonably good shape.
MG27 (27 foot (Mid 1980''s) under $20K)
Nice little fractional rigged English boats. They seem to be well mannered and have an interior layout similar to my Laser 28. They have a diesel aux. But tiny tanks that will need to get upgraded.
Oday 28 & 30 (28 feet and 30 feet(late 1970''s and early 1980''s) $12-20K)
These were not the best built boats or the fastest boats in their day but are common and sail reasonably well.
1970''s vintage Tartan 30''s, (30 feet( 1970''s) under $20K)
These are my favorite masthead sloops of that era. They are good all around boats. Most still atomic 4''s but you can find them with diesels.
Late 70''s/ early 80''s Hunter 30''s, (30feet (15-20K)
These are under appreciated boats. We have had two in my family and again it is a matter of finding one that has been upgraded and is in good clean shape. My Dad raced his in PHRF and went for a couple years without finishing lower than a first or second. They are roomy and surprisingly fast.
70''s vintage Pearson 30''s (Not Flyers)
These are very venerable racer/cruisers on the Chesapeake. They have an active one-design class and are also good boats for cruising the Bay. Of course they come in all kinds of condition from really well maintained and up graded with good racing hardware and a diesel engine to stripped and trashed. You can buy them from under $10K (but you would not want any in that price range) to something approaching $20K. You should find good boats in the high teens.
Ranger 29 (29 (early 1970''s) 10-18K)
These are good sailing and nice cruising little boats. They should be adequate for club racing and are certainly good boats. They were not the best built boats and so you should be looking for a clean and updated version. Still they offer a lot of bang for the buck.
Wylie 28 and Wylie 30 (28 and 30 respectively(late 1970''s to early 1980''s) 10-15K)
These are neat little boats that sail well and are really pretty interesting. The few that I have seen have good hardware and have had simple but workable interiors. They came in fractional and masthead rig versions. There was a masthead version that did quite well on the Bay. There was a one design version called a Hawkfarm but they never caught on the Chesapeake but are still raced in S.F. Bay.
If you want something that is more of a performance boat than cruiser, you might look at :
Shockwave (also called Schockwave 30, or Wavelength 30 )
If you want some thing more traditional:
C&C Redwings and Corvettes
Pearson 35''s, Coasters, and Wanderer''s
Chesapeake 32''s and Vanguards
Now you will find that more traditional boats have less room and will have older equipment but they should cost less money and for some applications may be better (albeit slower and wetter) sailing boats than some of the newer boats on the market today.