Just tossing out a few names:
Freya (esp. the 39)
Some of Chuck Paine's midsize designs
Trouble is, sailboats are priced to some extent on tonnage (ferro excepted
). The boats above are going to be difficult to find under $100 in good condition. They hold their value because they appeal to a small but stubbornly committed population of full keel enthusiasts.
Also, boats with long keels (and attached rudders) are always, always going to sail poorly to weather because neither foil lifts worth a darn. To go upwind, you need deep, short-chord appendages.
Here's an interesting cutter
builder called Horizon. New to me. Quel
salty. Ain't going to point too high with that keel, but the split rig could make sailhandling easier. Mizzens are great for drying laundry, too.
Certainly in your price range.