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This appears to be a small daysailer, most likely a Herreshoff-style design, and it resembles a Haven 12 1/2 or possibly a Cape Cod Herreshoff 12 1/2. These boats are classic gaff- or marconi-rigged sloops with beautiful lines and are popular for their elegant design and excellent sailing characteristics.

Clues:

The varnished coaming and tiller

The fractional sloop rig with a furling jib

The small, classic cockpit with thwarts and internal halyard routing

The lapstrake-style hull (if visible), common in classic designs


That said, this specific boat may also be a Buzzards Bay 14, Cape Cod Bullseye, or even a Fiberglass reproduction of a classic wooden boat — several modern builders like Cape Cod Shipbuilding and Edey & Duff have produced fiberglass versions of these.

To get a precise ID:

Look for a builder's plate or HIN (Hull Identification Number) at the stern.

Or check with a local sailing club — this boat has a loyal following and is usually well known in local harbors.