Ridgefield Fire Chief Heather Burford said the plane clipped the tops of several trees before flipping over and landing on its roof on a front lawn.
She said the pilot, a man in his 50s, had reported his engine was out shortly before the plane went down.
Burford said the man was treated for non-life threatening injuries at a local hospital.
The Connecticut Post identified the pilot as Robert Baldwin. His wife, Frances Baldwin, told the paper her husband was "fine."