The R44 is a single-engined helicopter with a semi-rigid two-bladed main rotor and a two-bladed tail rotor and a skid landing gear. It has an enclosed cabin with two rows of side-by-side seating for a pilot and three passengers. Tail rotor direction of rotation on the R44 is reversed compared to the R22 for improved yaw control authority. On the R44 the advancing blade is on the bottom.

Designed during the 1980s by Frank Robinson and his staff of engineers, the R44 first flew on March 31, 1990. The R44 Astro was awarded an FAA Type Certificate in December 1992, with the first deliveries taking place in January 1993. In January 2000, Robinson introduced the Raven with hydraulically-assisted controls and adjustable pedals. In July 2002, Robinson introduced the Raven II featuring a more powerful, fuel-injected engine and wider blades, allowing a higher gross weight and improved altitude performance.

In 1997, a Robinson R44 was piloted by Jennifer Murray for the first helicopter circumnavigation of the world by a woman, covering a distance of 36,000 miles in 97 days. Chilean president Sebastián Piñera owns one of these choppers, and has made several public appearances flying it. Since 2002, Belgian Prince Philippe flies a red R44 for personal leisure, with the unique registry code "OO-PFB", which stands for "Prins Filip België".  British singer Jay Kay also owns an R44 (registry code G-JKAY), which he pilots in the music video to the song White Knuckle Ride.