Corrected entry: The bench used in Mrs. Farrel and Annie's duet number has wheels that are plainly visible. The chair that Annie spins in likewise has wheels, where all other chairs in the room don't.
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Correction: Casters on furniture were patented by David A. Fisher in 1876 (and have been around since even earlier). Specifically designed to move furniture across hardwood floors, they were made from glass or leather and were very heavy. They definitely would have been on chairs and benches when Annie was set. As for Miss Hannigan only having one chair that rolls, she may have felt she didn't have room for more than one or she may not have been able to afford more than just one (remember that she doesn't make or get that much money).