Winter increased the meager income from his congregation by establishing an Academy in 1783 and charging tuition. One of his pupils was William Jay. At most the Academy had twelve students   Winter's Academy in Marlborough, in operation 1783-1788, was one of England’s Dissenting academies for training Dissenting clergy. Cambridge and Oxford were closed to Dissenters by the Act of Uniformity of 1662. Winter used an “informal manner” of teaching. Lectures were replaced by “reading and a tutorial or seminar”. The Academy had a balance between “practical and theoretical elements of training”. As part of the practical training, Winter had his students preach in area churches very early in their course. After a decade at Marlborough, chronic illness forced Winter to close his Academy and lose that income. Furthermore, his major benefactor was in “declining health” and his sons were hostile toward Winter. Thus, when a congregation at Painswick in Gloucestershire requested his services, he accepted. The congregation of Christ Church nonconformist chapel at Painswick already knew Winter and his preaching. He and his wife moved there on 2 August 1788. During his tenure in Painswick, Winter rebuilt the chapel in 1803 and established a Sunday school. He also bequeathed two cottages to the congregation that were later used as the site of a school”  In 1910, a story about the closing of Christ Church in the Painswich newspaper spoke of Winter as a “very influential pastor at Christ Church”. As he had done at Marlborough, Winter established an Academy at Painswick, which operated from 1788 until his death. Sunday, 13 December 1807, was the last time Winter preached. On the following Friday evening, lying in bed, Winter “stretched himself out, laid his arms at length upon his body, and indistinctly said,"Come Lord Jesus;" and died. Winter’s interment was January 19. Some thirty ministers of various denominations attended. His remains were placed in the vault beneath the pulpit. People of different religious beliefs opened their homes to those “who came from a distance”. The rector of the parish apologised for not attending, as he put it, “the funeral of the ‘ever to be lamented’ Mr. Winter”. Rowland Hill expressed his opinion of Winter, by affirming that "he would make the very worst devil of any man on earth".