The present research examined remains found from the Winchester Site in Winchester, MA that have evidence for postmortem alteration. The author compared the assemblages from Point San Jose (Hart et al. 2019; Willey et al. 2018), Holden Chapel (Hodge 2013; Hodge et al. 2017), Medical College of Georgia (Blakley 1997; McFarlin and Wineski 1997; Terrell and McFarlin 1997), Milwaukee County Institutional Grounds (Dougherty and Sullivan 2017), Newcastle Infirmary (Chamberlain 2016), and Blockley Almshouse (Crist et al. 2017; Hynes 2005) regarding patterns in bone modification and their potential causes. The sawn assemblage consists of 1365 adult remains, 67 juvenile remains, and 13 nonhuman remains. The human adult sawn Winchester Site sample is composed of 19.7% cranial remains and 80.3% postcranial remains. The postmortem alterations found on the remains from the Winchester Site lack pathological changes surrounding them. Eight of the 17 (47.0%) nearly complete crania exhibit evidence for craniotomy. Postmortem trephinations are seen in three crania. Repetition of surgical procedure training is seen through the 349 transverse complete kerfs located on the postcranial remains. There are 125 sternal segments and 133 rib segments with evidence of sharp force trauma, potentially from thoracotomy. The postmortem alteration within the faunal assemblage can be attributed to butchery on the elements from cow, sheep, and unidentified mammal, and dissection on the elements from the dog and red fox. Implements utilized on the skeletal remains were a flat-bladed saw with 18 teeth per inch (TPI) and a trephine. The remains from the Winchester Site exhibit experimentation with kerf locations, most likely originating from surgical training practices.