Around 35 staff are understood to have been made redundant by insolvency specialist FRP.
The Kirkcaldy family-owned firm specialised in groundworks, drainage and plant hire and celebrated 50 years in business this year.
FRP Advisory partner Callum Carmichael said: “James Penman struggled to maintain its financial obligations which stemmed from the pandemic and, regrettably, has entered liquidation.
“Our job now is to focus on supporting all staff that have been impacted with their applications to the redundancy payments service as we wind down the remaining business.”