Cypress Group announces sale to PE-led investment group

An investment group led by lower middle-market private equity firm Milestone Partners Management Co. LP is acquiring the majority of Jacksonville, Fla.-based Cypress Group Holdings Inc.

Insure Homes Holdings LLC, which the private equity firm formed in December 2020, invested in the recapitalization of Cypress Group and its affiliated insurance service technology companies, Cornerstone Operations Group, Allied Restoration and reinsurance brokerages Access Re and Vista Re.

The change of control is subject to the approval of the domestic regulators of Cypress Group's insurance subsidiaries that include Cypress Property & Casualty Insurance Co. and Access Home Insurance Co.

Cypress Group owns managing general agent and insurance carrier subsidiaries that serve homeowners in the Gulf Coast and the southeast region.

Citizens Bank NA led a senior credit facility with Hancock Whitney and CIBC to support Insure Homes in the transaction. Troutman Pepper LLP was the legal adviser of Insure Homes and Milestone Partners, while Stonybrook Capital was the investment banking adviser of Cypress Group.