
Highstreet Insurance Partners in Traverse City, a community-based insurance brokerages and financial service firm, has announced its acquisition of Winder Insurance Center headquartered in Winder, Ga. Terms of the deal were not disclosed.
The transaction, which adds an office with expertise in business and personal insurance solutions, is part of a growth phase for Highstreet Insurance.
Last year, the firm announced its partnership with Wingert Insurance Agency in Mill Creek, Wash., which provides employee benefits and property and casualty solutions to clients across the local Washington area.
In 2024, Highstreet Insurance announced it had acquired Flagler Insurance Agency in Palm Beach, Fla. The transaction added three offices in Florida to Highstreet’s portfolio — Cape Coral, Clearwater, and Palm Beach — along with an office in Lexington, Ky. Flagler provides commercial, personal, and private client insurance solutions.
In addition, Flagler specializes in serving the equestrian, commercial real estate, and financial services industries.
Winder, under the leadership of Russ Shepley and Brett Gamblin, has become a leading player in the Georgia insurance market. The company focuses on serving clients personal and business insurance needs with additional expertise in commercial real estate, professional, and contractor risks.
Russ and Brett will continue to lead the Winder team out of the Winder, Ga., office and will join Highstreet’s Southeast Region, headed by Alyssa Rockwell, regional president.
“Winder’s expertise and ability to provide wholistic coverage to their clients will help support Highstreet’s strategy in the Georgia market and the entire Southeast Region,” says Rockwell. “We’re excited to have Winder join the Highstreet team.”
A full-service independent insurance agency, Highstreet Insurance was founded in 2018. The company provides a broad array of business insurance, employee benefits, personal insurance, retirement services, and specialty risk solutions delivered through community focused agencies.
For more information, visit hsip.com.



