Cross Insurance of Windham

Cross Insurance of Windham is an insurance agent in Windham, Maine, serving individuals and businesses with a wide range of personal and commercial insurance solutions. The agency offers auto, home, renters, boat, motorcycle, ATV, RV, and snowmobile insurance, as well as life, umbrella, and specialty policies. For businesses, it provides commercial property, general liability, workers’ compensation, cyber insurance, professional liability, and employment practices liability insurance (EPLI). The team also supports employee benefits, surety and bonding, and student health programs. With a strong local presence and a reputation built on trust, the agency serves customers across Windham and surrounding areas. It holds a 4.40 rating based on 23 reviews, reflecting consistent customer satisfaction.

Rooted in a legacy that began in 1954 at the kitchen table of Woodrow Cross, Cross Insurance has grown into one of New England’s largest independent insurance intermediaries, with over 40 branches across the Northeast. The agency has expanded through the acquisition of more than 150 operations and now employs over 1,200 professionals. As a family-owned business, it emphasizes integrity, hard work, and community commitment, supporting local initiatives such as food drives and youth programs. The agency has been recognized as the 2nd Largest Insurance Broker in Massachusetts across multiple years and ranked among the Top 20 Property & Casualty Agencies in 2025 by Insurance Journal.

Located on Roosevelt Trail in Windham, the office sits just 0.1 miles from the Windham Post Office, approximately 0.3 miles from the Windham Fire and Rescue District 2 and Manchester Elementary School, and within a short distance of Tandberg Trail. The area is part of the North Windham neighborhood, with Roosevelt Trail serving as a primary access route.

Cross Insurance of Windham is known for its reliable service, deep expertise in both personal and commercial insurance, and long-standing commitment to its community. Its standing reflects a trusted, locally rooted business with a national footprint. In Windham, it stands as a dependable partner for residents and businesses seeking comprehensive, personalized coverage.