About Us

The Rand Difference

Rand Insurance is one of the largest independent insurance agencies in southwest Connecticut. For over 80 years, we have been a steadfast shield against uncertainty, the unknown and the unexpected.

Our people are what set us apart – innovative staff with the insight, experience and imagination to plan for every curve life can throw your way. We embrace the understanding that in the real world, claims and losses are inevitable. Solely on that basis, we are committed to help you lessen your exposure to certain risks and attempt to reduce the likelihood of their occurrence. When you work with Rand, you have a team dedicated to understanding your needs, not just selling you a policy. Whether it’s personal or commercial insurance, life or health insurance, we can custom-design solutions that are right for your unique circumstance.

With offices in Riverside/Greenwich, New Canaan, and Darien/Rowayton and Florida, and licensed in over 45 states, we’re ready to help every client prepare for a more prosperous, secure future. Communication is essential and a key element in making every Rand relationship important. We’re always ready to talk – and more importantly, always ready to listen.

Our Mission Statement

Committed to Service Excellence With Understanding and Innovation

At Rand Insurance, we are committed to excellence in every facet of our work and will strive to provide tailored, quality insurance products best suited to protect our customers’ assets.

Our commitment is to serve our clients first and foremost. We not only listen to, but understand our clients’ needs and measure our success by our customers’ satisfaction.

Our History

Rand Insurance started small in Greenwich, CT in 1938. We weren’t the largest agent around, so we dedicated ourselves to being the smartest, with personal service and innovative thinking that helped our clients reach their goals. Better service wasn’t just a slogan; it was the cornerstone of our company’s culture.

As the 3rd generation Rand and after leading and building the business for 50 years, Stanley “Sandy” Rand retired in 2019.   His legacy carries on with his daughter, Lindsay Rand McGuckin, as she continues to represent the family and help Rand Insurance flourish and be one of the largest independent insurance agency in southwest Connecticut with offices in Greenwich / Riverside, New Canaan, and Darien / Rowayton.

Sandy Rand and Lindsay Rand McGuckin

Representing Trusted Names

What Our Clients Say

We’ve Got You Covered

Protect yourself against the unexpected. Rand can provide the answers and insights you want, and we can design the custom insurance solution you need.

Riverside / Greenwich

1100 East Putnam Avenue PO Box 900 Riverside, CT 06878

Darien / Rowayton

30 Old King’s Highway South Darien, CT 06820

New Canaan

51 Locust Avenue Suite 204 New Canaan, CT 06840


45 Sherman Street, Fairfield, CT 06824