We’re Hiring! Join the Winters-Oliver team!

Experience the
Winters-Oliver Difference

Choice. Expertise. Innovation. Service.

The origins of Winters-Oliver Insurance Agency date back to 1945, when E. Ray Winters Sr. founded an independent insurance agency in the Broad-Grace Arcade building near Grace & 5th Streets in Richmond. Today, Winters-Oliver is a specialty insurance agency offering property & casualty insurance and employee benefits to small and middle market businesses.

Business

Insurance solutions tailored to fit your unique lifestyle

Personal

Insurance solutions tailored to fit your unique lifestyle

Employee Benefits

Insurance solutions tailored to fit your unique lifestyle

Specialty

Insurance solutions tailored to fit your unique lifestyle

Professional Affiliations

Arbor is proud to have professional affiliations with some of the insurance industry’s most respected organizations. We are also an active supporter of the Lehigh Valley business community and are committed to the future of area businesses.

Home

Home

Home

Home

Home

Home

Winters-Oliver took the time to understand our business and saved us significant premium dollars on our workers compensation. We have been so happy with the team at Winters-Oliver, we moved our general liability and umbrella policies to them as well. They are proactive and always respond quickly to our service requests. I appreciate their partnership and highly recommend them!

Julie McGlothlin, Owner
Rain Guard Roofing LLC
Elkton, Virginia

We began working with Sherwood Bowditch for our commercial insurance and employee benefits when our distillery was in a time of growth and we needed more support and expertise for managing our risk. Sherwood helped us arrange our insurance and risk management in a way that made much more sense for our distillery. His understanding of our industry and proactive support has made him a trusted advisor that we value greatly.

Dave Cuttino
Reservoir Distillery
Richmond, Virginia

Winters-Oliver has been servicing our business insurance needs, including commercial liability, malpractice, workers compensation and employee group health insurance since 2017. We are very pleased with the level of service we receive from everyone at Winters-Oliver. They are knowledgeable professionals who are really engaged with their customers and quickly respond to support needs. They have consistently advocated to ensure we are appropriately insured at the best rates by quality carriers. I highly recommend Winters-Oliver for all of your business insurance needs.

Erika Eades, Human Resources Manager
Strategic Therapy Associates
Lynchburg, Virginia

In November 2020, the waste line collapsed between my house and the street. I received bids ranging from $6,000 to $10,000 for the cost of replacement. I did not expect this to be covered by insurance but I called Winters-Oliver just to be sure. They reviewed by policy and found coverage for the cost of excavating the yard to access the broken pipe which saved me $4,000! I was so thankful that Winters-Oliver placed my homeowner’s with a reputable company providing such broad coverage. They truly saved the day (and Christmas) for my family!

Rebecca W.
Richmond, Virginia

We Love Hearing From Our Clients!

We love hearing from our clients!

Were you happy with your Arbor experience? We’d love to hear about it! Please tell us about your experience with a Google review!

I have been close friends of the Hackers for many years. I know their character and am sure they would offer the best product possible. I have never been disappointed with any of the dealings I have had with Arbor. I would gladly recommend their service to anyone

Rev S.
customer since 2001

I have been close friends of the Hackers for many years. I know their character and am sure they would offer the best product possible. I have never been disappointed with any of the dealings I have had with Arbor. I would gladly recommend their service to anyone

Rev S.
customer since 2001

I have been close friends of the Hackers for many years. I know their character and am sure they would offer the best product possible. I have never been disappointed with any of the dealings I have had with Arbor. I would gladly recommend their service to anyone

Rev S.
customer since 2001

I have been close friends of the Hackers for many years. I know their character and am sure they would offer the best product possible. I have never been disappointed with any of the dealings I have had with Arbor. I would gladly recommend their service to anyone

Rev S.
customer since 2001

I have been close friends of the Hackers for many years. I know their character and am sure they would offer the best product possible. I have never been disappointed with any of the dealings I have had with Arbor. I would gladly recommend their service to anyone

Rev S.
customer since 2001