Welcome to Stateline Senior Services

Let Us Help You Understand Your Future

Founded to specialize exclusively on the insurance and investment needs of the retired and soon to retire, Stateline Senior Services, LLC can help you find the best Medicare Supplement and Medicare Advantage plans for your situation.  Since 1983 our founder, Bill McCloskey has worked to  help our clients with retirement and investment planning.  We design income plans and can help with advanced long term care planning as well as crisis planning. We are a Fiduciary regulated by the state of Connecticut and never charge fees for consultation or planning services. Our trained staff is equipped to service our clients in North Central Connecticut and the surrounding communities in Connecticut throughout the year at our convenient Somers location.



Learn more about what Stateline can do for you.


Register for workshops held throughout CT.


Answer financial questions with our calculators.


Contact us for a free consultation.

Prepare for your future. Contact Stateline Senior Services for more information and a free consultation today.


Dave Ramsey’s Financial Peace University

daveramsey.comA biblically based curriculum that teaches people how to handle money God’s way.


The Macie Grace Foundation, Inc.


The Macie Grace Foundation, Inc. supports families that have been given a diagnosis that their child is critically ill.

Privacy Notice    |    Terms of Service    |   Do Not Sell or Share My Personal Information

Stateline Senior Services is not endorsed by government agency or Medicare.

We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options.

Investment Advice offered through William Joseph Capital Management, LLC, a Registered Investment Advisory Firm (RIA) registered with the U.S. Securities and Exchange Commission (SEC). William McCloskey is an Investment Advisor Representative of William Joseph Capital Management, LLC. William McCloskey provides insurance services separate from William Joseph Capital Management LLC. Stateline Senior Services is not affiliated with William Joseph Capital Management LLC.

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