Chicago is where Windsor planted its roots in 2012, and it remains our home today. From the Loop to the suburbs, we’ve helped Illinois policyholders unlock the hidden value of their life insurance policies — always with independence and integrity at the core.
Not every company plays it straight. Some buyers run multiple life settlement “marketing companies,” creating the illusion of choice while pushing you toward a single buyer and a smaller check. Others use tactics like “expiring” offers or artificial deadlines to pressure policyholders into accepting less than they deserve.
Windsor rejects that model. As a full-service, independent life settlement broker, we represent you — not the buyers. We introduce your policy to a wide network of institutional investors who compete for it, and we guide you through every step with clarity and transparency.
Policyholders across Chicagoland turn to Windsor because we bring independence, strategy, and results to the life settlement process.
Better Offers Through Competition – With multiple investors bidding, policies often sell for far more than direct offers.
No Pressure Tactics – We never use “expiring” offers or high-pressure sales. You decide on your timeline.
Full-Service Representation – From valuation to negotiation, Windsor manages the process from start to finish.
Chicago Roots, National Reach – With more than a decade headquartered here, we pair local accountability with the strength of a national investor marketplace.
For Chicagoans, Windsor means more than a transaction — it’s a trusted partner committed to delivering the best possible settlement.
From downtown to Oak Brook, Naperville, and the North Shore, Windsor works with policyholders across the entire Chicagoland area. Our process is designed for convenience: you can review offers and make decisions from home while Windsor handles the details behind the scenes.
Being headquartered in Chicago means more than geography. It means accountability, accessibility, and a deep connection to the community we’ve proudly served since 2012.
If you’re a Chicago policyholder considering a life settlement, don’t let a direct buyer or life settlement “marketing company” dictate your outcome. Windsor ensures your policy reaches true competition — without deadlines, gimmicks, or pressure. Just full-service representation focused on you.