Len Benefico
About Len
A lifelong Chicagoan with nearly 35 years of experience in residential real estate, Len is a trusted name in the Chicago market. A consistent multi-million dollar producer and recipient of the Legend's Chicago Magazine Five Star Award for service excellence for 10+ years and counting, Len has built a business rooted in results, referrals, and long-standing client relationships.
Known for his thorough market knowledge, patience, and practical advice, Len is a true partner to his buyer clients whether they’re buying their first home, moving up, downsizing, or investing in apartment buildings of any size. He guides clients through every step of the process with clarity, professionalism, and a commitment to making their goals the priority.
Sellers benefit from Len’s strategic pricing, staging insights, and sharp negotiation skills, all aimed at maximizing value and ensuring smooth, profitable sales.
Outside of real estate, Len has enjoyed playing and coaching both volleyball and basketball and leisure time in Wisconsin at his summer cottage.
Whether you’re buying, selling, or simply exploring your options, Len brings decades of experience and a personal touch to every real estate journey.
The Benefico Sullivan Group’s Past Sales
The Benefico Sullivan Group’s Exclusive Real Estate Listings
See what people are saying about Len
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Thao D. Lenny Benefico was instrumental in helping me purchase my first home located in Skokie back in 2005. Despite a challenging bidding war where I initially ranked third out of eight buyers, I maintained the same re-bid under Lenny's expert guidance and ultimately secured the home. Since then, it has been and will be the only place I call home. Fast forward to 2024, Lenny now partnered with Chrissy, once again worked their magic by assisting with selling my mother's charming vintage home in Chicago. Their unparalleled expertise, combined with their charisma, keen eye for design, meticulous attention to details, and insightful renovation advice, led to a verbal cash offer during a tour and swift closing, all while in the typical slow fall season. Both experiences were seamless and transparent. They genuinely care for their clients and all parties involved. Lenny and Chrissy are my trusted realtors for life!
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SalknoNorth Park Len was exceptionally helpful from the very beginning as he responded within minutes to my inquiry for the purchase of a condo in Chicago. He paid close attention to my needs and was ready to arrange visits as soon as something in my area of interest arose. Anytime Len noticed something of concern, he was in touch offering suggestions for how I go about addressing any problems. His attention to every detail and expertise in helping me navigate terrain I was unfamiliar with was most appreciated.
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Natalie P. Len made our home buying experience easy and fun! As first time home buyers, we were nervous to start our search in the midst of chaos (started looking in March at the onset of the pandemic). Len was able to ease our concerns through his knowledge of the housing market and his years of experience in the industry. Throughout the process, we talked with Len almost every day! He was always available to talk, answer questions, provide us with information on next steps and his ideas on how to progress our search. He found us a perfect home and worked the negotiations seamlessly! I can't thank Len enough for all the support he provided to us throughout our search. We are so happy in our new home and have him to thank for that!
