Downsizing & senior transition specialist
As a designated Seniors Real Estate Specialist® (SRES®), I’ll help you plan the next steps.
Watch
Selling a longtime home, buying the next one, or doing both, here’s what working together looks like.
Free self-assessment
A self-assessment to help you decide.
Answer 20 questions across four categories to discover if downsizing might be right for you. This takes about 5 minutes.

Your Chicago real estate advisor

As a licensed REALTOR® and designated Seniors Real Estate Specialist® (SRES®), I represent homeowners and buyers throughout Chicago’s North Side and Evanston. I understand the financial, logistical, and emotional considerations that can come with leaving a longtime home.
My role is to listen carefully, communicate clearly, and handle the transaction from start to close while staying in step with everything else happening in your life.
More than a transaction
Practical help deciding what to keep, share, donate, or move, at your own pace.
Connections to organizers, movers, attorneys, financial professionals, and home service experts.
Thoughtful guidance on accessibility, aging in place, and neighborhoods that fit daily life.
Resource areas
A senior transition involves a lot more than real estate. I’ve pulled together trusted resources across the services that tend to come up most.
SRES® guidance on pricing, timing, and selling a longtime home on Chicago’s North Side and in Evanston.
Introductions to senior move managers, professional organizers, and estate sale and cleanout services.
Introductions to elder law and estate planning attorneys, financial advisors, and tax professionals.
Community programs, local services, and support groups for you and the family members helping you.
Local contractors and specialists for home modifications that help you stay comfortable where you are.
What to look for in a next home, from step-free entries to main-floor living and walk-in showers.
Not sure where you stand? The free downsizing self-assessment takes about 5 minutes.
Begin assessmentCommon questions
An SRES® is a REALTOR® with specialized training in the real estate needs of clients age 50 and older, including the financial, legal, and emotional considerations that can shape a move.
Start with a conversation. We’ll talk through where things stand, who is part of the decision, and what needs to happen first. Many families reach out while a parent is still weighing options, and others call once a timeline is set. Either way, I can keep everyone informed, including relatives who live out of town.
Deborah Libby is a licensed REALTOR® and SRES® designee based in Rogers Park, specializing in senior real estate transitions on Chicago’s North Side and in Evanston. You can schedule a free consultation here.
It depends on the condition of the home, the current market, and the timeline of the transition itself. On Chicago’s North Side, well-prepared homes in good condition typically go under contract within a few weeks. The fuller answer comes from understanding your specific situation, which is what we work through together.
Good things start with a conversation
Book a free 45-minute Zoom call. We'll talk through where you are, where you want to go, and how to get there.