Chicago · North Side · Evanston
Downsizing or buying after 50? Let’s plan your next move.
Whether you’re selling a longtime home or buying the next one, I help Chicago adults 50+ and their families move forward with calm, clear guidance.
A friendly conversation in plain language about what matters to you, and a practical plan for what comes next.
Real estate representation for 50+
The right support, whether you’re selling, buying, or doing both.
Selling a home
Honor the memories. Prepare for what’s next.
I help you understand the market, prepare the property, evaluate offers, and manage every detail through closing. When downsizing or outside support is needed, I can coordinate that, too.
Let’s discuss your optionsBuying a home
Find a home that fits the life you want now.
From lower-maintenance living to a more walkable neighborhood, I help clarify what matters, evaluate each property, negotiate confidently, and guide you to the closing table.
Learn more about buyingHow we work together
A clear path forward for one of life’s bigger moves.
Before anything else, we talk. I listen to the whole story, then help put the pieces in the right order.
We start with your story
We talk through your timeline, priorities, and everything already in motion.
We make a clear plan
Together, we identify what needs to happen, when, and in what order.
I bring in trusted help
I connect you with the right local professionals for each part of the transition.
I manage the real estate transaction
Whether buying, selling, or both, I guide the transaction from first step to closing.
Your Chicago real estate advisor
Deborah Libby
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 a move after 50.
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.
- Seniors Real Estate Specialist® (SRES®)
- National Association of REALTORS®
- Chicago Association of REALTORS®
- Illinois license #475.212662
- @properties Christie’s International Real Estate
- Scott Stavish Group, CAR Top Producer Team
More than a transaction
Trusted resources for the rest of the transition.
Downsizing with less stress
Practical help deciding what to keep, share, donate, or move, at your own pace.
A trusted local network
Connections to organizers, movers, attorneys, financial professionals, and home service experts.
A home that works for you
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.
Seniors Real Estate Expertise
SRES® guidance on pricing, timing, and selling a longtime home on Chicago’s North Side and in Evanston.
Decluttering & Downsizing Assistance
Introductions to senior move managers, professional organizers, and estate sale and cleanout services.
Legal & Financial Resources
Introductions to elder law and estate planning attorneys, financial advisors, and tax professionals.
Senior Support Networks
Community programs, local services, and support groups for older adults and the families helping them.
Resources for Aging in Place
Local contractors and specialists for home modifications that help you stay comfortable where you are.
Accessibility at Home
What to look for in a next home, from step-free entries to main-floor living and walk-in showers.
Common questions
A few helpful answers before we talk.
What does a Seniors Real Estate Specialist® (SRES®) do?
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.
Where do I start if a family member needs to 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.
How do I find a Seniors Real Estate Specialist in Chicago or Evanston?
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.
How long does a senior home sale typically take in Chicago?
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.
A conversation is the first step
Let’s talk about what comes next.
One conversation is often enough to bring real clarity to a big decision. Bring your questions, and I’ll help you see the path forward.
Schedule a one-on-one call