“It’s just a house,” people say. But when you’ve lived in a home for decades, it’s much more than that—it’s your memories, your milestones, your story.
Selling a longtime home in Chicago is not just a financial transaction—it’s an emotional transition. And if you’re considering downsizing or rightsizing, you deserve more than just a standard real estate agent.
As a Senior Real Estate Specialist (SRES®) and trusted guide for Chicago homeowners, I work with clients who are navigating the complex emotions of leaving a beloved home. With years of experience and a wealth of resources, I’m here to make the process smoother, more manageable, and aligned with your next chapter.
1. Acknowledge the Emotional Weight
You’re not just leaving a building—you’re leaving a life stage. Whether it’s the home where you raised a family, hosted holidays, or simply found your rhythm, the emotional ties can be strong. It’s okay to feel grief, fear, or even guilt. Allow yourself space to feel.
Tip:
Journal your favorite memories. Taking stock of your experience can help bring emotional closure and a sense of gratitude.
2. Get Clear on the “Why”
Understanding why you’re moving is the key to moving forward. Are you downsizing for simplicity? Moving closer to grandchildren? Reducing expenses? Rightsizing isn’t about giving up—it’s about gaining freedom and clarity in your next phase.
Tip:
Make a “vision list” for your next chapter—what do you want more of? Less of? This can anchor your decisions when the emotional fog sets in.
3. Don’t Go It Alone: Work with a Specialist
As an SRES® designee, I’m trained to support older adults through the home-selling process with empathy, patience, and skill. I don’t just market homes—I provide concierge-level service, including:
-
Trusted referrals to downsizing consultants and estate planners
-
Moving and clean-out resources
-
Guidance on tax implications, capital gains, and timing
-
Strategies to minimize disruption and maximize value
This is about your life—not just your listing.
4. Say Goodbye on Your Terms
Before handing over the keys, take time to say goodbye intentionally. Host a farewell gathering, take photos in every room, or simply sit quietly and reflect. Closure doesn’t have to be grand—it just has to be yours.
5. Focus on the Future, Not Just the Farewell
There’s beauty in beginnings. Imagine waking up in a lower-maintenance condo in the Loop, or walking to your favorite coffee shop in Lincoln Park without worrying about shoveling snow or leaky gutters. A new home can offer peace of mind, flexibility, and ease.
As someone who specializes in Chicago’s luxury and historic home markets, I help my clients transition not just out of their longtime homes—but into spaces that reflect who they are now.
You’re Not Alone—Let’s Make a Plan
Selling your longtime Chicago home doesn’t have to feel overwhelming. With compassion, clear planning, and expert guidance, we’ll walk through each step together.
📞 Let’s talk when you’re ready—whether that’s now or a year from now. You don’t have to do this alone.
Anne Rossley, SRES®
Helping Chicagoans downsize, rightsize, and embrace their next chapter—seamlessly.
Resources for Rightsizing:
- National Association of Senior Move Managers
- PS Lehman – staging, organizing, decluttering
- Humble Design
- Open Books
- Chicago Furniture Bank
