Naperville Downsizing Guide  ·  02 of 06

Sell First or Buy First?

The question that keeps Naperville downsizers up at night — answered honestly.

By Joe Graham  ·  February 2026  ·  ← Full Downsizing Guide

Ask ten Naperville homeowners this question and you'll get ten different gut reactions. Some want to sell first — they can't stomach the idea of carrying two mortgages. Others want to buy first — they've already spotted the condo they want and they're terrified it'll be gone.

Both instincts are reasonable. And both approaches work in Naperville's 2026 market — if you go in with the right plan. Here's how each one plays out.

Path A: Sell first

Path B: Buy first

Path C: The coordinated close (what most people don't know about)

For most of my clients, the best outcome comes from coordinating both transactions to close within days of each other. You're not stuck in limbo. You're not carrying two mortgages. You move once. It takes planning — and an agent willing to manage both sides with care — but it's very doable in Naperville's current market.

With homes selling in a median of 28 days and inventory tight, we can actually predict your sale timeline closely enough to coordinate your purchase contract around it. That's the conversation I have with every downsizing client before we do anything else.