When to sell your home
Selling because you're moving cities, right-sizing, or genuinely cannot afford the home — almost always right. Selling "because the market is at a peak" — almost always wrong. Markets are peaks and bottoms only in retrospect.
For most people, the choice isn't "should I sell" but "when do I sell, once I've decided to." Once the decision is made, do it efficiently: a competent agent, correct pricing, staging, and responsiveness beat trying to wait for an ideal number.
The IRS §121 primary-residence exclusion is one of the most generous tax exemptions ordinary households can use: up to $250K of gain ($500K married filing jointly) is tax-free if you've owned and lived there 2 of the past 5 years. Don't sell at year-1.9 of ownership if you're close to the threshold — wait the few months.
If you're selling to upgrade, run both transactions side by side. The transaction-cost drag of selling and buying in the same market is roughly 8–12% combined. Make sure the lifestyle gain is worth it.