How to Navigate Selling and Buying at the Same Time in Regina Real Estate

There is no perfect answer, but there is a right plan for your family.

This guide walks through how selling and buying at the same time in Regina works, so you can move forward with confidence.

Should You Sell First or Buy First in Regina?

Many families cannot financially carry two homes at once. To take possession of the new home, their current home needs to be firm sold. That creates the main worry: if they buy first and their home does not sell, or does not sell for the amount they need, they are in a tough spot. That is why many people choose to sell first. But selling first comes with its own pressure. Once the current home is sold, families need somewhere to go, and they can end up making concessions on their purchase because they are in a rush.

There is no perfect answer. A strong mortgage broker who knows what they are doing and gets your paperwork right is important. A Regina REALTOR® who can confidently guide the process and advise you on which to do first will make all the difference.

Regina Sell and Buy Checklist
Use this as your planning list. The sections below explain each step.

✓ Understand current Regina market conditions
✓ Get a home evaluation
✓ Talk to your mortgage broker first
✓ Decide your order of operations
✓ Plan possession dates
✓ Prepare a backup plan

When Should You Start Planning?

Start three to six months before you want to move. That gives you time for a home evaluation, a conversation with your mortgage broker and getting your home ready before you commit to either side.

1. Understand Current Regina Market Conditions

In August 2026, the Regina Moose-Mountain region reported 2.85 months of supply. The Saskatchewan REALTORS® Association describes three to five months as comfortable, so the market is still tight. That works in your favour when you sell, but it can limit your choices when you buy.

2. Get a Home Evaluation

Knowing what your home is likely to sell for tells you how much equity you have and what you can spend on your next home. Your Regina REALTOR® can give you a realistic number based on recent sales in your neighbourhood.

3. Talk to Your Mortgage Broker First

Ask about qualifying for your next home, bridge financing, porting your mortgage and any penalties for breaking it. These answers often decide which approach is realistic for your family. Our guide to the true cost of upsizing in Regina explains how your equity works for you.

4. Decide Your Order of Operations

Your mortgage broker and Regina REALTOR® can look at your finances and current market conditions together and recommend whether selling first or buying first makes the most sense for your family.

Kelsey's Seller Tip
Decide your order before you fall in love with a house. It is much harder to think clearly afterward.

5. Plan Possession Dates

When we sell your current home, we will often ask for a possession date 60 to 90 days out. That gives you time to search for your new home and get through the conditions period. Once you buy, you usually end up with about three to six weeks before possession on both homes.

6. Prepare a Backup Plan

Know what you will do if one side takes longer. If your family is open to it, putting your belongings in storage and staying with family for a couple of weeks can give you a lot of breathing room. That will not work for everyone, and that is completely understandable, but it is worth considering.

Kelsey's Real Estate Perspective

Moving Up or Down? The Order Matters More Than the Speed.

Most families who sell and buy at the same time worry most about timing. The best results usually come from deciding the order early and building flexibility into possession dates. Every approach carries some risk. The goal is to choose the one your family is most comfortable managing. The more useful question is often "Which risk are we willing to carry?" Our guide on how to upsize in Regina walks through every step.

Talk Through Your Timing Options.
Kelsey and Kyle are self-proclaimed upsizing specialists, and in 2026 they have helped at least 15 families upsize. Kelsey Smith and the Regina Real Estate Group help families coordinate both sides of a move, from pricing your current home to finding the next one.