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You're ready to move—but here comes the big question: is it better to sell first or buy first?
It's a decision that every homeowner faces, and the answer depends on a few key factors. In this guide, I’ll walk you through a detailed framework to help you decide with confidence, reduce risk, and move forward smoothly.
Whether you're upsizing, downsizing, relocating, or just looking for something new, the right strategy depends on three crucial elements:
Current market conditions in the areas you’re buying and selling
The type of home involved in the transaction
Your financial situation, risk tolerance, and back-up options
Understanding Real Estate Market Conditions: The Key to Timing Your Sale or Purchase
Market conditions can heavily influence your strategy. But it's not just about knowing whether it's a buyer’s or seller’s market overall—you need to understand your specific market conditions. That’s why working with an experienced local REALTOR® is essential. They’ll help you interpret current trends, pricing dynamics, and the pace of the market in the neighbourhoods you’re buying and selling in.
In a seller’s market, there are more buyers than homes available. Properties often sell quickly, sometimes above asking price, and bidding wars are common. If you're selling in this environment, you may want to buy first because your home will likely sell fast. But if you're buying in the same hot market, competition can make finding your next home more challenging.
In a buyer’s market, there are more homes for sale than buyers. This leads to longer selling times, more negotiation room for buyers, and potentially lower prices. If you're buying in a buyer’s market, you might consider writing an offer that is subject to the sale of your existing home. Sellers may be more flexible in this environment, and this condition can protect you from the risk of owning two homes at once. Just keep in mind: not all sellers will accept this condition, especially if they receive stronger, unconditional offers.
Real estate markets can vary by region, neighbourhood, and even property type. For example, starter homes in a popular school district might sell quickly, while large rural properties may take longer. An experienced REALTOR® will analyze comparable sales, days on market, absorption rates, and local demand trends to guide your timing strategy.
A word of caution: Some REALTORS® or brokerages may promote "guaranteed sold" programs that promise to buy your home if it doesn't sell in a certain timeframe. While this may seem like a safety net, these programs often come with strings attached—such as a much lower sale price, strict conditions, or higher fees. Be sure to read the fine print and discuss all the implications before relying on this type of offer. It’s always wise to get a second opinion from a trusted, independent real estate professional.
What Kind of Home Are You Buying or Selling? Why It Matters More Than You Think
The type of property you’re selling—or hoping to buy—has a big impact on whether it makes sense to buy or sell first.
Selling a common home (like a standard three-bedroom in a popular neighbourhood)? These tend to attract many buyers and sell quickly, especially if they’re priced right. You may feel more confident buying first since there’s a good chance your current home will move quickly once listed.
Selling a unique or luxury property? These often take longer to sell because they appeal to a smaller buyer pool. Think of custom homes, acreages, high-end condos, or character homes in niche locations. If your current property falls into this category, it’s usually safer to sell first so you’re not left carrying two mortgages.
The same goes for the home you want to buy:
If you’re looking for something that comes up often, you have more flexibility and may prefer to sell first.
If you're seeking something rare—like a walkout bungalow, lakefront cottage, or a home with a legal suite—these don’t come around often. In these cases, it might be smarter to buy first, so you don’t miss the opportunity.
In either case, your REALTOR® will be your best asset in helping you understand how long it might take to buy or sell each property type and what the competition looks like.
What is Bridge Financing, and How Does It Work?
Bridge financing is a short-term loan that helps you cover the gap between buying your new home and selling your current one. It's a useful tool for buyers who want to purchase a home before their existing one sells.
Here’s how it works:
You buy your next home and need the funds from your current home to close.
Your lender gives you a short-term loan (typically for up to 90 days) using the equity in your current home.
Once your old home sells, the proceeds are used to pay back the bridge loan.
Important details to know:
Bridge loans are usually only approved if your current home has a firm sale agreement (e.g. the buyer has waived all conditions).
Most lenders require less than 90 days between possession dates—meaning your home sale must close within 90 days after the purchase.
Interest rates on bridge loans are higher than traditional mortgages, and some lenders charge an additional administration fee.
Bridge financing can be a helpful solution—but it’s not without its risks. If your home sale falls through, or if there’s a delay in closing, you could be on the hook for repaying the bridge loan without the proceeds from your sale.
This is why it’s essential to work with both a knowledgeable mortgage advisor and a REALTOR® who can coordinate timelines and closing dates to minimize your risk.
Buying First: The Risks of Carrying Two Mortgages
Buying first gives you the freedom to search for your next home without the pressure of having already sold. But if your current home doesn’t sell on time, you could be faced with the financial burden of owning two homes at once.
Risks include:
Double mortgage payments, property taxes, utilities, and insurance
Needing to reduce your asking price to sell quickly
Difficulty qualifying for financing due to increased debt load
The emotional stress of having two homes and no sale date
Some buyers overestimate how quickly their home will sell, especially in a shifting market. That's why it's important to budget conservatively and have contingency plans in place.
One risk: You may not be able to port your current mortgage if your home doesn’t sell within the required timeframe set by your lender—usually 30 to 90 days. This could result in losing a great interest rate, paying a mortgage penalty, or being forced into a new mortgage at a higher rate. Be sure to confirm your porting conditions with your mortgage broker or lender before making any decisions.
In a worst-case scenario, you may need to ask a co-signer (such as a parent, sibling, or trusted friend) to help qualify for the mortgage temporarily. Co-signers assume legal responsibility for the loan, so this option should be used only after careful discussion and legal advice. It can offer a financial safety net, but it’s not a substitute for a solid sale strategy.
A word of caution: Some REALTORS® or brokerages may promote "guaranteed sold" programs that promise to buy your home if it doesn't sell in a certain timeframe. While this may seem like a safety net, these programs often come with strings attached—such as a much lower sale price, strict conditions, or higher fees. Be sure to read the fine print and discuss all the implications before relying on this type of offer. It’s always wise to get a second opinion from a trusted, independent real estate professional.
The Risks and Rewards of Selling First
Selling your home first gives you financial clarity. You’ll know exactly what you can afford, and you’ll avoid the risk of juggling two properties. This approach tends to be lower-risk, especially in uncertain or declining markets.
But it comes with its own set of challenges:
You may feel pressure to buy quickly to avoid moving twice
The perfect home might not be available when you’re ready
You could face short-term rental costs or storage fees
To manage this, many sellers:
Negotiate a longer closing period (e.g. 60-90 days)
Rent back their home from the buyer for a short period
Stay with family temporarily
Store their belongings and rent a furnished suite
Again, your REALTOR® plays a key role in helping you time your sale with your next purchase. They can help align closing dates, negotiate flexible terms, and guide you through each step.
Still Undecided? Use This 3-Step Framework to Plan Your Next Move with Confidence
To recap, here’s how to decide whether to buy or sell first:
Know your market – Is it a buyer’s or seller’s market in both areas? Are conditions changing? Your REALTOR® will help you evaluate this with current local data.
Understand your property type – Is it common or rare? Fast-moving or niche? What are the average days on market?
Assess your risk tolerance – Can you manage timing gaps, carry two homes, or qualify for bridge financing? Do you have a back-up plan?
Need Expert Advice? Let’s Talk.
This is one of the biggest financial decisions you’ll ever make. You don’t have to figure it out alone.
I’m Liz Taylor, and I’ve been a full-time Winnipeg Realtor for over 20 years. I specialize in helping clients navigate buying and selling with less stress, better timing and the right strategy. I know the Winnipeg market inside and out, and I’ll guide you every step of the way.
Contact me today, and put MY expertise to work for YOU!
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