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Challenges of Selling Your Home & How to Overcome Them

Wednesday December 10, 2025

Selling

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Selling a house can seem simple in theory. In practice, the process gets complex, especially in today’s fast-moving market. There can be life circumstances that complicate the transaction. Alternatively, a legal issue might arise.

Whatever the reason, it’s discouraging when a house sits on the market without getting the results you want. Fortunately, as long-time real estate experts in Hamilton, Burlington and the surrounding areas, there isn’t much we haven’t successfully overcome.

In this post, we’ll show you some of the ways you can deal with very specific obstacles so you can look forward to a successful sale and a streamlined transition.

An accurate, unbiased assessment is the foundation of your effective home-selling strategy. Start by booking your complimentary home evaluation with our experts.

Table of Contents

  1. Finding a Private Buyer
  2. Issues With the Title
  3. Selling a House in the Midst of Divorce
  4. I’ve Inherited a House: Now What?
  5. My Property Has a Tenant. Can I Still Sell It?
  6. Selling a House With a Stigma

Finding a Private Buyer

A home sale isn’t like any other commodity. Finding a buyer who can and will purchase your house almost always requires comprehensive marketing and assertive networking. However, as with any rule, there can be exceptions.

What happens if you already know someone who wants to buy your house? Maybe a friend or a family member has long admired your property and asked to be the first to know if you ever thought about selling.

At first glance, it’s the perfect situation, and you can’t believe your luck. It might seem as though you can save yourself a lot of time, trouble and expense in getting your house ready. Maybe you don’t have to go on a crazy cleaning spree or make those cumbersome repairs after all!

Before you breathe that much-desired sigh of relief, there are a few things to consider.

  • Will you be leaving anything on the table if you choose not to officially list your home? Without exposure, you really have no way of knowing how much interest your listing would generate from other buyers.
  • Perhaps even the buyer you’ve lined up might be willing to pay more if you took the time to prepare and stage your home in its best light.
  • Have you covered all of your bases legally? A slight misunderstanding over disclosure obligations, advertising claims, drafting the contract or the closing process could cause disruptions if you’re not careful. Even using images from a professional photographer you hired years ago could cause problems if permission to use them has expired.

Even if you find a buyer yourself, you might still need a real estate agent to protect you and streamline your closing process. For more information about private or FSBO (For Sale By Owner) transactions, read the posts below:


Issues With the Title

Some selling problems are easy to spot, like a house that hasn’t been updated since the 1980s or clear signs of a leaking basement. Others are a little harder to notice, but might turn up on a pre-listing inspection, like electrical or plumbing issues.

On the other hand, title issues are completely invisible. Some will come to light during the closing process as the lawyer reviews the deed. However, you want to be aware of how your title is set up in the first place.

  • Joint Tenants is the most common arrangement. There are no issues with the transfer of ownership as long as all owners agree to sell. Inheritance law is also more straightforward. If one owner passes away, ownership automatically transfers to the surviving partner.
  • Tenants in Common can be a little more complicated. To start with, succession works differently. Instead, it must go through probate before transferring to the beneficiary named in the Will.

In addition, listing a house under Tenants in Common is less straightforward. You can sell your share at any point, without permission from the other parties. However, finding a buyer who is willing to purchase a partial interest can be difficult.

Married couples and families make up the bulk of real estate purchases, and they may not be inclined to make an offer – unless all parties agree to sell. You may need to concentrate your efforts on investors. Alternatively, one of the other owners might agree to buy you out.

Do you have questions about how your title impacts your decisions later on? Learn all you need to know in  Can You Sell Your House Under Tenants in Common?

Selling a House in the Midst of Divorce

Selling a house and moving on to something bigger, more convenient or in a more desirable neighbourhood is one of the happiest transitions anyone can hope for. Unfortunately, not every home sale is easy, particularly when going through a divorce.

The first thing to do is to try to keep the situation as amicable as possible. If that seems like a tall order, remember that the sooner you sell your home, the sooner you can begin the healing process. Cooperation now won’t just make your transition less stressful, but also potentially more profitable. What can you do?

  • Start by connecting with a family lawyer to protect your interests. (As real estate agents, we can provide general information, but we can’t give legal advice. It is always best to consult a professional.)
  • Decide whether or not one spouse will buy the other out. Often, this is the simplest option, and it creates the least amount of disruption for any children involved.
  • Reach out to a real estate agent to streamline the selling process and help you get the best price and terms for the home. If the divorce is contentious, you may each want a separate Realtor®.
  • Clean and declutter thoroughly. Removing every personal touch helps buyers imagine the space as theirs. This step is especially critical during a divorce when there may be signs of conflict in the home.
  • Speed may be of the essence, but you’ll still want to perform any critical repairs and stage your home to impress potential buyers. When working with a full-service real estate team, we can handle most of these tasks on your behalf.

Do you want to know more about how real estate sales work during a divorce or separation? Start by reading the posts below:


I’ve Inherited a House: Now What?

Receiving a house in a Will is an incredible and overwhelming gift, especially as real estate becomes more unaffordable to the next generation. However, it does leave you with some decisions to make.

Should you keep the property and remodel it to your needs? Or is it better to sell the home so you can keep your eye on something more suitable for your lifestyle?

  • First things first, you will need to get through the probate process.
  • Next, you’ll want to know the rules around taxes and capital gains. If you are currently not a homeowner and this will be your primary residence, you should be exempt. However, you may be subject to capital gains when selling a second property that has increased in value.

Preparing the home for the market is one of your most critical steps. Even relatively new properties can benefit from a few updates. If the home has been in the family for many years, it may need even more attention. A real estate agent can help you decide what upgrades are likely to pay off and which ones you can skip.

Do you want to know more about what to do with an inherited home? Read Selling an Inherited Home next.

My Property Has a Tenant. Can I Still Sell It?

As the homeowner, you’re entitled to sell your home whenever you wish. However, a tenant on the premises does complicate the process. You still need to respect all terms on the lease, as will the new owner once they take possession. In other words:

  • You cannot evict the tenant just because you intend to sell the property.
  • The tenant does not have to make any repairs or stage the home.
  • You can show the home between 8 a.m. and 8 p.m. as long as you give the tenant at least 24 hours’ notice.

Once the transaction changes hands, the new owner will need to wait until the lease expires before they can move in. Alternatively, they could submit an N12 form stating that they or an immediate family member needs the home for their own purposes. Even then, the tenant can appeal to the Landlord and Tenant Board (LTB), which delays the process.

For the best results, communication is the key! A tenant who feels respected and listened to will be far more cooperative in helping you prepare and sell the home. You might even work out an arrangement to end the lease early by mutual agreement. This path uses the N11 form, sometimes known as “cash for keys.”

Do you want to know more about the steps to selling a tenanted property? Read Can You Sell a House When You Have Tenants next.


No matter what might be standing in your way, there is always an answer. Sometimes, you may need to adjust your expectations. Or you may need to level up your strategy. You’ll get even more valuable home-selling tips in the posts below:


Selling a House With a Stigma

A house could be beautiful, in perfect condition and priced to sell quickly and still sit on the market for weeks or even months on end. What went wrong? For some reason, there’s something about your house that makes buyers hesitate.

  • Maybe it’s supposedly haunted.
  • Perhaps a heinous crime once took place on the premises.
  • There may be nothing wrong with the home, but it has sat on the market too long, and now buyers are starting to wonder. (Note: This is why you must have an accurate and compelling price point right out of the gate.)

Whatever the reason, buyers like the house itself, just not the baggage that comes with it. What can you do?

You might be tempted to try to hide the stigma and hope the buyer doesn’t find out. This technique can backfire, however. Honesty is almost always the best policy, especially when it comes to real estate disclosures.

When selling a house with a stigma, extensive marketing is often the answer. Some people will not buy the house no matter what. Others will be less inclined to worry about the stories, especially if the price and presentation are on point. Still others might be intrigued and want to buy the house because of the stigma, not just in spite of it! If we can reach the right audience, your stigmatized house is as good as sold!

Do you want more details on how to deal with stigma in real estate? Check out Can You Successfully Sell a House With a Stigma?


Are you looking for answers to your unique situation? Our top agents in Hamilton & Burlington can help you overcome nearly any home-selling challenge. Reach out today with any questions you have, or call 905-332-9223 to connect with our office.

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