By Shaheen & Company

Luxury real estate in Toronto is a world of its own, offering unique opportunities, complex negotiations, and no room for guesswork. We’ve guided many clients through multi million dollar purchases, and one thing is always clear: informed buyers make better deals. Before you submit an offer on a luxury property, whether it’s a Yorkville penthouse or a stately Rosedale residence, there are essential questions to ask that go beyond price and square footage. Let’s walk you through what to consider before taking that next big step.

• Luxury properties often have complex ownership structures or restrictions
• Hidden costs such as taxes, maintenance, and fees can add up quickly
• Resale potential depends heavily on location, layout, and long term value
• Understanding why the seller is moving helps shape your offer strategy

Not all luxury listings include everything you see during a showing. In high end homes, certain features may be excluded or treated as negotiable. Clarifying this early avoids surprises later in the deal.

• Are all custom fixtures and built ins included in the sale?
• Will the appliances, wine fridges, or AV systems stay with the home?
• Are exterior elements like hot tubs, pergolas, or garden sculptures included?
• Has the seller itemised any exclusions in advance?

In Toronto, especially in vintage luxury homes, some high value finishes or features may have been imported or custom built, and sellers may prefer to keep them. It is essential to obtain a detailed list in writing.

Understanding why the seller is moving can give you an edge. It can also shape how aggressive or flexible you should be in your offer terms. While we’ll always gather as much intel as possible, it’s smart to ask directly when possible.

• Are they relocating or downsizing? Sellers in transition may be more flexible on closing dates or price.
• Is the home sitting vacant? That could indicate that carrying costs are building up, and the seller may be open to quicker negotiations.
• Has the property been on the market long? Older listings may reflect overpricing rather than a lack of interest.
• Are there other offers or expected interest? Understanding the competitive landscape helps you position your offer with confidence.

Luxury homes come with luxury level expenses. Beyond your mortgage, there are many other financial commitments buyers sometimes overlook. These can vary widely in Toronto depending on location, property type, and amenities.

• What are the annual property taxes? These are often significant in high end neighbourhoods like Forest Hill or The Bridle Path.
• Are there ongoing maintenance contracts (e.g. for pools, elevators, snow removal)?
• What are the average annual utility costs? This is particularly relevant for larger homes, especially those with radiant heating systems or extensive landscaping.
• Are there private road fees or shared services in gated areas?
• If it's a condo or townhouse, what are the monthly maintenance fees, and what do they include?

Zoning laws and heritage designations can affect your ability to renovate, expand, or even maintain a luxury property. At times, buyers are caught off guard after closing when knowledge regarding unexpected restrictions arises.

• Is the home designated as a heritage property? This may limit exterior renovations or require approvals.
• Can the property be used as a short term rental or home business, if needed?
• What are the rules for future expansion or demolition?
• Are there any easements or shared laneways that affect the property?

We always recommend a full review of zoning and title documents before moving forward, especially in Toronto neighbourhoods with strict development controls.

Whether or not you plan to remain long term, it’s wise to consider your exit strategy. Luxury homes don’t always move as quickly as mid tier properties, and certain features, or flaws, can affect future buyer interest.

• Is the layout functional and appealing to future buyers? Overly unique floor plans can narrow your resale audience.
• How do similar homes in the area perform on the resale market?
• Are there upcoming developments that could impact the property’s value, positively or negatively?
• Is the location adaptable to market shifts? Proximity to transit, parks, schools, or retail can insulate value over time. 

Yes. Luxury properties often have specialized systems, like elevators, radiant floors, or wine storage, that require niche inspections beyond a standard home review.

Absolutely. In Toronto, even high end buyers include conditions for financing, inspections, or legal review, especially if the property is complex or unique.

It depends on the market and the seller. We’ll analyse recent comparable sales and the property’s time on market to guide your strategy.

Luxury buyers deserve clarity, strategy, and expert guidance at every step of the purchase. Asking the right questions upfront gives you more than peace of mind, it gives you negotiating power and long term confidence in your investment.

Reach out to us at Shaheen & Company,  we’ll help you ask the right questions, uncover hidden details, and secure a luxury property that meets your needs today and holds its value tomorrow.