Sheldon Kiestin

Sheldon Kiestin

Broker

Sutton Group-Admiral Realty Inc., Brokerage *

Mobile:
416-809-0221
Office:
416-739-7200
Email Me

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Upsizing Playbook

UPSIZING IN THE GTA

A Buyer's Market Guide

Vaughan  •  Markham  •  Richmond Hill  •  Aurora  •  Newmarket  •  Toronto

 

Upsizing your home in the Greater Toronto Area — from the busy streets of Toronto to suburban communities like Richmond Hill — requires a solid plan, especially when the market favours buyers. A buyer's market occurs when there are more homes for sale than there are people looking to buy, shifting negotiating power to you as the purchaser.

This guide walks through the key financial, strategic, and timing decisions to navigate an upsize with confidence — and outlines exactly where I can help.

1.  Evaluate Your Needs vs. Wants

Before browsing listings across the GTA, determine whether you truly need more space — a growing family, a permanent home office — or simply want a larger property. Larger homes in Ontario come with added responsibility: higher property taxes, more expensive utility bills, and significantly more time spent on maintenance.

2.  Understand Your Finances

In a buyer's market you may have more room to negotiate, but financial preparation still matters:

  • The 28/36 Rule: to avoid becoming “house poor,” aim to spend no more than 28% of your gross monthly income on housing costs, and no more than 36% on total debt.

 

 

The 28/36 Rule

How much housing and debt your income can support

$10,000
Housing costs $2,800 max (28%)
 
Total debt (housing + all other debt) $3,600 max (36%)
 
 
Housing (28%) Other debt (up to 8% more)

Max housing budget

$2,800/mo

Max total debt budget

$3,600/mo

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  • Equity: ideally, you should have at least 20% equity in your current home before moving.
  • Closing Costs: budget for legal fees, moving expenses, and Land Transfer Tax — which can be significant on higher-value GTA properties
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  • https://www.sheldonkiestin.com/landtransfertaxcalculator

 

3.  Benefits of Upsizing in a Buyer's Market

Upsizing when inventory is plentiful offers real advantages:

 

  • More Time to Shop: homes stay on the market longer, so you can view multiple properties across Richmond Hill, Markham, Vaughan, or Toronto without the pressure of an immediate bidding war.
  • Negotiating Power: sellers are often more motivated, meaning you can negotiate a lower purchase price or request repairs.
  • Protective Conditions: you have a better chance of including a “subject to sale” condition in your offer — your purchase only closes if your current home sells, which greatly reduces financial risk.
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  • 4.  Detriments of Upsizing in a Buyer's Market

    While buying is easier, selling your current property becomes the primary challenge:

    Difficulty Selling: your current home may sit on the market longer than expected. If you find your dream home but haven't sold yours, you could face carrying two mortgages at once.

  • Lower Sale Proceeds: you may receive less than expected for your current home, which can impact the budget available for your larger purchase.
  • Need for Perfection: to stand out in a crowded market, your current home must be decluttered, professionally cleaned, and staged.

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    5.  Choosing the Right Strategy

    Sell First, Then Buy  (Recommended in a Buyer's Market)

    •  You know exactly how much you have to spend

    •  You shop as a cash buyer — a stronger negotiating position

    •  Lowest financial risk of the two approaches

     

    Simultaneous Close  (Most Convenient, Most Complex)

    •  Sale and purchase close on the same day

    •  Minimizes moving disruption and double-carrying costs

    •  Requires a solid backup plan in case either deal is delayed

    Strategies for Success

    To make the most of a buyer's market while minimizing risk:

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  • Sell First, Then Buy — experts generally recommend selling before buying in this type of market, so you know exactly how much you have to work with and can shop with confidence.
  • Follow the 28/36 Rule — even on a great deal, keep total housing costs below 28% of gross monthly income, and total debt below 36%.
  • Prepare for a Wait — be patient, and ensure your home is impeccably cleaned, decluttered, and staged to stand out from other listings.
  • Get Professional Advice — work with an expert who understands the specific trends in your GTA neighbourhood, since conditions can vary block by block.
  •  

  • Ready to Plan Your Upsize?

    •  With 39 years serving the GTA and York Region, I can help you time your sale and purchase, negotiate confidently, and avoid carrying two mortgages.

    •  Let's build a strategy tailored to your street, your timeline, and your budget.

     

  •  

  • Sheldon Kiestin, Real Estate Broker

    Sutton Group-Admiral Realty Inc., Brokerage  •  1206 Centre Street, Thornhill, ON

    Direct: 416-809-0221

  • sheldonkiestin.com

    “Your Goals Are My Business”

 

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