Buy first or Sell first?

What's a unicorn got to do with Real Estate?  Read on to find out! 

This question is one of the biggest ones I get when I sit down with clients, and that is whether it’s better to buy first or sell their current home first. 

Even if new clients aren’t thinking this through; especially in fluctuating markets this is definitely something that should be given careful consideration.  

There’s no one size fits all answer, but there are definitely ways to figure out the best answer for you.  In no particular order, here are some things to consider when mulling this question over….

What’s your risk tolerance?

If you’re comfortable carrying two properties at once (even for a short period), buying first may be an option. However, if carrying two mortgages is not financially feasible or too stressful, selling first ensures you know exactly what to budget for your purchase.   

How do you judge your risk tolerance anyway?  Here are some questions to ask yourself: 

•    How is your financial stability?  If you lost your job, would you have enough savings to cover your expenses for a few months, or do you manage paycheck to paycheck.  If you have a healthy emergency fund and a steady income, you might tolerate more financial risk, like carrying two mortgages temporarily.  If unexpected expenses (like staging costs, temporary housing, or bridge financing fees) would put a strain on your finances, selling first might be the safer option.

•    What is your emotional Response to Uncertainty – How would you respond to this? Imagine you’ve booked a vacation but don’t yet have a hotel reservation. Are you comfortable finding one last-minute, or does the uncertainty stress you out? If you need things planned in advance, you might struggle with the unpredictability of buying before selling.  

At the time I’m writing this, the world is an uncertain place.  We are feeling it in real estate as many buyers are sitting on the sidelines just waiting to see what’s going to happen.  Imagine you buy a new home first, but your current home sits on the market longer than expected.  Would you stay calm knowing it will sell eventually, or would sleepless nights and stress take over? If uncertainty makes you anxious, selling first could be the smarter choice.

•    How do you invest?  Do you prefer putting your money into high-risk stocks or experiment with cyber currency for big potential returns, or do you stick with safer options like fixed rate GICs? If you naturally gravitate toward safer investments, you may prefer selling first to avoid financial strain.  

•    Decision-Making Style  - When making a big purchase like a car, do you research for months and test-drive multiple options, or do you go with your gut and buy the first one that feels right? If you take time to make careful decisions, you might be more comfortable selling first to know exactly what you can afford.  

Do you think you’ll be more comfortable if you view 10-15 homes to find the perfect home, or can you make quick decisions under pressure? If you like to explore many options before deciding, buying first might be best so you don’t feel rushed after selling. But if you’re confident making fast decisions, selling first can work because you’ll be able to move quickly when the right home comes up.  You’ll be making some fast decisions in real estate that may make you uncomfortable anyway, so this is important to think through

•    Past Experiences with Risk -- Have you ever taken a big risk—like starting your own business or moving to a new city without a job lined up? If you’ve handled uncertainty well in the past, you might feel confident in buying before selling.  

Have you handled big financial risks well in the past, like buying an investment property or flipping a home? If so, you may be comfortable with the short-term risk of owning two homes. But if past financial risks caused stress or losses, a safer approach—selling first—might suit you better.

How particular are you about your next home?

If you have very specific needs—like a certain school district, a unique property style, or a hard-to-find neighborhood—you may want to buy first. Otherwise, you risk selling your current home and not being able to find the right one when you’re ready.

How reverse engineering may help you predict how long it will take you to find a specific home

Smart realtors will take your needs and wants and look back in history to analyze the sales data over the past few years.  Going back 5 years you can apply your criteria to a reverse property search to find out:

•    How many homes like that have sold in the past

•    What prices did they sell for

•    Did they sell in competition because they are rare?

•    What did they look like inside

•    How often do they come up for sale

This way you can give yourself a ‘reality check’.   It helps to know a few things that just make sense, like:

•    In a low turnover neighbourhood or condo where people live a long time it’s less likely to find something sell that’s renovated

•    In a demand school district homes will be more expensive than in the catchment districts that border it

•    New construction may sell for a higher per sq ft price than resale

•    A renovated home will cost more than an unrenovated home

A good example of this is a reverse search I did for a senior looking to rent in a specific condo building.  A reverse search showed that there are very few condos that rent privately (2-3 every 4 years)   Therefore it’s unlikely a condo in their budget would be available when they wanted to move.  That way they could adjust their plans.  

What’s the market like? 

For many people, the sale price of their current home determines what they can afford to buy next. If the market is in flux, it makes sense to sell and buy in the “same market” – that way market conditions will benefit you (whatever they are) on both transactions.    

How do you know what the market is like? 

Because news articles may focus on the negative & real estate can be very specific to neighbourhood it’s best to talk to a realtor that has listings, is active with buyers and sellers and is familiar with your area.  Or has been recommended to you.    

In slow markets, if you’re like most people you don’t want a realtor that will make unrealistic promises just because they are hungry for business.  

If you're house hunting in Toronto, there are a couple of other realtors that write excellent blogs with market information; many of these have articles on a variety of topics going back years.  

Toronto Realty Blog - if you can get through his style of writing (long wind-ups to the meat & a bit of pretention) there good information

The Refined Real Estate Team Blog - Jeff is a colleague at my brokerage and his analytical style of examining the market shows his financial background.  He looks at thing with not only a "what happened" but "what did it feel like" view.  His focus is really on central Toronto. 

The BREL team Blog - another central Toronto blog; but I find the real estate articles are on a wide range of topics and written in a straightforward style.  

Are you unicorn hunting?

If your dream home is a rare find—such as a waterfront property, a century home, or a condo in a specific building—waiting to sell before buying might mean missing out.  In this case, you may choose to buy first;  prepare your home when you start your search, so once you’ve put in an offer so you can list right away.  

If you’re unicorn hunting, a reverse engineering approach may be helpful.  It’s also helpful to keep an open mind and look not only at a 100% unicorn, but see if a 50% horse/50% unicorn may work for you as well.    Or perhaps you can buy a horse and transform it over time to your personal unicorn! 

Buying before selling 

Allows you to take your time finding the perfect home without feeling pressured to settle. You can move in at your own pace and avoid temporary housing. However, this approach carries financial risk—you may need to qualify for two mortgages or rely on bridge financing. If your current home doesn’t sell as quickly as expected, you may be stuck covering two mortgages for longer than anticipated.

Pro Tip: If you're interested in what homes are selling for to do research, my website has a 'sold' feature that's really helpful.  You can set up a property search that will only send you homes that have sold in your area, community or neighbourhood.   It's a great way to stay on top of pricing! 

Just sign up here:

www.SueAnfang.com   You can even download a GPS enabled app to your phone that will bring up sold & available properties when you're out and about.


Selling first 

This eliminates the risk of carrying two mortgages and provides a clear budget for your next home. You’ll know exactly how much equity you have to work with, reducing financial uncertainty. However, it also means you might need temporary housing or feel pressured to buy quickly, which can lead to settling for a home that isn’t quite right.  

If you're interested in what homes are selling for in your area, my website has a 'sold' feature that's really helpful.  You can set up a property search that will only send you homes that have sold in your area, community or neighbourhood.   It's a great way to stay on top of pricing! 

Just sign up here:

www.SueAnfang.com   You can even download a GPS enabled app to your phone that will bring up sold & available properties when you're out and about.


Is Bridge Financing Right for You? 

Bridge financing is a short-term loan that helps cover the gap between buying a new home and selling your existing one. It can be a good option if you have firm closing dates that don’t align or if you need flexibility. However, bridge loans come with interest costs and eligibility requirements, so it’s essential to discuss this option with your mortgage advisor before deciding.

Pro tip: Have a backup plan

Whichever way you go, it’s smart to have a contingency plan. If you buy first, consider bridge financing or a rental option if your home doesn’t sell right away.  If you sell first, consider a long closing, or look into short-term rentals or family accommodations in case you need extra time to find your next home.

Ask an expert

While the answer may be different for everyone,  discussing your situation with a knowledgeable realtor can help you decide the best approach. If you have questions about your own situation, or if you’re helping a family member navigate a move, feel free to call me at 416-562-5002. My website blog and YouTube channel also have lots of helpful articles.

About Sue Anfang


Apr 01, 2025

Recent Blog Posts

Sep 29, 2026

The Landlord and Tenant Board (LTB) in Ontario had some major updates and legislative changes that took effect September 21, 2026.   Thes introduce significant procedural shifts for both landlords and tenants in Ontario, and should improve delays.

Key updates of the September 21 2026 LTB Changes are: 


Shorter N4 Notice Period (7 Days): The notice period for an N4 form (Notice to End a Tenancy Early for Non-Payment of Rent) has been reduced from 14 days to 7 days for monthly, yearly, and fixed-term tenancies. This compresses the window a tenant has to pay missed rent before a landlord can file an L1 application with the LTB.

N12 Personal-Use Eviction Compensation Exception:  Landlords serving an N12 notice (for personal use by themselves, a purchaser, or close family members) can now waive the standard requirement to pay one month's rent as compensation, provided they give at least 120 days' notice and the termination date aligns with the end of a rental period or term.

Persistent Late Payment has been defined (N8): Regulation changes establish a clear, written benchmark for persistent late payment under an N8 notice—defined specifically as "three or more occasions of rent being paid more than seven days late" within a six-month lookback period.

T5 Application Deadline Update: The deadline for a tenant to file a T5 application (for bad faith evictions or related issues) has been updated to two years after the date the tenant moves out

(Note: Other concurrent administrative shifts surrounding LTB reviews, fine structures, and general procedures have rolled out through mid-2026 to streamline case processing timelines.)

What these changes mean if you're a landlord:

These updated regulations provide sharper tools to manage cash flow and streamline property operations when challenges arise. With the N4 notice period compressed to just seven days, you can address non-payment of rent much faster, reducing the window of financial exposure. Additionally, the option to waive the one-month compensation fee on an N12 notice—provided you give at least 120 days' notice—offers welcome flexibility when transitioning a property back for personal or family use. Meanwhile, the clear benchmark for persistent late payment under an N8 removes previous gray areas, making it straightforward to document chronic payment issues and take decisive action.

What these changes mean if you're a renter: 

The shifting landscape means timelines and procedural windows require your utmost attention to protect your housing stability. Because the N4 notice period for missed rent has dropped from 14 days down to seven, you have a much narrower window to catch up on arrears before a landlord can file with the LTB. On the plus side, clarity around rules like the two-year deadline for filing T5 bad-faith applications gives you a solid, predictable timeframe to hold landlords accountable if an eviction turns out to be unlawful. Staying proactive with your communication and keeping meticulous payment records are your best defenses under these tighter rules.

Maximum Prosecution Fines for Landlords in Ontario:

For severe violations of the RTA—such as illegal lockouts, bad-faith evictions, or shutting off vital services—landlords can be prosecuted. Maximum fine thresholds are:   

  • Individuals: Up to $100,000   
  • Corporations: Up to $500,000  

Bad Faith Evictions (N12 / N13): If a landlord evicts a tenant for personal use or renovations and fails to follow through (e.g., re-renting the unit out immediately at a higher rate), a tenant can file a T5 application. Penalties ordered by the LTB can include:   

  • Paying the tenant up to 12 months of their last rent charged.   
  • Covering the difference in rent between the old unit and the tenant’s new home for up to one year.   
  • Covering reasonable out-of-pocket moving, storage, and related expenses.  

Other landlord behaviours that may result in fines or penalties are:  Illegal Lockouts, interfere with reasonable enjoyment, changing locks without following proper legal eviction processes, or harassing a tenant to force them out, are major offenses., intentionally cutting off or interfering with the supply of heat, electricity, fuel, hot/cold water, or gas is strictly prohibited.   Unlawful Rent Collection: Charging rent above allowable guidelines without an approved Above-Guideline Increase (AGI), illegally retaining deposits, or failing to pay annual interest on rent deposits results in mandatory rebates to the tenant (via T1 applications).   

For more information on Bill 60 & the Residential Tenancies Act visit: 

Ontario Government Website bill 60

Ontario Residential Tenancies act 2006

Landlord and Tenant Board of Ontario

Landlord Tenant Board Decisions through OpenRoom

LTB of Ontario Decision Data Catalogue

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Sep 20, 2026

The core concern for most Toronto downsizers: 

Downsizing from a long-time family home is as much an emotional hurdle as it is a logistical one. Sellers often ask how to sort through a lifetime of accumulated possessions without feeling completely overwhelmed.  

In the Greater Toronto Area, this has led to a massive demand for specialized local resources. Families frequently ask how to vet professional senior move managers, how local online estate auctions (such as those servicing Ontario via platforms like MaxSold or Transition Squad) handle a large volume of items items, and what local charities or consignment options will accept remaining items.  

My personal experience as a Seniors Real Estate Specialist:

My clients are often overwhelmed with the task of sorting through a lifetime of accumulated possessions (and collections) without feeling completely overwhelmed.   Here are some tips I have learned helping many of my sellers through this exact process:

  1. Start as early as possible - if you’re planning a move start a year before.  Sort into piles of ‘junk’, ‘sell’ & keep. 
  2. Tackle one room at a time starting with an unused guest room. Use the cleared room to stage the items from other rooms so your house stays organized.
  3. Use the "pomodoro' method - remember the little tomato kitchen timers?  Set a timer to 20 minutes - work through as much as possible - then take a break.  Admire your progress.  Repeat for another 20 minutes.  Breaking up the tasks makes things easier. 
  4. Selling things?  Do your resarch beforehand  The value of your items & the modern methods of selling may be vastly different than you imagine.  A little research ahead of time will help you understand what works best for you.  
  5. Bring in professionals to consult - a decluttering expert or realtors like me (who work hands on) will help you and your family break down the process, work with you to come up with a plan so you don’t have a nervous breakdown!

The main ways to sell a lot of belongings in Toronto if you're downsizing  

Personal on-line sales like Kijiji & Facebook marketplace:

Garage sales:

On-line platforms like Carrot, E-bay etc. 

On line auction houses/estate auctions like Transition Squad or MaxSold 

Consignment Stores:

Auction houses like Sotheby's

On-site estate sales

Pros and cons of each method of selling:

 Personal on-line sales like Kijiji & Facebook marketplace:

  • Pros:  you can set your own prices, take your own pictures & write your own descriptions - you have full control, you keep 100% of your sales
  • Cons: strangers show up to your door; they may haggle or "ghost' you - ask a lot of questions then become unresponsive, it may take a long time to sell things

Garage sales:

  • Pros: you can sell a bunch of things at once, it all happens in one day and people will leave with their purchases, often there are neighbourhood sales organized that will draw bigger crowds, you keep 100% of your sales
  • Cons:  if you don't like haggling, this is not for you, advertising is usually limited to your neighbourhood, weather may not co-operate

On-line platforms like Carrot, E-bay etc. 

  • Pros:  you can set your own prices, take your own pictures & write your own descriptions - you have full control
  • Cons: strangers show up to your door; they may haggle or "ghost' you - ask a lot of questions then become unresponsive, it may take a long time to sell things, both are not as popular as Facebook marketplace, there is a fee for selling items, you have to arrange pack & to ship items by mail to buyers that are not local - so not good for larger, heavy items

On line auction houses/estate auctions like Transition Squad or MaxSold 

  • Pros:  people bid on your items & pay on line.  No haggling.  Pick up is generally a specific and limited window.   A great way to sell a lot of items at once.  You can manage your own auction (pictures, descriptions & posting) or pay a service to have someone else manage it for you. 
  • Cons: The auctions charge a percentage which is non-negotiable.  Managing an auction is labour intensive, so expect to pay by the hour for someone to do it for you.  MaxSold starts all auctions at a dollar, with no reserve - but has a large database of potential buyers.  Transition Squad has reserve bidding, but a much smaller database of potential buyers

Consignment Stores:

  • Pros: good for higher end items that may sell for more but not in the fine art/antique category.  Buyers will pick them up from the store so you don't have to deliver.
  • Cons: they are picky and will only accept items that they know they can sell (apply with pictures to the consignment store to find out if an item is acceptable), generally the longer it take to sell the less you will make, the consignment store will have a fee, you have to arrange to get your items to the store & pick them up if they don't sell.  There are not as many consignment stores as there used to be. 

Auction houses like Sotheby's

  • Pros: they sell books, furniture & decorative Art, Jewelry, Paintings & Sculpture, Sports Collectibles, the sell on line or also at auctions, either live or on-line
  • Cons: generally for high end items or fine jewellery, there is a process similar to consigning to see if they will sell your item; they judge condtion and provenance, too.  Fees are about 20% of finaly price, They take about 3 weeks for consideration of an item to sell

On-site estate sales - honestly I am not sure if anyone does these in Toronto anymore! 

Buying household contents in Toronto or the GTA is an urban myth

I see people asking this question all the time on-line.  There is no service in Toronto that will pay you in bulk for a household of items

Any way you would like to sell your items, understand that there is a glut of 'baby boomer' stuff out there.  Younger generations simply don't live the lifestyle of their parents or grandparents - so they don't have space for, or appreciation of things like: Dining room sets, heavy carved furniture, matching bedroom suites, 'good' china, silver or crystal.  With a glut of these items on the market, set your expectations accordingly! 

For more hints and tips, please check out:

How to sort through a lifetime of pictures & slides

30 Day Declutter worksheet

Tips for a smooth move



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Sep 14, 2026

Spectacular ravine setting

Craving something that’s not a cookie-cutter home?  Set on an extraordinary ravine lot, this home is packed full of character and unlike any typical East York bungalow.   With 2 bedrooms upstairs along with a full bath and sunroom overlooking the ravine this home has an open concept main floor with vaulted ceilings. 

Descend the incredible reclaimed wood stairs to the lower level (the basement is on-grade) with a 3rd bedroom/rec-room and 4 pc bath. Also on this level is a walk-out to the back deck, yard and ravine. 

On the other side of the lower level there's a jr 1 bedroom suite with separate laundry, 2 separate entrances, a deck, kitchenette & bedroom with 3 pc ensuite & egress window. It's completely separated from the rest of the house and has been carefully and thoughtfully designed with privacy in mind - right down to a separate outdoor space. 

The serene back yard has lots of table land and ultimate privacy - there's no public space beyond.  If you want to enjoy the Taylor Creek Park system the entrance is at the end of the block. 

Surrounded by established homes & new builds, this is your chance to own a very special home that speaks to calm, stillness and nature in the heart of the city. 

Incredible character and features

The main floor features 100+ year old wide plank reclaimed hardwood floors, an open concept living space with vaulted ceiling & skylights - all overlooking the ravine that dips down to a tributary of Taylor-Massey Creek.

The kitchen ceiling is vaulted with 2 skylights creating an incredible light filled home.  The lower level, accessed by a gorgeous reclaimed wood staircase has a room that can be used as a 3rd bedroom or rec room.  There's a full 4 pc. bathroom, and the entry is heated with a wet bar/kitchenette and dedicated yoga space.  

Video tour of 124 Glenwood Terrace

Privacy & income potential 

Another unique feature of the home is that the the other side of the lower level has been converted into a jr 1 bedroom suite with separate laundry, 2 separate entrances, a deck, kitchenette & bedroom with 3 pc ensuite & egress window. 

It's completely separated from the rest of the house and has been carefully and thoughtfully designed with privacy in mind - right down to a separate outdoor space and deck with privacy screen.  

The ravine

The serene back yard has lots of tableland and ultimate privacy - there's no public space beyond. If you want to enjoy the Taylor Creek Park system the entrance is at the end of the block.  With a gently sloping yard, there's lots of space to enjoy.   Set back from the other homes, it's a truly private oasis. 

Surrounded by established homes & new builds, this is your chance to own a very special home that speaks to calm, stillness and nature in the heart of the city.

For a private showing, message me at 416-562-5002

Craving more details about 124 Glenwood Cres?

Check out the links below:

Full listing details with all the photos

Property Website for 124 Glenwood Cres

Search for Ravine properties in Toronto



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