Ep. 75 - When To Sell At A Loss: The Biggest Challenge In GTA Real Estate In 2026

Ep. 75 - When To Sell At A Loss: The Biggest Challenge In GTA Real Estate In 2026

Send us Fan Mail [https://www.buzzsprout.com/2361917/fan_mail/new] In this episode of the Last Honest Realtor, David Fleming draws on his own experience investing during the tech boom and bust of 2001-2002 to ask an important question: “How and when should you exercise a loss?” David also analyzes a recent media article about sellers who exercised a massive loss on a home in Peel Region and explains why the loss never should have been that large to begin with. In this episode we explore why people struggle to "exercise a loss," how emotions cloud financial decisions, and why sometimes the best investment move is accepting a loss and redeploying your capital elsewhere. In This Episode: * 01:35 — The investing mistake that changed my life * 09:32 — Why I wanted to sell—and didn't * 15:16 — The danger of hindsight * 16:23 — The Brampton home that lost $950,000 * 31:30 — Why sellers must stay ahead of a falling market * 34:39 — Reinvesting instead of holding on * 38:36 — Why real estate owners struggle to sell at a loss * 40:08 — When selling at a loss can actually make financial sense Whether you own a condo that's fallen in value, an investment property, or you're simply trying to understand the roller coaster of the Toronto housing market, this episode offers an honest look at one of the toughest decisions investors face. Support the show [https://www.buzzsprout.com/2361917/support] Subscribe and Follow: Toronto Realty Group Website [https://torontorealtygroup.com/meet-the-team/] Toronto Realty Group YouTube [https://www.youtube.com/@Torontorealtygroup] Toronto Realty Blog Instagram [https://www.instagram.com/torontorealtyblog/] Toronto Realty Blog Twitter [https://x.com/TORealtyBlog] Toronto Realty Blog Facebook [https://www.facebook.com/torontorealtyblog]

Ep. 74 - Has the Toronto Real Estate Market Finally Hit Bottom?

Send us Fan Mail [https://www.buzzsprout.com/2361917/fan_mail/new] Has the Toronto real estate market finally hit bottom? It's one of the most searched questions in Canadian real estate, but it's also one of the most misunderstood. In this episode, David Fleming explains why market bottom can only be identified after it's already happened, why buyers almost always purchase on the way back up (even at higher prices), and how psychology—not statistics—drives most real estate decisions. Using historical market cycles, media headlines, investment examples, and real Toronto housing data, David breaks down why trying to perfectly time the market is a game almost nobody wins. In This Episode: * 02:05 — Why nobody can identify the bottom in real time * 04:17 — Why buyers always purchase on the way back up * 13:18 — Are Toronto condos hitting new lows? * 16:00 — Interest rates and the "affordability bottom" narrative * 22:14 — Fear of losing more vs fear of missing out * 31:12 — Condos, detached homes, and different market bottoms * 33:26 — What the data actually says about Toronto condos If you're waiting for the "perfect time" to buy in Toronto, this episode may completely change how you think about the market. Support the show [https://www.buzzsprout.com/2361917/support] Subscribe and Follow: Toronto Realty Group Website [https://torontorealtygroup.com/meet-the-team/] Toronto Realty Group YouTube [https://www.youtube.com/@Torontorealtygroup] Toronto Realty Blog Instagram [https://www.instagram.com/torontorealtyblog/] Toronto Realty Blog Twitter [https://x.com/TORealtyBlog] Toronto Realty Blog Facebook [https://www.facebook.com/torontorealtyblog]

Ep. 73 - The Craziest Toronto Real Estate Stories of 2026 (So Far) with Anya Ettinger

Send us Fan Mail [https://www.buzzsprout.com/2361917/fan_mail/new] This week is another crossover special as David Fleming is joined by friend and colleague Anya Ettinger (Who's In My House?) for their inaugural Spring Market Awards. David and Anya dive into real stories from the trenches that defined Toronto's 2026 spring real estate market. From bidding wars and difficult negotiations to heartbreaking losses and unexpected victories, they hand out awards for the best, worst, and most memorable transactions of the season. Along the way, they discuss buyer psychology, multiple-offer dynamics, and the lessons that emerge when real people navigate an increasingly complicated housing market. In This Episode: * 02:11 — Best House * 06:20 — Toughest Deal * 12:43 — Best Deal * 18:10 — Biggest Heartbreak * 23:01 — Biggest "I Told You So" * 31:37 — Best Villain Award * 37:40 — My New BFF * 43:28 — Best High * 48:28 — Worst Low * 55:34 — Best Turnaround Support the show [https://www.buzzsprout.com/2361917/support] Subscribe and Follow: Toronto Realty Group Website [https://torontorealtygroup.com/meet-the-team/] Toronto Realty Group YouTube [https://www.youtube.com/@Torontorealtygroup] Toronto Realty Blog Instagram [https://www.instagram.com/torontorealtyblog/] Toronto Realty Blog Twitter [https://x.com/TORealtyBlog] Toronto Realty Blog Facebook [https://www.facebook.com/torontorealtyblog]

Ep. 72 - Spring 2026 Recap: 10 Lessons Learned In The Toronto Real Estate Market

Send us Fan Mail [https://www.buzzsprout.com/2361917/fan_mail/new] In this episode of The Last Honest Realtor, David Fleming looks back at Toronto's 2026 spring real estate market and shares his biggest observations from the first five months of the year. While headlines continue to focus on falling sales, weak condo performance, and economic uncertainty, David explains why the reality on the ground is far more nuanced. From multiple offers on $4 million homes to the growing shortage of move-up inventory, this episode explores where buyers are active, what properties are commanding premiums, and why turnkey homes continue to outperform everything else. Using recent transactions and client stories from across Toronto, David breaks down what's selling, what's struggling, and what these trends could mean for the rest of the year. In This Episode: * 03:15 — Why High-End Move-Up Product Is Still King * 06:09 — The Move-Up Inventory Shortage * 09:11 — Why Lower-End Move-Up Buyers Are Still Active * 17:03 — The Rise of Exclusive Listings * 18:58 — Condo Sellers Cutting Corners * 24:02 — The Problem With Two-Bedroom Houses * 26:17 — Offer Night Psychology in the 905 * 29:37 — Why Turnkey Homes are Winning * 33:30 — Sales, Prices & Inventory: The Spring Market Recap #TorontoRealEstate #TorontoHousingMarket #SpringMarket #TorontoHomes #TheLastHonestRealtor Support the show [https://www.buzzsprout.com/2361917/support] Subscribe and Follow: Toronto Realty Group Website [https://torontorealtygroup.com/meet-the-team/] Toronto Realty Group YouTube [https://www.youtube.com/@Torontorealtygroup] Toronto Realty Blog Instagram [https://www.instagram.com/torontorealtyblog/] Toronto Realty Blog Twitter [https://x.com/TORealtyBlog] Toronto Realty Blog Facebook [https://www.facebook.com/torontorealtyblog]

Ep. 71 - The Future of Toronto Real Estate: Industry Ethics, Consumer Experience, and AI with Special Guest Christan Bosley

Send us Fan Mail [https://www.buzzsprout.com/2361917/fan_mail/new] This week on The Last Honest Realtor, David sits down with Christan Bosley, Broker of Record of Bosley Real Estate, to unpack one of the most disruptive periods the real estate industry has faced in decades. With evolving industry business models and the rise of AI, this conversation breaks down what’s actually changing (and what isn’t) in Canadian real estate. Christan shares an expert perspective on industry ethics, consumer protection, and why experience and full-service representation still matter in a changing market environment. In This Episode: * 02:02 — Why independent brokerages still matter * 03:57 — Traditional brokerage model vs. changing consumer perception * 12:05 — Why cheaper service isn’t always better * 17:41 — Mentorship and training agents at a brokerage * 22:10 — Consumer protection & regulatory oversight * 29:18 — The impact of technology on real estate workflows * 36:40 — Social media’s influence on agents * 53:10 — AI enters the real estate conversation * 55:32 — Future of the Realtor role This episode is for buyers, sellers, and anyone curious about where real estate is heading next. Support the show [https://www.buzzsprout.com/2361917/support] Subscribe and Follow: Toronto Realty Group Website [https://torontorealtygroup.com/meet-the-team/] Toronto Realty Group YouTube [https://www.youtube.com/@Torontorealtygroup] Toronto Realty Blog Instagram [https://www.instagram.com/torontorealtyblog/] Toronto Realty Blog Twitter [https://x.com/TORealtyBlog] Toronto Realty Blog Facebook [https://www.facebook.com/torontorealtyblog]