Author: Nick Tenev

Rabinowitz v. 2528061 Ontario Inc., 2026 ONCA 21 A recent Ontario Court of Appeal decision offers a trio of lessons that transactional real estate lawyers cannot afford to overlook: the limits of specific performance, the dangers of failing to plead damages as an alternative remedy, and a cautionary tale about mortgage interest clauses. Although the case was litigated, the core problems arose at the drafting table or, more precisely, from what was left off it. The Background The appellant buyer, Naftali Rabinowitz, entered into a commercial agreement of purchase and sale with the numbered company respondent. To facilitate the deal…

StreetCity Realty Inc. v. Paner House III Inc., 2026 ONSC 292 The Court rejected the vendor’s arguments by which he attempted to justify his refusal to close, and awarded damages to the real estate agent and attempted buyer. In the fall of 2017, a London, Ontario chiropractor (Dr. Seksek, through his company 2221736 Ontario Inc.) agreed to purchase a commercial office building at 1408 Ernest Avenue from Paner House III Inc., controlled by a retired psychiatrist, Dr. Botros. The deal was facilitated by Bill Rashmawi of StreetCity Realty, who represented both sides. The purchase price was $1.6 million. The first…

Austin v. MacFarlane, 2026 ONSC 463  A recent Ontario Superior Court decision serves as a timely reminder that a vendor’s representations, from the MLS listing all the way to closing warranties, carry real legal weight. In Austin v. MacFarlane, Justice Bellows awarded a purchaser over $129,000 in damages after finding that the vendor negligently misrepresented a North Bay home as “move-in ready” and “very well maintained,” when in fact the property had a long and hidden history of water infiltration and foundation damage. For transactional real estate lawyers, the case offers practical lessons about vendor warranties, the reach of MLS…

Ponesse et al. v. Astoria Homes Inc. et al. (2026 ONSC 541) Introduction A recent Ontario Superior Court decision serves as a timely reminder that vendor-protection clauses in agreements of purchase and sale (APS) must either be exercised carefully and on time, or not at all. In Ponesse et al. v. Astoria Homes Inc. et al. (2026 ONSC 541), Justice Akazaki granted summary judgment ordering specific performance of a $2,530,000 APS for a country home in Hall’s Lake Estates, Caledon, despite the builder’s claim that pandemic-driven cost increases made the project uneconomical. For lawyers who draft, review, or negotiate new-home…

This week’s case review examines 2642948 Ontario Inc. v. Jonny’s Antiques Ltd., 2025 ONSC 2059, a decision addressing power of sale, certificates of pending litigation (CPLs), and peaceable possession under a commercial mortgage. The dispute arose after a vendor take-back mortgage matured and the mortgagor continued making interest-only payments for several years without paying down the principal. When the mortgagee ultimately moved to enforce its rights, the mortgagor sought and obtained an ex parte CPL and claimed an oral agreement allowed indefinite interest-only payments. The court set aside the CPL, finding material non-disclosure on the ex parte motion. It reaffirmed…

Gyimah v. The Roman Catholic Episcopal Corporation of the Diocese of Hearst in Ontario, 2025 ONSC 3876 Transactional real estate lawyers handle closings routinely. But a recent Ontario Superior Court decision serves as a stark reminder that even straightforward purchases can spiral into costly litigation when basic closing mechanics go wrong and when parties make poor decisions about handling funds afterward. The Facts: A Simple Purchase Gone Wrong In May 2019, Anthony Gyimah agreed to purchase property in Cochrane from the Diocese of Hearst for $65,000. Gyimah lived in Toronto. He paid a $9,000 deposit and, on the scheduled closing…

Bennett v. Chadwick, 2025 ONSC 3603 The Setup Picture this: your client calls, frustrated. They’ve enjoyed convenient access across their neighbour’s driveway to their cottage property for years. Now there’s a fence blocking their route, and they can’t get their vehicle through. Surely, they have a right-of-way, don’t they? The recent Ontario Superior Court decision in Bennett v. Chadwick illustrates why assumptions about long-standing informal arrangements can lead to expensive litigation and disappointing results. The Facts This dispute arose within Cressview Lakes Corporation, a non-profit corporation that holds 19 cottage lots. The Bennetts owned shares giving them exclusive possession of…

Shakil v. Heffernan, 2025 ONSC 3279 The Nightmare Scenario What started as a routine month-long Airbnb booking in April 2020 turned into a five-year legal battle that should serve as a wake-up call for anyone involved in short-term rental properties. In Shakil v. Heffernan, the Ontario Superior Court of Justice finally granted possession to property owners Ahmad Shakil and Anjum Qadiri after their “guest” lived rent-free in their Toronto condo unit for 54 months. The Facts The applicants owned a condominium unit at 12 York Street in Toronto, which they managed through Simply Comfort Estates Inc. for short-term rentals on…

Halton Standard Condominium Corporation No. 534 v. Antunes, 2025 ONSC 3377 For transactional real estate lawyers advising condominium corporations or unit owners, a recent Ontario Superior Court decision offers an important reminder: winning doesn’t always mean full cost recovery, even when your condominium declaration says it should. The Background In Halton v. Antunes, Justice Parghi had previously ordered Christine Antunes to permanently vacate her condominium unit within 120 days, finding that her conduct and that of her mother Coralia (the unit owner) violated the Condominium Act, 1998 and the corporation’s Declaration and Rules. The June 2025 endorsement dealt solely with…

Crampton v. Lightfoot, 2025 ONSC 3902 The recent Ontario Superior Court decision in Crampton v. Lightfoot, 2025 ONSC 3902, offers transactional lawyers a stark reminder of what can go wrong when parties skip proper documentation. The case involved a romantic couple who purchased vacant land together, but only one party appeared on title. When the relationship ended, litigation followed, resulting in a court-ordered sale under the Partition Act. The Facts Claire Crampton and David Lightfoot were dating when they decided to invest in a piece of vacant railway land in Cayuga, Ontario, listed at $150,000. Lightfoot lacked sufficient funds and…