Executive Summary: Key Legal and Evidentiary Issues

• Central dispute concerned damages flowing from a failed residential real estate transaction and the proper measure of those damages.
• The plaintiff’s attempt to bring a second summary judgment motion for loss-of-value damages was challenged as barred by res judicata (issue and cause of action estoppel).
• Evidentiary sufficiency on damages was pivotal, particularly the absence of qualified expert valuation evidence to prove alleged loss of market value of the Caledonia property.
• The court scrutinised whether the plaintiff had put his “best foot forward” on the first summary judgment motion, given the limited listing period and lack of reliable market valuation proof.
• Interpretation and scope of Rule 20.07 were in issue, including whether it permits a plaintiff to relitigate a head of damages already addressed in a prior summary judgment.
• The second motion was also assessed as a potential abuse of process, given the plaintiff’s attempt to re-advance a previously dismissed damages claim based on newly obtained appraisal evidence.

Background and facts

The litigation in Webster v. Dinardo arises from a failed residential real estate transaction involving a property in Caledonia, Ontario, owned by plaintiff Keith Webster, and a subsequent purchase of a replacement home in Alberta. The defendant, Enrico Dinardo, agreed to purchase Webster’s Caledonia property under an Agreement of Purchase and Sale but failed to close the transaction. The defendant did not dispute that he breached the agreement by failing to close.
As a result of the failed sale, Webster claimed that he suffered several categories of loss. First, he alleged that the value of his Caledonia property had dropped by approximately $90,000 (later framed as a $100,000 alternative claim) after the scheduled closing date, in a significantly deteriorating housing market. He asserted that he was unable to sell the property due to market conditions and continued to own it. Second, he claimed damages of $212,800 based on the difference between the agreed sale price of the Caledonia property and the price he was obliged to pay to purchase his new home in Alberta, arguing that this shortfall was a foreseeable consequence of the failed sale.
No insurance policy or contractual indemnity clauses beyond the standard real estate agreement play any role in the reasons provided. The decisions instead focus on the general principles of contract damages for breach of an agreement of purchase and sale, and the procedural doctrines governing summary judgment, res judicata, and abuse of process.

The first summary judgment decision (2024)

In 2024, the plaintiff brought a summary judgment motion seeking damages for the defendant’s admitted breach of the purchase agreement for the Caledonia property. In his factum on that motion, the plaintiff expressly claimed: (a) $212,880 representing the difference between the Caledonia sale price and the Alberta purchase price, or, in the alternative, (b) $100,000 for the loss of value of the Caledonia property between the date of agreement and the date of breach/closing. His affidavit evidence and written submissions confirmed that these were the core damage theories he wanted adjudicated.
The defendant, for his part, argued that the plaintiff had failed to adduce proper evidence of his damages. He contended that the plaintiff’s alleged loss of value of the Caledonia property was speculative because there was no expert valuation evidence, the property had been re-listed for only a short three-week period, and there were no actual sales or offers that could anchor a reliable market value at the breach date or thereafter. He also characterized the claimed linkage between the failed Caledonia sale and the Alberta purchase price as remote and not the proper measure of contract damages for breach of a real estate agreement.
Justice Goodman, hearing the first summary judgment motion, accepted that the defendant had breached the agreement but carefully evaluated the plaintiff’s proof of damages. He rejected the plaintiff’s attempt to recover $212,800 based on the difference between the Caledonia sale price and the Alberta purchase price, finding that this was not a proper measure of damages for breach of the Caledonia contract. That head of damage was considered too remote and not within the reasonable contemplation of the parties at the time of contracting. In effect, the Alberta purchase was treated as a separate transaction whose pricing could not be used as the benchmark for the seller’s loss vis-à-vis the Caledonia deal.
On the alleged loss of value of the Caledonia property itself, the plaintiff argued that a $100,000 diminution had occurred and that, if anything, his claim was conservative. Nonetheless, Justice Goodman concluded that the plaintiff had not provided reliable or cogent evidence to prove any loss of value. The property had been re-listed only briefly, and the evidence consisted mainly of a realtor’s market valuation with a limited window for receiving offers. The judge held that this did not amount to qualified expert opinion evidence sufficient for a summary judgment determination on valuation. He emphasised that parties on summary judgment must “put their best foot forward” and adduce the necessary expert or objective evidence if they wish to have damages determined at that stage.
Despite rejecting the large claimed amounts tied to the Alberta purchase and the alleged diminution in value of the Caledonia property, Justice Goodman did award the plaintiff certain other damages. Specifically, he allowed: (1) $38,005 for costs the plaintiff incurred in resolving his own breach of the Alberta purchase agreement on reasonable terms after the Caledonia sale collapsed, and (2) $5,000 as compensation for interest, closing costs, and related expenses connected with the failed Caledonia transaction. Justice Nightingale’s later reasons summarize that Justice Goodman ultimately granted judgment in favour of the plaintiff in the amount of $43,500 plus applicable interest, while dismissing the other claimed heads of damage. That judgment, including costs, was not appealed and the defendant paid it in full.

The second motion and res judicata ruling (2025)

Following his partial success in 2024, the plaintiff later brought a second summary judgment motion, this time focused squarely on recovering damages for the alleged loss of value of the Caledonia property. He argued that this head of damages had not truly been before Justice Goodman on the original motion and relied on Rule 20.07 of the Rules of Civil Procedure, which provides that a plaintiff who obtains summary judgment may proceed against the same defendant for “any other relief.” In support of the renewed claim, he filed new evidence in the form of a retroactive appraisal and a comparative market analysis prepared by the realtor who had unsuccessfully relisted the property after the breach.
The defendant responded with a motion under Rule 21.01(3)(d) to strike out the plaintiff’s second summary judgment motion. He maintained that the loss-of-value issue had already been advanced and decided in the first summary judgment motion and that the plaintiff was barred from relitigating it by the doctrine of res judicata, including both issue estoppel and cause of action estoppel, as well as by the related doctrine of abuse of process. He further argued that Rule 20.07 could not be used to reopen or re-prosecute a head of damages that had been previously determined on a final basis.
In the 2025 decision, Justice Nightingale agreed with the defendant. He carefully analysed the record of the first summary judgment motion and concluded that the plaintiff’s loss-of-value damages claim for the Caledonia property was squarely put before Justice Goodman. The statement of claim included loss of value as part of the overall $290,000 general damages for breach of contract. The plaintiff’s original factum and affidavit expressly sought either the Alberta-related differential or, in the alternative, $100,000 for loss of value of the Caledonia property. Justice Nightingale emphasised that Justice Goodman had not only acknowledged this claim but also substantively addressed and rejected it on the evidence.
Although Justice Goodman had prefaced one paragraph by observing that “the relief related to damages for the alleged loss of value in the Caledonia Property is not pleaded for this motion,” he went on in the same paragraph to state that, even if he was wrong on that point, the plaintiff had failed, on the evidence adduced, to establish any loss of value or to prove the market value of the property as required. He criticised the reliance on a realtor’s limited-window valuation as insufficient expert opinion evidence and concluded that the plaintiff had not discharged his onus to prove that head of damages on a balance of probabilities. Justice Nightingale therefore read the 2024 reasons as clearly dismissing the loss-of-value claim, not leaving it open for future litigation.
On that basis, Justice Nightingale held that issue estoppel applied. The same issue—whether the plaintiff was entitled to damages for the alleged loss of value in the Caledonia property—had been raised and decided in the prior summary judgment decision, which was final and involved the same parties. He also found that cause of action estoppel applied, relying on appellate authority that parties must advance every claim and defence they wish to have adjudicated in the earlier proceeding. Since the loss-of-value claim was part of the original cause of action for damages arising from the failed Caledonia transaction, and either was argued or could have been argued with reasonable diligence, the plaintiff could not bring a second proceeding to re-litigate it.
The court also characterised the second summary judgment motion as an abuse of process. Having failed to present expert valuation evidence on the first motion, the plaintiff was effectively attempting to “try again” with new opinion evidence to support the same head of damages that had already been dismissed. Justice Nightingale underscored that summary judgment is intended to provide finality when a party has chosen to seek a determination and has had a full opportunity to put forward its best case. Accepting the plaintiff’s approach would undermine that finality and invite repetitive litigation whenever a disappointed party later obtained stronger evidence.

Interpretation of Rule 20.07 and pleading requirements

A further issue concerned the scope of Rule 20.07. The plaintiff contended that, having obtained summary judgment in 2024, he was entitled under this rule to proceed against the same defendant for “any other relief,” which he said included the loss-of-value damages supported by the new appraisal. Justice Nightingale rejected this interpretation. He held that “other relief” in Rule 20.07 refers to relief not already claimed and adjudicated in the original summary judgment motion. In this case, the plaintiff’s statement of claim and his 2024 summary judgment materials clearly encompassed the loss-of-value damages.
Rule 25.06(9)(a) was also considered. It requires that a pleading containing a claim for relief must specify the nature of the relief claimed and, where damages are claimed, set out the amount claimed for each claim. The court noted that the plaintiff had in fact pleaded general damages for breach of contract of $290,000, a figure embracing the loss-of-value component. Because that head of damages was already part of the original relief sought, Rule 20.07 could not be used to evade the application of issue estoppel and cause of action estoppel or to reopen a previously dismissed claim.

Outcome and monetary consequences

In the result, Justice Nightingale concluded that it was “plain and obvious and beyond doubt” that the plaintiff’s second summary judgment motion for loss-of-value damages concerning the Caledonia property could not succeed. He applied the doctrines of res judicata (both issue estoppel and cause of action estoppel) and abuse of process to strike out the second motion. The defendant’s Rule 21 motion was granted, and the plaintiff’s second summary judgment motion was dismissed. Justice Nightingale ordered the plaintiff to pay the defendant $7,500 in costs, inclusive of HST and disbursements, for the 2025 motion. Taken together, the two decisions yield a split success: in 2024, the plaintiff was the successful party and obtained judgment of $43,500 in damages plus applicable interest and an unspecified amount of costs, while in 2025, the defendant was the successful party on the res judicata and abuse of process motion and received $7,500 in costs; because the reasons do not disclose the precise amounts of interest or the earlier costs awarded with the 2024 judgment, the total monetary recovery in favour of each party beyond those specified figures cannot be determined from the available decisions.