Mass. Appeals Court hears dispute over whether offer to purchase created binding contract in 5 Middle Street sale

The Massachusetts Appeals Court on Zoom heard oral argument in case number 2453460, 5 Middle Street LLC v. Robert Alexander, a dispute over whether a standardized offer to purchase created a binding contract and whether the Superior Court erred in granting summary judgment and ordering the sale of a three‑family residence.

Appellant Robert Alexander, through attorney Matthew Lamoth, told the panel the offer to purchase contained multiple defects and post‑signing communications that under Massachusetts precedent demonstrate the parties did not intend to be bound. "The issue before the court . . . is whether considering the facts and precedent and standards for summary judgment and specific performance, the lower court erred," Lamoth said, arguing for remand for additional discovery and that genuine issues of material fact remain.

Lamoth emphasized several facts he said weigh against treating the form as a binding contract: the seller repeatedly refused to sell before the purported offer; a buyer entity (65 Middle Street LLC) did not exist until after the parties' exchange; the form contained handwritten changes, crossed‑out terms and missing seller initials; the stated acceptance deadline was altered and the document was not executed until after the deadline; and the deposit check post‑dates the purported execution. He also argued there were communications about structuring the sale to avoid capital gains tax that were not reflected in a finalized purchase‑and‑sale agreement and that the limited discovery period below (about two months after default was removed) prevented meaningful fact development.

Plaintiff 65 Middle Street LLC, through attorney Jason Menikus, countered that the dispute turns on well‑settled contract and equity law and that the standard form used here "creates binding obligations." Menikus argued that when the buyer's agent transmitted the completed form by DocuSign on September 9 and the seller executed and returned it within about an hour, that sequence amounted to a valid post‑deadline offer and timely acceptance or, at minimum, a new offer capable of prompt acceptance. He told the court that the signature lines and initials on the form identify the buyer (appearing in the record as David Pogorel) and that it is routine in real estate for purchasers to take title in single‑purpose LLCs.

The court's questioning focused on several contested evidentiary and legal points: whether a form stating it expired on September 8 could be treated as effective if executed on September 9 via DocuSign; whether the buyer's signature or initials on the form sufficiently identify the buyer; whether assignment of the contract to 65 Middle Street LLC prior to closing requires seller consent (counsel agreed assignment documents are not in the record); and whether a text message among brokers referencing a trust transaction creates, or permits a reasonable inference of, an undisclosed condition material to the agreement. Counsel disagreed about the evidentiary weight of post‑signing broker communications and whether those communications were ever objectively manifested to the seller.

Both sides cited Massachusetts decisions addressing when offers to purchase are too vague to bind parties and when post‑signing negotiations undercut an intent to be bound. Lamoth pointed to a line of cases in which courts declined to enforce offers that lacked material terms or showed no meeting of the minds; Menikus relied on decisions that have enforced standard form offers and ordered specific performance. Both attorneys acknowledged unpublished decisions they relied on are in the record or addendum to briefs.

Counsel also debated discovery below. Lamoth argued that the brief discovery window and a motion to quash depositions prevented the defense from obtaining testimony from witnesses (including the seller's broker and other participants) who could corroborate the seller's claimed lack of intent. Menikus said the plaintiff identified in interrogatory answers the persons who would have relevant information and argued additional discovery would not alter the legal conclusion supporting summary judgment.

The court did not rule from the bench. After questioning both counsel, the panel accepted the arguments and the matter was "submitted," closing the argument.

The appeal will turn on (1) whether the offer form and the sequence of DocuSign transmission and signatures constitute a binding agreement under Massachusetts contract law; (2) whether objective manifestations and post‑signing communications about tax‑avoidance or trust structures create material unresolved terms; and (3) whether the limited discovery below produced a genuine issue of material fact sufficient to defeat summary judgment.