Brookline's Cottage Farm neighborhood just reminded everyone why it sits at the very top of the local market. In early June, two stately single-family homes in the exclusive enclave changed hands in back-to-back deals that added up to roughly $18.7 million, putting them among the priciest closings in Massachusetts for the week.
The bigger trade was at 22 Worthington Road, an approximately 8,000-square-foot Georgian that closed for $10 million on June 8, 2026. That deal ranked as the top-priced luxury home sale in the state for the week, according to NBC Boston.
A day later, 90 Ivy St. followed suit. The roughly 4,700-square-foot Cottage Farm home sold for about $8.7 million on June 9, 2026. The Warren Group's weekly sales roundup, summarized in Banker & Tradesman, captured the transactions and listing details, while public listing pages on sites such as Zillow show the homes' square footage.
Cottage Farm's historic pull
Cottage Farm is a tightly preserved 19th-century pocket of large-lot mansions just a short walk from Fenway and Allston, and that kind of pedigree helps explain why buyers keep paying up. The Town of Brookline's Local Historic District materials lay out the neighborhood's origins and why intact properties there so often command top dollar, especially when they rarely hit the open market, according to the Town of Brookline.
Public records and property-data sites show that 22 Worthington's 2025 assessed value was roughly $7.85 million, so the $10 million closing represents a notable premium. Those assessment figures and recent tax history are available on property-data pages such as Realtor.
What the sales suggest
Together, the two closings highlight how steady demand remains at the very top of Greater Boston's single-family market. Buyers are still paying for proximity to the city, generous private lots and historic character, even as prices at that level leave little room for hesitation.
Weekly transaction roundups and local reporting, including Boston Business Journal coverage republished by NBC Boston and the Warren Group's listings cited by Banker & Tradesman, point to other eight-figure deals around the region this year, suggesting that the high end is still very much in play.
For neighbors, the back-to-back sales are another reminder that Cottage Farm remains a tightly held market where historic parcels near Boston carry a serious premium. Any follow-up activity, such as renovation permits or fresh listings, will show whether the new owners keep the homes largely intact or reshape them for the next chapter.
