Chestnut Hill's Zoning Vote Passed. The Timeline Didn't.

"We don't plan to wait. We're planning to keep going full speed ahead."

That's Cliff Kensington, City Realty's director of acquisitions, talking to reporters minutes after Brookline's Special Town Meeting approved the Chestnut Hill Commercial Overlay District on May 28, 2026. His company had just cleared the single biggest zoning hurdle standing between it and a redevelopment of the old Chestnut Hill Office Park at 1280-1330 Boylston Street, a project once pitched at 1.2 million square feet before years of revisions reshaped it. The vote wasn't close. Then, in the same breath, Kensington told those same reporters the project won't break ground before spring of 2028 at the earliest, and that's the optimistic version.

If you're weighing a purchase near Route 9 in Chestnut Hill right now, both of those facts matter, and they point in opposite directions. One says the biggest zoning fight in the neighborhood in a generation is over. The other says the thing everyone's picturing when they hear "redevelopment" is still years from becoming a construction site, let alone a finished building. Treating this as one piece of news instead of two is the mistake I'd want a buyer to avoid.

A vote that wasn't close after all

Town Meeting approved the zoning change 217 to 20, and a related agreement authorizing the town to enter into a tax certainty arrangement with City Realty passed 230 to 6. Both margins cleared the two-thirds threshold required for zoning changes by a wide margin. That kind of lopsided result usually means one of two things: either nobody cared enough to organize opposition, or the real fight happened earlier and got resolved before the vote ever hit the floor.

Here, it was the second one. The Chestnut Hill Commercial Area Study had been grinding through community advisory group meetings, design guideline drafts, and transportation studies since at least December 2025. By the time articles reached Town Meeting, the Select Board had already negotiated a Memorandum of Agreement with City Realty and amended the zoning language twice, once in April and again in May. The lopsided vote wasn't a surprise ending. It was the visible tail end of months of quieter negotiation that most residents never saw.

One piece of friction did survive to the floor: a motion to strip the district north of Boylston Street out of the overlay entirely. It failed, and that parcel stayed in the zoning as written. Worth knowing if you're looking at property on that side of the street specifically, since it means the taller-building rules apply there too, not just on the south side where the office park sits.

The building that shrank before it was approved

Here's the detail most people who only read headlines miss. Earlier public materials, including reporting from as recently as April 2026, described City Realty's plan as a 783-unit mixed-use project. That number circulated widely enough that it's probably still the figure in a lot of buyers' heads.

It's not what got approved. By the time the developer finalized its plans for Town Meeting, the project had been revised down to three buildings, 14, 12, and 7 stories, containing a 200-room hotel, 266 apartments and condos, medical office space, and ground-floor retail. The unit count most people quote isn't the unit count that exists in the approved zoning. Plans on a project this size move between concept and approval, and the version that clears Town Meeting is rarely the version that generated the first round of news coverage. If you're comparing what you've heard about this project against what a listing agent tells you today, ask which version they're describing.

The zoning itself splits the district into subdistricts with different height ceilings. The core commercial parcel allows buildings up to roughly 14 stories. A transitional buffer subdistrict, covering ground closer to Hammond Street, caps height around 7 stories, specifically to soften the edge between the commercial corridor and the residential streets behind it. Projects can earn bonus height for including a hotel use or for making at least half their units affordable, which is one reason the final massing landed where it did.

Two projects, two very different clocks

The 1280-1330 Boylston megaproject isn't the only redevelopment on this stretch of Route 9, and it's useful to hold it up against the other one to see how differently these things actually move.

	1280-1330 Boylston Street (City Realty)	1180 Boylston Street (Chestnut Hill Investments)
Site	Former 1960s office park, 5-acre parcel	Former gas station, single corner lot
Scale	Three buildings, 14/12/7 stories	One six-story building
Program	200-room hotel, 266 apartments/condos, medical office, retail	50 age-restricted (55+) apartments, ground-floor retail
Affordability	Bonus height tied to affordable unit share	10 of 50 units at or below 50% AMI
Status as of zoning approval	Cleared zoning May 2026, earliest groundbreaking spring 2028	Broke ground years before this vote, with demolition and foundation work already done

A short walk down the same corridor, and one project already reached a construction phase the other hasn't started. Chestnut Hill Investments, led by principal Raj Dhanda, began transforming a long-shuttered service station at the corner of Boylston and Hammond into a six-story building built by Nauset Construction, with a unit mix of one, two, and three-bedroom apartments restricted to residents 55 and older. Ten of those fifty units are set aside as affordable housing. It's a fraction of the scale of what City Realty is planning next door, but it's the kind of project that actually moves dirt on a predictable timeline, while the larger one is still working through permitting, design review, and financing before a single foundation gets poured.

If your mental picture of "Chestnut Hill is about to change" is built around the big number, you're pricing in a timeline that's several years further out than the small project already under construction down the same street.

Why the loudest objector had its own redevelopment to protect

The most visible opposition to City Realty's project came from WS Development, which owns The Street, the shopping and entertainment complex directly across Route 9. Its stated concern was parking. On the surface, that's a narrow, almost bureaucratic objection. Underneath it, the timing tells a more useful story.

The Street completed its own Sasaki-designed renovation years ago, and it's still in the process of filling storefronts today. Next Health recently opened an East Coast flagship location there. Sweetish Fish opened its first permanent location. Madras Dosa Co. opened its doors. The RealReal is set to open its first Massachusetts location there in late 2026. A retail complex still leasing up years after its own redevelopment has every reason to want every nearby parking spot reserved for its own customers, whether or not that's the argument it makes in a permit filing. It doesn't take much reading between the lines to see why a landlord protecting a multi-tenant investment would push back hard on a competing project's parking ratios right next door.

None of that means the parking objection was wrong on the merits. It means the fight over parking standards was also, quietly, a fight over who gets first claim on a limited resource during a period when both properties need it most.

What this actually changes if you're buying near Heath or Hammond Street

A few practical questions worth asking before you write an offer near this corridor:

Ask which subdistrict a specific parcel falls into. A 14-story neighbor and a 7-story neighbor create very different daylight, noise, and resale conversations, and the zoning map draws that line street by street, not block by block.
Ask what the Memorandum of Agreement and tax certainty agreement actually commit the town and the developer to, and over what time horizon. These documents shape how commercial tax growth from the project gets treated, which matters if you're weighing long-term tax stability in the area.
Ask your agent for the current, post-revision version of the project, not the version that made headlines a year ago. The unit count and building heights have already moved once between initial announcement and approval.
Don't assume "approved" means "under construction." The developer's own stated earliest groundbreaking is spring 2028, and that assumes financing conditions improve from where they sit today, with elevated interest rates and construction costs already slowing projects across the region.

FAQ

Will this project affect my property taxes if I buy nearby? The town and City Realty signed a tax certainty agreement as part of the approval, which is meant to lock in predictable terms for how the project contributes to the commercial tax base over time. The details of that arrangement are public through the town's Chestnut Hill Commercial Area Study page, and worth reading directly if property tax exposure is a factor in your decision.

How tall can buildings get under the new zoning? Up to roughly 14 stories in the core commercial subdistrict, with a 7-story cap in the transitional buffer subdistrict closer to Hammond Street. Bonus height is available for hotel components or for projects that commit at least half their units to affordable housing.

Is now a bad time to buy near this stretch of Boylston Street? It depends what you're pricing in. If you're expecting the retail and walkability upside promised by the megaproject to show up in the next year or two, that's not realistic given the stated spring 2028 earliest groundbreaking. If you're evaluating the neighborhood on what already exists today, The Street's completed renovation and the project already under construction at 1180 Boylston are the more relevant near-term reference points.

Chestnut Hill isn't one story right now. It's two, moving at two different speeds, and confusing them is the easiest way to misprice a decision on this stretch of Route 9. If you're weighing a purchase near Boylston Street and want a read on a specific address rather than the neighborhood in general, that's a conversation worth having before you write an offer. David Gordon Group can walk through what the zoning actually means for a specific parcel. Let's Connect.