What Happens to the Taylor Block Depends on a Survey That Closes November 29

Who decides what goes into the empty storefronts on Washington Street? Some windows on the Taylor Block in Wellesley Square have been covered in brown paper with "for lease" signs since Comina and Panoply left. Rice Burg, Old School Pizzeria and Tutto Italiano are still open on the same strip. The block's owner is a Quincy investment firm that rarely speaks in public. It has said it is in no hurry. Over the next few months, the most active planning in the Square is coming from Town Hall and from residents who answer a survey before Sunday, November 29.

One owner, four Wellesley holdings

Jumbo Capital is a privately held commercial real estate firm in Quincy. Jay Hirsh founded it in 2009. Over about three years it has become one of Wellesley's larger commercial property owners.

Bisnow reported in 2023 that 40 Grove St. accounted for $15 million of the portfolio price. Hirsh told the Boston Business Journal, as Bisnow relayed, that the tenant mix of small medical, law, accounting and financial services businesses drew him to the buildings, and that rents were "slightly below-market." That first purchase was about office income. The Taylor Block and 888 Worcester are a different kind of holding. One sits in the middle of the Square's retail, and the other is a roughly 6-acre site on Route 9 that the owner wants to rebuild.

The Taylor Block sits behind 888 Worcester in the queue

The Taylor Block covers about 1.2 acres. Its roughly 70,000 square feet hold retail, office, residential and auto repair space. When Jumbo bought it from longtime owners Sullivan & Co. of Braintree, Hirsh described it to Banker & Tradesman as a long-term hold and said no major changes were planned in the near term.

"A lot of the retailers are beloved, and I don't want to do anything to lose any of those tenants."

The same article said the sale brochure suggested the block could hold roughly twice its current density. Hirsh answered that higher uses might come "down the road." The parcel sits in one of Wellesley's MBTA Communities zoning districts. The Boston Globe had reported earlier that the block offers limited redevelopment potential for new housing.

The town has since put a timeline on "down the road." At the September 29 All Board meeting, Executive Director Meghan Jop said Jumbo intends to finish 888 Worcester St. first. The minutes say development of the Taylor Block is not expected for about five years. In its coverage of the October 14 public forum, The Swellesley Report added that Jumbo is expected to bide its time on the block until it sees how the town's Wellesley Square plan shakes out.

That sequence explains the papered windows. A landlord planning a five-year wait has little reason to sign long leases or start construction now. The design for the sidewalks, crosswalks and parking in front of its storefronts is also still open.

What the town is drawing around the block

The Wellesley Square Improvement Project is led by the Department of Public Works. Toole Design is the lead consultant, and BETA Group provides support. According to the project's StoryMap, its goals include:

• safer pedestrian connections
• better traffic flow at key intersections
• more parking for visitors, customers and merchants
• new open space and gathering places
• updated lighting, benches, meters and crosswalks
• tying together the Central/Washington, Church/Washington and Grove Street business areas

The work is planned to take 20 months and ends with a construction funding request at Town Meeting in 2027 or 2028.

The first engineering focus is two intersections, Central/Washington/Grove and Central/Crest/Railroad. The Taylor Block's Washington Street frontage runs along the corridor those intersections control. Decisions on curb lines, turning lanes and metered spaces will shape the block's storefronts before Jumbo draws anything of its own.

So far, the public turnout has been small. The Swellesley Report counted 30-plus people at the October 14 session at Hunnewell School. Town staff and consultants made up a high share of the room. The survey had drawn more than a hundred responses by mid-October, and the project team had met separately with about two dozen businesses. The concerns raised are familiar to anyone who drives through the Square. Businesses don't want to lose parking, the main intersections are dangerous, and people want more places to sit outside. One attendee pointed to the five-way intersection near the church and Anderson's Jewelers, where people try to cross Washington Street. Another, who lives near the Square, described the drive to Roche Bros. as like "going around the Mulberry bush."

The room also raised a larger question. Under an emerging plan for a new fire department headquarters, the Central Street fire station would close. Attendees asked whether the building could become an arts space. The block, the fire station and the street layout are all unsettled in the same stretch of months.

Two calendars running side by side

Jumbo's timeline and the town's line up closely. Here are the dates as the town and Jumbo had set them at the end of October 2026:

1. Sunday, November 29, 2026. The Wellesley Square public survey closes.
2. Thursday, December 10, 2026, 7 p.m. The town and its consultants hold the next public meeting at Hunnewell School, 28 Cameron Street, to review data and consider design options.
3. Late January 2027. The preferred design concept is presented.
4. Spring 2027. The Square's final design and next steps are scheduled. Jumbo also hopes to bring a rezoning of 888 Worcester St. to Annual Town Meeting this spring, though the proposal still had to be worked out within a couple of months of mid-October.
5. Around mid-2027. The town land-use departments still working out of 888 Worcester, the building that served as temporary Town Hall, plan to move out.
6. 2027 or 2028. A Square construction funding request goes to Town Meeting.

The 888 Worcester plan is still a proposal. According to The Swellesley Report's October 21 coverage, Jumbo's Tom Powers told the Planning Board on October 19 that Life Care Services would operate the site's independent living, assisted living and memory care community. An earlier presentation to the town cited 150 to 200 units. Board member Tom Taylor supported the project but raised concerns about the zoning. He said the town may need a new zoning district that could apply to other properties, not just a change for this one site. No board vote has been reported. Every month the Route 9 project takes adds a month to the Taylor Block's wait.

The Square this month

In the meantime, the block is operating as a set of short-term arrangements. The vacancies are listed for lease, and the remaining tenants are open for business. A few doors down, the Square shows another way empty retail space gets used. The Cashmere Sale, back for its 16th year, opened October 16 in the former Dover Saddlery at 595 Washington St., next to The Village Bank. It has metered parking out front and free parking in back. The Swellesley Report notes that the pop-up has used at least a half-dozen locations in town over the years.

The survey and the December 10 meeting will shape the street the Taylor Block's storefronts face, and Jumbo is expected to wait for that design before making its own plans. The town's project StoryMap posts the October 14 presentation video and will carry updates as the design alternatives come in. The survey link is on the town's Wellesley Square notice until November 29.

If you own a home within walking distance of the Square, the changes coming over the next few years could matter to your property. Molly Campbell Palmer follows each redesign meeting and Town Meeting vote and can explain how they could affect a home near the Square. You can start with an instant home valuation.