Built to Last:

Penny Glassmeyer and the Power of Positive Spaces

By PAMELA DEY VOSSLER

Grove Street Plaza / photo by Kyle Norton


Penny at one of her building sites 
/ photo by Carol Guthrie

Perhaps you’ve heard her name. Maybe you’ve even met her. Most likely not. She’s kept a low profile as she transformed the blights in our town to things of beauty. But you absolutely know her. Better than you might imagine.

Builder, visionary, decades-long Darien resident, wife and mom—Penny Glassmeyer and her work surround us—incommercial properties such as Grove Street Plaza, 1292 Post Road, 17 Old King’s Highway South and 745 Boston Post Road,to name just a few of the places she has reclaimed. Homes too. If it’s beautiful,made from the finest materials and looks like it’s always been there, chances are she built it, renovated it or inspired it.

You’ll know her best through Grove Street Plaza. Perhaps you’ve met a friend there for coffee, brought your kids to the multigenerational Darien Summer Nights concert series, decamped there to work or just “be,” and then run into people you know from all walks of whatever claims your interest in town.

In a morphing world that allows for less and less time together, Penny has savedspace for us to still have what made families and communities close before social media, sports on weekend mornings, meetings at night and our “always-on” lives shredded our days into disjointed bits.

“She created a place for people to connect. That creates pleasure, that creates kindness,” said recently retired State Representative Terrie Wood who has known Penny professionally and personally for 30 years. “Grove Street was a game changer for our town. There was no place like it before,” she added, describing what she calls “the power of positive spaces” and Penny’s ability to conjure it.

Any moment you’ve enjoyed at Grove Street is thanks to Penny. Fifteen years ago, it was a tumble down, ramshackle wreck of a place, nothing to note …which most of us who lived here at the time didn’t.

Grove Street before

Who would have thought it could be anything more? The town didn’t. Not at first. It took them three years to approve Penny’s plans. So, who would take a flyer on such a long shot?

Someone with vision. Someone with conviction. Someone with the tenacity to see it through.

“Penny has a fantastic eye for properties,” said Carol Guthrie, Penny’s landscape architect for 25 years on all her projects, including Grove Street, “and then turns them into something great,” she continued.

Grove Street after.

“She never quits,” said Darien native David Genovese, founder of Baywater Properties who, in partnership with Penny, is developing The Corbin District downtown, adding new layers to a relationship with the Glassmeyer family begun when he was five years old and just starting a lifelong friendship with Ward, the oldest of Penny’s five children. “She never gave up (on Grove Street)…. She knew what it could be, so she trusted her gut. She has enormous conviction and patience,” he added.

In rescuing Grove Street from the mess it was and replacing it with structures built from the highest quality materials using the best type of construction, true to her uncompromising commitment to exacting excellence, she set the course for David’s rebuild of Ten Twenty Post and its sister structures. She also sparked the revitalization of downtown Darien.

“The Bevolo gas light fixtures that you see on Grove Street Plaza or 1020 Poston Post Road and our other buildings in downtown Darien? That started with Penny,” explained David.

And those bricks! Each one handmade in Virginia, authentic, beautiful—the kind that last …similar to those Penny chose for Grove Street.

Already influenced by his own high standards and his volunteer work with the Darien Revitalization Initiative (DRI) which he’d been asked to join after leaving his career in real estate investment banking to pursue commercial real estate development in 2001, David’s commitment to quality was cemented by Penny’s work. He took it with him as he moved on with her to design and break ground for The Corbin District.

“It all kind of emanated from Penny’s overarching philosophy to do it right,” said David of the trajectory of The Corbin District and the Grove Street-like spaces it will have for gathering. “Penny set the bar.”

“The typical financial partner is focused on maximizing the economic outcome of each investment,” he explained. “In the case of Mrs. G. (as David still calls her), it is never that. It’s how do we create a sufficient economic outcome and the best possible project for the Town of Dairen and its residents. If I didn’t have a partner like Penny, The Corbin District would look very different. (No matter what I may want), I would have had to convince a financial partner to look at that with me and it’s unlikely that a typical investor would allow us to design and build the project at the high quality we are today,” he said.

Penny with Hoby Baker, her right hand man

If you’ve been to Flour, Water, Salt—the baker in Grove Street Plaza, you’ll know another side of Penny.

“She’s tough. You respect her,” said Ed Glassmeyer, Penny’s husband of 58 years.

Just try to keep her in a meeting for longer than the shortest amount of time required to cover the issues at hand and you’ll understand what he means.

“She is a woman on a mission,” agreed David. “She doesn’t like long meetings. She’s like ‘What are we here to talk about? Let’s do this. Let’s go.’ She does not labor over decisions,” he continued.

“But she’s very empathetic,” Ed added as he related the story of her investment in the extensive equipment Flour, Water, Salt owner Rob Van Keuren needed to get his bakery up and running in the space he was to rent from Penny.

Given the bakery’s great success since the day it opened, it’s hard to imagine the leap of faith it was back then to make that big cash outlay based solely on her belief in Rob and his vision.

Penny, right, on site at her Knobel Hill project, a multi-house development for empty nesters on Locust Road

Was she nervous about it? Sure. “It was a dance studio before, with no fixtures. The only thing there was a bar along the walls and a bunch of wood,” said Ed, explaining just how anxious Penny was about it, and just how much she trusted her gut to give it a go in spite of it.


“How very lucky we are to have someone so focused on the long game, someone who can see what others may not—in a space, a building, a business, a person.”


“She gives people a chance,” said her son Ward of the path she paved for people to pursue their dreams through the breaks she gave them. Not just Flour, Water, Salt, but the Melting Pot, Neat, A Little Something White, and other small business owners who are now so central to our town. “But she doesn’t believe in a wishful way,” said Ed. “She’s a tough person to win approval and respect from. But she has this amazing combination of that and giving people a fair chance,” he added.

And she cares, endlessly, though you have to look a bit beyond her focused, no-nonsense approach to see just how much.

It’s in what she does when no one’s looking, randomly stopping by one of her buildings to see to a planter, or a mat that needs fixing—rolling it up herself and putting it in the back of her car to bring it to the people who will mend it; or getting down on her hands and knees to paint the small protective pads beneath the legs of an antique console in the lobby of 17 Old King’s Highway South so that they match the wood.

17 Old King’s Highway before

“She is an artist,” said David commenting on Penny’s ability to see the big picture and the details simultaneously, and the driver behind all that conviction and tenacity. “Her emphasis is on the art of what she builds. Penny is into the details of the aesthetics, the materials and the place that she is creating.”

“But she’s very practical when she needs to be,” said Carol, recalling her “complete calm” when things did not go as planned, when it truly was unrealistic to backtrack.

17 Old King’s Highway after

She believes in people, respects them and they love her for it. “She treats people fairly and with respect regardless of where they came from or who they are,” said David. Her contractors? Her crew of carpenters, electricians plumbers, sheet rockers and masons? They were her partners, and her friends.

“Penny really is like a second mom to me,” said Garry Ford who started working with Penny in 1995 as a carpenter. “We had similar opinions on how to bring her visions to life and I respected her goal of keeping things authentic and beautiful…. Penny holds a special place in my heart and I’m so grateful for all that she has shared and taught me over the years.”

“She is an unbelievable gatherer of opinions,” David said. “While she has her own opinions, she always sought the opinions of a huge cast of characters, and wove that into her thinking.” She spoke to everyone—her friends, her builder, people in town. “She loved to get advice from as many people
as possible,” he continued. “She is (also) incredibly capable of spotting competent, talented people and then giving them free rein to do their best and because of that everybody gave her 110%,” said
Carol who holds an MBA from Columbia and describes Penny as “the best manager I ever encountered.”

“Penny was always in control, but never control-oriented,” she added….

and good at getting people to get things done. Just ask any of her kids’ friends, now adults, who raked leaves, stacked wood, mowed lawns, seeded grass—whatever Mrs G. asked, when they’d gather at the Glassmeyer home.

“We were lucky we still had friends after that,” recalled Ward, laughing.

“Their house was where we went the most to play street hockey and hang out and Mrs. G. would always put us to work if she had chores. She was old school. Really old school. She’d say, ‘Hey guys, take a break and come help,’” recalled David. “She liked me the most because I worked the hardest,” he joked.

Where does all this come from? Some by way of DNA, of course. Her uncle and grandfather developed Rye Brook and other properties in Westchester in the mid 1900s. Her father was a tenacious adventurer, determined to prospect for uranium, which he did – in Utah, moving Penny, her mom and three siblings from Larchmont, where Penny was born, to Wisconsin and Texas.

And she comes to it by way of grit and an instinct to provide for those she loves—the kind you get when you lose a dad you’re very close to when you’re just 16 years old and you’re the one best equipped to take over the care of your mom and siblings.

“She was the second child but the other siblings weren’t up to taking command of the family and give their mother support so Penny did,” explained Ed. She also comes to it through a sharp intelligence that took her through Berkeley to a B.S. in Business/Math in California where the family moved after her father died.

It’s in her quiet yet fierce drive to do her best in her work, the paddle she played in flight one of the town league, the golf and bridge tournaments she won. It was in her tough, no-nonsense confidence in her kids as they grew up. She believed in their ability to make decisions, get to where they needed to be and make the most of their talents. It cuts widest in the good humored, non-negotiable positivity with which she lives her life.

In a time of disposable everything, where convenience rules and even messaging lasts just nanoseconds, how very lucky we are to have someone so focused on the long game, someone who can see what others may not—in a space, a building, a business, a person, someone who is willing to
go against the grain so that others may see it too, and become better themselves for it…. Someone who knows how to build things that last, someone like Penny Glassmeyer.