Drive along Route 302 past 765 Roosevelt Trail this fall and the plaza looks different than it did two years ago. The beige facade is gone. There's a hot dog joint with its own dedicated seating area. Through one storefront window you can see golf simulators lined up in a row. Another space has the look of a co-working lounge, complete with a smoothie counter. None of this reads like a plan a chain retailer's real estate team would draw up. It reads more like someone filled the building with businesses they already knew.
That's close to what actually happened.
The anchors that never left
According to Mainebiz, before any of the renovation started, two tenants had already been at the North Windham Shopping Center for four decades: the U.S. Postal Service branch and Windham Jewelers. Add in State Farm Insurance, US Cellular, and Miracle Ear, and you get a plaza that spent years running on the kind of steady, unglamorous businesses that don't need foot traffic gimmicks to survive. People come in for stamps, batteries for hearing aids, an insurance question. That was the baseline.
What's changed sits around those anchors, not in place of them.
Two brothers, $6.3 million, and no outside investors
The property's current owners are Mark and Eric Giguere, brothers from Westbrook who bought and renovated the shopping center entirely with their own money. By the time Mainebiz reported on the project last November, that investment had reached $6.3 million, covering the purchase and a full facade overhaul designed by CWS Architecture. As of that report, the upgrade on one building was 95 percent finished, with work on the second building planned to start the following spring.
The pace of leasing surprised even the people running it. Once word got out that the plaza was getting a new look, the brothers say they filled available units within 45 days of a space going vacant. Juliana Tonini, the leasing agent from EME Commercial Real Estate handling the property, summed it up for Mainebiz in three words: "Windham is booming."
Why the tenant mix looks like it does
Here's the part that explains everything else about this plaza. Eric Giguere isn't a career commercial landlord. He spent more than 20 years in finance at Sappi and Fairchild Semiconductor before becoming a Planet Fitness franchisee in 2007, first in Windham and later in Biddeford. In 2016 he bought the building next door at 759 Roosevelt Trail specifically to house that gym. He sold the Planet Fitness locations in 2023 to focus on commercial real estate. Mark spent 13 years in Maine's retail auto business, then built two reinsurance agencies, one focused on auto dealers and one on credit unions, before selling both to a New York private equity group in 2021.
Neither brother came up through a leasing office. They came up running businesses that depend on local relationships, gym memberships, dealership networks, insurance referrals. So when a space in their new plaza needed a tenant, they didn't run a demographic study. They talked to people they already knew. Eric described one of the bigger leases to Mainebiz this way: "One of the bigger spaces we just leased, it was a deal that happened on the golf course."
That single sentence tells you more about this shopping center than any square footage figure. The businesses that ended up here didn't arrive because an algorithm flagged Windham as underserved in indoor recreation. They arrived because the landlord plays golf with people who run businesses, and one of those conversations turned into a lease.
What actually moved in
The result is a tenant list that would look random on paper and makes complete sense once you know how it was built:
- Cormier's Dog House, a Chicago-style hot dog counter opened by Ryan Cormier of Waterboro, serving Vienna beef dogs and burgers out of a space next to the post office.
- Big Swing Golf Sim, an indoor golf simulator business now operating out of the plaza, giving Windham golfers a way to keep swinging through a Maine winter.
- Blended, which combines co-working desks, conference rooms, and private offices with a smoothie bar, a combination that only makes sense if you assume the same person might want to close a laptop and order a drink without leaving the building.
- Maine Dance Center, a dance school relocating into the plaza from its previous location.
None of these businesses compete with each other for the same customer at the same hour. A parent dropping a kid off for dance class can grab a smoothie next door. Someone finishing a golf sim session can walk over for a hot dog. The mix works because it was assembled by people thinking about how their own days actually move through a plaza like this, not by a leasing matrix sorting tenants by category.
Still a work in progress
The renovation isn't finished. The facade work on the second building was planned to begin in the spring following that November report, which means parts of the plaza have likely looked different building to building through this year as work has progressed in phases rather than all at once. If you've noticed scaffolding on one side of the property and a finished look on the other, that's the sequencing, not a stalled project.
The Gigueres have said plainly that they expect the region to support more of this. "There is no question the region can and will support additional businesses," they told Mainebiz. "Build it and they will come." Given how quickly the current round of spaces filled, that's less a prediction than a description of what's already happened twice.
Part of a bigger stretch of Route 302
The North Windham Shopping Center doesn't sit alone. It's part of a cluster along Route 302 that includes the Windham Mall, anchored by Renys and Marshalls with Smitty's Cinema and Portland Pie Company nearby, and the Windham Shopping Plaza next door, home to Bull Moose and the Busy Bee Laundromat. If you already run errands along this corridor, the new plaza tenants slot into a route you're already driving, not a new destination that pulls you out of your way.
One more reason to be in the area this month
If you're near the plaza on September 24, there's a separate but related sign of how much is happening in Windham's food and coffee scene right now. Milk & Honey Café, the coffee shop in town, is teaming up with Tandem Coffee out of Portland and Crouse House Coffee out of Lewiston for a latte art competition running from 5:30 to 8 p.m. It's a small event, but it's another data point on the same trend line as the shopping center renovation: local operators betting that Windham has room for more of this kind of thing, and betting on each other to fill it.
The plaza at 765 Roosevelt Trail is a small story on its own. But it's a useful one if you want to understand how growth actually happens in a town like Windham. It's rarely a single big announcement. It's landlords who used to run a gym leasing space to a guy who makes Chicago hot dogs, because they know each other, and because enough people kept showing up that it made sense to keep going.
If you're watching Windham change and want to talk through what any of it means for your own plans, whether that's timing, a specific street, or just understanding what's coming next, Real Maine Living is a good place to start. Let's Connect.
