Drive Route 302 through North Windham and it is easy to miss what happened at 765 Roosevelt Trail. The building still reads as a strip mall. The parking lot still fills the same way it always has. But walk into the tenant spaces that opened over the last year and you are looking at a different bet entirely, one about what 60,000 people in the Lakes Region have been driving an hour to find.
That is not an exaggeration for effect. It is the number the plaza's new owners used to justify spending $6.3 million on a building most people had stopped noticing.
The number that explains the renovation
Brothers Mark and Eric Giguere bought the North Windham Shopping Center at 765 Roosevelt Trail in June 2023. Both are Westbrook natives with backgrounds outside retail real estate. Eric spent two decades in finance before becoming a Planet Fitness franchisee, eventually selling those gyms in 2023 to focus on commercial property. Mark spent 13 years in the auto retail business before building reinsurance agencies across 14 states, which he sold in 2021.
Neither brother came from shopping center development. What they saw when they looked at the two buildings totaling 58,000 square feet was a math problem. The Lakes Region, they told Mainebiz, is underserved in retail and restaurant space relative to its population, and residents were regularly driving up to an hour away to meet needs that should have been available closer to home.
That is the thesis the entire renovation rests on. Not "this plaza needs new paint." More like: North Windham is close to becoming the commercial center of gravity for a region that currently has nowhere close by to go.
What actually changed, and how fast
The renovation itself has been incremental. As of last fall, the facade and storefront glass work on one building was already 95 percent complete, with planning for the second building's exterior upgrade slated to begin last spring. That is the visible part.
The number that matters more is the speed of leasing. The Giguere brothers told Mainebiz they expected roughly half of the plaza's square footage to turn over within 18 months of purchase, and when that space came open, they filled it within 45 days. That is not a typical retail leasing timeline. A vacancy that gets filled in under two months signals demand that was already there, waiting for the right space to open up.
Juliana Tonini of EME Commercial Real Estate, the property's leasing agent, put it plainly: "Windham is booming."
Who actually moved in
Here is where the plaza stopped looking like a generic strip mall and started looking like a cross-section of what Windham residents are actually asking for.
| Tenant | What it offers | Status |
|---|---|---|
| Windham Jewelers | Jewelry retail | 40-year tenant |
| U.S. Postal Service | Mail and package services | 40-year tenant |
| Cormier's Dog House | Chicago-style hot dogs | New addition |
| Big Swing Golf | Five indoor golf simulators | New addition |
| Blended | Co-working space, private offices, conference rooms, smoothie café | New addition |
| Maine Dance Center | Dance instruction for all ages | Relocating from Raymond |
The mix tells its own story. Windham Jewelers and the Postal Service have anchored this plaza for four decades, which means whatever else changes, there is still a version of the building that feels familiar to anyone who has shopped there since the 1980s. Everything else is new, and everything else points toward a specific kind of everyday use: a place to work outside your house, a place to bring your kids after school, a place to grab dinner without driving into Portland, a place to practice a golf swing in February without leaving Cumberland County.
Blended's founder, a merchant mariner's wife who runs the business with her husband, also a merchant mariner, already operated a mortgage brokerage out of the same space. When she knew the surrounding square footage was coming open, she told Mainebiz she started thinking about what the neighborhood was missing rather than just filling the lease. Her answer was co-working, six private offices, ten private workstations, three conference rooms, and a smoothie bar built around real fruit with customizable add-ons. It is a small business decision, but it is also a bet that North Windham has enough people working from somewhere other than a traditional office to support a dedicated space for it.
Why the anchors matter as much as the newcomers
It would be easy to write this as a before-and-after story: old boring plaza, new exciting plaza. That misses what is actually interesting here.
The two businesses that have stayed for 40 years, Windham Jewelers and the Postal Service, are not decorative holdovers. They are the reason the plaza had steady foot traffic to build on in the first place. The Giguere brothers were not renovating an empty building. They were renovating a building that already had a customer base, and using that base to justify bringing in tenants that customer base did not previously have reason to visit.
That is a different story than "developer builds something new." It is closer to "developer notices an underused asset and fills in what is missing around it." The distinction matters if you are trying to understand how North Windham's commercial strip is actually evolving, because it suggests the growth is additive rather than a full teardown-and-rebuild. The jeweler and the post office window you have used for years are still there. What is different is everything around them.
What this means if you live nearby
If you live in North Windham, the practical version of this story is simple: a plaza you may have been driving past for a routine errand now has more reasons to stop. You can drop off a package, grab a smoothie, hit a few buckets on a golf simulator, and work out of a private office before picking your kid up from a dance class, all without leaving the same half mile of Route 302.
The Giguere brothers were explicit that they see this as the start of something larger, not a finished project. They pointed to the town's own infrastructure investments, including sewer expansion and bypass roads, as part of what will keep supporting growth in the area. Whether that plays out exactly as they expect is not something anyone can promise. What is verifiable right now is that a plaza most people had stopped noticing just got a new identity, filled it fast, and did it by betting on a regional shortage that had been sitting there the whole time.
Windham has been absorbing this kind of change for a while now, in ways that show up more in daily patterns than in headlines. If you want a broader sense of what is shifting across the town, the Windham neighborhood guide is a good next stop.
For everything else happening in Southern Maine's neighborhoods, from Scarborough to Gorham to Kennebunk, The Scoville Foley Team keeps a close eye on the kind of local detail that never makes it to the portals. If you have questions about what a shift like this means for a specific street, a specific town, or a specific home, reach out and we will give you the straight answer.
