A ten year lease, negotiated in the dark

In early 2026, Winter Garden was mourning a bookstore.

Writer’s Block had been at 32 W. Plant Street for five years before its lease ended, and the closure moved through local social media the way these things do, as a small civic grief about a street changing faster than the people on it.

While that conversation was happening in public, a negotiation for the same address was already underway in private. We were running it. And we were not allowed to tell anyone which building it was. Not the city, not the architect, not the contractor.

Cosa Nostra had one shot at a second location.

The Clermont flagship was working, a franchise model was in development, and the second site would either prove the concept travelled or stall it for a year. Plant Street is one of the most contested retail corridors in Central Florida. Over the preceding year, entities linked to outside investors had put more than $40 million into acquisitions in Winter Garden’s historic district, and rising values had already pushed out a series of long standing independent tenants.

Space on that street does not sit vacant. When it opens, it rarely reaches a public listing at all.

There was no listing, no bidding process, and no open market to enter.

The property owner, represented by Millenia Partners CRE, required a non disclosure agreement that prohibited any mention of the address. Any mention. That included routine permitted use questions to the City of Winter Garden.

For months, every piece of due diligence had to be conducted around the address rather than through it. We could not call planning and ask whether the use would be approved at number 32. We could not confirm what the space would allow the normal way. We worked the questions from the outside in, verified what we could through other means, and kept a signed client moving forward on a space we were forbidden to name.

We had known this client since before they had a storefront.

We met the owners in October 2022, when Cosa Nostra was a food stall inside West End Plaza on West Minneola Avenue in Clermont. A small footprint, a serious product, an authentic Italian identity. The stall became a proof of concept, and in late 2024 the proof of concept became a restaurant when the flagship opened at 798 W. Montrose Street in historic downtown Clermont, to a reception that told us the concept could travel.

So when Plant Street surfaced through a relationship rather than a portal, we were not starting from a requirements list. We already knew the economics, the kitchen, and the kind of environment the brand needed to work. That is the only reason we were in position when the second location mattered.

The search itself began in June 2025. Over the months that followed we looked at roughly a dozen locations across Central Florida and took eight of them through serious evaluation. None of them were right, and saying so is most of the job. A second location that opens in the wrong place does more damage to a growing brand than no second location at all.

Here is what the confidentiality actually cost.

We negotiated substantially all of the main business terms without being able to bring the client’s professional team into the building. No architect walking the space to confirm the layout would work. No general contractor pricing the build out from inside it. No consultant standing in the room where the kitchen had to go.

Every question those people would normally answer in an afternoon had to be worked around, inferred, or verified indirectly. And at the end of it, the client had to decide whether to commit to ten years on a property their own build out team had never set foot in.

That is not a normal transaction. It is a decade long commitment made with most of the usual instruments switched off, and it only works if the tenant trusts their broker completely and the broker has done the work to deserve it.

Size

2,900 SF

Lease term

10 years

Starting base rent

$58.00 per SF per year

Annual escalation

Approximately 3.5%

Search began

June 2025

Sites evaluated

8, from roughly a dozen locations

Publicly listed

No

We represented

The tenant

Base rent only. Operating expenses and additional rent are separate.

Cosa Nostra Italian Deli signed at 32 W. Plant Street with no public listing and no open market competition. The second location is expected to open in late 2026. The Clermont flagship remains at 798 W. Montrose Street.

For context on what they bought into: Winter Garden has grown past 50,000 residents, and the Plant Street core is anchored by two demand drivers most corridors would envy. The West Orange Trail, a 22 mile multi use path, draws an estimated 150,000 visitors a month. The Winter Garden Farmers Market brings 3,000 to 5,000 people to the street every Saturday.

Number 32 sits in the middle of it, steps from the trail, surrounded by independent restaurants, breweries and boutiques, with consistent foot traffic seven days a week.