Winchester . . . “the definition of small-town America”

A conversation with Adam Kidd

Adam Kidd describes him­self as one of “a group of young, eccen­tric fel­lows all with dif­fer­ent back­grounds.” He is refer­ring to DAM Holdings LLC, a Winchester real estate and devel­op­ment com­pa­ny chang­ing the sky­line of down­town Winchester. Literally.

Adam and his two part­ners found­ed the com­pa­ny five and a half years ago with the sim­ple goal of devel­op­ing real estate in Winchester. Along the way, they have shift­ed pri­or­i­ties and adapt­ed to chang­ing con­di­tions as they sought to bal­ance earn­ing a liv­ing with being respon­sive to the needs and wants of the com­mu­ni­ty they serve.

Says Adam, “We are doing every­thing in our pow­er to build a bet­ter com­mu­ni­ty. At the same time, we’re try­ing to build bet­ter build­ings. We’ve said since day one, we could have come in and gut­ted and stripped every build­ing in Winchester, rebuilt it, made it fan­tas­tic, won­der­ful in every way, and it would have sat empty.”

Instead, he says, the com­pa­ny focused on “grow­ing the com­mu­ni­ty” as they grew their buildings.

“We try to part­ner with dif­fer­ent com­mu­ni­ty orga­ni­za­tions at the same time we part­ner with dif­fer­ent busi­ness­es in the com­mu­ni­ty, [and] at the same time we work on our real estate endeav­ors. So we split our inter­est and it . . . keeps us as busi­ness own­ers more engaged and more interested.” 

The “crown jew­el” of the com­pa­ny — and its cur­rent head­quar­ters — is Winchester’s McEldowney Building on Cleveland Avenue, just across the street from the Clark County Courthouse. Adam says he want­ed to take on the biggest pri­vate­ly-owned build­ing in down­town Winchester as DAM’s first big project.

“We as com­pa­ny own­ers . . . are a group of young guys des­per­ate­ly try­ing to impress our fathers. When we set off in real estate, we went with the ‘go big or go home,’ and if you’re going to fail, you’d bet­ter fail big.

“This build­ing is almost 30,000 square feet, and at the time, it was 30,000 square feet of derelict, con­demned. Like so many of the oth­er build­ings in down­town Winchester, the McEldowney Building fea­tured all the great ameni­ties of 10 years ago: miss­ing win­dows, col­lapsed roof. It was rough.”

And today?

“It is a 30,000 square foot tes­ta­ment of a hun­dred-year-old struc­ture. It’s a beau­ti­ful build­ing in down­town Winchester. It’s hous­ing 26 dif­fer­ent busi­ness­es cur­rent­ly. And we’re hap­py to have it. It real­ly is the cen­ter point of the build­ings that we hold in Winchester.”

But it is far from the only one. The com­pa­ny cur­rent­ly holds six prop­er­ties just in the down­town dis­trict of Winchester. Much pub­lic atten­tion has recent­ly been paid to two prop­er­ties at the south end of the “high side” block of Main Street at the inter­sec­tion with Lexington Avenue.

In September 2023, DAM Holdings pur­chased 63 South Main Street, adja­cent to the vacant cor­ner build­ing (71 South Main) that had expe­ri­enced a roof col­lapse months ear­li­er. When it became clear that they would not be able to ren­o­vate 63 while the build­ing next to it fell into fur­ther ruin, they also stepped up and pur­chased 71.

“It was nev­er our inten­tion to tear down a build­ing,” Adam says. But they soon dis­cov­ered that the build­ing could not be saved, so ear­li­er this year, they demol­ished the cor­ner build­ing as they worked to save and restore as much as pos­si­ble of the oth­er one.

Losing anoth­er build­ing on Main Street just a few years after los­ing the Spharr Building on North Main was painful for many of us. However, it was unavoid­able after the pre­vi­ous own­ers of 71 South Main had allowed the build­ing to dete­ri­o­rate beyond the point of repair fol­low­ing the roof collapse.

But Adam and his part­ners are deter­mined to make the most of their inher­it­ed situation. 

A build­ing boast­ing one of the many hand­some Victorian facades that line the high side of Main Street along­side a now vacant cor­ner lot opens up a myr­i­ad of pos­si­bil­i­ties for an attrac­tive and func­tion­al space in the down­town core.

In our lat­est Voices of Winchester pod­cast, I sat down with Adam Kidd to dis­cuss these things. We talked about the high-side ren­o­va­tion project, the prob­lem of the lack of afford­able hous­ing in Winchester, the vision of for­mer city man­ag­er Mike Flynn, Adam’s vision of a “fra­ter­ni­ty of busi­ness own­ers,” and the announce­ment of a new venue for live music.

Listen to the pod­cast for all the details!