Praying for Snow Every Day: David Waldman Talks Everything Westport

On a recent Thursday David Waldman, perhaps today’s major force in redeveloping Westport’s downtown, offered Y’s Men a rapid-fire, almost stream of consciousness overview of a career dedicated to making Westport “one of the best towns in Connecticut.” 

For years Waldman has been an aggressive advocate for Westport’s “Golden Triangle” — Main Street, Elm Street and Church Lane — for making it a magnet for shoppers, preserving and incorporating the town’s historic buildings into its future, creating a more cohesive whole, and overturning dated restrictions that left the town behind both Fairfield and Norwalk as an evening entertainment venue.

His 27 year old firm, David Adam Realty, raised its visibility by in 2004, with its acquisition, renovation and preservation of the Westport Bank & Trust building on Post Road East — now Patagonia’s home. 

The bank was on Connecticut’s Register of Historic Buildings when he bought it. Waldman called the renovation “historically adaptive commercial reuse.’’ The task included preserving the lobby murals and keeping the huge safe in place. He and the building won an award from Westport’s Historic District Commission, and the building earned a place on the National Register of Historic Places.

This success helped him win the 2006 bidding for the Westport-Weston Family Y building. Its repurposing, he commented, “has consumed the last 12 years of my life,” what with the collapse of financial markets, the stream of meetings with town boards, and, ultimately the substantial scope of the construction itself.

Timing being what it was, the Y found itself up in the air, and Waldman became a bit of a bad guy. He closed on the sale after the town had refused the Y’s plan to move to Baron’s South, yet before it had received permission to build at Mahackeno. And, there were some who felt the project was just too big.

As work on this project was going on, he bought and repurposed historic buildings on the south side of Church Lane, creating attractive homes for The Spotted Horse and Urban Outfitters. And he relocated the Kemper-Gunn House to Elm Street as the flagship store for Serena & Lily.

The Spotted Horse also led to something of a personal turning point. He acquired the 1802 Sherwood House to use its land as a parking lot. After being denied the right to raze the structure he worked with Historic District commissioner Maggie Feczko to preserve it. It too, received the Award of Merit by the Connecticut Trust for Historic Preservation.

Today, with work nearly completed, Bedford Square is a reality, a 110,000 square foot retail, restaurant and residential mall, and perhaps the cornerstone of downtown Westport. And with the Church Lane businesses only enhance the Golden Triangle.

Done yet? Hardly. He’s torn down the Fonda Del Sol building and swapped its land for space to build behind Lux, Bond and Green. He bought and is sprucing up Sconset Square. And he is converting the Save The Children Building on Wilton Road to luxury condominiums.

Yet Waldman expressed some apprehension about the future: Too many retail vacancies, the rapid growth of online retailing and the potential impact of the scheduled October, 2019 opening of the upscale SoNo Collection, a 700,000 square foot “vertical mall” and “entertainment and food venue” at Connecticut Turnpike exit 15.

He already hears merchants ask “Why am I going to be on Main Street?” 

And as construction at SoNo continues, he joked, “I pray for snow every day.”


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