Roger Leifer’s Love Letter To Westport

I was lucky in 1978 when I decided to move to Westport to start my entrepreneurial and legal careers after serving as a Federal Prosecutor in Washington, D.C., during the Carter administration. I wanted to be a real estate developer and lawyer, and Fairfield County at that time had the third-highest concentration of Fortune 500 Company headquarters in the country, behind New York and Chicago. It was poised for growth.

At 28 and single, I partnered with my college friend Jim Randel to establish a small law firm specializing in real estate. Our goal was not only to master the practice of real estate law but also to renovate and develop new buildings in an arts-centered community. Our initial project was to convert the former Convent at the Assumption Church on Riverside Avenue into Westport’s first condominiums in order to save the historic building. We went on to be awarded multiple Historic Preservation Awards and Beautification Awards in Westport.

I have seen so many changes in Westport during the last 46 years, many brought about by me and my team. Imagine: there are now sidewalks along the Post Road and gorgeous trees lining the boulevard, which wasn’t the case in the early ’80s. It was quaint then and it’s a little more polished now. It was a great place to live, work and visit then, and is even better today!

Approximately 850 new millennial families have moved to town in the last three years and they have discovered what my septuagenarian peers have known for over a generation: that you can’t choose a better place to live and raise a family than Westport, which I’m told is also the “hottest” place in the tri-state area for young families to settle.

What’s not to love? Paramount is our excellent public school system (with pre-and private-school options also available), natural beauty, like most of Connecticut; three beaches and parks on beautiful Long Island Sound; myriad fine dining choices; live music venues at The Levitt Pavilion, the Black Duck, Church Lane, and Walrus Alley; live theater entertainment for adults and children at The Westport Country Playhouse and Staples Players; a world-class,  cutting-edge library and event space; all the brick-and-mortar retail choices one would need within three miles; sports activities for children and adults, i.e., soccer fields, baseball fields, outdoor and indoor basketball, tennis, pickleball, and padelball courts; and a skating rink; an amazing 100,000-square-foot Y with three pools with other physical activities galore; at least a dozen private gyms and training facilities; a sailing and windsurfing school to go with public and private marinas and golf courses; a world-class rowing club; a nearby Scandinavian Club; a community garden; a model airplane airport (did you know that?) at Sherwood Island State Park; a cool new private social club for car aficionados (Autostrada); a Modern Art Museum (MOCA); the Historical Society Museum; an amazing large senior center with over 40 weekly classes and activities; a Mandarin language school; music and dance schools; all the necessary physical and mental health medical practices and dental offices, and three first-class hospitals within minutes away. Amazing. Lucky us!

I am proud that Westport has a very active civic-minded local population with community volunteer involvement. Virtually every issue that affects our townspeople gets vigorous full hearings. Our responsible town boards serve an important role in our local government, which in my opinion affects our lives more directly than the national government, and I urge the new members of our community to get involved.

We also have committed, hardworking and honest local officials who run this town so responsibly, efficiently and well. Even presidents stop by. I was fortunate to join Bill Clinton when he came for lunch twice as president and once as a candidate, and Hilary, who also had three independent fundraising stops here during her political career.

Westport has been very good to me and my family, and I continue try to give back. I take pride in having  served on the building committees for the following, which I believe each have made Westport a better place to live, visit and work: Compo Beach Playground (which consisted of only two swings, a small slide and a rocking horse on a spring in the ’80s before we redesigned and rebuilt it twice); the Westport Country Playhouse (rebuilt 15 years ago under the leadership of Joanne Woodward and Paul Newman, when we raised $31 million for that effort); Paul Newman’s  Dressing Room Restaurant, now elegantly redone as Gabriele’s; The Conservative Synagogue and its day school; The Learning Community; the new outdoor Levitt Pavilion for the Performing Arts (rebuilt 10 years ago at a cost of $10 million.)

I also try to reciprocate by continuing to serve as one of the longest tenured members of the nonprofit Boards of Directors of The Playhouse, The Levitt Pavilion, and The Downtown Merchants Association.

I love to create and construct beautiful buildings and spaces for Westport, for its cultural institutions and for our Leifer Properties’ tenants. I have a personal relationship with all our tenants. I am blessed to have an exceptional and loyal team in a collaborative effort. The five of us have a cumulative 150+ years working together. What an amazing support system and I love them all! Thank you staff.

It is a privilege to be able to work and live here as well. I want to make it as special as I can for everyone! I am now lucky enough to be partners in business with my son Max, who grew up in Westport. He has helped us diversify our business from solely Westport to now include Austin, Texas, which is a new exciting journey for us. I will never retire, as there is something always to do, to create, to improve and work with my son and our tenants and partners.

Westport has never been better than it is today. I hope you all will work to make it a better, kinder, more beautiful and special place for us all to enjoy together.

Thank you, Westport.



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