From Starter Home To Downsizing: The Westport Housing Arc

More than 30 years ago, Rick Shelman and his wife Maryanne visited Westport. They got ice cream (he can’t remember where). His wife said, “This would be a nice place to live.”

Their oldest child was 5 years old. The Shelmans learned the school system was excellent — and home prices were high.

But they found a house they could afford. It was near the Post Road, and a bit noisy. After 4 years they moved to a bigger home, off Sturges Highway. They were there for 17 years.

Rich had his own computer supply company. As the industry changed, he embarked on a 2nd career: real estate.

A few years ago, when the youngest of their 3 children left for college, Rick and Maryanne looked around. Their 5-bedroom ranch house sat on an acre of land. They’d spent so much time ferrying their kids to various activities around town, they knew their neighbors only to wave hello.

The Shelmans always wanted to live near the water. They found a fixer-upper on a side street between Soundview and Bradley. Soon, they were in their 3rd Westport home.

The Shelmans' Compo Beach home.

The Shelmans’ Compo Beach home.

The family’s trajectory — starter house, upgrade, downsize — mirrors that of many Westport fsamilies. Despite frequent complaints that there is nowhere for empty nesters to go here (except for condos), Rick says the Compo neighborhood is perfect.

“There’s always something going on here. People are walking, jogging or out with their dogs. On Halloweeen we have 1500 kids.”

The calmness of the water balances the summertime action.

Best of all, it’s a neighborhood. “We really know people here,” Rick says of one of the few places in town with cheek-to-jowl zoning. “We look out for each other.”

His neighbors are a mix of retirees and families with young children. Some houses have been renovated (and raised, to avoid hurricane damage). Some still need to be updated.

Rick and Maryanne Shelman love the neighborhood aspect of Compo Beach. They also don't mind 1500 trick-or-treaters -- many from outside the neighborhood, drawn by the denseness -- every Halloween.

Rick and Maryanne Shelman love the neighborhood aspect of Compo Beach. They also don’t mind 1500 trick-or-treaters — many from outside the neighborhood, drawn by the denseness — every Halloween. (Photo/Lynn U. Miller)

Living at the beach requires a certain mindset, Rick says. “We raised our house for a 100-year flood. A young couple across the street bought their home knowing full well Sandy had destroyed the 1st floor. They want to be here. When they can afford to, they’ll raise it.”

He thinks many Westporters in his age group — folks in their 60s and 70s — would like to downsize, and stay in town. “If they could afford to move to the beach, they would,” he says. “A lot of people have asked me for advice.”

Rick notes that the Compo neighborhood is not the only place to go. Smaller houses can be found in other areas, like Bauer Place and Oak Street — and for a lot less than the going price by the beach.

Those places will continue to be attractive for empty nesters, and young families looking to get into Westport.

Three decades ago, Rick and Maryanne Shelman were just starting out in town. They’re still here, in their 3rd home.

They have no plans to leave.

22 responses to “From Starter Home To Downsizing: The Westport Housing Arc

  1. It’s getting tough just to find a 3 bedroom house. Try Westport’s sister town,,, Weston. Better values and schools.

  2. Janette Kinnally

    My family has lived here for almost 50 years. My mom and dad moved here in 1967. They lived in their house for over 40 years and decided it was too much to keep up for them. They moved in with us two years ago (to be near their two only grandchildren). And when they feel it is time to find a retirement community, they will find a condo in the area. My only concern is how expensive it is for old time residents to find another place to live in this area. Very expensive to live here and not getting any tax cuts any time soon.

  3. Brad, that’s interesting because Westport was just ranked the #1 school district in the state. Sounds like someone’s upset they can’t afford Westport.

  4. Depends on who is doing the ranking. Not much difference, but some.

  5. Michael Calise

    Great story! I suspect that within the claimed “20%” (of seniors) there is a silent majority which are handling there living needs in a positive manner as Rick and Maryanne Shelman have done. They are a testament to the standards of most Westport Seniors

  6. Bobbie Herman

    When my husband and I decided to downsize in 2001, we looked at every possibility in Westport. Unfortunately, we found nothing. The builders get to them first. It’s a double hit for the realtors — they sell the teardown to the builders (without listing it) and then get the listing of the new McMansion. Two sales, two commissions. We finally found a lovely ranch in Fairfield just over the town line. We still participate in many Westport activities, but it’s not the same.s

  7. Ben, yes…”better value” means you pay less for a still very good or excellent situation. Some folks have to take these things into consideration.

  8. don l bergmann

    My wife and I did the same thing, moving to Sherwood Drive, and consider it one of the best decisions we ever made. Cost is an issue, in part because so many variances are granted that, in essence, escalate the value of the land wrongly and artificially, That can be stopped by challenging variances and prevailing in Court. We did just that to prevent a tear down of a pleasant modest home which a builder sought to replace with an “edifice”. “Edifice” is the word the Judge used in deciding for us. Unfortunately, lawsuits cost money and the builders usually have the greater financial interest.
    Don Bergmann

  9. I lived in Westport my entire life. Always a “water person,” we moved closer to the Sound as our family grew. With the first of three kids in college, I decided to look around for a smaller waterfront home in Westport. Not only were the prices insane, but there was always a road or a cobweb of ugly power lines in the way. Only one of our kids was in public school, so that wasn’t a priority. We found a magical, affordable home ON the beach in Fairfield, with no street or power lines between. Hurricane Sandy had opened a door, which had begun to close. We jumped on it. Best decision ever.

  10. Are these “outlier” incidents ( an inappropriate relationship, and 2 pellet guns) that some of you are referencing intended to prove which school is better? So silly. They are both excellent schools for goodness sake. Once schools are this good, the rest is up to the students. You get out of it what you put into it.

  11. Seems like Bill Miller is ‘a little too proud’ to have been able to afford to buy something in Westport. An element that’s getting old really fast these days. Oh the Westport of past. Sigh.

    • So now people can’t be proud of where they live? What’s getting really tiring is how sensitive everyone is.

      • By all means be proud of your town. However, “Sounds like someone’s upset that they can’t afford Westport” is not a statement of pride. It is a statement of arrogance.

        • I wasn’t trying to come off arrogant; instead I was disheartened with the comment, Weston has better value and schools, when that’s not really true. Brad should try and find a Weston blog instead of posting that on 06880.

  12. Westport and Weston are very close sisters. I think of them as almost the same town.. we share the same Y, used to share the same High School, share the same Board of Realtors, same Red Cross chapter.. etc, etc. Weston is so gorgeous, I want it to be part of Westport instead of a separate town. How does Westonport sound? Westporton? And Weston and a big part of Westport used to be Fairfield. Westfairport sounds good too.

  13. Tom Feeley Sr.

    Rick & Maryanne were THE BEST neighbors‼️