Sunday, October 18, 2026

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WestportNow Teardown of the Day: 258 Hillspoint Road

258 Hillspoint Road, Westport, CT 06880
Westport building officials received an application for a permit to demolish the home at 258 Hillspoint Road. The 2,271-square-foot, one-story, raised ranch house was built in 1966 and is located on a .98-acre property with a water view. The property changed hands in January for $4 million. (CLICK TO ENLARGE) Dave Matlow for WestportNow.com

4 thoughts on “WestportNow Teardown of the Day: 258 Hillspoint Road”

  1. This house was built (I think) by Michel (Mike) and Matilda (Til) DeSantis, friends of my parents and their daughter, Margarita DeSantis Read, is still a good friend who makes exquisite jewelry in Rhode Island and she and her glass-blowing-artist husband exhibit each year to the Westport Craft Show at Staples.  Mike was a talented artist and art director, and Til taught piano to many Westport students over the years.  They lived for many years on Wilton Road, but moved to Hillspoint and loved their house with a view of the water.  When the house was built across the road (the only one on the water side between Hillspoint Road and the water), they lost most of their view.  They moved to Vermont or NH and are now both deceased.  Wouldn’t they be amazed at $4mm for a teardown?  Just a bit of Westport history.

  2. I sent this WestportNow article to my friend and she couldn’t figure out how to post a comment but asked me to do so for her:

    “I am Margaret de Santis & my Dad, Michele de Santis, designed & built this house around 1965. We all loved the water & sailed Long Island Sound so the glass front of the house brought in that wonderful vista of sky & water. I have many happy memories living there. There was a beautiful old elm tree on the property which was eventually cut down. Spring & summer on the deck enjoying grilled clams with drinks while watching the sun set brought joy to the soul. It’s sad that it’s going to be demolished. It is kinder that my Dad has long passed on so he can’t see his dream being destroyed.”  margarita@margaritadesigns.com

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