Sunday, October 18, 2026

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WestportNow Teardown of the Day: 108 Cross Highway

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An application for a permit to demolish the house at Westport’s 108 Cross Highway is in process. Built in 1805-1806, the two-story vernacular, known as the Henry Munroe House, has 2,872 square feet and is situated on a 1.02-acre property. Westport Historic District Commission records cite it as “one of the few 19th century dwellings documented as being built by a free black. Henry Munroe, a farmer, purchased the parcel from John Burr in 1802 and in 1807, he conveyed the property ‘with buildings’ to his sons, Henry Jr and Alexander. The house first appeared on the tax rolls in 1806. In 1827, Alexander passed his interest to Henry Jr. Henry Jr, (died 1881) and his wife Phoebe were members of the Green’s Farms Church. His sister Amelia was the housekeeper for Peter Sturges who resided at 93 Cross Highway. After Amelia’s death in 1883, the house was sold to Peter Sturges. The west wing was added in 1969.” Because the house was built more than 50 years ago, the application will be reviewed by the Westport Historic District Commission. (CLICK TO ENLARGE) Dave Matlow for WestportNow.com

31 thoughts on “WestportNow Teardown of the Day: 108 Cross Highway”

  1. When I lived in Wyoming- and was much younger- I thought old, rustic cabins from the 1890’s was exciting. Since I have been living on the East Coast, seeing signs with dates from ‘16’ or ‘17’ so and so really instills a sense of marvel and historical pride.
    This particular house not only has all of those elements, but the African-American aspect makes it even more relevant.
    I, too, hope that the HDC realizes this.
    Joyce Joiner

  2. Outrageous. It seems that if there is any time this ‘commission’ would intervene, it would be now. As owners of a historical property, I would think there would be a natural sense of responsibility to maintain it’s historical attributes rather than total destruction.

  3. Perhaps the historic commission needs to have a condemnation clause for houses like this – in order to demolish it, it must be condemned.  As a previous comment noted – there are scads of houses for sale in town.  This one is noteworthy for several reasons. It could be added onto instead of being torn down.

  4. Was this house recently purchased solely to be torn down? There are so many houses for sale in town that could be replaced but who would buy a house with this unique and proud history solely to tear it down?  It is so difficult to believe that someone would want to do this.

  5. The new buyer doesn’t need a new house, they need history lessons!  I mean seriously…welcome to “The Constitution State.”  Being a carpenter who renovated something much older than this, there are so many options here.  Typical.  Another Westport atrocity on the way…can’t wait to see the next routine photo of the excavator jaws crunching it up.  Unbelievable.

  6. I agree with all the comments thus far, it is just so sad to see this happening almost on a daily basis here. Where is the New England Westport that we have all come to know and love? Main Street has become 5th Avenue and historical homes have become McMasions….Hopefully, our history for future generations will not be remembered as such.

  7. When I go West to Marin County, just across the Golden Gate bridge to Belvedere (Island), I walk
    around the roads.  Hardly a house has changed since I was a child. …. some few houses have been repaired or improved to some degree but the essence of the personality of the house has been preserved.  Breath-taking views of
    San Francisco and the East Bay. 
    What is wrong with us so that we allow this destruction happen?

  8. The statute provides no real protection to these historic structures.  The town has no incentive to stop the McMansions because they are able to charge much higher property taxes on a new large structure than on the old one.  Many of the tear-downs are post-war garbage and I agree they should go, but this house should have had some protection.  This saddens me because I have driven past this one hundreds of times and admired it.  I would like to see some real zoning protection, no more studies, no more inaction, no more wasting our time and money.

  9. This is the 5th or 6th owner of this home over the last 10 or so years – perhaps there is a problem with the property that is not evident to the public. I agree that this property should be protected, especially with the historic relevance of this particular parcel but perhaps there is more to this story.

  10. If ever there was a case to STOP the teardown, this is it.  We see so many “an application will be reviewed by the Westport Historical District Commission” and yet I cannot recall ANY of these reviews resulting in a denial of demolition.  WHO is on this commission anyway? Not an elected position as far as I know.  What a sham(e).  SAVE THIS PROPERTY!!

  11. I don’t understand what indeed is the purpose of going before the Historic District Commission if they have no authority to preserve history.  Why review the application at all? This house is not only about Westport history, but New England as well.  Its going to take more than just expressing our concern on this site to preserve this house. The community of Westport has rallied before to preserve homes of historical significance, and we will do so again. Thanks WestportNow for alerting us.

  12. Property owners who think their property is worthy of preservation can ask the RTM to declare it a protected Historic Landmark Property (Sec. 38-24 of the Town Code).  The process begins by going to the Historic District Commission.

    I don’t believe there is any evidence that listed properties decline in value. In fact, anecdotally, I have heard that it actually increases maket value. All it takes is a willing property owner to make the intial request.

  13. Greetings,

    If you visit the HDC’s page on the town’s website at http://www.westportct.gov, you’ll find the following paragraph:  “The Commission has a mandate, as a CLG, to be an advocate of historic preservation planning throughout Westport.”

    Let’s assist the HDC’s efforts to preserve and protect the character, charm and history left in our town by attending their meeting at Town Hall on Tuesday, 12/13 at 7pm.

    See you there!

    Sandi C. Martin

  14. For people who care about their historic homes, preserving them for future generations should be incentive enough. Tax credits means it all about money.

  15. It is incentive enough to have an historic home – but it costs an owner more to maintain and renovate than it does a builder to tear down and build new. While older/historic homes are wonderful, they do present more of a burden, especially financially, to the owner.
    Let’s help roll that boulder uphill!

  16. Perhaps this might add some clarity to what the role of the HDC is:

    The only time the HDc can actually prevent the teardown of a structure is if that structure is part of a Local Historic District or designated as a Local Historic Property. Both of these designations occur only when either the neighborhood (in the case of an LHD) or a property owner (in the case of an LHP) actually agree to put their homes under the protection of the HDC. When a structure is not designated, the only thing the HDC is able to do is impose a 180 day waiting period (which is the longest demolition delay in the State) which is designed to foster a conversation concerning alternatives to demolition.

  17. Good to see so many passionate comments, but again, sad to see all the “red tape” ends mostly in destruction of history all due to physical age of something.

  18. If tax breaks for the owners of historic properties will keep the allure of McMansion builders at bay, then I’m all for it.  At the end of the day, it’s a win/win for the preservationists and for the town of Westport—visitors and residents alike.

    I applaud and thank Mr. Loffredo’s willingness to take a stand and make a difference.

  19. So can we ask the HDC for the 180 day waiting period so that the community can indeed have conversations, and hopefully take action against demolition?  Surely, if there was ever a need for the HDC to take steps to delay, its with this house.

  20. Owners of historic houses who are on the fence (want to preserve the character of the town but have had some Realtors tell them that they may get less money when they sell) might be willing to preserve their homes if there WERE a tax credit.  It’s difficult when this is an asset you want to save for your children’s futures, and some people have said that the value of your house will go down if it’s listed as a historical property.

  21. Something interesting I found regarding the Monroe family.

    From the book Greens Farms Connecticut, the Old West Parish of Fairfield, pg 59 in the chapter
                                  Slaves

    “Aunt Lazette Hyde (Lyzette Monroe) lived in her own little house on the back road off the Turnpike, now the home of Michael Bowers. Notwithstanding her pipe, which Mr. Birge remembers her smoking as she sat in his grandmother’s kitchen, telling stories with great gusto with his grandfather and Betsy, Aunt Zette had the dignity and manner of a cultured lady, for she had served in the family of the Norwalk Bissels and the Jesups. Her name indicates that she had come from slaves of the Hyde family.”

    Take a look at the 1820 census (Fairfield , CT pg 243 M33_1: image 178 enumeration date Aug 7, 1820) for Henry Monroe’s son : there is one person listed as free Colored under 14 and 5 listed as slaves.

    1820 United States Federal Census
    about Henry Monroe
    Name: Henry Monroe
    Home in 1820 (City, County, State): Fairfield, Fairfield, Connecticut
    Enumeration Date: August 7, 1820
    Free Colored Persons – Males – Under 14: 1
    Slaves – Males – 14 thru 25: 2
    Slaves – Females – Under 14: 1
    Slaves – Females – 14 thru 25: 2
    Number of Persons – Engaged in Agriculture: 1
    Total Slaves: 5
    Total Free Colored Persons: 1
    Total All Persons – White, Slaves, Colored, Other: 6

    Our history began in the Colonies with a pursuit of freedom. What better way to help preserve a small part of that history than by saving this house, a symbol of freedom.

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