This feature submitted to the Westport Journal chronicles how Bob Weingarten, the house historian for the Westport Museum for History and Culture, identified the historic gate houses of the former Richard H. Winslow estate, now known as town-owned Winslow Park.

WESTPORT — The long-forgotten second Richard H. Winslow gate house was honored with a Westport Museum plaque last August.  

This structure, now on Evergreen Parkway, was moved in the 1930s from its original location on Evergreen Avenue.

The estate’s other gate house was discovered on Washington Avenue in 2008, through efforts by Bob Weingarten, the Westport Museum’s house historian. 

Both gate houses were built by Richard H. Winslow in circa-1855 after purchasing an 18-acre property from Benjamin L. Waite in 1853. The Winslow property is now  better known as Westport’s Winslow Park property, aka the “Dog Park.”

Prior to becoming a town park, the property extended from the two gate houses to Post Road East at the west corner of Compo Road North, with the main Winslow house called the “Compo House.”

At the time of the property’s purchase by Winslow, a house with Ionic columns was already on site, but he remodeled the building with more elaborate columns and added two wings. Winslow also added a billiard house, barns, stables, bath house, ice house, as well as the two gatehouses.

Winslow’s wealth came from his success in banking, stocks and money exchange. He also was involved in developing the railroad and was a state and Congressional representative.

Winslow sold the property to Stephen Alden in 1865, and it subsequently was owned by several others over the years until the home was demolished in 1973 and the site became  known as Winslow Park.

The two gate houses were forgotten until Weingarten, the house historian for the Westport Museum (formerly, the Westport Historical Society), found a reference to the structures in a 1951 Judge Adams document on all the real estate in Westport.   

Under the section on Main Street, Adams stated, “The next house, long known as the Stone Cottage, was the upper gate house of the Stephen H. Alden and later Richard H. Winslow property. The road now known as Washington Avenue was just a private road leading around to the gatehouse on Evergreen Avenue.”

While Judge Adams’s recall was imperfect, deed searches confirm that Winslow actually sold his property to Alden in 1865, after having purchased the property from Waite in 1853.  

The documented information identified both gate houses, one on Washington Avenue, just off Main Street, and one on Evergreen Avenue.  

The Washington Avenue gatehouse was easy to spot — a “stone house” on the corner of Washington and Main. Using deeds and tax records, the “stone house” was determined to be one of the Winslow gate houses.

The owner, Sheila Keenan, agreed in 2008 to obtain a Westport Historical Society plaque to honor the heritage of this Winslow gate house.  

Finding the second gate house was more difficult since no style information was provided by Judge Adams. The only description was, “until forty or fifty years ago Evergreen Avenue was comparatively a short street. It extended to a gate house standing where the Sylvester Foster home now is. This was a rear entrance to the extensive grounds of Stephen H. Alden and later of Richard H. Winslow.”

Once again, Judge Adams made the same mistake on sequence of ownership, but that was not an issue. The main issue is that his wording of “where the Sylvester Foster home now is” implied the house was no longer standing.  

As a result, no further research was done until 2013 when a resident on Evergreen Parkway sent a note to the Westport Museum asking to confirm his research. He contended that the original location of the Evergreen Avenue gate house was at 14 Evergreen Ave., but moved in the 1930s to Evergreen Parkway.

Once again, Weingarten got involved and after three years of additional research, using the homeowner’s research as a base, he confirmed that the house on Evergreen Parkway is, in fact, the Winslow gate house moved from 14 Evergreen Ave. in the 1930s.  

In 2018, the Evergreen Parkway gate house was sold to Amanda Freeman and Trey Ellis. This year, they decided to order a Westport Museum plaque to commemorate the heritage of their house as the other Winslow gate house built circa-1855.   

The plaque was presented to the owners in August.

Mysteries related to historic houses can take years to solve, requiring careful analysis of evidence found in unusual places. Eventually, with considerable research and dedication, facts can be established and mysteries solved.