Living History on Shippan Point

Stunning water views, private beach access, family gatherings and clambakes…Live every day like a vacation day at this iconic Victorian landmark in the city of Stamford. Formerly known as the famous Chesterfield Inn, the now converted, five-bedroom single family residence is up for grabs in the rental world. So strike now while the deal is hot! Qualified tenants are presented with a once-in-a-lifetime chance to enjoy luxury and history in the exclusive waterfront community of Shippan Point for $10,000 per month, while its current residents spend a year abroad.


Originally constructed in 1865 as part of a 30-acre estate, the house at 1404 Shippan Avenue, which has since undergone extensive restoration, operated as the ever-popular Chesterfield Inn for more than a century. The nine-room hotel is widely regarded as an architectural centerpiece of the quiet city enclave, for years providing community members and visitors with a prime coastal retreat. Now offering many modern amenities and features including two home offices, a gym and wine room, the incredibly transformed structure continues to maintain much of its historic detail and charm.

“A truly remarkable experience awaits all those who appreciate casual elegance, sunlit rooms and an interesting historic past,” said Stamford agent June Rosenthal, who is co-listing the rental with Linda Sentementes, another agent from our Stamford brokerage. “Its owners are seeking very special people to temporarily live in their truly wondrous estate, which comes fully furnished and will be ready for occupancy in later July.”


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Shippan Point is a peninsula comprising over 800 acres extending into the Long Island Sound. The community contains some of the area’s wealthiest neighborhoods, with large estates boasting their own private beach and surrounding water views. Multiple beach and yacht clubs, including the Stamford Yacht Club, can also be found here, adding to its abundance of lifestyle offerings. The Shippan Point Association was formed in 1902 to protect the integrity and beauty of this exclusive coastal location through neighborhood events, regular meetings, tree planting, police patrol and much more. This voluntary, non-profit organization encourages all to become involved in its cause to preserve and enhance the unparalleled tranquility and value of one of Stamford’s most highly acclaimed historic neighborhoods.

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“Take it all in—savor the beautiful setting of this magnificent home from the comfort of its inviting wraparound porch and sandy shores,” added Sentementes. “This is an opportunity to actually live history instead of just read about it—a legendary Shippan Point mansion and beloved city icon.”



For more information on the property for rent, located at 1404 Shippan Avenue, please visit our website here. You can also contact Stamford agent June Rosenthal by email at Jrosenthal@williampitt.com, or by phone at 203.536.7470. Linda Sentementes can additionally be reached by email at Lsentementes@williampitt.com, or by phone at 203.940.0275.

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