The Mailands Estate, once a grand Gilded Age mansion, is located in Fairfield, Connecticut, and is now part of Fairfield University. Built in 1906 by Oliver Gould Jennings, whose wealth was derived from Standard Oil, the estate originally spanned 120 acres of rolling hills, farmland, and forest. Designed by the architectural firm Flagg & Chambers, the elegant French Renaissance-style mansion sat atop Osborn Hill, offering commanding views of the surrounding landscape. Mailands was conceived as both a luxurious retreat for high society guests and a working farm.
A member of the influential Jennings family, Oliver’s wealth stemmed from Standard Oil, a company co-founded by his father in partnership with William Avery Rockefeller Jr. His family played an integral role in Fairfield’s development, and their name is memorialized in numerous locations throughout the town, including Jennings Beach and Jennings Elementary School.
The estate was constructed at an estimated cost of $1 million. Mailands replaced an earlier mansion Jennings had built on the same site. The decision to demolish the first home to construct an even grander estate was controversial among some Fairfield residents. Although Jennings recognized the farm as a luxury rather than a commercial enterprise, it played a key role in supplying both Mailands and the family’s townhouse on East 72nd Street in Manhattan with fresh produce, meat, and flowers year-round. A notable feature of the farm was Jennings’ prized Jersey cattle, including his favorite bull, humorously named “Interested Laddie.”
Oliver Gould Jennings passed away in 1936. His widow and two sons continued to use Mailands as a summer home for five years before deciding to sell the property. In 1941, the Jesuit order of priests, seeking a location for a new educational institution, acquired the 76-acre estate for $43,879.
Following the Jesuits’ acquisition, Mailands was repurposed as the first building of Fairfield College Preparatory School and later Fairfield University. The mansion was renamed McAuliffe Hall in honor of Bishop Maurice F. McAuliffe of Hartford, who played a crucial role in securing the location for the new educational institutions. The building housed classrooms, laboratories, a cafeteria, a library, and a chapel.
Over time, McAuliffe Hall transitioned from an academic facility to an administrative building for Fairfield University. Although modifications have altered some aspects of the original structure, including the removal of the semi-circular portico, its historical significance endures.
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Doug Cress
(212) 203-5251
doug@cress.co
License #RES.0832278
Fairfield County, CT
Enterprise Realty Inc.
License #REB.0751297
45 Huntington Plaza
Shelton, CT 06484




