Sasco Hill

Delight in the pleasure of sun-filled days and spectacular sunsets in the exclusive hilltop enclave of Fairfield’s Gold Coast known as Sasco Hill. This frequently sought-after neighborhood, ideally located with a southwest exposure overlooking the Long Island Sound and Southport Harbor, has strong roots that date as far back as the descendants of Southport’s original settlers. Many of these settlers were farmers who strategically benefitted from the area’s rich soil and, of course, inherent beauty that still so powerfully remains.

Only a few key houses dotted the landscape of the Sasco Hill area during the 19th century. The majority of the surrounding acres were open and leased by gentleman farmers, who used the land for cultivating the globe onion for export. The Wakeman Home, a Federal-style home with Colonial massing located at 209 Sasco Hill Road, was built in 1809, making it one of the neighborhood’s earliest residences. Offering a more recent construction, 775 Sasco Hill Road, built in 1963, is an example of the later homes added to the area that purposely uphold the Colonial style and quality of the neighborhood’s historic foundation. What then, can be attributed to this residential transformation from a rural agrarian past?

Sasco Hill
209 Sasco Hill Road
Sasco Hill
775 Sasco Hill Road

Industrialist Oliver Gould Jennings owned most of the region’s land at the time. As a descendant of railroad tycoon Jay Gould, and son of Oliver Burr Jennings, a scion of the Southport shipping family and one of the founders, with Rockefeller, of Standard Oil, Jennings was bound to think outside of the box. By 1880, the export of onions began to dwindle, providing Jennings with a new vision for this large tract of land. Being highly aware of the increased demand for luxury summer options for wealthy New Yorkers, Jennings began his quest to subdivide this stunning coastal area into lots within walking distance of sandy beaches and a newly developed links golf course along the water. Now recognized as the Country Club of Fairfield, this golf location is one of the top links courses in the region. The Pequot Yacht Club, a premier sailing and racing club, also began here, offering some of the state’s finest summer recreation opportunities around.

In order to lure in wealthy businessmen and professionals, Jennings wisely laid out plans for residential developments bordering these highly appealing clubs and courses on the western slope of the hill. With the majority of this construction taking place during the “Golden Age,” fine architectural quality in a Colonial Revival-style, with detailed Georgian touches, grace each home with a distinct 1920s brilliance.

Sasco Hill
402 Sasco Hill Road

Among some of these homes are 402 Sasco Hill Road, which was built in 1934 for Henry Rennell, the President of Bridgeport Savings bank, as well as 794 Sasco Hill Road, constructed in 1937 by architect Louise Conrad Rosenberg. This home features a prominent hipped roof in addition to symmetrical massing of the manorial style, and enjoys views of Southport Harbor. The John Hamilton House at 828 Sasco Hill Road was built in 1927 by architect Francis Hamilton, and boasts an English style with views of the water as well. This brilliant residence frequently served as the Connecticut retreat of celebrated playwright, composer, director and actor Noel Coward.

Sasco Hill
794 Sasco Hill Road
Sasco Hill
828 Sasco Hill Road

These are just a few of the many incredibly elegant properties located in this enclave of long-lasting appeal and exceptional beauty known as Sasco Hill. Experience it for yourself! Make an appointment with a listing agent today to visit this wonderful neighborhood of Fairfield, Connecticut.

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