A 1927 cottage, thoughtfully reimagined.

For nearly a century, The Flirt has welcomed guests to
Lake Waramaug.

Designed for modern lake living,
The Flirt honors
the spirit of the original cottage
while beginning a new chapter.

Every detail invites you to slow down,
settle in,
and simply enjoy being here.

Whether you’re lingering over coffee on the porch, gathering around the table with friends,
or watching the sun slip behind the hills,
we hope you’ll find yourself settling into
the simple rhythm of lake life.

Every old home has a story.
We hope you’ll become part of The Flirt’s.

The Flirt.

The Flirt - 1880's tugboat on Lake Waramaug
The Flirt - 1880's tugboat on Lake Waramaug

The Flirt at Wright’s Landing, 1880s. From A History of Lake Waramaug by Mary Harwood. Photograph by Walter M. Pickett, Jr. Digitally restored for Waramaug Living.

Flirtation Avenue - 1927 Lake Waramaug cottage

The Flirt, 2026.
Ready to welcome its next century.

Story Behind the Name

Long before there was a road around Lake Waramaug, visitors arrived by boat.

One of those boats was The Flirt, a steamboat that carried guests to the lake's inns and cottages.

Nearly a century later, The Flirt once again
welcomes guests to this same shoreline.

The vessel changes.
The welcome remains.

A black and white photo of a dirt road winding through a wooded area with bare trees.
Street sign reading 'Flirtation Ave' on the corner of East Shore Rd in New Preston, CT.