Logo
Real EstateReal Estate

1 of 9
Snag this Connecticut estate for just under $3 million.
Snag Tony Award-winning director Jack O'Brien's 20-acre spread for just under $3 million. Ren Nickson
Snag this Connecticut estate for just under $3 million.
Ren Nickson
Advertisement
Snag this Connecticut estate for just under $3 million.
Ren Nickson
Snag this Connecticut estate for just under $3 million.
Ren Nickson
Snag this Connecticut estate for just under $3 million.
Ren Nickson
Advertisement
Snag Tony Award-winning director Jack O'Brien's 20-acre spread for just under $3 million.
Ren Nickson
Advertisement

Tony Award-winning Broadway director Jack O’Brien is listing his New Milford, Connecticut, estate for $2.8 million.

O’Brien, a former Old Globe Theatre artistic director, has credits including directing “The Full Monty” and “Hairspray.”

Known as Imaginary Farms, his 19.95-acre property at 51 Bear Hill Road — designed by architect Peter Wooster — is as theatrical as one might expect.

Jack O’BrienWalter McBride/Getty ImagesJack O’BrienWalter McBride/Getty Images

The three-bedroom, five-bathroom, Colonial-style main house, built in 2005, opens with a foyer featuring an “ancient Chinese pavement stone floor” and a David Rockwell-designed mechanical glass chandelier “hovering over the foyer,” according to the listing.

Next is a wood-paneled great room with floor-to-ceiling, built-in bookcases and a large fireplace surrounded by glass. There’s also an open kitchen and dining room with a fireplace, and a staircase that leads to the second-floor master suite.

The master suite features a Rockwell-designed bed that rotates 180 degrees “to take advantage of the changing seasons.” Think of it as your own theater in the round!

There’s also a screened-in porch, a terrace in the back of the house and stunning grounds featuring a freshwater pond, a pool, a Japanese garden and a meadow with crab apple trees.

You’ll also find an antique barn with a “partially finished” two-floor apartment, including an open kitchen/living room with a fireplace.

The listing brokers are Ira Goldspiel and Steve Pener, of William Pitt and Julia B. Fee Sotheby’s International Realty.

Comments
anonymous profile image
Powered by RoundtableBuilt on infrastructure designed for real-time media. Learn more at RTB.io.© Roundtable 2026. By using this site you agree to the Terms of Use and Privacy Policy