249 Greens Farms Road, Westport

$3,750,000 • 7 Bedrooms • 6 | 3 Baths

2% to Buyers Agent

Storied and superbly restored, 'The Lookout' at 249 Greens Farms Road blends the grandeur of a 1907 Colonial Revival with today’s modern luxury. Privately set among perennial gardens and antique copper beeches, this iconic 16-room residence offers a gracious floor plan with elegant formal spaces. Original architectural details shine alongside impeccable updates.

As you approach, the inviting wraparound veranda captures your attention, providing south and west-facing views perfect for relaxing afternoons. A charming rear porch and multiple balconies also extend the living space outdoors, while offering views of magnificently landscaped grounds, and luxurious pool.

A standout feature is the tower, extending from the lower level to the third floor. This circular space houses a sauna adjacent to the workout area, a handsome bar for entertaining, a cozy sitting room adjacent to the primary suite and a study offering panoramic views of Nyala Farms at the top.

Main Floor Elegance: The grand foyer leads to a spacious living room with multiple seating areas, a striking fireplace and solarium/bar area. A formal dining room connects to a distinguished library, both featuring wood burning fireplaces. The well-appointed kitchen opens to a sitting area and welcoming breakfast room, with easy access to poolside enjoyment.

Bedrooms & Baths: Located on the second floor, the spacious primary suite includes a fireplace, spa bath, custom closets and sitting room, creating a private sanctuary. There are three additional ensuite bedrooms and two more bedrooms, sharing an adjoining bathroom. A laundry room, with dual washer and dryer sets completes this floor. The third floor hideaway includes a bedroom suite and a study in the turret crown with elevated, tranquil views.

The two car garage leads to the home’s lower level, featuring ample storage and a kitchen prep area with freezer and sink. Oenophiles will appreciate the expansive wine room.

Outside, relax by the sparkling pool or host gatherings on the lush, landscaped lawn. The property includes an adjacent lot for added privacy or future expansion. This Greens Farms gem stands as one of the premier examples of Victorian architecture in Westport, Connecticut. Steps from town, schools, and rail, this is a rare opportunity to own an estate rich in location, character and comfort. Shown by appointment.