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If Southport is known for tightly packed Victorians overlooking the harbor, Greenfield Hill is definitely its country cousin, with sprawling horse farms and grand estates socked away on so many landscaped acres that they're hidden from view. Broker Al Filippone, of Al Filippone Associates, says Greenfield Hill is the least well known of Fairfield's prestigious neighborhoods--and that the residents like it that way. Most of what you can see from its winding roads looks a century old, from the grand estates with their stone walls to the horse farms with their split-rail fences.
"It has more history, more character and more charm," says Filippone, comparing it to the backcountry enclaves of New Canaan and Greenwich, adding that the neighborhood only feels remote. In fact, one of his current classic Greenfield Hill listings is a short drive to the Southport station with its 70-minute train rides into Grand Central. The 7,000-square-foot Nantucket shingle-style estate on 12 acres has a "Ralph Lauren-style" aesthetic, says Filippone, thanks to the antique materials deployed throughout. The foyer, for instance, features an oversized mahogany door and antique limestone underfoot, which gives way to the reclaimed chestnut floorboards and pillars used on the first floor. This time of year, one of the most welcoming rooms is the posh library, featuring cherry cabinetry, a coffered ceiling and a slate fireplace. The master suite is also on the first floor, boasting a 20-foot-high cathedral ceiling and a cupola, a fireplace, a luxury master bath (with steam shower and whirlpool tub) and French doors onto a stone terrace. On the second floor there are an additional four bedrooms, each with an en suite bathroom and an entertainment wing that includes a billiards room, gym and kids' playroom. Al Filippone, who has offices in Southport and Fairfield, can be reached at (203) 256-3264.