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There's also an authentic-looking English pub attached to a billiards room, a pine-paneled library with a Gothic fireplace surround and a kitchen with a hidden hatch door leading to a lower-level wine cellar. The property is listed with Nancy Dauk of Wheeler Real Estate in Darien (203-656-6501)
Green's Farms, Westport, $3,675,000
We're not supposed to have favorites, but if pressed we'd readily admit that this former onion farm is our It house. Part of our penchant stems from its rags-to-riches story. The tidy, circa-1760 Jessup Wakeman House, as it's called, survived a torching at the hands of British soldiers in 1779, only to fall prey to such profound neglect that when current owners Jill and Stephen O'Shea bought it in 2005, they had to dismantle it completely. Fortunately, the O'Sheas do this for a living, having bought, restored and sold several homes in the area. They're now selling this one with an option to purchase all of its furnishings (for an additional $100,000). Jill is careful to call her work a "revival" rather than a true restoration, as she opened up walls and added antique and salvaged materials (floorboards, door hardware, antique glass) where needed to create the lofty, family-friendly home. She also built a gorgeous pool and terrace, as well as a handsome, glassed-in walkway that connects the main house to the barn-style, three-bay garage, which is topped by a teen dream of a hang-out space. The neighborhood's heaven, too: minutes from Martha Stewart's estate (also for sale), the area looks as if it's been art directed by Ms. Stewart and a crew of her Omnimedia minions. The Jessup Wakeman House is represented by Jean Studwell and James Love Lee of William Pitt Sotheby's International Realty in Westport (203-221-7990).
Southport Village, $6,995,000
Sure, the massive mansions lining Southport's Sasco Hill and Harbor Road are swell. But there's something pleasing about the winding lanes that encircle this charming, pedestrian-friendly town. To be clear, Southport center is a village in the same way that Newport, Rhode Island, is—still plenty grand, with housing prices to match. One of the most admired homes is a 22-room, Queen Anne-style Victorian built in 1882.