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A Few Drop-Dead Gorgeous Houses from New York's Hudson Valley

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Since the colonial era, New York urbanites have been heading north to the Hudson Valley to stake their claim, either to make their fortunes or, more recently, to spend a fortune in the bucolic countryside. Perhaps no fortune was better spent in this region than on Taghkanic House, an ultra-modern glass and steel construction on 350 acres in Taghkanic, N.Y., a 2.5-hour drive from NYC. The 8,800-square-foot spread was designed by Thomas Phifer and Partners, who concealed much of the structure's bulk beneath a planted green roof, leaving a glassy aerie on top to house the living and dining rooms. The result is a massive house that doesn't seem too large and blends into the surrounding countryside. The estate, with its six bedrooms, media room, stainless steel kitchen, wine cellar, refrigerated cheese room, and indoor and outdoor pools, is on the market for $9.75M.

? Clapboard farmhouses are almost a dime-a-dozen in the Hudson Valley, so when we happened upon this brick colonial with remarkably high ceilings in Clermont, N.Y., we figured it was something special. Built for New York Assemblyman and physician Dr. Thomas Broadhead in 1804, the 13-room house—for sale at $825K—now occupies a 1.8-acre plot surrounded by farms and retains some of the finest period features, like nine fireplaces, pine floors, and original moldings, doors, and mantles.

? Deeper pocketed buyers can get a similarly impressive house, but with more than just a couple acres. The $9.9M Hoffman Farm on tongue-tying Shekomeko Lane in Pine Plains, N.Y. offers up a restored 1800s farmhouse that measures 5,000-square-feet and 360 acres of prime upstate real estate. The land is sub-divisible, but even the broker is rooting for someone to conserve this spread: "Opportunity to extinguish development rights, resulting in substantial tax benefit."

? Getting less than half the acreage of the last place for nearly three times the price might not sound like a deal, and well, it probably isn't, but Sky Blue Farm in Millbrook, N.Y. is well equipped for equestrian pursuits and that generally means a serious premium. There's an 18-stall barn, 20,000-square-foot indoor riding ring, and 144 verdant acres of private land for the riding. For the humans, there's a six-bedroom main house, a 3,200-square-foot guest house and a caretaker's residence. All this multi-species luxury costs $27M.

? Now this last one requires a leap of faith—the house hasn't been built yet—but the impressive renderings and quiet treed lot should woo someone into dropping the necessary $1.5M on this Woodstock, N.Y. home. The broad panes of glass, a privacy concern most anywhere else, seem to make sense with the dense forest outside.

· Taghkanic House [Sotheby's]
· Broadhead House [R.H. Blackburn]
· 85 Shekomeko Lane [Houlihan Lawrence]
· 123 Fraleigh Hill Road [Houlihan Lawrence]
· 1 Van Dale Road [Trulia]