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Location: Newport, R.I.
The Skinny: Built long before the fashionable "cottages" of the Vanderbilts and their ilk, the estate now known as Rocky Farm was a prime feature of the Newport waterfront. The main house, a charming center-hall colonial, dates to 1695, but the guest house on the property is even older. Built in 1668, the stone cottage was originally a sheep barn for lands owned by the founder of Newport, Governor William Brenton. Now, 345 years later, the estate enjoys the same sweeping views of the Atlantic and is steps to Newport's most popular beach. The three-bedroom compound, on 3.4 acres, is currently listed for $4.7M.
· 121 Ocean Ave [Zillow]