The summertime haven of Fishers Island, located off the eastern Connecticut coast but belonging to New York, has been a retreat for blue-blooded preppy types for years, in part due to its out of the way location. Commuting from NYC requires a three-hour drive to New London, Conn. (two-hours from Boston) and a ferry or private plane service into Elizabeth Field. Convenient for those who draw their checks from a family trust, not so much for the workaday nouveau riche. The real estate, however, is alluring, the product of old money's penchant for preservation, and you'll get more for your money here than in the highway-, train-, and Jitney-fed Hamptons. This waterfront estate—5,000 square feet on 11.4 acres—features a deep-water dock, seven bedrooms, and an unusual outbuilding—a stellar observatory built in 1930, complete with refracting telescope—for $3.5M.
? Lacking a true water view, the Hilt House, as this shingled manse is known, comes in at a much lower price point than the sprawling estate above, but it makes up for the wooded views with classic architecture and unmolested interiors. The wall-to-wall carpeting will have to go, but one has to assume there's some gleaming hardwood hiding under there. The three-story five bedroom is asking $775K.
? This place might have the wood floors already exposed, but the rest of the house could use a little work. At least that classic facade is still largely intact, though some of the more ornate detailing has gone by the wayside. How do we know this? This listing agent is kind enough to include a yellowed photo of the house in its heyday. The $519K price tag should leave enough for the touch ups.
? This six-bedroom house might not be furnished to everyone's taste, but the interiors are well-kept and the swimming pool, with its surrounding stone patio, cabanas, and hedges, is one of the best on the island. If you want the best, expect to pay. This island pad, despite having no water view, is priced at $1.8M.
? This classic cottage, though it sits on just a third of an acre, commands a $1.5M price tag thanks to a peek at Long Island Sound through old growth trees. The location on Mansion Hill across from the Hay Harbor Club affords easy access to diversions like golf and tennis and proximity to the docks, while seven bedrooms ensure the next owner could fill his or her score card for the summer.