Setting: Old Saybrook lies on Long Island Sound just west of the mouth of the Connecticut River. It is 105 miles northeast of New York City, 32 miles east of New Haven, and 43 miles southeast of Hartford. Average high temperatures reach 25 to 30 degrees in winter, mid-80s in summer.
Attractions: Despite Old Saybrook's status as a bedroom and resort community (the year-round population of about 9,700 more than doubles in summer), there's plenty of civic spirit. The business district along broad Main Street makes this a cozy, self-contained New England village. Natural surroundings are superb, with Long Island Sound and (once you cross U.S. Highway 1) the bucolic Connecticut River Valley.
Drawbacks: Former city dwellers might find the town "a little quiet," says one resident. Others fear overdevelopment might become a problem.
Housing Options: North of U.S. 1, the inland section of town tends to be more heavily wooded, with 1-acre zoning. Main Street and the surrounding blocks are within walking distance of shopping, with many 18th- and 19th-century homes. Houses near the sound and along the east shore of Saybrook Point trade lot size for marsh and water views. The exclusive Fenwick area features grand homes that seldom come on the market.
Your Next-door Neighbors: Nonagenarian Katharine Hepburn, the town's most famous resident, has a secluded Fenwick home. A few Yale professors, executives from eastern Connecticut's big casinos, and workers at Pfizer and General Dynamics' Electric Boat Division commute from here.
What It Costs: Some modest properties, particularly to the north, go for less than $200,000. Figure on $300,000-$600,000 in neighborhoods convenient to Main Street. Waterfront properties and 200-year-old homes along North Cove Road easily exceed $1 million.
Where You'd Spend Free Time: Water-oriented activities are the big draw, with the protected sound ideal for sailing, powerboating, sea kayaking, and the pursuit of bluefish and striped bass. There are two town beaches. Hammonasset Beach State Park, one of New England's finest saltwater beaches, is only 12 miles away. Golfers can play a 9-hole course in town and several 18-hole courses in the area. There are bike paths, and Great Cedars Conservation Area has hiking trails. The historic Goodspeed Opera House and Ivoryton Playhouse theaters are a short drive away.