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Living a Boating Lifestyle in Old Saybrook, Connecticut

Old Saybrook, Connecticut is an idea boating community that combines New England history, a vital downtown, pristine beaches, and a friendly, small town feel. Located where the Connecticut River empties into the Long Island Sound, this charming old town of just over 10,000 (founded in 1635 ) was one of the original 3 colonies in Connecticut. Strategically important, it has the ruins of a fort built during the French and Indian War. There are docks and moorings on the Connecticut River and in the many harbors and bays in town. From here it is an easy cruise up the river, down the coast to Block Island, or through the Gut to Long Island. Old Saybrook’s most celebrated resident was Katherine Hepburn, who lived in a private community at the mouth of the river called Fenwick.

Old Saybrook's downtown is bustling with good restaurants and interesting stores. In an unusually cohesive mix, the Wal-Mart and plenty of other big box shopping is just one block away from main street. There is a major Amtrak station downtown, which also connects to New York’s Metro North.   Welcome to Old Saybrook.

Where to Retire in Old Saybrook and Home Prices

Retirement community housing choices for active adults 55+ are very good, ranging from private homes to condos. Quiet residential neighborhoods with a mixture of cottages and year round homes lead to community beaches. Some retirees live here for the summer, and then migrate to a warmer climate. There are several small condominium projects that have sweeping river or bay views. Prices are high by Midwestern standards, but a relative bargain compared to other parts of Connecticut. There is a very good assisted living facility in nearby Essex (Essex Meadows).
The median home value was $467,660 in late 2021, according to Zillow.

What Is Special about Old Saybrook

• Consistently chosen as a "Best" town • The majestic Connecticut River • Beautiful beaches and harbors • Fenwick – an unusual private community • Fort from the French and Indian War • Friendly atmosphere • Great library • Solid tax base due to several large companies and strong commercial base

What Is Not Special about Old Saybrook

Traffic in season can be heavy; it is not inexpensive; it's a small town

Climate and Physical Environment

The area experiences a 4 season climate. Water is just about everywhere and Old Saybrook is surrounded on 3 sides by the river, bays, and Long Island Sound. The area is low with forested hills forming as it goes away from the Sound. Thanks to the moderating presence of Long Island Sound, Old Saybrook winters are several degrees warmer and summers cooler than just a few miles inland.

Restaurants & Cultural Scene

Antiquing is good in the area. Theatres include the Katherine Hepburn Center for the Cultural Arts, a new facility downtown which is also the home of the Salt Marsh Opera Company and their wonderful productions. Area theatres include the Bushnell in Hartford, the Goodspeed in East Haddam, and New Haven’s Shubert, Long Wharf and Yale Rep. The Old Saybrook public library was recently expanded and is first rate. Choral groups such as Con Brio add additional entertainment opportunities. Very close to the active Lyme and Old Lyme art scene,  home to the American Impressionists.


Crime in Old Saybrook is very, very low - a little over a third the national average.

Medical Facilities

Lawrence and Memorial Hospital is 20 miles away in New London. Middlesex Hospital is about 20 minutes away in Middletown. Middlesex Emergency Clinic is about 8 miles away in Essex.


Bradley Airport is about 50 miles in Hartford. Green Airport is 60 miles away in Providence. Amtrak and the Shoreline Express stop in Old Saybrook (railroad). There is also bus service along the shoreline to New Haven. Route 95, a major Northeast Highway, goes through Old Saybrook, but doesn't detract from it's beauty; only adds to its convenience.

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