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Living a Small town Lifestyle in Guilford, Connecticut

Guilford is the quintessential old, small town in Connecticut.  It has one of the finest greens (squares) in New England - a huge expanse of lawn and trees surrounded by stores, churches, restaurants, and a brand new library expansion.  The Guilford Fair is an annual event that evokes old time fairs and brings this close knit community together, as do the high school soccer and football games. Yet even though a small town, from the new train station here one can be in New York City in just over 2 hours, making day trips there easy.  Fishing and boating are excellent. There is a town owned par 3 golf course, with other public courses in Middletown and Hartford.

Where to Retire in Guilford and Home Prices

The neighborhood near the green, while expensive, is one of the best places for retirees since they can walk or bike to stores and restaurants. There is one very nice condo building there, with others sprinkled around town.   Prices are high and during early 2013 reached close to $400,000.  However, according to, the median selling price was $340,800 in mid-2019.

What Is Special about Guilford

Guilford is one of the prettiest towns in New England with its historic green, beautiful homes, and beaches and harbor on Long Island Sound. It also has great transportation and an active art scene.

What Is Not Special about Guilford

Prices of homes are expensive, as are taxes. Very nice homes near the water will be over $1million.

Climate and Physical Environment

Guilford is on the Connecticut coast about midway between New York and Boston. The median January temperature is about 30. Here near the water it is warmer in winter and cooler in summer than just a few miles inland. The town is very deep as it goes away from the Sound, covering a large expanse of territory.

Restaurants & Cultural Scene

Thanks in part to the Greene Gallery and the Guilford Handcrafts Center, the town has a lively arts scene. The Guilford Fair and the Guilford Crafts Fair are 2 of the highlights of the season. Many artists and writers live and work here. The newly expanded library on the green is spacious and inviting. The new Community Center downtown is well used by citizens of all ages. Many interesting restaurants downtown, either just on or off the Green. The Stone House on the harbor is always a great place for the food and the view.


The crime rate is very low thanks to its affluent citizenry and well-financed Police Department.

Medical Facilities

Guilford is fortunate to have an Emergency Room and Clinic that is a branch of Yale-New Haven Hospital.


I 95 runs through town. The Guilford Train Station's Shoreline Express has frequent departures for New Haven, where one can take Metro-North to New York City or switch to Amtrak and go anywhere in the country. New Haven Airport is close and convenient, although it has very few flights.

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