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Cheshire Crossing – Wallingford, CT

This area of beautiful homes in Cheshire, CT was actually settled in 1780. Newly constructed homes are located 15 minutes from the Boston downtown area; there are many gorgeous family dwellings in this New England styled settlement.

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This neighborhood has the popular Sleeping Giant State Park and Lyman Orchards Golf Club located near the district to keep anyone relaxed, and busy. With the Gouveia Vineyards near really kick back and enjoy the evening.

Area Schools

Parents with school age children will find the Cheshire school district a great place to educate their children. There are three public schools and one private, all in close proximity of these beautifully designed homes.

  • Sheehan High School
  • James Morgan Middle School
  • Cook Elementary School
  • Cheshire Academy Private School

This area holds some great colleges. There are almost twenty in the area, St. Joseph, Yale College, Fairfield, Central Connecticut State, New Haven and the list goes on. Therefore, whether you need schools for the little ones or a college close to home, Wallingford, CT has an educational facility close by.

Cheshire Crossing


Cheshire has two modes of transportation moving residents in and out of the area easily. The Greyhound Bus Line is a reliable mode of transportation bringing residents from across the country and the Arrow Line Peter Pan is a local bus line transporting customers around the area.


This lovely area is filled with activity for culture or worship. Stores of all types are open for convenient shopping, churches for worship, theaters, opera and cinema.

The stores, scenery and people are special in this environmentally community. If you love natural beauty, Cheshire Crossing Wallingford, CT is the place to live.

Main Attractions

Yale Cabaret has fantastic shows everyone can enjoy, listen to jazz music or see other dramatic performances. These are wonderful actors and the space is intimate. If fame and fortune should arrive for one of these entertaining folks, you can say you rubbed elbows with the greats. A glass of wine before the show matched with great entertainment makes for a pleasant $10 ticket.

Have a fabulous time at Sea Tea Improv, the local comedy club in the area; it is a great place to laugh and have a good time. The action is located at Steam City Brewery. Eat a little food and forget about your cares. There is a once a month free show if budgeting is a problem. Everyone gets to have fun and have a good laugh.

This is a beautiful setting for a home. Foliage is gorgeous any time of the year, particularly in the fall. Add to this by making a visit to the Claypen and design your own decorative seasonal delights with plates and vases of many colors and designs. This shop is a great stop for locals and visitors looking for unique items for home use.

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