Middlefield, CT —
“Fielders” Have More Fun

Growing up, my Dad used to tell me that Middlefield was once a part of the city of nearby Middletown but a tax difference between the urban “Towners” and the rural “Fielders” caused tensions and so, the towns split apart. Although I haven’t found anything to back up his claim, Middlefield remains a sacred place to me and now, to my own family.

"Yes, our little town has ski slopes! They offer lessons and tubing as well."

Special Features

Fun facts to put you “In The Know”:

The Town Seal is divided into quadrants and is meant look like the town is being watched through a gun sight. The four sections of Middlefield, in a nutshell.
1) Aside from the gun-sight view, one quadrant represents the old pistol shop that was a large part of Middlefield commerce.
2) Another quadrant represents the orchards and farmland.
3) The third quadrant represents the outdoor activities Middlefield offers such as hunting, fishing and skiing.
4) The last quadrant represents the saltbox-style homes of the 1700’s that still dot the landscape.

There is it! We “Fielders” just have more fun!

Residents here will tell you that the Lyman family is embedded in the DNA of this town. In 1741, farmer John Lyman bought a 37-acre parcel of land here. Now, his family farm covers more than 1,100 acres and is host to countless family attractions. Whether you are picking your own fresh apples, finding your way through the fall corn maze, trying their award-winning pies or enjoying any of their three golf courses, it’s nothing short of a good time.

Featured Listings

1143 Sasco Hill Road, Fairfield (Sasco), CT

$14,000,000
ONE OF THE SINGLE MOST ANTICIPATED, MAGNIFICENT, AND BREATHTAKING ESTATES ON THE GOLD COAST HAS JUST HIT THE MARKET! This architecturally brilliant and elegant home was built for entertaining and lavish gatherings in Gatsby-Esque style. A rare opportunity to own nearly 3 acres of property on Fairfield County's most prestigious address, with SPECTACULAR views of Long Island Sound, Sasco Beach, and the Country Club of Fairfield's Golf Course. Refreshed to its grandeur, with no expense spared by the owner, you will be impressed the moment you enter this estate. Presenting 19,000+ SF on 4 levels of living, 30+ rooms each with its own unique features and design, 9 Bedrooms, 13 Baths, Elevator servicing all levels, PLUS a 6 car Garage/Carriage House with staff apartment above. A private oasis and yet minutes to Fairfield and Southport center, train, library, harbor, restaurants, and shopping. Ideally located and 53 miles to New York City. This is a once in a lifetime opportunity.

1A Pratt Island, Darien (Pratt Island), CT

$15,600,000
One-of-a-kind direct waterfront proposed new construction on Pratt Island! This 2+-acre utopia has a protected deep-water dock in Noroton Harbor. Hop on your boat at a moment's notice! Water lovers will delight in the 200' private sandy beach. Be lulled to sleep by the waves & watch thunderstorms roll down Long Island Sound. Enjoy the endless wildlife surrounding you. Prepare to be amazed by the high-end finishes of this house. The Nantucket shingle design boasts a classic layout, 9'+ ceilings with an open floor plan & an abundance of natural light throughout. This 5500SF home has 3 finished floors, fireplaces, 3 garages, generator, irrigation, central vac, and more. A large pool & spacious yard are perfect for entertaining or just relaxing. Beach life is calling you! Photos are from builders previous project. Colisted with Keiley Fuller

1 Pratt Island, Darien, CT

$15,600,000
One-of-a-kind direct waterfront proposed new construction on Pratt Island! This 2+-acre utopia has a protected deep-water dock in Noroton Harbor. Hop on your boat at a moment's notice! Water lovers will delight in the 200' private sandy beach. Be lulled to sleep by the waves & watch thunderstorms roll down Long Island Sound. Enjoy the endless wildlife surrounding you. Prepare to be amazed by the high-end finishes of this house. The Nantucket shingle design boasts a classic layout, 9'+ ceilings with an open floor plan & an abundance of natural light throughout. This 5500SF home has 3 finished floors, fireplaces, 3 garages, generator, irrigation, central vac, and more. A large pool & spacious yard are perfect for entertaining or just relaxing. Beach life is calling you!

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