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

1093 Pequot Avenue, Fairfield (Southport), CT

$13,900,000
Magnificent DIRECT WATERFRONT - A Coastal Masterpiece awaits at 1093 Pequot Avenue! As you arrive to the gated entry & private drive to your estate, you are keenly aware that this is a special & rare find! Southport's premier 2 year young home is set on a level full acre of direct waterfront w/ unobstructed panoramic views of Southport Harbor & Long Island Sound. Brilliant architecture & craftsmanship highlight the water views in all rooms. Abundant natural sunlight throughout the first floor w/ the wall of glass doors that span the width of home. This modern day floor plan spared no expense w/ custom high end finishes, lighting, window treatments, mill work, and impressive details. Three levels of living, 9000+ SF, 17 spacious Rooms, 6 full and 2 half Baths, 5 en-suite Bedrooms including the Primary with a Sitting Room, his/her walk-in closets, and private Deck overlooking the water, 2 car Garage with 2 car lifts that services a total of 4 cars, 2000+SF unfinished lower level (not often found in water front homes) ideal for storage & whole house generator. The back yard features multiple Patios/Terraces and seating areas that surround your salt water Gunite pool which of course has magnificent water views. Spend your days watching the boating activity from the Harbor, wake up to amazing sunrises and sip coffee from your balcony and enjoy all this resort-like lifestyle truly offers. Minutes to Southport Beach, Village, Harbor, Train and Library.

1099 Pequot Avenue, Fairfield (Southport), CT

$9,950,000
Spectacular builder's own custom waterfront home on private Rock Point Road off Pequot Avenue in historic Southport Village. Magnificent views of Long Island Sound from all major rooms in this 11,000+ square foot home. Beautiful pool and pool house look toward Beachside Avenue and the Manhattan skyline in the distance. Walk to the beach, train, restaurants, and shops. Waterfront living at it's very finest. 1 hour to NYC.

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.

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