Field Guide To The Most Massive Mansions In Connecticut

CONNECTICUT — Who wants to own a home when you can afford a compound? Why suffer squeezed into two or three floors when you can spread out over six?

You can't take it with you, so you might as well spend it on a little more elbow room.

With that in mind — and fresh from Mega Millions dreaming — we did a deep dive into the new Patch Real Estate listings to find the biggest and most bodacious homes in Connecticut.

These aren't necessarily the most expensive homes in the Nutmeg State, but they are the largest on the board, each holding over 14,000 square feet of living space.

Click on the photos for even more photos, and the complete listings.

All the best estates have names ("Wuthering Heights" wouldn't be nearly as successful if Bronte called it "544 Oenoke Ridge"), and one of the best-named Connecticut estates is Orchard's End, in New Canaan. At 25,000 square feet, it's the largest mansion in Patch's Connecticut listings. At just under $15 million, it's also one of the better values among the excessively extravagant homes.

The estate was built in 1929 and designed by New York architect William B. Tubby, whose other named homes include Waveny House in New Canaan, Dunnellen Hall in Greenwich and William H. Childs House in Brooklyn.

In 2014, the current owners of this 12-bedroom, 16-bathroom mansion retained world renowned architect Dinyar Wadia for a 3-year $6 million makeover. Builders expanded upon a brand new 4-bedroom guest house, along with a custom designed 5,000 square foot wellness center, a custom pool with spa and new terraces.

The same folks who brought you the TV series "Happy Days," "Laverne & Shirley," "Mork & Mindy," "Bosom Buddies," "Full House," and "Perfect Strangers" are also responsible for the second-largest home on the list. This 22,282 square foot palace was the country estate of executive producers Thomas Miller and Robert Boyett, built just 20 years ago in Salisbury. It's on the market now for $15.7 million.

The home, with its nine bedrooms and 14 bathrooms, sits on more than 470 acres and boasts magnificent western views of the Berkshire Mountain Range. There's also a 1,900 square foot caretaker's cottage, a spa that seats 15, warehouse, art storage building and a log cabin that the listing suggests offers "the best views of the Twin Lakes in the county."

At just $8.2 million, this 18,811 square foot home in Washington is a steal, especially given it sits atop 106 acres. The home's modern style makes it something of an oddity on a list of Big Money Connecticut real estate, but all those glass walls offer unobstructed views from every room, so why complain?

If the five bedrooms (each with their own wood burning fireplaces and spa-inspired baths) aren't enough, you can sprinkle your weekend visitors out among a three bedroom guest house and bunks for four in the grass-roofed tennis house. The indoor activity center with a saltwater pool, hot tub, sauna, showers, squash court, movie theater, family room, and game room guarantees they'll have plenty to do once they wake up.

You'll pay nearly four times as much for about the same amount of house down on the Gold Coast. This 18,068 square foot Greenwich estate is on the market for an even $30 million.

The original estate was built in 1900 and enlarged over the years, with the grandest addition in 1991. That nearly doubled the size of the home, which sits on almost 6.4 acres and boasts 11 bathrooms, and nine full baths. Two 1-acre lots have been subdivided to create a compound in addition to the guest house, and a cottage flanking the driveway.

How much of this 17,878 square foot estate on Pecksland Road in Greenwich is left for people to live in, once you remove all the space for cars? We're not sure, but it's clear the original owner did love his automobiles. A 3-car garage only hints at a lower level that can accommodate up to 30 cars.

On the main levels, you'll find multiples of everything: dining rooms, living rooms, guest suites, offices, walk-in closets — and all of them super-sized. There are 10 bedrooms and 19 bathrooms all told, and all for $33.8 million.

Renowned Westport architect Roger Ferris designed this distinctively deep home on Saco Hill Road in Fairfield, packing 17,735 square feet of living space up and down six floors. Residents bustle between the "soaring space that is the Gallery with its mesmerizing marmalade marble floor" and the lowest level's 75-foot-long Italian marble lined indoor pool with a glass skylight roof.

The floor-to-ceiling windows throughout take in crazy-spectacular views of Southport Village and Harbor, Country Club of Fairfield, Long Island Sound and the Manhattan skyline. In between are 10 bedrooms, 18 bathrooms, multiple living, playing and working spaces, all for $17.9 million.

If it all starts feeling a bit claustrophobic and you need to spread out a bit, sneak off to the guest house with its own living room, kitchen, two bedrooms, two full bathrooms and 2-bay garage.

Sitting atop one of the most-elevated lots in Greenwich, this 16,359 square foot home "harmoniously combines modern and tradition aesthetics," according to the listing. It certainly checks all the standard boxes for a Gold Coast gated estate: views of Long Island Sound from multiple rooms, over-the-top kitchen, media room, large gym, 4-car-garage, and no fewer than seven bedrooms and 13 baths.

The price is golden as well: just under $35 million, making it the most expensive mansion on the list.

If you're buying yourself an island, you better be certain you have enough bedrooms for all the family and friends who'll be inviting themselves over to help you appreciate it. This 13-bed/12-bath Stamford property on Long Island Sound has you covered.

For just under $8 million, the buyer can enjoy 14,149 square feet of living space designed like an English manor, and sited like a lighthouse. Outside amenities include a 200-foot pier with dock, heated salt water lap pool, expansive flagstone terraces, sandy beaches, stone walkways, koi pond, Lord & Burnham greenhouse, 3-bedroom stone guest cottage and a carriage house with two apartments.