If you’re fan of modern architecture, you’ll never be bored in Manhattan.

Around every corner you’re bound to stumble across a building designed by say, Philip Johnson or entire blocks styled by Rosario Candela, or a Harlem church inspired by Le Corbusier’s Ronchamp.

Which, don’t get me wrong, is great and all, but there are almost no opportunities to actually live in a historically significant building.

That’s because in the 1940s and 50s ambitious young architects from Yale and Harvard all seemed to settle and build in a place like New Canaan, Connecticut.

If you drive through New Canaan in the spring it’s easy to see why.

It’s a quaint town with miles and miles of wooded suburbs to build their utopian homes, and the well heeled Manhattan doctors, lawyers, and business leaders who could afford to pay for them.

It wasn’t (and still isn’t) quite Greenwich. And that’s the point. In New Canaan you could take risks, and boy did those risks pay off.

Breuer House by Elliot Noyes

The only problem on our end is that there were three houses on the market this week that we all fell in love with. Asking us to choose would be like asking a mother to pick her favorite child.

So instead, we decided to make all three our listings of the week. Once you’ve seen them I think you’ll agree.

Address: 31 Chichester Road, New Canaan, Connecticut
Asking price: $1,295,000 (Pending)
Listing Agent: Fran Snelwar
Listing Brokerage: Halstead
Year Built: 1956
Architect: William F Pederson

First up is 31 Chichester Road, which is something of a Champs Elysees for jaw-dropping mid -century architecture in New Canaan.

Still, 31 Chichester stands out from the crowd, and it only takes a quick scroll through the listing photos to discover why.

Right from the start, you’re hit with all the goodies that mid-century architecture is known for. White gravel, a flagstone patio, low-slung rectangular shapes, and a very carefully planned integration between interior and exterior space.

Once you’re inside, the atomic age charm really starts to kick in. The main living space boasts huge picture windows that frame the wooded yard beautifully.

new caanan fireplace

Take a step back, and you can see one of the design innovations that carries over into today’s luxury homes. The central fireplace with exposures on two sides. Not only do you get views of your fireplace from multiple angles, but you also get heat from both sides.

The furniture here is also a perfect fit, which helps with the overall feel of the place.

Virtually staged? We can’t tell. Can you? Either way, it shows just how great splashes of color look in well-designed minimalist homes.

As an added bonus, the lucky buyer of 31 Chichester gets this absolutely adorable screened porch for dinner parties, or just relaxing.

Fondue set and Burt Bacharach records not included.

PS: Looks like someone has an accepted offer on this place, so you might have to schedule your dinner party somewhere else.

Luckily, 729 Laurel checks all the same boxes, has a much bigger lot (~3 acres vs Chichester’s 1 acre), and even has a more famous architectural pedigree.

Let’s take a look:

Address: 729 Laurel Rd New Canaan, CT 06840
Asking: $995,000
Listing Agent: Christine Williams
Listing Brokerage: William Pitt Julia B Fee Sotheby’s
Year Built: 1952
Architect: John Black Lee

From the front we’re getting the same tingly feeling we got from 31 Chichester. Flagstone walkway, minimal rectangular shapes, and the same interior/exterior integration.

Once we zoom out with the drone, the comparisons end. The lot here is nearly three times as large, and densely wooded.

While the interior space is smaller, (1500 sq ft vs ~3,000 sq ft,) in our eyes the lot more than makes up for the size difference. Since it’s built on a hill, a lower, cantilevered level would seem like a no brainer addition.

Of course, with exterior lines like these, and a large detached garage that would make a killer studio/office, you might want to just leave it as is.

While the owner’s furniture here kind of detracts from the vibe a bit, it’s easy to imagine an Eames lounge chair and some nice built-in shelving to bring the space back to its stylish roots.

The garage, or if we bought the place, our new office/art studio:

The best part about 729 Laurel is that you get all the cachet of owning a historical mid-century home, without the eye-watering price tag. A below million dollar home in this area, in this condition, with this pedigree is actually a bargain. Don’t believe us? A Philip Johnson designed house is also on the market in New Canaan for $8.5 million.

Address: 126 Chichester Rd New Canaan, CT 06840
Asking: $1,390,000
Listing Agent: Inger Stringfellow
Listing Brokerage: William Pitt Julia B Fee Sotheby’s
Year Built: 1963
Architect: James Evans

Last but certainly not least, we’re back on Chichester Road for a look at an uber charming early 1960s home that is as warm and cozy as Grandma’s house. Well, maybe a cool grandma who makes abstract collage art and knew Jack Kerouac back in the day…

There’s just something about those stained, beamed ceilings that draws us in. Truly amazing how form over function can look so beautiful.

Instead of a rectangular box, this house has a gorgeous sloped roof that adds some drama to the space.

The living area boasts a natural flagstone fireplace, floor to ceiling windows, and built-in shelving.

Off the kitchen, there’s huge sliding glass doors that lead out to, you guessed it, a flagstone patio.

The bathroom has what looks like original blue mosaic tile and large window.

The kitchen looks more Shaker than Breuer, so it’s safe to assume this is a newer reno. It has a nice cozy vibe, but seems a bit out of place here. An easy fix though.

Outside there is more of a traditional suburban backyard, which is a bit of a shame, but there’s a pond and plenty of room for swing sets and jungle gyms.

Over to You

Which New Canaan Mid-Century gem would you rather live in? Let us know in the comments!

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