Bucking ‘In-Town’ Trend, Realtors Turn to New Canaan’s ‘Upper East Side’


Kelly Kraus says that when she came to New Canaan in 1999, prospective homebuyers moving here overwhelmingly wanted homes on four-acre lots north of town.

Then in 2004, the sale of a home at 110 South Ave. (and soon after, another on Brooks Road), kickstarted a trend of tearing down and building anew “in town”—call it above Farm Road to about St. Mark’s, and as wide as a walkable distance to the business district.

Realtors hyper-focused on that geography—driven by the tastes of prospective residents as well as New Canaanites already here who were seeking to downsize to more manageable properties after, say, their kids moved out, Kraus said.

Yet while riding the wave of homebuyers seeking to live “in town,” Realtors may have neglected other parts of New Canaan, Kraus said—particularly what a group that gathered this week refer to as the ‘Upper East Side’ (call it east of Smith Ridge Road and north of 106).

Kelly Kraus of Barbara Cleary's Realty Guild in New Canaan. Credit: Michael Dinan

Kelly Kraus of Barbara Cleary’s Realty Guild in New Canaan. Credit: Michael Dinan

“We’re just trying to reacquaint people with how pretty that section of town is, instead of just automatically saying ‘I want to live in town’ when in reality, New Canaan is not that big and you are never far away [from downtown],” Kraus, of Barbara Cleary’s Realty Guild, said Wednesday afternoon, hours after pulling together Realtors from nearly every real estate office in New Canaan to discuss the situation. “And really all these people who are buying on Woodland, they are not walking to town. They’re still driving to town. So it’s a question of driving two minutes or seven minutes. And it’s nice to see agents from a broad spectrum of offices cooperate and say, ‘We may be partly to blame for this ‘in town’ trend, because we have been so concentrated on selling this in-town building boom that we need to get people focused again on all of New Canaan.”

And on the ‘Upper East Side,’ in particular. It’s an area that Kraus said offers not just more value and a great quality of life, but also more inventory and in a wider range of styles, including Mid-Century moderns, Colonials at $1.5 million, larger homes at $3 million.

Following this week’s meeting of the minds—itself a very rare step, Kraus said—Realtors are planning a cross-agency Open House Day for the area, from 1 to 4 p.m. on Sunday, Sept. 28.

John Engel, a lifelong town resident who works as a Realtor out of Barbara Cleary’s, crunched some numbers that, in many ways, demonstrate the value in New Canaan’s ‘Upper East Side.’ Breaking out two years of closed listings data by school district (all of East School is east of Route 123), Engel found that the average price per foot at South came to $384, compared to $400 for East School district and $513 for West.

Asked whether the discrepancy can be attributed to lot sizes, Engel said: “I think that East and West both have a fair amount of 4-acre zoning and 2-acre zoning and 1-acre zoning, so I don’t think that there’s a huge difference between East and West school districts. I do think in the South School district, you’re going to find smaller lots and that’s why you see smaller house size, because you have smaller lots.”

And the South School district—geographically, a Trival Pursuit-like wedge (see map here) that starts in the center of town and opens as it moves away, past the YMCA and toward (and slightly below) the Merritt—includes much of what is termed “in town.”

Here’s more data that Engel broke out, article continues below:

House Sales by Neighborhood in New Canaan

Original Asking$1,571,742$1,861,635$2,350,986
Final Asking$1,543,084$1,784,402$2,265,602
Sold Price$1,489,605$1,702,498$2,129,125
Pct of Original 94.77%91.45%90.56%
Avg 'Town Hall Feet'3,872 4,2484,143
Price per Foot$384$400$513
Avg Age of House196219571967
Source: John Engel, Realtor, Barbara Cleary's Realty Guild

* Data based on 520 sales between Sept. 17, 2012 and Sept 17, 2014


Denise Gannalo, sales vice president for William Raveis Real Estate, said that while homes located within walking distance of the downtown have seen a “meteorite rise in popularity and values over the last several years,” the area east of 123 and north of 106 “is presenting some excellent values.”

“For a family moving to New Canaan from the city or other urban areas, this part of town is a welcome retreat, where quiet tree lined streets foster children playing safe from traffic and the allure of the lush green lawns is a welcome sight for many urban dwellers,” she said.

Gannalo also spoke to the relatively high amount of inventory there.

Right now, there are 68 homes on the market in the “Upper East Side” of New Canaan and an additional 12 properties have accepted offers or are pending, Gannalo said—compared to 44 active properties and 11 pending in the South School district.

“In northeast New Canaan, you can typically buy a 4,000-square-foot Colonial about 20 to 30 years old, on two acres, with a nice yard and renovated kitchens and baths,” she said. “The home could even have a swimming pool. The median price would be around $1,600,000. In town, a buyer would not be able to find such a large home in good condition with some property.”

Laura Costigan of the New Canaan office of Berkshire Hathaway HomeServices New England Properties said there’s not only more square footage for your money in the “Upper East Side”—for example, for families with a dog or dogs—but also “a more peaceful existence when you want to get out of town.”

“Because town can get pretty crazy, too, and some people want to get out of town just so they can hear the birds sing,” Costigan said.

The “Upper East Side” has other major selling points, Kraus said, such as proximity to St. Luke’s School and Wilton Center.

“People who live there can take advantage of both Wilton and New Canaan, and it really has some of the prettiest areas in town, with the reservoir,” she said. “It has much more of a New England feel.”

[Editor’s Note: The table originally had East and South School district information in the other’s category. It’s been updated.]

5 thoughts on “Bucking ‘In-Town’ Trend, Realtors Turn to New Canaan’s ‘Upper East Side’

  1. It would be wonderful if we could move the focus of those families that are looking to build “in town” to the North East area, and stop the “pillage of the village” charm. I live a walkable distance to town but still drive because it’s too dangerous to walk.

  2. Correction. Please note that the square feet numbers were transposed above from the figures on my website. South homes are smaller, on average.

    East = 4,248 square feet
    South= 3,872 square feet
    West= 4,143 square feet.

  3. If people on Woodland Road aren’t walking to town, why did the town spend hundreds of thousands of dollars installing sidewalks on Main Street?

    • And why does the Plan of Conservation and Development include more sidewalks in the area. If people aren’t walking to town, why put in more sidewalks?

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