The Best Streets in Town (Published in Greenwich Magazine, April 2007)
Some of smartest people I know in real estate (not as low a barrier as you might think) advised me against taking this assignment because, they warned, I’d be bound to offend hundreds of homeowners who expect their own address to be included among the best streets in town. Offend hundreds of people at once? That’s the kind of challenge I relish, so here goes.

First of all, of course, there is no such thing as “the best street in town”. Individuals and their desires are far too idiosyncratic to allow that kind of ranking. For every desperate striver who would gladly sell his first-born in exchange for a huge house in a prominent location that simply shrieks, “look at me!” there’s another who, like Garbo, wants to be alone. A Back Country house may be perfect for a hedge fund trader who’s chauffeured to work every day but a mother of five who is the chauffeur might prefer a house in crowded Riverside, where her kids can walk to school or their friends’ houses without parental supervision (although these days, observing the nearly-empty bike racks at Riverside School, I wonder if that happens any more). With that caveat, here are some of the streets in town that command a premium.

Field Point Circle
David Ogilvy, speaking of the entire Belle Haven community, says that it “retains the feel of a summer community that just happens to be attached to Greenwich”. Grand old summer-houses with great architecture and all long-since converted to full-time residences. There’s high security and a neighborhood club (as a sailor, I won’t vouch for its harbor but, in this case, that’s a quibble and beside the point). I’d suggest that Field Point Circle should be at or near the top of anyone’s list of best streets in town, even though it’s approached via the Grass Island sewer plant (there are compromises involved in every scrap of Greenwich real estate). While it doesn’t hold the record for the highest sales price achieved (Conyer’s Farm, at $45,000,000 has that distinction) I think, year in and year out, this address holds the most prestige and commands the best prices. One thing of note: my brother Gideon once researched sales in this neighborhood to see if the “international marketing” pitch some firms tout as the way to sell Field Point Circle homes actually worked. Turned out that, out of twelve recent sales, eleven of the buyers were relocating within Greenwich. Sometimes you have to live in town awhile to appreciate or at least understand its high market prices.

Maher Avenue
Other than the Brunswick traffic and the great Halloween invasion, when half the town and all of Westchester descends on the place, this is a great, family neighborhood littered with grand old houses, almost all of which have been renovated. Owners who live here seem to gladly put up with Brunswick (and some actually enjoy the Halloween frenzy) in exchange for living in beautiful houses and having good friends on either side.

Park Avenue/Park Place (Greenwich)
One of my very favorite streets. Big yards, dignified houses of all ages and a really convenient location. Without spending too much time on research (okay, no time on research) houses here seem to sell rapidly and well. You or your agent will have to keep on top of new listings if you want to live here.

Parsonage Road
I only know this street from my bicycling tours but its western half, beginning after the parsonage itself, holds some of the best-looking houses in town. I like it a lot but one potential buyer, eying St. Mary’s graveyard behind and the Nathaniel Witherall down the road protested, “I’ll be living between the dying and the dead!). Aren’t we all. Get over it.

Back Country Roads
Cathy Adams still sounds wistful remembering her commute, pre-real estate days, to IBM via these roads. “I’d drive up Clapboard to Round Hill, cross Porchuck to John Street. When the leaves were turning …”. These are all still nice streets but, to my eye, they’ve lost some of their lush beauty as, one-by-one, the 100-acre estates have been chopped into 4-acre ranchettes and high, towering walls have blocked the views of what were once rolling meadows. It’s your call but, in my opinion, we’ve lost something here.

Quintard, Keofferam
Almost any street in this section of Old Greenwich is a winner. A huge stock of large Victorian summer homes all long-since winterized and updated and, although lot splits are becoming more common, still some very nice, big yards. There’s easy access to Tod’s Point, Old Greenwich School and the train. Riverside native Mary Karlan has lived on Keofferam since 1998 with her nine (!) kids – okay, it’s a blended family – and loves the street: “there are lots of kids, everybody’s really nice and if you like to run at the beach, walk your dog or walk your kids to school, this is the place.”

Club Road/ Gilliam Lane
These parallel Riverside streets present a bit of a quandary. My editors chose Club Road while, no doubt because I grew up on Gilliam, I prefer the latter. Club Road is busier in the summer due to the daily stampede of cars delivering and picking up kids at the Riverside Yacht Club but, for now, the houses are mostly larger and more impressive. I suspect that will change as the tear-down boom continues its sweep through Riverside but you can’t lose on either street.

Up and Coming?
Perhaps Arch Street, right next to Binney Park. This area starts off with some so-so 1960s contemporaries but four new, expensive and good-looking houses have been constructed recently (Peter Fusaro, of Riverside, got the ball rolling with a nice one on the corner of Wesskum Wood that sold for around $2.4 million a few years ago – it’s worth at least $1 million more today) and, as prices climb, you’ll see more such projects. The latest mind-blower was 30 Arch, built by Doran Sabaag two years ago and recently listed for $6,250,000. Several of us thought the sellers would get their price, others, also very experienced agents, thought that someone had sucked a bit too long on the old bong. Turned out we were all wrong and the house went in just two days for, rumor has it, $6,400,000. Mr. Sabaag is one of the best builders currently working in Greenwich and, if anyone’s creation is going to draw a premium, his is, but still – astonishing.

Start High, Finish Low
There are a number of streets that provide a friendly, close neighborhood experience that approaches or surpasses that offered by Field Point Circle. Fado Lane in Cos Cob, for instance, is a dead end street that gets closed off for neighborhood block parties on a regular basis. Its houses are not going to win any architectural awards but you can get your family into a house here for under $1,000,000. These days, that qualifies as a starter home. And, by way of amends, may I suggest Cary Road which I once described as the worst street in Riverside? (I heard about that, believe me). A tiny, crowded street abutting the Mianus River with, it turns out, and notwithstanding the tone of their letters to me, some of the nicest folks in town. Without the river, it’s not much but the water yields skating, boating, fishing and swimming, all for far less than you’d pay to belong to the Belle Haven Club.