5 homes for autumn on the Upper West Side, à la ‘When Harry Met Sally’

Experience Billy Crystal and Meg Ryan’s New York with these cozy digs

(Illustration by Alexis Manrodt for The Real Deal)
(Illustration by Alexis Manrodt for The Real Deal)

Who can forget the pandemic walks? When the insides of our houses (and heads) drove us insane, New Yorkers masked up in socially distanced droves to stroll the city streets and parks and enjoy the fresh air — or enjoy anything, really.  

There were days when living in the then-desolate city didn’t seem worth the effort. On those days, it helped to think of movies that celebrate the simple joy of walking through New York. When it comes to on-screen strolls, nothing captures it quite like Nora Ephron and Rob Reiner’s quintessential 1980s romcom, “When Harry Met Sally.”

As the leaves turn and the air chills, you can’t help but catch some borrowed nostalgia for autumnal New York. One of these five Upper West Side homes, curated and showcased by TRD‘s Select Spaces team, might just be your real estate soulmate. Because, to paraphrase Harry Burns, when you find the apartment you want to live in for the rest of your life, you want the rest of your life to start as soon as possible.

A walk in the park

151 Central Park West | 4 BR | $21.5 million

Relationships are no walk in the park, unless you’re Nora Ephron.

The second time Harry met Sally was on a plane in 1982. Harry annoyed Sally from the seat behind her and gleefully swapped with a stranger to sit beside her. The third time was a charm — 1987, Shakespeare & Co. bookstore.

After Sally was unsuccessful in avoiding Harry at the bookstore, the two went for the first of many long Central Park walks. Just 15 minutes from the former bookshop — and about 10 seconds from the park — is this unit on 151 Central Park West.

The Kenilworth co-op is perfectly situated for someone who loves both the look of autumn leaves and the feel of crisp fall air. Three windows in the living room of this unit overlook Central Park, a view that can also be enjoyed from the formal dining room. Stick a bay window seat in the park-facing bedroom and sip a mug of tea while watching the leaves turn. Dark wood floors and wainscoting warm up the space, as does the fireplace in the den.

Shakespeare & Co. sadly shuttered its 81st Street location in 1996. Still, the neighborhood has no shortage of indie bookshops. This is excellent news considering the glass-paneled built-in bookcases lining the living room of this co-op. Showcase beloved titles and thrifted tchotchkes here as memorabilia from autumn walks through the Upper West Side.

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Living luxe

1 West 72nd St. | 3 BR | $10.9 million

Ephron’s whip-smart dialogue shines in the scene at Café Luxembourg on West 70th Street. The titular characters set each other up with their friends Jess and Marie for a double-date gone awry — Jess and Marie end up together while Harry and Sally fumble through another year as “just friends.” The iconic eatery where Sally ordered a grilled radicchio (dressing on the side, no doubt) is just a couple blocks from this apartment at 1 West 72nd Street.

Designed by the same architect as the Plaza Hotel, the space combines opulence and intimacy. Little details like the beveled, gold-inlaid ceiling and intricate mahogany of the fireplaces elevate “just hanging out” to an aesthetic experience. This unit is in The Dakota, one of Manhattan’s most famous luxury buildings (much to the liking of Sally Albright), and promises as many Ephron-esque walks in the park as the heart desires and a homey space for drinks and chats after a dinner date at the nearby cafe. 

Double-dating from home? Even better. Restaurants are loud — order takeout and have a walk down Central Park West while you wait for your food. Plate it on some fancy china when you get home and enjoy a meal together in the formal dining room. Energy-efficient, sound-proof windows won’t have you yelling across the table.

Wagon wheels welcome

271 Central Park West | 3 BR | $19.5 million

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Not far from the restaurant where they first met, Jess and Marie moved in together in an Upper West Side brownstone — 32 West 89th Street, to be specific. Harry and Sally helped their friends set up their new home and decide what to do with a polarizing wagon wheel coffee table. At the time, Harry was in the throes of divorce, leading to a meltdown on the stoop about the pointlessness of cohabitation, marriage and love.

Around the corner from the Jess-and-Marie Residence is 271 Central Park West. This full-service, pre-war co-op has a private elevator landing, so there’s no need to schlep up the stairs with a wagon wheel coffee table — and then all the way back down again when your spouse objects. Just stick it in one of the building’s private storage spaces, along with any other decor you can’t see eye-to-eye on.

Westerly views of the park make this a tranquil space, as does the open concept foyer-living room. With six bedrooms, a couple would feel anything but claustrophobic. Turn one into a guest bedroom — arguments happen, but no one should have to sleep on the couch. If your partner enjoys long showers and making you late for work, the seven full bathrooms in this home eliminate any bickering. And of course, if you need to walk it off, the biggest park in Manhattan is right outside your front door. Sometimes, all a couple needs is more space!

Have yourself an 80s rom-com Christmas

141 West 95th St. | 6 BR | $13 million

“When Harry Met Sally” is just as much a holiday movie as it is a rom-com. Sally is seen not once but twice at PlantShed on the Upper West Side, struggling with an unwieldy Christmas tree. If the PlantShed is where you plan to get yours this year, I can think of no better place to showcase it than 141 West 95th Street.

This home plays with color, texture and contrast in a way that invites a variety of styles. If you’re pro-wagon wheel coffee table, all I’ll say is that relationships are about compromise and it would look beautiful on the patio where no one has to look at it. 

The all-white kitchen with a pop of teal on the backsplash invites all decorating possibilities. And nothing represents our strictly platonic duo better than the sophisticated chandelier and rustic exposed brick wall of the dining room — polar opposites harmoniously occupying the same space.

It’s a 10-minute walk from PlantShed, probably longer if you’re carrying a tree. Just ask a “friend” to help you bring it home and see where the night takes you.

Nine extra floors

145 Central Park West | 2 BR | $6 million

“When Harry Met Sally” is spliced with interview footage of elderly couples reminiscing on their own origin stories, including the ones who famously never met… until they finally did.

In a delightful example of cooperative overlapping, one couple recounts their elevator meet-cute at the Ambassador Hotel in Chicago. “I rode up nine extra floors just to keep talking to her,” the husband says with the smile of someone who’s spent decades waking up next to the love of his life.

Ride up a few extra floors in the San Remo and you’ll find this apartment on 145 Central Park West. The building itself is an architectural masterpiece and, much like Mr. and Mrs. Nine-Extra-Floors, has decades of rich history. If these walls could talk they’d no doubt be “co-operative,” speaking in turn about the Great Depression and the building’s famous residents like Tiger Woods, Steven Spielberg, Demi Moore and Bruce Willis. Even the Court of Versailles-patterned floors would have loads to say, each piece measured, cut and laid down individually.

Art Deco-style light fixtures hearken back to an earlier time. This one’s also got custom built-in nooks and crannies to hold all your books, keepsakes and memories. The park is right there, but three terraces offer three different views of the autumnal city on the days you prefer to stay home. Create memories here with the person for whom you’d ride nine extra floors, or ride a couple extra floors by yourself — you never know who you’ll run into.

Bonus listing: Single in the Village

240 East Houston St. | 1 BR | $1.6 million

This East Village one-bedroom apartment is a bit of a departure from the luxurious park-facing properties of the Upper West Side. Still, it’s more than enough space for a single person, which is allegedly what Harry and Sally were until the very end of the movie. The skylights, private terrace and ample closet and storage space are undoubtedly enviable.

The best thing about this apartment on 240 East Houston, though? It’s a five-minute walk to Katz’s Deli.