Photo Credit: Warburg Realty

This 5,000-square-foot penthouse at 303 East 57th Street in the Excelsior co-op tower is the sort of apartment you see in your favorite 20th-century New York City films. Asking $4,995,000, the duplex is wrapped by 2,500 square feet of terrace and offers 360-degree views from four exposures including Central Park and the East River.

Take the grand tour

Photo credit: Al Siedman of VHT, courtesy of The Corcoran Group

It’s easy to overcomplicate things when it comes to real estate, but this Upper East Side co-op at 333 East 66th Street keeps things simple. It’s basically an alcove studio, but custom-designed built-in storage makes great use of every inch of space. A recent designer renovation makes it easy on the eyes, and a high floor means light and city views.

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As 6sqft asked when the 39th floor at The Pierre Hotel at 795 Fifth Avenue hit the rental market two years ago, if you’ve got the cash, why buy when you can rent for $6 million a year? Now that opportunity to refresh your enormous outlay every month is again seeking a renter at $500,000/month, keeping its title as the city’s most expensive rental. The massive 4,786-square-foot space has merely a butler’s kitchen, but the assumption is, of course, that you wouldn’t want to be slaving over a hot stove in a full-service hotel anyway. And that service includes twice-daily maid service, an on-call physician, room service, two restaurants and a chauffeur-driven Jaguar.

See what this hefty price tag gets you

The Upper East Side is home to a plethora of elegant residencies, and the interior of this 79th Street apartment from the design firm S.R. Gambrel is luxury at its best. Each room is impeccably outfitted to tell its own story, individual in point of view, but still fits together into one cohesive aesthetic. From the vivid color palette and wall decor to the ornate light fixtures and floor textiles, everything in this home is vibrant, lively and not to be missed.

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If you’re fan of the elegant, old-fashioned Upper East Side, pre-war co-ops and stylishly-decorated interiors, you can’t go wrong with this five-room, two-bedroom-plus home at 563 Park Avenue. The seller is the former editor-in-chief of Travel + Leisure magazine (and before that, Condé Nast’s House & Garden, where she replaced Anna Wintour as EIC), Nancy Novogrod and her husband, John, an estate attorney; so we’d expect that show-house-worthy interiors are a given.

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When you’ve got a house that’s just a hair over 13 feet wide, you’d better know a good interior design pro. Fortunately the owners of this slender 1899 townhouse at 259 East 78th Street took that caveat to heart when they purchased it for $2 million in 2009. It’s now on the market for $5.5 million, and every inch of its 2,600 square feet has been put into use with enough warmth, character and smart design decisions to keep any “narrow-minded” thoughts at bay. And there’s nothing skimpy about the location on a gorgeous townhouse-lined street just a few blocks from Central Park on the Upper East Side.

Have a closer look inside this charmer

Though we so often hear that an eye for interiors–or a good decorator–can make even the smallest apartment feel like a gracious home, we love to see real-life examples that aren’t in magazines shot by highly-paid photographers. This slender Upper East Side one-bedroom co-op at 330 East 94th Street with a relatively manageable $435,000 price tag is an inspiring example. In addition to the fact that with ownership comes the right (co-op board willing of course) to transform the space with any number of clever solutions, it would take far less to create a charming pied-a-terre, for example, without that level of effort or expense.

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We’ve pretty much seen it all when it comes to no-holds-barred luxury in an Upper East Side townhouse, and this five-story, 7,000 square-foot specimen at 17 East 83rd Street is by no means the most opulent. But when the listing starts with “elevator townhouse,” you know you’re probably not in for a lot of skimping. And when you learn there’s a “separate service entrance/mudroom with paw washer,” and a “mail center,” well, Billionaire’s Row is looking a just a bit like Dogpatch…

The current owners of this Manhattan mansion—an investor and an interior designer—purchased it for $2.9 million in 1998, which, sure, was 20 years ago, but if they get anywhere close to their ask of $24.5 million, it’s still quite a payday. A tidy sum, it’s true, must have been spent on renovations in this townhouse-that-treats-you-like-a five-star-hotel–though now that we think of it, where’s the pool?

Take the tour (good thing there’s an elevator)

There are some apartments in New York that leave you at a loss of words. This one, a triplex co-op at 403 East 87th Street in the Upper East Side, has a decor that definitely stands out. The best we could come up with in describing it was “medieval castle,” with its wood detailing, dark red furniture, and antique collection of books. Even the backyard space has some distinctive lighting and decor. If that’s your thing, it is now on the market for $1.795 million.

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Back in 2006, this 3,500 square-foot four-story Upper East Side townhouse first surfaced on the rental market, and again three years later; in 2010, its owner attempted to find a renter for the winter holiday season (a portion of December) apparently without much luck. After bouncing through several different agencies, 127 East 78th Street landed at Sotheby’s in 2011 with the intent of marketing the house as a summer rental for $25K; not much luck there either, as townhouse renters tended to want something more long term. A lesson seems to have been learned here, as there are no short-term stipulations mentioned in its new listing for $27,500.00 a month.

What is mentioned is more interesting: The townhouse once belonged to famous fashion photographer Milton Greene–known for his collaboration with Marilyn Monroe on photo shoots as well as their joint film production company–and his wife, Amy. Marilyn considered the home a sanctuary among friends when she was in town. And though its interiors have likely been updated since Marilyn’s day, the elegant Upper East Side enclave still retains the aura of an East Coast refuge for Old Hollywood.

Take a look around