A rolling stone gathers no moss, but can a $17.5 million townhouse gather a buyer?

When Jann and Jane Wenner split in 1995, the coupled stayed married,  putting off the legal wrangling that would inevitably arise when they split their publishing empire. Mr. Wenner borrowed $7,500 from his own family and from the family of his wife to found Rolling Stone, and once it grew into an empire worth hundreds of millions of dollars and includes Men's Journal and Us Weekly, it would be understandable if the vagaries of divorce just didn't seem worth it.

Until, that is, 2011. Mr. Wenner had been living with his partner, Matt Nye, a former Calvin Klein model 19 years his junior with whom he's raising three kids, and Ms. Wenner finally wanted out. (There was speculation that the divorce was finalized because Mr. Wenner and Mr. Nye wanted to formally marry each other, but despite the legalization of gay marriage in New York, that never came to pass.) There was a little acrimony in the divorce, including a lawsuit filed by Ms. Wenner's Amagansett groundskeeper, but things seem to have gone as smoothly as a divorce can be expected to go and Jane Wenner got to keep the couple's Upper West Side townhouse, at 37 West 70th Street.

Now, after three years of holding onto the property, Ms. Wenner wants to cash out. Though she acquired Mr. Wenner's stake in the home in 2010 for a bit more than $4 million, now she wants much, much more: $17.95 million. At nearly $2,500 per square foot for the 7,200-square foot home, the asking price is nearly double the Upper West Side townhouse average.

Once owned by Perry Ellis, the 20-foot-wide, five-story townhouse dates back to 1891, when it was designed by architect Gilbert A. Schellenger, who built townhouses from Harlem to Crown Heights. It was most recently renovated by American designer Ward Bennett—a distinction that no new homes will be able to claim, given that he passed away in 2003.

"The bathrooms are outfitted with the Art Deco treasures of the London Savoy Hotel," reads the listing—Wolf Jakubowski of Brown Harris Stevens has the exclusive. The home has five bedrooms, but where it really shines are the fireplaces: it lays claim to a whopping ten, nine of which are wood (or back issues of the glossy magazine) burning.

She's a survivor.

Robert A.M. Stern's 15 Central Park West may be the hottest building in New York, but the good fortune hasn't crept up the western edge of the park, which still plays second fiddle to the Fifth and Park when it comes to closing prices. There are some standouts, though, and the townhouse at 247 Central Park West is most definitely among them. Whether it stands out tall enough to get its $37 million ask is another question entirely.

Built in 1887, it's the first townhouse you encounter on Central Park West—a rare holdout to withstand two waves of rapacious early 20th century redevelopment. The first, around the turn of the century and the construction of the city's first subway on Broadway, saw developers raze townhouses and tenements all around No. 247 and its two neighbors on the block to erect apartment houses of a dozen or so floors. During the second boom, around the time the IND Eighth Avenue Line was being built underneath Central Park West and right before the Great Depression, the pressure mounted and builders strove for even loftier heights, with buildings as tall as the 30-story El Dorado eating away at what remained of the low-slung real estate.

But through a combination of luck and placement higher up along the avenue (it sits between West 84th and 85th Strets), 247 CPW made it to the late 20th century, meeting the warm embrace of the Landmarks Preservation Commission, which ensured that no would-be Dakotas or San Remos will ever again threaten this six-story townhouse.

Would you care for a lap pool with your archway?

And for its fortitude, 247 Central Park West has earned another accolade: it was the most expensive townhouse on the Upper West Side when it sold back in 2009. Abigail Disney, filmmaker, philanthropist—and yes, Disney heiress—sold the house to Coach exec Keith Monda for $15.5 million in 2006, who went on to set the West Side townhouse record (or maybe the citywide record if you don't include extra-wide Upper East Side mansions) three years later with his $22.4 million sale to a mysterious LLC named Top Estate (NY) Corp.

After trying to rent it out for a staggering $110,000 per month back in early 2012, the owners—chatter among the brokers is that they're Russian—wants to set the record again.

With a pool in the basement, an in-home theater and a massive skylight, it's no doubt an impressive house, but is it worth $37 million? We've seen a lot of ambitious asks since the $88 million condo at 15 Central Park West, but no new records. It's likely that Sotheby's Vannessa Kaufman can set a new Upper West Side record, given the limited pool of comparable houses (basically limited to 247's next-door neighbors) and its track record in a less ebullient time, but a more than 60 percent return over three years may be a check that this townhouse can't cash.

The Columbus Avenue bioswale.

The sidewalks of Manhattan are famous for surprises—outré fashions, bizarre dog breeds and outlandish happenings (where else would an underwear-clad cowboy have a hard time turning heads?)—but it's not often that the sidewalks themselves cause double-takes.

Recently, though, an unusual sidewalk/curb/tree pit combo by the corner of Columbus Avenue and 76th Street has been catching the eyes of local passerby. At first glance, the elongated tree pit doesn't appear all that different than its Upper West Side peers: a delicate sapling protected from the large population of neighborhood dogs by a shin-high iron railing. But on closer examination, the odd characteristics pop out: rather than a standard curb, a border of rocks rings the pit, broken up by two big notches cut out of the curb. Manhattan's first bioswale, according to the Columbus Avenue BID which installed it.

A bioswale, or bioretention swale, is basically a tiny, curbside garden designed to act like a big sponge, sopping up rainwater and street runoff that floods the city's sewer systems during storms and compromises the health of local waterways. The low notched curb is designed to catch water, which is is filtered through layers of stones to purify it and protect the hardy plants that it hydrates.

A close-up view of the bioswale.

While a number of bioswales have been installed in Brooklyn (in March the Department of Environmental Protection installed 29 in East New York to reduce pollution in Jamaica Bay), and hundreds more will be installed in the future as part of a $10 billion DEP green infrastructure overhaul of the wastewater system, the Columbus Avenue bioswale is one of the few to be built by an outside non-profit group and the first to be built in Manhattan.

The bioswale installation came about as part of a broader effort to transform the block between 77th Street and 76th—dominated by a vista of concrete, blacktop and the chain link fence of a nearby schoolyard—into something a little more lush. Coming at the end of a corridor that takes hordes of tourists from Central Park and the thick greenery surrounding the Museum of Natural History to the shops and restaurants of the Upper West Side, the stark streetscape has long been a jarring, and incongruous sight.

The new makeover aims to change the block into a shade-filled oasis where tourists and locals will linger, with nine new trees and elongated 10-foot tree beds, ergonomic benches, in-ground solar lighting and a solar-operated compacting trash can. Overall, the project cost about $100,000 and spanned 10 years of fundraising and planning, according to Barbara Adler, executive director of the Columbus Avenue BID.

Solar lights are also part of the streetscape.

"I sometimes though it would never come to fruition," Ms. Adler told The Observer as she pointed out the improvements on a recent afternoon. "Some were calling it Barbara's folly."

While the Columbus Avenue bioswale's performance during stormy weather has yet to be assessed, the DEP said that their bioswales (they warned that the building specifications, and therefore performance, of other bioswales may vary) soak up 2,244 gallons during storms.

The bioswales built by the DEP are aimed at reducing the untreated sewage overflow into specific waterways like the Gowanus and Jamaica Bay—an unfortunate side effect of New York City's combined sewer system, which mixes sewage and rainwater together. After years of investing in "grey" infrastructure, like building huge holding tanks to keep storm overflows until they could be treated safely discharged, the DEP has increasingly focused on greener, more cost-efficient solutions like bioswales, which help to minimize the pressure on the system and ultimately, the pollution of local waterways.

New York's aging system funnels, on average, $1.3 billion gallons of wastewater a day through 7,500 miles of sewers to water treatment plants, a system that has the capacity to handle twice that capacity in dry weather, according to a DEP spokesperson, but one that is easily overwhelmed during storms. When more than an inch or rain falls an hour, the excess rainwater gets discharged, untreated, into local waterways.

While the amount of rainwater that the Columbus Avenue bioswale soaks up might seem like a drop in the bucket, it will mean a slightly less strained sewer system. And maybe more importantly, a glimpse of how the city infrastructure might be changed for the better in the future—a  lesson in sustainability for the local children, who were, on the afternoon that The Observer checked out the revamped block, busy sketching Columbus Avenue from the other side of the school's chain link fence.

One of the character-stripping branches. (DNAinfo)

In recent years, the Upper West Side has been besieged by bank branches, with countless TD Banks and Citibanks, Chase Banks and Banks of America gobbling up once-vibrant street corners, the dull gleam of their ATM screens casting an eerie glow on the empty sidewalks late at night.

There has been hand-wringing, there have been outcries, there is even a zoning ordinance that prohibits banks from having storefronts wider than 25 feet. And unlike the cancerous spread of Duane Reades across every corner of our fair city, which for all their colonial tendencies offer a certain languorous refuge for the stressed city dweller, no one can quite understand what is driving the bank branches' spread. Aren't we always told that people are doing more and more banking online? Other than withdrawing cash from the ATM, how often do most of us really visit the bank?

But now there is some good news for bank-beleaguered Upper West Siders: the number of bank branches in the United States is falling and is at the lowest it has been since 2007, according to the Wall Street Journal. Last year, 2,267 branches closed, bringing the number of hopelessly bland, generic outposts to 93,000. Best of all, the number of U.S. bank branches is expected to drop to 80,000 over the next decade, which should put us somewhere close to 2000 levels.

The change, The Journal reports, is a reversal from the wild expansion that was seen over the last three decades, when the number of bank branches doubled. The industry has reduced branches only three times in the last 77 years, when the FDIC started monitoring such changes.

Maybe now the Upper West Side will finally be able to accommodate more of the children's boutiques and the sad, weird bars that have been longing to move there? Alas, it seems unlikely that the most-missed establishments, the dives and the hardware stores and eclectic, reasonably-priced restaurants will be able to return to the neighborhood. Although a decrease in the number of deep-pocketed national companies eager to sign leases might help some beloved institutions stay—retarding rent increases—it's not as though the neighborhood would or could revert back to its former self. Broadway is increasingly home to other upscale, dead-souled national retailers and Columbus is blighted by cookie-cutter cafes with book-like wine lists and prices that start at $11 a glass.

And, while the decrease in the number of bank branches is ostensibly connected to the increase in online banking—it now accounts for 53 percent of all banking transactions, compared to 14 percent for in-branch visits, according to the AlixPartners statistics quoted by The Journal, ironically, it's the more rural, less-connected towns that are losing their banks rather than iphone-cluttered urban centers.

The closures are concentrated in small towns like Athens, Michigan and in the states that were hardest hit by the mortgage crisis—Nevada, Georgia. The kinds of places where communities not only like, but treasure their one bank branch. Athens even sent letters to 20 different banks and threw a pizza party to try to attract a new bank after losing its branch.

Meanwhile, in places like the Upper West Side, despite the high costs of retail space, online savvy and general hostility to them, banks continue to open new branches, at least for now. Last spring—during the time frame when other areas of the country lost more than 2,000 branches, four banks announced plans to open Upper West Side branches within a 20-block radius of one another. And at least now the new branches will be limited to 25-feet on Amsterdam and Columbus Avenues.

kvelsey@observer.com

Don't mind the smoke billowing out of the ninth floor—that's just Ms. Wells.

The El Dorado (our sincerest apologies to the Spanish language) was home to one of New York's cattiest co-op dramas of 2012, when the co-op board took heiress Diane Wells to court over her formidable smoking habit and fumes they claimed were leaking into neighboring ninth-floor units through a gaping hole in her apartment. "On multiple occasions," the complaint read, "the cigarette smoke and odor [have] filled the entry halls on at least the ninth and 10th floors of [the] building, requiring shareholders to traverse a cloud of smoke between the elevator and their apartment entrances."

Though the board ultimately succeeded in forcing Ms. Wells to allow repairs to her apartment, the board was not able to get her to stub out her cigs—something that apparently didn't worry Gretchen Pusch and Richard Bayles, who just picked up a classic six on the tenth floor for $2.4 million (down from a $3.3 million ask two years ago—so maybe the cigarette issue persists?). The sale was brokered by Daniel Douglas and Eileen LaMorte at Corcoran.

The unit was sold by Toni Pagano Rosenfeld, widow to the late advertising great Ronald Rosenfeld. And Toni herself was no slouch—she was featured in promotional video for Mad Men discussing her work in the industry, where she created Kodak's "Life is short, snap it up" campaign.

While some classic sixes—named after their six rooms, including a kitchen, formal dining room, living room, two bedrooms and a maid's room—have been modified to bring them up to more modern standards, Ms. Pusch and Mr. Bayles's new apartment still has its warren-like kitchen, pantry and maid's quarters. Domestics have, by and large, been replaced by a coterie of part-time staff, so we don't suppose they'll be needing that room for the help. Ms. Pusch—a flutist who once played at Carnegie Hall and now teaches at Julliard—could well use the 7 foot by 13.5 foot room for a practice space, although the neighbors might be extra sensitive to any nuisance after the smoke debacle.

The apartment does contain at least one modern touch: a massive restaurant-sized Garland range and Salamander broiler. Perfect for cooking grilling large amounts of fish, in case the new owners get into a war-of-odors with their downstairs neighbor.

Central Park West Enemy No. 1: Columbia Grammar and Preparatory School.

The meeting started out, as these meetings tend to, with loud admonitions from the audience to speak loudly into the microphone. “We can’t understand you!” one man shouted. “You do need the mic!” was a common refrain as speakers tried to get by on projection alone. (There was eventually a backlash, with one woman hissing, “Don’t start shouting!” at a particularly vocal and ornery man. Thereafter he resigned himself to disgusted head shakes.)

The crowd was assembled at an Upper West Side community center to discuss a zoning variance that the Columbia Grammar and Preparatory School was seeking for a modest expansion of its campus, which is bounded by West 92nd and 94th Streets and Central Park West and Columbus Avenue. The school wants to make room for a separate middle school, adding a cafeteria (lunch currently starts at 10:20 because of a lack of space) and more classrooms.

The two extra stories the school is looking to tack onto one of its buildings would still leave it smaller than its prewar neighbors, and the architects are not using the property’s total allotted square footage. But because of arcane zoning rules, the school must ask the Board of Standards and Appeals for a variance. Community Board 7’s role is entirely advisory.

The audience’s concerns were mostly unrelated to the variance. One committee member asked the audience to “do one of those Occupy Wall Street thingies” with their hands if they would be satisfied should the school decide to build within the existing zoning envelope, without a variance. Barely anybody did the Occupy Wall Street thingy.

Dr. Richard Soghoian, the school’s headmaster, was adamant that the school was not looking to expand enrollment, but the audience was unpersuaded.

“Is my word assurance enough?” asked Dr. Soghoian, to which the audience responded in unison, “No!”

One resident shouted to the elderly headmaster, “Well it won’t be you doing it!”—a point that could have applied just as well to the assembled crowd. (A gaggle of urban planning students from Hunter College, compelled to attend by their professors, were the youngest there by at least a decade. They left 30 minutes into the three-hour meeting, presumably to change majors.)

"I love Armenians, but I don't like him."

Dr. Soghoian was a frequent object of derision. Whispered one Upper West Sider: “I love Armenians, but I don’t like him.”

The crowd was particularly exercised about the issue of traffic (“Your chauffeur-driven SUVs idle for 10 to 15 minutes!”), as some students commute from New Jersey and Westchester. Traffic, however, will not be considered by the Board of Standards and Appeals.

The portion of the meeting devoted to the fate of neighbors’ lot-line windows also stoked audience passions. One of the architects insisted that only a couple of windows would be blocked, at which point the audience proceeded to plumb the ontological depths—“What’s your definition of ‘blocked’?”

“I bought my apartment because I thought they’d never be covered,” said one woman, who had moved in one year ago.

The architect conceded that yes, the expansion would block some light even if it didn’t completely cover the windows, comparing the situation to an old law tenement’s air shaft. “But this is the 21st century!” an audience member protested.

And it wasn’t the only time the project was likened to Industrial Revolution-era development. One neighbor claimed that apartments would be “totally removed of light and air” by the two-story expansion, and that the school was “creating a 19th-century condition.” (No word on whether neighbors would be forced to use backyard outhouses.)

Residents of the Turin, at 333 Central Park West, made the strongest showing. The 12-story co-op began its life in 1909—like nearly all the concerned citizens’ buildings, it was built before New York City had any zoning code at all.

Margot Adler, a Wiccan priestess and NPR correspondent residing at the Turin, suggested that the building doesn’t need to split its younger and older students at all. She fondly recalled her own child’s experience at the Dalton School, where having middle and high schools under one roof “gave a chance to have a buddy system.”

Toward the end of the meeting, bowing to realities, the conversation turned to mitigating the effects of construction. Many people wanted the Department of Buildings to forbid contractors from working on Saturdays, and one woman asked if the school would pay for any damage to neighboring properties.

Yes, the project’s defenders responded, they had insurance that would cover damages.

“Except for the urn,” mused one woman, presumably in reference to her late husband’s cremated remains, though we may have missed the joke. “And my petunias!” chimed in another.

As the crowd shuffled out, the Transom approached Mark Diller, chairman of Community Board 7, and inquired as to whether he had fun at the meeting.

“I love engaging my community,” he responded, without missing a beat.

Tiny boxes.

As we ponder the arrival of micro-apartments, it's worth noting that the woman who may well have been the city's most famous small apartment advocate has moved into a much, much larger space. It is all of 500 square feet, Gothamist reports.

Felice Cohen, who briefly became famous for living in a 90-square-foot studio back in 2011, has bought a one bedroom. And while she may have defected from the ranks of shoebox dwellers (shoeboxes being defined, as per the Bloomberg administration, as anything under the legally-allowable 450-square feet) she's still fully committed to the cause, as a new video from Fair Companies reveals:

Ms. Cohen became a micro-dwelling media darling not only because she lived in a meticulously organized micr0-apartment (she was a part-time professional organizer), but for her cheerful embrace of extremely cramped living conditions. She admitted to having a panic attack the first night she awoke in her lofted bed, but demonstrated how a single person can adapt with aplomb to apartments much, much smaller than Bloomberg's micro-units, which are between 250 and 375 square feet.

Alas, Ms. Cohen didn't leave her Upper West Side studio, for which she had been paying $700 a month, willingly. Her landlord saw the video and, in light of the fact that she had taken over the apartment from a friend and wasn't on the lease, tried to double her rent. Ms. Cohen admits that she considered simply paying twice as much, but decided to purchase a one-bedroom apartment instead. At 500-square feet, it's modest, but looks palatial in comparison to her old place.

There are some good things about the new apartment: she doesn't need to turn sideways to sit on the toilet. "I can sit and my knees are no longer black and blue," Ms. Cohen explains. But, honestly, she seems less than thrilled about the new space and the lack of challenge it presents. She has even pared down her possessions since moving, a rejection of living large even if she is living larger.

"It's about making any space your home," Ms. Cohen says in the first video, explaining how so many New Yorkers were unaccountably angry about the dimensions of their apartments. "I want to fill life with experiences more than stuff, that's the goal."

And living in a tiny apartment was worth the sacrifice for Ms. Cohen, who finished a book about her family history there—a project that she says she was able to do because she was paying $700 a month. After all, accumulation of experiences, rather than the accumulation of stuff is, in large part, what draws people to New York.

There's just one problem with living in a Bloombergian micro-unit: it doesn't come cheap. Apartments reserved for low- and middle-income New Yorkers are expected to cost between $940 and $1,800 a month. Micro-apartments, in other words, are no longer a sacrifice that a New Yorker makes to pursue artistic goals, but the reward of pursuing a stable, middle-income career.

kvelsey@observer.com

Big Nick's (NY Mag).

Big Nick's might not  be to everyone's liking, but it has certainly made an effort to suit everyone's tastes. In a city of increasingly "curated" dining experiences and foraged vegetable tasting menus, Big Nick's offers not only hamburgers, pizza and assorted Italian favorites, a vast assortment of sandwiches, chicken barbecued, fried and broiled oreganate, but also Greek standbys, salad platters, a full breakfast menu and a surf-and-turf shack selection of seafood.

So it will come as sad news to many an Upper West Sider that Big Nick's, which has been open for 24 hours a day for the last 50 years at 2175 Broadway Avenue may soon be no more, reports The West Side Rag. The reason is not a lack of fans—although the Upper West Side's DNA has changed considerably since the greasy spoon opened—but, you guessed it, a rent hike.

The restaurant, which is located in a ground-floor space at West 77th, has been told that its rent will be going from $40,000 to $60,000 a month. "I can pay the $40,000 per month I am paying now. I just can't pay $60,000. It is only 1000 square feet (and you know how small my place is)!" owner Nick Imirziades lamented on the restaurant's Facebook page.

That means that Big Nick's would need to earn approximately $2,000 a day on its low-end restaurant items just to make the rent.

Apparently, the building owner is counting on renting not only Big Nick's space, but also Bra Smyth and News Inc.'s for a huge corner storefront clocking in at 3,100 square feet. The space is listed with RFK Partners brokers David Abraham and Zach Winkler with an availability date of February 1.

Mr. Imirziadess told The West Side Rag that he hadn't intended to take the news public, as he's still trying to negotiate with the landlord, but that he felt the need to respond to the rumors that were flying.

Even if Big Nick's leaves, it is unclear if building owner, Lophijo Realty, can cash in on the corner space. When reached on the phone, Bra Smyth manager Angela Cukar told The Observer that the store had no plans to leave, especially given that it has a few more years left on its lease.

"Yeah, good luck, I don't see it happening," Ms. Cukar said of the store's departure, adding that she was willing to entertain large lease buyout offers, but didn't expect one given that she hasn't seen any potential tenants sniffing around the commercial space. Not for $21,000 a month.

Mr. Abraham declined to comment on the situation and an email sent to the owner has yet to be returned.

While the restaurant has another location on West 71st Street (couples who can never agree on a cuisine need not give up hope!) it's a bad sign for a neighborhood where so much of the retail space has already been gobbled up by banks, big-box pharmacies or luxury retailers. And yet another sign that even popular, long-enduring, independent businesses are an endangered species in this city.

kvelsey@observer.com

Imagine all the people, living life in peace.

Are the days of airing the Dakota's dirty laundry finally nearing an end? Hedge fund manager Alphonse Fletcher Jr.’s lawsuit against the board of the fabled Upper West Side co-op still stands, but he and the lawsuit are standing all by themselves.

The two law firms representing Mr. Fletcher have been allowed to withdraw from the case, according to The Wall Street Journal, citing unpaid bills and irreconcilable differences—the culprits that seem to end every once-happy relationship.

The unpaid bill part is particularly bad news from Mr. Fletcher, given that the crux of his lawsuit against the co-op board is that he was financially fit to buy another apartment neighboring his own and that the board's denial of his bid amounted to discrimination (Mr. Fletcher is black). The board has claimed that the turn-down was the result of Mr. Fletcher's shaky financials.

Mr. Fletcher has, apparently, had problems paying off his legal teams in the past. The Journal reports that court filings by Mr. Fletcher's fund show that when it filed for bankruptcy-court protection, it owed more than $2 million to law firms.

The allegations in Mr. Fletcher's lawsuit extended well beyond his own personal situation (he claimed, among other things, that the board made ethnic slurs against prospective residents and denied another black resident, Roberta Flack, the right to install a bathtub in her apartment), but it could be much harder for Mr. Fletcher to win his suit if there are strong indications that the board had good reason to think he couldn't afford to carry a third apartment.

Moreover, finding another firm to take the case pro-bono seems unlikely. Law firms don't usually do charity work for Wall Street tycoons who are miffed that their application to buy a third apartment in a tony c0-op was rejected.

Mr. Fletcher has until December 20 to hire a new lawyer, although extensions often allow lawsuits to live on for years and years, so we don't necessarily expect to see much change in the next few weeks. But who knows? Maybe Mr. Fletcher will drop the lawsuit, maybe co-op board president Bruce Barnes will decide he doesn't want to sell his palatial apartment for $29.6 million after all, maybe by next year's autumn potluck the building, if not the world, will live as one.

kvelsey@observer.com

The home, which made its market debut at $8 million in April 2006, in the midst of massive renovation intended to set buyers’ hearts aflutter, has lingered there ever since. A handful of renters have come and gone, but none have wanted to sign the deed. Not for $8.5 million (the highest ask), not for $6.45 million (the lowest and most recent ask) and not for anything in between. It’s now listed for rent at $25,000 a month.

When The Observer visited 129 West 20th Street on a recent afternoon, we found an apartment that was many of the things it has claimed to be over the years: “glamorous, dramatic and refined,” just as the first Corcoran listing had promised, as well as “cinematic in scale and scope” like the Prudential Douglas Elliman listing bragged a few years later. (It had, in fact, starred alongside Keira Knightly and Eva Mendes in Last Night and Mariah Carey in an AT&T commercial.)

We couldn’t argue with the first Brown Harris Stevens listing that pronounced it “modern yet ultra-chic, exceptionally spacious and yet welcoming,” or with the second, which declared the condo “a singular home with dramatic potential.”

But after six years of showings and rentals, the celebrated design was starting to show its age: the floors were scuffed, the dust bunnies were reproducing like, well, bunnies, and the handle of a glass door to the terrace came off in our hand. A broker there to scope out the apartment before showing it to her clients—a family with three small children relocating from Canada—wondered why no one had bothered to paint, repair a warped piece of kitchen cabinetry, or sweep.

The owners were probably exhausted by their ongoing stewardship of a property that they’d expected to offload years ago, a place where they’d never lived and upon which they continued to spend $9,000 a month in maintenance and taxes.

Properties between $4 million and $9 million that sold in the third quarter of 2012 spent an average of 161 days on the market, or about five and a half months, according to Streeteasy data, to the Chelsea penthouse’s six and a half years. Was it simply asking too much, or was there something more? How else to explain a highly desirable space that no one seemed to desire, in a city where real estate is an obsession, vacancy rates hover near zero and battles over square footage are fought by the inch?

The penthouse of 129 West 20th Street numbers among a handful of Manhattan luxury properties that aren’t just slow-sellers, they are no-sellers. Not just for sale, but forever for sale.

Take, for example, the ten-room spread on the fourth-floor of the Dakota—one of the most legendary co-ops in New York (where else can one mingle at an annual October potluck with both Lauren Bacall and Yoko Ono?)—that has been on the market since October 2006.

The $14.5 million apartment lacks park views, and its décor is a bit theatrical, but it has 4,500 square feet, six fireplaces, and a shaving closet. Still, after so many years, even the Warburg listing sounds fatigued, sapped of the energy to string clauses and descriptions into proper sentences; it ends with a semi-coherent fade out: “One of a kind. Function and glamour.............As fabulous as your fantasy.”

A few dozen blocks north, on Central Park West, the turreted, red-brick condo conversion at 455 CPW has had a terrible time trying to lure buyers. The former nursing home and New York Cancer Hospital has undergone an impressive makeover, but No. LM17 and LM19 both hit the market in December 2006, where they remain to this day, asking $5.6 million and $3.8 million respectively. Manhattanville isn’t the most prestigious address, and buyers may have an aversion to moving into a building where most residents once left in body bags. But can that really explain a half-decade of snubbing?

And what of the penthouse at 425 East 63rd Street, listed since February 2007? Doesn’t anyone want a $5.6 million penthouse on Lexington and 63rd Street, even if it does look like something out of a Jackie Collins novel? The long-suffering broker, Debra Forest of AIB Management Corp., admitted there were a few things that might not appeal to potential buyers: the penthouse is actually two separate units that would need to be combined, and the décor is “circa the 1980s.” But she remains confident someone will be thrilled to snap it up. “I’m definitely not worried,” she said. “The owner is not worried.”

There might be any number of deficiencies or problems with apartments that linger, according to Jonathan Miller of appraisal firm Miller Samuel, but the only real problem is price. “There’s always a price to match a buyer,” he said. “Even when someone is murdered in an apartment, there’s a price it will sell for.”

What’s more, overpricing can backfire. A study Mr. Miller did with the Furman Center at NYU found that the closer the seller lists a property to its actual market value, the higher the price it actually sells for. And conversely, he said, “if you throw a property on for an absurdly high price, you end up getting less than you would have if you had listed it close to market value.”

Vanity and ego are the two major driving factors behind many outrageous asking prices. Take, for example, the townhouse at 22 East 71st Street, purchased by Aby Rosen for $15.6 million in 2004. After completing a partial renovation, the real estate tycoon relisted it for a whopping $75 million in 2008, making it the most expensive townhouse listing at the time, (that honor now belongs to the $90 million Woolworth Mansion). Mr. Rosen, who never lived in the home, eventually dropped the ask to $50 million in 2011 and the property is now said to be in contract to the Qatari prime minister for $47 million.

“Aby is Aby,” said one high-end broker. “It’s ego.”

Nobody who has had their property on the market for more than three years really wants to sell, claimed Fred Peters, the president of Warburg Realty. Some sellers are parading a trophy, some are testing the market and some are simply delusional. But, said Mr. Peters, “at some point, the pain becomes too much. It all depends on where the threshold is.”

At this point, the seller frequently moves on to a second broker (indeed, most lingering listings leave a string of jilted brokers in their wake), for whom he or she is often willing to lower the price. The Chelsea penthouse, for example, burned through nine different brokers and four different brokerages. And that’s not even counting the rental brokers.

Other reasons that places sit: a fussy co-op board kills a low offer, or it’s an estate, notoriously difficult to sell because the apartments often need renovation and bickering heirs are reluctant to lower prices. But most brokers blame dust-covered listings on unrealistic sellers and the brokers who are only too happy to tell them what they wanted to hear in exchange for a wildly expensive exclusive listing and the publicity that comes with it.

One broker angrily told us that he’s missed out on more than a few listings by being honest with sellers rather than peddling a fantasy number. Brokers who do that “screw up the market,” he complained. “They agree to overprice a property because it’s what the sellers want to hear.”

Moreover, once a listing becomes stale, buyers start to think that there must be something wrong with it. Then, even if and when the seller drops the price, buyers can be leery.

“It’s like seeing a piece of jewelry displayed at a store,” said A. Laurance Kaiser IV of high-end brokerage Key-Ventures Realty. “If it’s been in the window for six years, unless it’s the most exquisite thing that no one can afford, you think there’s got to be something wrong with it.”

More expensive properties do take longer to sell because the pool of potential buyers is much, much smaller for trophy penthouses and sprawling $40 million townhouses. A property between $10 million and $20 million spent on average 225 days on the market this quarter; for properties over $20 million, that number falls to 212 days, according to Streeteasy data. But that’s still shy of a full year.

Not all sellers are greedy, though—some of them are just so infatuated with their homes that they can’t see them objectively. “Psychologically, the problem is that everyone loves their own house the most,” said Kirk Henckels, the executive vice president at Stribling.

Expensive, custom renovations are particularly tricky. One broker spoke of an owner who’d poured millions into a meticulous renovation and felt like he absolutely had to get the money back when he decided to sell. The architect and designer encouraged him to stand firm: after all, what did it say about their design if it didn’t bring in a fawning public?

What happens to these market dinosaurs? Does anyone ever come along to rescue them from listing purgatory, the endless parade of critical buyers judging their views, frowning into their bathroom mirrors and peering into their cabinets?

For a few, five or six years down the road, the market finally catches up to an asking price. The townhouse at 41 East 70th Street, for example, spent seven years on the market before it sold this fall for $25 million—the price it tried, and failed, to get in 2005 before reaching ever higher—$30 million, then $35 million.

Perhaps the buyer, steel magnate Leroy Schecter, felt a pang of sympathy for the overreaching townhouse. He had, after all, just re-listed his apartments at 15 Central Park West for $95 million—a full $40 million more than he’d been asking the year before.

So what’s responsible for the spinsterhood of 129 West 20th Street?

“It’s a luxury loft in a non-doorman building—there’s your start. Nothing in the building is that size, and it’s a very, very taste-specific,” said a broker who was familiar with the property. “I brought a lot of people there who really, really loved it, but it didn’t fit their lifestyle. And they didn’t want to pay for a renovation that if they bought it, they’d have to destroy.”

He cited the cantilevered steel staircase—which would make most parents of small children convulse in fear, the kitchen with unusual zebrawood cabinetry (stunning) and unusually small European appliances (not so stunning) and the fact that the master bedroom and its terrace faced an office building. It was a temperamental beauty whom everyone wanted to date but no one wanted to marry. Not to mention that the Chelsea of 2006 was not the High Line, Google-hosting, gentrification juggernaut it is today. If it made its market debut today, it could probably get $6.45 million, just as it could have back in 2006, but it’s no longer the fresh-faced debutante it had once been.

“The owner really spent a lot of money in the materials and the design,” said another broker. “But in real estate, your dream penthouse is not someone else’s dream penthouse.”

Indeed, although the staircase didn’t worry the broker representing the Canadian family (the children already lived with one) she fretted aloud that the layout—with the bedrooms right off the entertaining areas—would keep the children up if the parents had parties.

Eran Cohen, a rental broker in the building, was more blunt. “I think it’s a great, great unit, but it won’t go for that price,” he said, adding that the owner keeps toggling between renting and selling, which may suggest indecision. Said Mr. Cohen: “He has no patience.”

kvelsey@observer.com