#25 Jim Chanos' historic triplex
Estimated value: $23.1 million
Title: President and Founder, Kynikos
The hedge funder bought his 7,700 square foot triplex condo for $20 million in 2008. The fourteen-room penthouse in the historic Stuart Duncan House overlooks Central Park and has perfect views from the massive terrace. You may recognize Chanos' neighborhood from the '90s TV show "The Nanny," as the neighboring building at 7 East 75th Street was used for exterior shots of the Sheffield home.
"The going square foot price for a property of this quality and size today is between $3,000 to $4,000 per square foot," said Patricia Cliff, a licensed associate real estate broker at Corcoran and author of The Art of Selling Real Estate, which would put the value of the home at around $23.1 million.
"Although it would be very difficult to estimate the present value because of the uniqueness of the property," she added.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#24 Joseph Baratta's new Upper East side townhouse
Estimated value: $26 million
Title: Global Head of Private Equity, Blackstone Group
At the end of last year Baratta was in contract to buy the Upper East Side townhouse for $26 million from music mogul (and Tory Burch's boyfriend) Lyor Cohen, according to the New York Post. The six-story building off Fifth Avenue is 25 feet wide, with an 1892 Cass Gilbert facade and six bedrooms, an elevator, patio, and eat-in kitchen that opens out onto the garden.
The master bedroom suite takes up a whole floor by itself, adorned with a planted terrace and overlooking the beautiful Central Park reservoir.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#23 Marco Birch's Shelter Island getaway
Estimated value: $28.5 million
Title: Partner and Senior Portfolio Manager, Moore Capital Management
Earlier this year, Birch put his exquisite, 23,000-square-foot Shelter Island mansion up for sale, asking $28.5 million. The home, which is accessible by sea plane, has 10 bedrooms, 12 bathrooms, a heated pool, three-car garage, deck spa, tennis and squash courts, and a 100-foot dock.
But the basement of the home is where the action is, with a gym, sauna, eat-in wine cellar, home theater and nightclub. The nightclub also includes what Curbed called a "stripper pole" in the basement, though a spokesperson for the home has said that the basement has never been used as a strip club.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#22 John Paulson's Aspen Lakes ranch
Estimated value: $29.9 million
Title: Founder and President, Paulson & Co.
Paulson's Aspen Lakes Ranch, which he bought barely three years ago for $24.5 million, is back on the market for $29.9 million. The 13,068-square-foot home has seven bedrooms and 10 bathrooms, as well as gorgeous mountain views and lakes perfect for fishing.
This is not the only Aspen home Paulson owns; last summer Paulson purchased Hala Ranch from Saudi Prince Bandar bin Sultan for $49 million.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#21 Steve Feinberg's mansion in a former mission
Estimated value: $30 million
Title: Founder, Cerberus Capital Management
Feinberg purchased his Upper East Side home in 2003 for $19.75 million. Feinberg's East 67th Street ultramansion spreads out over a massive 17,000 square feet of space—space which used to belong to the Egyptian mission. Not much else is known about Feinberg's digs, as the Cerberus Capital founder tends to keep a very low profile.
Patricia Cliff, a licensed associate real estate broker at Corcoran and author of The Art of Selling Real Estate, believes Feinberg's place is most likely worth at least $30 million today, though "possibly more, depending upon the renovation which was done."
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#20 Marc Lasry's celeb-approved townhouse
Estimated value: $35 million
Title: CEO, Avenue Capital Group
Lasry's six-floor, Upper East Side townhouse is centrally located just steps from Fifth Avenue. Formerly the home of late celebrities like Michael Jackson and artist Marc Chagall, the Lasrys gutted the 12,000+ square foot home, which is now equipped with a 36-foot parlor, formal dining room, wet bar, and library. The fifth floor is home to a three-room guest apartment and billiard room, while the sixth floor is reserved for the home gym.
"It's a beautifully renovated home, most likely worth in excess of $35 million," Cliff said.
The Lasrys have also been known to completely deck out their house every Halloween with cobwebs, statuettes, and the famous "Superfreak"-singing pirate skeleton guarding the door.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#19 Boaz Weinstein's architecturally stunning penthouse
Estimated value: $35.5 million
Title: Founder, Saba Capital
The founder of Saba Capital owns a pricey Upper East Side apartment at 907 Fifth Avenue, one of three that was once owned by the late recluse and copper heiress Huguette Clark. Weinstein bought the top floor in May 2012 for $25.5 million—$1.5 million over the asking price. It has four bedrooms, four bathrooms, and separate quarters for staff.
Real estate broker Patricia Cliff said that while Weinstein's apartment is architecturally stunning, it required extensive work. She estimates that it could be worth up to an additional $10 million post-renovation, making it a pretty penny per square foot.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#18 Stephen Freidheim's ultraluxe duplex
Estimated value: $36.75 million
Title: CIO and Senior Managing Partner, Cyrus Capital Partners
Freidheim purchased the Woolworth Estate Penthouse at 1020 Fifth Avenue for $26.75 million in 2011. The apartment had been on the market since 2008; it was listed for $46.5 million, but was subsequently reduced down to make the price more recession-friendly.
The penthouse, which has unobstructed views of the park and the Metropolitan Museum across the street, had previously been two apartments on the thirteenth and fourteenth floors.
However, Cliff said that the layout was awkward and the apartments were "un-artfully combined," so she imagines that Freidheim has invested at least $10 million in renovations. "[I] presume that he would get his money out, but perhaps not much more, given the intrinsic negatives of the property," she said.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#17 Daniel Benton's Park Avenue palace
Estimated value: $39 million
Title: Co-founder, Andor Capital Management
The Andor Capital Management co-founder purchased the penthouse at 730 Park Avenue in December for $39 million—$4 million over the asking price, according to Curbed.
The apartment has four bedrooms, an enormous living room, solarium, greenhouse breakfast room with a glass ceiling, and five terraces. There's even a terrace in the maid's room—not too shabby.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#16 Lloyd Blankfein's 15 CPW duplex
Estimated value: $40 million
Title: CEO and Chairman, Goldman Sachs
Goldman Sachs CEO Lloyd Blankfein paid $26 million in cash for the penthouse duplex at 15 Central Park West, where some the most famous and affluent people in the world own homes, back in 2008.
The apartment has 6,136 square feet of indoor space, with four bedrooms and six and a half bathrooms, and an astounding 1,128 square feet of terrace space.
Nick Jabbour, Senior Vice President at Nest Seekers International, said that there are properties currently for sale at 15 CPW asking $7,000-$8,000 per square foot, and recent sales on lower floors from about $5,000-$7,000 per square foot.
"From where I sit, I would speculate that a value in the mid-$40 millions may be considered a bit high," he said.
Blankfein also purchased a massive Bridgehampton estate for $32.5 million this past winter, according to the New York Post, which has an 8,000-square-foot house and enough land on the property to build a second home.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#15 Gene "Tiger" Sykes' La Belle Vie
Estimated value: $42.5 million
Title: Co-head of Global Mergers and Acquisitions, and Chairman of Global Technology, Media and Telecommunications Investment Banking, Goldman Sachs
Sykes bought his 35,000-square-foot palace in Bel Air, Calif., for $40 million in the spring of 2011—in cash, according to the Real Estalker.
The eight-bedroom, 21-bathroom mansion, which he calls La Belle Vie, has a gym, pool, wine cellar, beauty salon, media room, billiards room, tennis court, staff wing, and three kitchens.
Jonathan Miller, President and CEO of real estate appraisal and consulting firm Miller Samuel, said that, according to the latest FNC Home Index, a home like Sykes' could have seen a 6.2 percent increase since he bought it two years ago, putting it at approximately $42.5 million.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#14 Carl Icahn's Hamptons hideaway
Estimated value: $44 million
Title: Investor and Founder, Icahn Associates
Lily Pond Lane is known for being one of the most elite streets in East Hampton, and it's home to billionaire Carl Icahn's seven-acre estate which consists of not one, but three houses. It's also equipped with two tennis courts and massive ocean frontage.
Many celebs, like Martha Stewart, Steven Spielberg, and Jon Bon Jovi, have all owned property in the area at one point or another.
Susan Breitenbach, a broker at Corcoran in Bridgehampton, estimated that the price of Icahn's high-end home has increased by about 10 percent from last year, putting it at around $44 million.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#13 Robert Bass' Upper East Side apartment
Estimated value: $47 million
Title: Co-founder, Oak Hill Capital Management
In 2012 Oak Hill Capital Management's co-founder bought the twelfth floor at 834 Fifth Avenue from Damien Mezzacappa, another hedge funder, for $42 million.
Patricia Cliff, a licensed associate real estate broker at Corcoran and author of The Art of Selling Real Estate, estimates that it has increased between 10 and 15 percent since last year, putting the current value at about $47 million.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#12 Howard Marks' adjoining duplex penthouses
Estimated value: $62.9 million
Title: Co-founder, Oaktree Capital
The Co-founder of Oaktree Capital bought two adjoining duplexes in May 2012 at 740 Park Avenue for $52.5 million, setting the record for the most expensive co-op ever sold in New York at the time.
The duplex apartment, which occupies the 12th and 13th floors of the luxury building, has 30 rooms, including eight bedrooms, 10 bathrooms, a private elevator, elliptical staircases, two libraries, seven fireplaces, and an expansive view of Central Park. His neighbors include fellow finance giants Stephen Schwarzman and Charles Stevenson.
The property is worth about $62.9 million today, according to the NYC Property Assessment Final Roll of 2013.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#11 Eddie Lampert's exclusive island home
Estimated value: $64 million
Title: Chairman, Sears Holdings Corporation; Founder, Chairman, and CEO of ESL Investments
Last year, Lampert bought a 17,000-square-foot mansion on Florida's Indian Creek Island, an exclusive, ultrawealthy neighborhood for $40 million. The home sits on 2.7 acres.
Jonathan Miller, President and CEO of real estate appraisal and consulting firm Miller Samuel, told us that according to the Q2 2013 Miami Element Report, the value of a single family home in a luxury market like Lampert's could increase up to 50 percent. Miller estimated that Lampert's home could be worth about $64 million today.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#10 David Tepper's palatial Sagaponack home
Estimated value: $66 million
Title: Founder, Appaloosa Management
The founder of Appaloosa Management famously bought and tore down an enormous $43.5 million Hamptons home in 2011 and has been rebuilding what will be a house twice the size.
Construction has been ongoing, but aerial photos taken early this year show just how big it will be. The estate covers six and a half acres and includes 500 feet of ocean front.
Susan Breitenbach, a Corcoran real estate broker who specializes in Hamptons properties, said that Tepper is likely putting at least $15 million into the construction of his new home, and that the value has increased this year by about 10 percent since last year. She valued Tepper's Hamptons getaway at about $66 million.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#9 Ron Perelman's Hamptons estate "The Creeks"
Estimated value: $77 million
Title: Chairman and CEO, MacAndrews & Forbes Holdings, Inc.
One of billionaire Ron Perelman's most valuable properties is his luxurious, Gatsby-esque East Hampton estate called "The Creeks," which is located on 57 acres on Georgica Pond in the Hamptons. The property includes a 40-room house and a mile of land fronting a coastal lagoon.
The New York Times once called The Creeks “the largest and most spectacular estate in the Village of East Hampton, with more than a mile of frontage on Georgica Pond and a view of the Atlantic Ocean beyond.”
Perelman bought the 19th century estate in 1990 for $12.5 million, but today it would be worth much, much more.
Susan Breitenbach, a broker at Corcoran in Bridgehampton, estimated that the value of the home had increased about 10 percent since last year, putting the home at $77 million.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#8 Henry Kravis' 26-room Manhattan residence
Estimated value: $80 million
Title: Co-founder, Kohlberg Kravis Roberts & Co.
Kravis owns a massive 26-room apartment in a swanky Park Avenue building equipped with a gallery, ball room, dining room, and 68-foot-long rec room. He bought the apartment for $15 million in 1994 from Iranian Princess Ashraf Pahlavi, according to the New York Observer.
Patricia Cliff, a licensed associate real estate broker at Corcoran and author of The Art of Selling Real Estate, estimates his apartment to be worth about $80 million.
Kravis also owns property in Palm Beach and Southampton, among other places.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#7 Bruce Kovner's Georgian mansion
Estimated value: $80 million
Title: Founder and Chairman, Caxton Associates
Kovner bought his mansion at 1130 Fifth Avenue for $17 million over 10 years ago and reportedly invested another $10 million to make it his private residence. Today it has a soundproof media room, two-story master bedroom, book vault, and more.
The home comes with a lot of history: Built in 1915 by Willard Straight and designed by the architect Delano Aldrich, various private owners used the home as their residences until the International Center of Photography bought the building in 1973 and used it as their museum until 2001 when Kovner purchased it.
"Given the architectural splendor of this home, and its uniqueness, it is probably worth north of $80 million to the right buyer," Cliff said.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#6 Bill Ackman's investment property at luxurious One57
Estimated value: $90 million
Title: Founder and CEO, Pershing Square Capital Management
Billionaire hedge funder Bill Ackman is buying a $90 million penthouse duplex at One57, a luxury residential building overlooking Central Park that is currently under construction.
The deal for the apartment, which occupies the 75th and 76th floors, is still in contract. An unnamed source told the Wall Street Journal that Ackman does not have plans to move into the apartment; instead, he's using it as an investment.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#5 Phil Falcone's vanity mansion
Estimated value: $100 million
Title: Founder, Harbinger Capital and LightSquared
Phil Falcone and his wife Lisa purchased the 25,000-square-foot Upper East Side townhouse in 2008 for $49 million, and have since been renovating it, spending $10 million or more for outrageous features like a Roman-inspired indoor pool, heated sidewalks, and even marble columns with his face carved in them, according to Curbed.
Cliff said that the renovation was "a gut job," and if the renovations appealed to another buyer, this place could be worth close to $100 million.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#4 Dan Loeb's multimillion dollar 15 CPW penthouse
Estimated value: $100 million
Title: CEO and Founder, Third Point LLC
The hedge funder was reportedly quietly shopping around his 15 Central Park West apartment for $100 million last year. Though it's not on the open market, the apartment is still reportedly up for sale and there are no reports of a sale or any drop in the initial asking price.
The penthouse, which Loeb bought in 2008 for $45 million, features 360-degree views, servant's quarters, an expansive deck, and a library over 10,500 square feet.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#3 Steve Cohen's behemoth Upper East Side apartment
Estimated value: $115 million
Title: Founder, SAC Capital Advisors
Cohen is currently selling his massive Upper East Side penthouse at the illustrious One Beacon Court for $115 million. The 9,000-square-foot apartment has 6 bedrooms and 6.5 bathrooms, 24-foot ceilings, maple floors, and Venetian plaster molding.
He bought the duplex for $24 million back in 2005, and hired the late architect Charles Gwathmey to renovate it.
Cohen recently bought a house in the Hamptons for $60 million and a triplex apartment at The Abingdon, a luxury building at 607 Hudson Street in Manhattan, for just over $23 million.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#2 Steve Schwarzman's ritzy triplex penthouse at 740 Park Ave.
Estimated value: $120 million
Title: Chairman, CEO and Co-founder, Blackstone Group
Back in 2000 Schwarzman paid somewhere between $35 and 40 million for his triplex penthouse apartment at at 740 Park Avenue, one of the ritziest buildings in Manhattan, which has 11 fireplaces, 37 rooms, 43 closets, a gym, sauna, steam room, billiards room, screening room, and servants' quarters, according to the New York Observer.
Cliff said that Schwarzman's apartment "is, without question, one of the largest and most beautiful apartments in the city." Former residents include Jackie O. and John D. Rockefeller.
She believes it would be worth around $120 million today, if there were a buyer.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.
#1 Ira Rennert's 110,000-square-foot Hamptons estate, the largest private home in the country
Estimated value: $247.8 million
Title: Investor and businessman
Rennert, an investor and business mogul, built his 110,000 square-foot estate, called Fair Field, in the late '90s, making it the largest private home in the country.
The home itself is 66,000 square feet, with 29 bedrooms, 39 bathrooms, a dozen chimneys, a 91-foot long formal dining room, a basketball court, a bowling alley, two tennis courts, two squash courts, and a $150,000 hot tub on 63 acres of manicured, Atlantic-viewing landscape. Curbed reported this year that Rennert is adding on a pilates studio to his monstrous manor.
The Suffolk County Assessor's Office estimated the home to be worth a cool near-$250 million in the 2013 final assessment roll. Susan Breitenbach, a broker at Corcoran in Bridgehampton, confirmed that the value had increased by at least 10 percent since last year, bringing it to about $247.8 million.
To estimate the approximate current value of the homes, we looked at recent sales and public assessors' records, and we spoke to expert realtors and appraisers in these homes' markets.