The 27-foot-wide, seven-story townhouse at 39 East 72nd Street is iconic even without the celebrity claim; a sandstone-clad facade and copper cornice cast an ethereal glow, yet blend with the stately homes on the Upper East Side block. Mansion Global reports that also-iconic socialite and businesswoman Gloria Vanderbilt lived in the home in her “Poor Little Rich Girl” childhood. The options for this pristine property are many. It’s currently set up as three separate condos, but a combo would make a Vanderbilt-worthy manse.

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Photo credit: Yale Wagner for Sotheby’s International Realty.

On the market for the first time in over 60 years, asking $17.995 million, this 20-foot-wide Beaux-Arts mansion stands among the most desirable blocks of the Upper West Side. Designed by the architectural firm Welch, Smith and Provot–the firm also designed the Duke-Semans Mansion on Fifth Avenue later owned by Carlos Slim–the six-story, 9,575-square-foot home at 5 West 73rd Street is one of the neighborhood’s most architecturally significant houses; among its most compelling features are iconic views of  another Upper West Side classic, the Dakota.

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The 25-foot-wide carved limestone mansion at 35 East 68th Street on the Upper East Side is a standout even on a block lined with historic architecture. The 13,000-square-foot Beaux Arts mansion, known as the Dunham House, was built as a private residence for physician Dr. Edward Kellogg Dunham and grain fortune heiress Mary Dows by Carrere & Hastings, the architecture firm who designed the Frick Collection and the New York Public Library. 6sqft featured this historic home in 2016. The two-bedroom duplex co-op is back on the market for $4 million.

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Just over a year ago, The Real Deal reported that Tony Award-winning Broadway producers Janet and Howard Kagan (“Tuck Everlasting,” “Pippin”) had put the 25-foot-wide, 12,729-square-foot mansion at 11 East 82nd Street, purchased for $24.5 million in 2009, on the market, asking $44 million. The impressive Upper East Side limestone-and-brick townhouse was also known for having previously belonged to financier Ron Perelman. The 1895 building in all its six-story, elevator-enhanced, Gilded Age glory has just been relisted for $29.5 million, a hefty haircut from last year’s ask.

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Bedford-Stuyvesant‘s most expensive home has sold for $6.3 million, setting a record price for the neighborhood and sending a message that rising property prices are making their way further into Brooklyn, according to the Wall Street Journal. At nearly twice the previous record sale of $3.3 million in 2017, the Renaissance Revival-style John C. Kelley mansion at 247 Hancock Street is the most expensive single-family house ever sold in Bed-Stuy. The 8,000-square-foot, 10-bedroom townhouse was built in 1887 for water-meter magnate John Kelley, designed by noted architect Montrose Morris and modeled after a Gilded Age Vanderbilt mansion along Fifth Avenue.

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While owning a waterfront castle might seem presumptuous even for the former Yankee captain and current Miami Marlins owner, this 50,000-square-foot upstate compound on four acres at 14 Lake Shore Road in Greenwood Lake, NY, was more than just a random luxury buy. Tiedemann Castle, as it is known, has a family history for Jeter: According to the New York Post, his grandfather Sonny Connors, adopted son of John and Julia Tiedemann, who purchased it in 1952, was raised on the property. Jeter bought the estate 15 years ago for $425,000, so even after being “lovingly restored, with unparalleled attention to detail,” the current $14.75 million price tag is a hefty hike.

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Built in 1887 by local builder William Noble, this remarkable Queen Anne mansion at 248 Central Park West has been painstakingly restored by its owners in a $10 million gut renovation, with its stunning details preserved and every modern luxury–including an elevator, a 50-foot lap pool in the cellar, a top floor penthouse, a home theater and a gym. As the New York Times tells us, it’s one of only three houses built in the surrounding Upper West Side historic district at the time. On the market for the first time since 2004, it’s asking $29 million.

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Built in 1927 for Andrew Carnegie‘s daughter, the 34,000-square-foot estate in Millbrook, NY known as Migdale Castle was modeled after Carnegie’s Skibo Castle in Scotland. Beginning in 2002, the home’s current owners spent four years renovating its four floors, the 100 acres it occupies, and another 100-acre adjacent plot, giving new life to one of Dutchess County‘s most distinguished estates. Migdale first hit the market for $25 million, making it the county’s most expensive listing, but a recent $8.1 million price chop resulted in the current $16.9 million ask.

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A sprawling 8.2-acre estate in Center Moriches once owned by the deceased Filipino President Ferdinand Marcos and his wife Imelda has hit the market for $4.99 million. The massive Long Island property, known as the Lindenmere Estate, at 16 Sedgemere Road features 14 bedrooms, 17-and-a-half baths, a glass-enclosed Pagoda pool house, and incredible views of the Moriches Bay. According to the New York Post, after a brokerage switch, the listing’s price dropped from $5.99 million last year.

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This undeniably grand home of pale carved limestone in the Beaux Arts style, designed by turn-of-the-20th-century architects Clinton & Russell, is in its element on what’s known as the most valuable corridor on the Upper East Side just across from Central Park. And unlike many of its kind, the interiors of the 25-foot-wide, 11,500-square-foot mansion at 7 East 67th Street are neither overly opulent and intimidating nor tastelessly renovated. There’s an elevator, gym, double-height library, two grand staircases, and decks and terraces around every turn. Why, then, has this home been seeking a buyer since 2009? It’s certainly possible that when other houses like this are asking less than half its current price of $36.5 million, an ask of $37 million nearly a decade ago that hopped to $49.5, fell to $42.5, and steadily dropped since then might have less appeal for buyers when the choices are many.

Take the tour, from the gym to the roof deck