Upper East Side

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Each part of town has several neighborhoods. Our residential-real-estate survey condenses its developmental highlights  through Manhattan’s boom-and-bust economic cycles.

In no way is its intention a complete history: rather, the survey reflects the overriding characteristics that remain (through its rise, fall, and then {often} subsequent gentrification).

Furthermore, the seven additional elements–our highlights, photographs, maps, and suchlike–aim to create a mosaic of the lifestyle and housing types throughout Manhattan.

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Time lines and Sidebars, Historic Maps, Neighborhoods, Upper East Side, Midtown East, Downtown East, Lower Manhattan, Downtown West, Midtown West, Upper West Side, Uptown, Upper Manhattan

 


Upper East Side

The northernmost point is East 96th Street (with an exception farther along upper Fifth Avenue), the end is at Central Park’s southeastern-most corner, Grand Army Plaza on East 60th Street, and extends from Fifth Avenue to the East River throughout. Indelibly bisected at Third Avenue, the residential neighborhoods, from north to south, are:

  • Carnegie Hill encompasses the northwest quadrant, from East 98th to 86th Street, spanning Fifth to Lexington Avenues.
  • Lenox Hill stretches from East 85th to 71st Street, between Fifth and Third Avenues, which contains the Metropolitan Museum of Art district, between East 84th and 78th Streets along Fifth Avenue, as well as the adjacent blocks to Madison Avenue.
  • The Social Sixties comprises East 70th to 60th Street, east of Central Park and west of Third Avenue, which takes in Tredwell farm, at the East-62nd-to-61st-Street mid-block, running between Second and Third Avenues.
  • And Yorkville, the eastern sector (originally) extending from the mid-East 90s to 77th Streets—nowadays some say, East 72nd, others East 60th Streets—and dominates Second Avenue to the East River.

Two (unequal) parts, essentially, has been fact for 150 years, since Central Park was created. Throughout its length, the neighborhoods along the park—referring to Central Park, in particular Fifth to Park Avenue as well as the immediate streets—are deemed Manhattan’s Platinum Zone. Location therefore differentiates the Upper East Side upper-crust resident from the longer, low-lying, eastern blocks denizen. At one time, the Third or Second Avenue Elevated Railroad trains (to New Yorkers, the El), buffered the western neighborhoods: “West of Third” says it all since.

The more lavish town house development off the westernmost avenues resulted in a museum, social club, and house of worship mix—among a predominant building type: 1920s 11-to-12-story, red-brick, avenue apartment houses, designed to be stately though not spectacular rental homes. One-third of these pre-war Fifth and Park Avenue apartment houses—125 buildings, with better than 7,500 units—were designed by two architects James Carpenter and Rosario Candela. It has been said that just two men shaped Fifth and Park Avenues’ essential character then, which is exactly as they remain.

Though much has changed, still, the single-family dwelling options in addition to the sumptuous, white-glove, Fifth and Park Avenue apartment houses are differentiated, as:

  • Opulent town houses;
  • Row houses, (made even more impressive after updates and renovations);
  • Single-family-brownstone-to-multiple-family-dwelling-usage conversions;
  • And limited mansion-to-mini-apartment-house transformations.

Madison and Lexington Avenues, though, have endured as ground-level shopping strips, mainly beneath 15-to-21-story apartment houses, sprinkled occasionally by 1890s brownstone strips, with stoops removed.

Diametrically opposed are the working-class row houses, tenement-apartment-house rows, and an array of five- and six-story multiple-family dwellings—many with unattended entries—which were built simultaneously east of Third Avenue. Moreover, drastically altering the eastern portion’s streetscape are the 1950-75 21-story-plus-penthouse, white- or red-brick apartment houses. Though peppered about on Madison and Lexington Avenues, these unadorned buildings, built densely—abutting one another along Third, Second, and First Avenues—are a distinct multiple-family dwelling type, dubbed post-war.

To complete the post-World War II-era picture: There was a sudden rash of pre-war Fifth and Park Avenue rental converts to co-operative ownership. By 1960, like rapid-fire and ever escalating to the mid-1970s, landlords east of Lexington Avenue—in fact, throughout Manhattan—opted for the ownership-conversion tax advantages, too. When the post-war residential-building-boom era ended (in 1975, concurrently with the conversion-tax advantage expiration), virtually every potential building site west of Third Avenue was a condominium tower or was assembled (awaiting, in developer’s lingo, no shovel in the ground yet) to scrape the sky. When the boom cycle reignited six years later, the easterly Upper East Side Avenues between Second and York Avenues were upscale rental tower strips, self-managed by their developer.

Carnegie Hill

Here’s how the indigenous village evolved into Andrew and Louise Carnegie’s urban vision. Beforehand, roughly the same peaceful seasonal patterns existed year after year when Henry Hudson came upon a large, deep, ice-free harbor, with the up-island Lenapehoking, “Lenape lands.” At the mid-Manhattan eastern apex, the Lenape, “the people” and to the Dutch Lenni-Lenape was “common people,” a Delaware dialect-speaking, Wappinger tribe of the Algonquian Nation, lived in their seasonal village, Konaande Kongh—a 40-to-50-man-woman-and-children band—stretching between East 98th and 93rd Streets, along present-day Park Avenue. The village was built on a hillside affording protection from rain and strong winds; and from its dome-shaped, bentwood and bark-covered long lodges, there was a commanding view of the rushing brooks, streams and creeks working their way to the river, and the surrounding outwash plain, Muscoota “the flat lands,” to the villagers, stretching two miles south and three miles north (East 59th to 159th Streets).

Additionally, the dense woods to the west were thick with maple stands for syrup and with blueberry bushes to pick in the spring and summer. To the east was a cultivated fertile plain—cleared by the slash-and-burn method—nearer the river’s richer loom, which provided abundant fruit, herbs, and vegetables, squash, beans, and corn. To the south, game such as deer, rabbit, beaver and bear were plentiful, while the gentle easterly slope accessed Harlem Creek, at East 119th Street, an oyster cove, where their fishing canoes were kept. Situated beside several intersecting running brooks, and on the north-and-south trade route to Shorakaprok, “place between the ridges,” where the Wiechquaesgeck confederation maintained a permanent fort guarding the North River trade routes and seasonal habitats within this tribal hunting reserve; or, to Kapsee, “sharp rock place,” at the harbor and to the Lower Manhattan village, Werpoles, sited at Collect pond, present-day New York City Hall Park, connecting several small seasonal neighboring tribe’s Manhatta trading villages. The well-worn walking trail forked 21st Street and Fifth Avenue, heading to Sapohanikan, “carrying place,” to the Dutch “tobacco field,” and trading post on the Hudson River. (This village, approximating Gansevoort Street, cultivated the very important commodity “smoked” at ritual ceremonies, which preceded clan and chieftain assemblies.)

(1600s)
Displacing the northern-portion inhabitants, a Delaware-speaking, Wappinger tribe among the Algonquin Nation, the Lenape, “people,” from their Lenapihonk, “traditional hunting and fishing reserves,” proved to be anything but a civilized transaction: the Wappinger position was tribal rights were not the (Long Island-based) Canarsie tribe’s to convey, the agreement was a sham, for various reasons. (Their negotiation strategy was to grant the land rights piecemeal, which required acquiring Manhattan by portions through later sales agreements. The final transfer took 75 years, and was completed by the British.)

Suddenly, and with swift consequences, a series of land rights and trading misinterpretations with the Native people—over use of verses ownership, over trade verses tribal rights to exchange—lead to struggles and uncertain truces, then scrimmages throughout 1643-55 broke out, with escalating ferocity. When a young squaw was found murdered, protracted bloody battles ended a relatively calm period, and resulted in fortifying the mid-island hamlet on the Hudson River, Nieuw Haerlem. Then-Governor Peter Stuyvesant, to defend New Haerlem’s scattered farms, ceded its freehold landowners Haerlem Common—Fifth Avenue and the land west included. His degree extended New Harlem from West 129th Street to East 74th Streets, river to river. Although the southeast tract, separated by swamps and rocky hills, with only one egress, McGowan’s Pass, was far from their hamlet, the villagers willing accepted Stuyvesant’s grant to start the first collective farm in North America. Subsequent-Governor Richard Nichols, Stuyvesant’s English replacement, reaffirmed Harlem’s clear claim to the entire Harlem Common.

Britannia’s Rule

After the British took complete control of the unprofitable Dutch colony, the largest tract encompassing Harlem Common land fell into one family’s hands, the Van Oglienis. Forty-eight years later, Mount Pleasant (renamed Prospect Hill, by the English) as well as the farmlands not within Harlem Common. were still owned by a few families. Shortly, the Waldron family would own the mid-East Nineties and southeast to East 87th Street between Fifth and Second Avenues. Baron Resolve Waldron passed his land to a son Samuel, and then it passed down to William, his son. Prior to the Revolutionary War, a spendthrift heir, Adolph Waldron, sold the fields and pastures piecemeal (for 800 pounds), with the majority purchased by Abraham Duricee, a New York Merchant; his heirs retained a narrow portion straddling East 91st Street, from Fourth to Second Avenues, where a marshy valley, formed by ponds, creeks and streams flowed into the converging East River and Harlem Creek, Hell’s Gate inlet.

The very irregular, mostly triangular tracts, which spread between East 94th and 87th Streets, had boundaries running northeast to southwest, and they were the estates of:

  • East 94th to 92nd Streets along Fourth Avenue, the northwestern tract, was owned by John G. Bogert.
  • East 92nd to 90th Streets, between Fourth and Third Avenues, a near east tract, was owned by the Douglas family.

The northeasterly, quite conical-shaped, parcel owners were:

  • East 94th to 91st Streets, Nathaniel Sandford;
  • And East 93rd to 91st Streets, Xaviero Gantro.

Due East:

  • East 90th to 86th Streets along Third Avenue, narrowing to East 93th and 91st Streets in the east, was shared by Mrs. Mary and Mr. William Rhinelander.
  • East 90th to 86th Streets along Third Avenue, narrowing to East 93th and 91st Streets in the east, was shared by Mrs. Mary and Mr. William Rhinelander.

To the southeast:

    • East 88th to 84th Streets, from Third to Second Avenues, the southeast tract on which the stone Waldron farmhouse stood, was retained by Samuel Waldron’s grandson, Benjamin.

Revolutionary and War of 1812 to the Civil War

On the eve of the Revolutionary War, the entire known population of New York, North America’s second largest city, had grown from a band of settlers to 20,000 residents, yet Prospect Hill’s population had not budged—maybe 15 additional people among the farm owners, their families and servants, lived in the present Carnegie Hill District. (With sketchy Dutch record-keeping, and after British control all transfer agreement records were removed to London, the exact settlement accounts were lost entirely or simply never returned.) Thirty years after the Revolutionary War, all Harlem Common lands, an incomprehensible swath, was owned by Lawrence and Sampson Benson (sixth-generation Bensons). Ownership outside the Common, however, did not transfer again—even after the 1818 city commissioners’ appointments: John Randel Jr. to hand draw and color Manhattan district maps, and Charles Clinton to survey northern Manhattan, for subsequent division into standard building lots.

Meanwhile, lower Manhattan’s rampant overcrowded conditions—caused by successive waves of immigration and poor housing, only worsening between epidemics and fires after the War of 1812—encouraged more and more New Yorkers with the 12.5 cent horse-drawn-tram fare to take a one-hour excursion from Prince Street Terminal to Prospect Hill. At East 93rd Street and Fourth (now Park) Avenue, Samuel Thomson erected Prospect Hall, initially a modest wood-frame building surrounded by a two-story piazza to serve as their destination; a large, 1837 dance hall was attached to accommodate assemblies and parties. At a nearby undeveloped tract, Observatory Place, sprawling between (present-day) East 94th and 89th Streets and from Fifth to Fourth (Park) Avenues—rich and poor New Yorkers alike could admire the sweeping Long Island and New Jersey views or walk through unfenced, untilled, uninhabited fields. This rural respite, with its maze of narrow dirt paths, was pronounced as “eliminated” by order of the New York State Legislature to accommodate upper Madison Avenue, which came about after 30 years. And, of course, Central Park’s creation took place, too. Records show that throughout 1850-60 the Benson family landholdings outside Central Park were subdivided: each Harlem Common lot was sold individually by one broker, Selden. Likewise, the Duricee, now Durye, and their neighbors’ estates were converted into lots—some owners sold large tracts before the grading process began. For instance—an eastern section was sold to a real-estate speculator, William Brady; likewise, a far smaller, southwestern strip (to East 85th Street) went to George M. Kay.

(1860s)
Throughout the 19th century, specific factors, occurring at auspicious moments, altered Carnegie Hill’s destiny and transformed it (gradually, seemingly begrudgingly), from tranquil and rural into a complex community: more often than not, each event had far-reaching implications before achieving its intended goal.

      • First and foremost was the New York City commissioners’ 1811 Grid Plan—urban plan: create city lots from farms—had a profound effect on Prospect Hill decades later.
      • Seventeen years later, still a dirt path, Fifth Avenue did open from East 106th to 90th Streets.
      • Ten years hence, real estate developer par excellence Samuel Ruggles convinced the commissioners to insert double-wide Madison Avenue between Fourth Avenue (the East Road), and Fifth Avenue; as well as Lexington Avenue, between Fourth and Third Avenues (the Eastern Boston Post Road)—though ordered would not happen quickly.
      • Commodore Vanderbilt’s New York-Harlem Railroad was chartered to connect lower Manhattan with Harlem—city plan: provide rapid transportation—convert horse-drawn cars to locomotive engines was mandated.

Along with locomotives, a partial tunnel was dug running between East 80th and 98th Streets with a bridge at each crossing that somewhat receded the tracks. (Since its inception, the tram from Prince Street stopped at East 86th Street near Lexington Avenue, entered a 596-foot tunnel from East 92nd to 96th Streets, where the cars emerged to complete a downhill run uptown to Harlem.) It took an additional 40 years of pressure before Vanderbilt submitted to submerging the tracks entirely—city enforced plan: eliminate danger, control nuisance, noise, smoke, and soot. Still obstinate, Vanderbilt took his (sweet) time completing the project, meanwhile Fourth Avenue squatters dug in and raised their lean-tos.

(1865-80)
As Central Park was enjoying unequivocal praise and surpassing expectations by the increasing New Yorker’s usage—urban plan: enhance New Yorkers’ quality of life. George Nowlan, Prospect Hall’s second owner and operator, meanwhile, sold the pavilion and 12 acres, with the splendid views: within three years, the retreat underwent extensive renovations to be a private residence for John Feldman, an emerging Duane Street merchant price. Little changed after the Civil War’s end, the entire commercial infrastructure on Prospect Hill was limited to a chemical plan and few small businesses, a piano parts shop and prosthetic limb manufacturer, for instance. On the other hand, there was impressive growth for the three large breweries to the east. Using the East River’s water for both brewing and transporting ale to the lucrative lower Manhattan tavern and restaurant markets, the three brewery owners—Jacob Ruppert, George Ringler, and George Ehret—amassed fortunes and could afford to build mansions on the “hill.”

Ehret (the nation’s second largest brewer) and Ringler bought Fourth Avenue Lots. Their homes (competed in the late 1870s) stood for years among a smattering of detached houses built in the farmhouse motif, with stables out back, and empty row-house lots, perpetually, in the planning stage. The typical nearby housing on Lexington and Third Avenues constituted crowded, tenement-apartment blocks occupied predominately by Irish immigrants: even so, it took five years when electric-train engines replace those that burned coal, for Fourth Avenue to be renamed (optimistically) Park Avenue.

Eventually, Jacob Ruppert, who was born in New York City, erected his mansion at East 93rd Street and Fifth Avenue, completing it as the expanding Metropolitan Museum of Art opened its second gallery. Surrounding Ruppert though were scattered gardens and several two-story brick affairs, with even fewer planned row houses than Fourth Avenue. “Old Jake” spent quite a while living between squatter shacks that sheltered unemployed immigrants and displaced park dwellers tending goats, slaughtering pigs, boiling bones, and quarrying rock. In a nutshell: southeast Harlem Commons had deteriorated into a hodgepodge, little more than a garbage dump.

(1880-86)
To the east, nearer Third Avenue, land speculation began with the1879 initial decision to build Second and Third Avenue El lines which remained chronically behind schedule)—city undertaking: expand public transportation. There too row-house-building came to a halt as financial panics caused several real-estate boom-and-bust cycles, delaying the El an additional decade. Gradually, the lots on and around Lexington Avenue evolved into a working- and middle-class enclaves for professionals, civil servants, and merchant families. Moving into these row houses, from East 95th to 90th Streets were: a bookkeeper, Robert Hebbert; Jewelers Horace D. and Lily Sherrill; wallpaper manufacturers George H. and Emilie Keim; liquor purveyor, Emil H. Kosmak and some such.

(1887-90)
Over 30 years, the population above East 40th Street multiplied fivefold, yet Highlands of New York (originally Mount Pleasant, for a time Prospect Hill, later Carnegie Center, and finally Carnegie Hill), with wood-frame houses still, remained a rural district. Even as the magnetic Metropolitan Museum of Art propelled New Yorkers to East 84th Street, few real-estate speculators halfheartedly assembled the vacant lots farther along Central Park. Fifteen years after Madison Avenue opened, few streets were being developed with multi-family flats buildings; one apartment hotel was under construction, with a second still in planning stages. Additionally, the low 90s in the Fifth-to-Madison-Avenue blocks, once Observatory Place, were morphing slowly (snail-like, indeed), into upper-middle-class-row-house-owner enclaves. On Fourth Avenue, without visible tracks for seven years and with its newest buildings cushioned by steel columns and vibration stabilizers, the shanties (finally) gave way to six-story tenement buildings.

Row House Development

As the tracks along Fourth Avenue were fully submerged and the cross-street overpasses eliminated, sparingly, the eastern parcels along the Park-to-Third-Avenue blocks were assembled for single-family row houses. Initially, these were 15 to 17-feet wide—sometimes less—and designed efficiently, sporadically, with minimal flourishes. Construction gradually accelerated, trotting along smartly and the pace continued unabatedly for 13 years. In some of these later years, the decade-old New York City Buildings Department processed 200 application filings for speculative row houses, usually in groups of two to six.

(1887-97)
Continuing throughout, the most prolific builder-developer emerged as Walter Reid—collaborating with architects J.C. Cade (fresh from his Metropolitan Opera House and American Museum of Natural History success), and A.B. Ogden, later with his son Walter Reid Jr.—who together erected better than 100 row houses, of which 40 have survived. During the row-house boom cycles, to increase profit by 20 percent, Walter Reid constructed several row house at once, using four lots for five houses and creating the 20-footer as an marketable option.

More than a few carpenters and masons formed partnerships during this boom cycle, including several family unions: William and John Walsh, Michael Duffy & Brothers, and John and Louis Weber, who worked exclusively with the architectural firm Weber & Drosser. The most popular and enduring styles erected were revival variations, including Gothic, Queen Anne, Venetian, post Renaissance, and neo-Federalist—ultimately allowing myriad inspirations. Their architectural vocabulary adjusting functionally to fit changing needs—for example, a simple invention, the 1894 dumbwaiter, permitted a family dining room on the parlor floor, instead of at ground level, and with this interior change the traditional outdoor egress, stairs (the stoop, to a New Yorker), became obsolete.

(1887-89 to 1987-89)
The tale of two Lexington Avenue historic district homes which, once renovated, were put on the market for $12,500,000 and $5,995,000, respectively, is telling. The first, at East 91st Street, 1380 Lexington Avenue, a south and east-facing corner row house with a stoop, designed by

Adam Weber, was built by “Old Jake” for Ruppert Brewery’s general manager (not for his daughter, as was once thought)—accordingly, as an upper-middle class dwelling example.

      • The front ground-floor dining room is on the avenue, while the kitchen service garden and garage are in back;
      • The soaring-ceiling parlor floor, accessed by its stoop, is two rooms:
      • a formal front living room (recently obliterated), originally adorned with ornate bas-relief wall projections, such as plaster scrolls or medallions,
      • a rear family library;
      • The family bedrooms are on the third and fourth floors;
      • A third-floor study, with a Juliet Balcony, in which film director Sidney Lumet, who purchased the house when it was 75 years old, co-penned Dog Day Afternoon, Serpico, and Prince of the City, all quintessential New York films.

Two blocks south, Andy Warhol concurrently owned 1342 Lexington Avenue, a second-class, single-family, speculatively built row house within the Hardenbergh/Rhinelander Historic District. Until his mother’s death, they shared the house—with 25 cats, all named Sam; Warhol, incidentally, did not sell the house—in fact, during his lifetime Andy barely acknowledged Mrs. Warhol no longer lived there. The diametric opposite of his “factory,” built too narrow to accommodate an exterior stoop, the house has an interior half-flight staircase directly off the avenue:

      • The dining room at the ground-floor and the rear kitchen entrée via the service garden, accessed by an alley—a city rarity—are down a steep, U-shaped staircase.
      • The parlor-floor front, actually, is a square foyer with a staircase leading to the second-floor bedroom:
      • The rear is the formal living room;
      • A small library faces the avenue. Warhol’s Campbell Soup Can—inspired, perhaps, by the variety Mrs. Warhol prepared for Andy’s lunch that day—as well as his Brillo and Do It Yourself series were painted in the front library.

What’s more, there are similar juxtapositions and contrasts on each Park-to-Lexington-Avenue-row-house block—for instance, on East 95th Street (Goat Path, 60 years prior), with his family, Mark Rothko, the abstract expressionist, living next door to the Broadway theater illustrator, Abe Hirshfield’s family. To their immediate south, throughout the 1950s Betty Comden, the Broadway lyricist, was sharing an East 94th to 93rd Streets, garden fence with actress June Havoc.

Over time, there are noticeably harmonious serious alterations to row houses, updates for changing lifestyles—the operative verb, to taste. And, these, too, have mellowed and incorporated themselves into a varied neighborhood streetscape. One case in point is 64 East 91st Street, a traditional 1887 classic, brownstone, designed by Gilbert A. Schellenger, and altered 40 years later, by John P. Volker, when every jutting exterior element (stoop, doorframe, window trim) were removed. Furthermore, during the Great Depression numerous row houses underwent a rasher reconfiguration: single-family homes to smaller units, accommodating a household size increase in the number of men and women living alone. Therefore, occasionally, the transformation included a ground-floor professional unit; less often, an entire row house became a boarding house. Fortunately, there are entire block-long stretches of unaltered row houses, especially throughout the East Nineties along the Fifth-to-Park-Avenue blocks. Meanwhile, the El lines neared completion and additional lots were gradually assembled for row houses: though, most remained unimproved lots.

It is true, of course, that 19th-century city interventions, a practical grid plan, Central Park’s grace and beauty, and an improved mass transportation system arriving, and then the submerged (Lexington Avenue) subway line paved the way; but, perhaps, the most significant and far-reaching event driving where the neighborhood would evolve was a Thanksgiving eve, when Andrew Carnegie and his wife, Louise, announced they would be moving from West 51st Street and building a new mansion, on Fifth Avenue, at East 91st Street (1900-05)

A reception (covered by the media) was held in the Windsor Hotel and hosted by a real estate broker, 22-year-old Lawrence B. Elliman, who isolated several properties for the Carnegie’s mansion: a riding-academy building and its stables, plus a few shanties. More impressive still, the Carnegies announced having purchased the remaining (some quite large), parcels on or adjacent to upper Fifth Avenue, as what amounted to the grandest (robber-baron worthy) of all land speculation gambles—an urban community created by selling building lots exclusively within their social circle, coupled with withholding large-scale Fifth Avenue parcels for later charitable land-grants to Church of the Heavenly Rest, at East 90th Street, by Mrs. Carnegie, and to the New York Academy of Medicine, at East 105th Street, by Mr. Carnegie.

This audacious Carnegie pronouncement was ultimately the overwhelming catalyst for subsequent development phases on upper Fifth Avenue—north of the Metropolitan Museum of Art—by: joining the town-house-and-mansion-building era, thereby, extending Millionaire Row beyond East 86th Street; and two-decades later, by a Court ordered re-zoning of upper Fifth Avenue for 15-story buildings, when luxury apartment houses would line Highlands of New York’s Fifth Avenue.

(1890-1910)
With more deluxe building materials, upgraded amenities, and innovations were added, these buildings became socially acceptable, at which point several apartment hotels (a Manhattan innovation), appeared in Highlands of New York, providing luxury at an affordable price. The 1890 landmark Graham Hotel was first, and the same year Chastiagneray Hotel opened, soon, renamed: Bibo, Bon Ray, Carnegie Hill and, pre-World War II, Wales Hotel, which was then the neighborhood’s sole transient hotel. The apartment hotel suites included two to four bedrooms with a bath, but no kitchen: taking meals in the common hotel dining room encouraged an even more abbreviated household staff. As the first 20th-century decade closed, the luxury-flats-building and apartment-hotel trend’s increasing popularity continued with renewed northward migration throughout the subsequent decade, and, with newer, more innovative and lavish housing concepts, all Highlands of New York was on the brink of blossoming.

The Carnegie’s announcement hardly brought an immediate super-rich surge to Highlands of New York. Regardless, investors did surface and skewed the per-lot price in a land-rush-like speculation: ending shortly in lost fortunes and property. Meanwhile, the Carnegies set about building their mansion, and they resold the additional lots among members of their social circle willing and able to adhere (by Covenant) to their architectural standards and requirements. Eight years passed, however, before a single plan was filed to build on these lots. (1906-18)

When building did begin, the grand, classic-style mansions, designed by the era’s renowned architects, were erected for bankers, in particular Otto Kahn and Felix Warburg, often with other lesser homes nearby for their children. Shortly thereafter, excavations had begun on several Vanderbilt mansions, and then for the Hammonds, multiple Sloane scions, as well as the Minneapolis Posts, Boston Minots, Philadelphia Drexels, and First National City Bank’s Bakers, who eventually assembled their complex at East 93rd Street, on Park Avenue—a remnant of the 1870s Feldman reserve.

Beginning with the Kahn excavation, merely to accommodate demand, the socially-acceptable border rapidly moved north from East 91st Street as Virginia Fair Graham Vanderbilt bought on East 93rd Street, off Park Avenue; and Edith Vanderbilt Fabbri built on East 95th Street, off Fifth Avenue. By then, social-pillar, Mrs. Amory S. Carhart was also town-house-building off upper Fifth Avenue, although in 1918, three years before Three East 95th Street was completed, she unexpectedly died. Soon East 96th Street was acceptable, too, when Lucy Drexel Dahlgren and Ogden Codman Jr. built homes on that Fifth-to-Madison-Avenue block.

(1920-35)
It did not take long for this new residential-real-estate craze to take hold. From the moment Carnegie made his intentions public, row house construction stopped—well, most anyway—and a new direction was sought. At first, existing specs (labor and materials costs) could be revised, with bigger budgets, by higher standards and better materials—Manhattan’s social elite wanted homes worthy of their wealth; soon, a new standard was needed—and town houses, not as opulent as befit a mansion nearby Central Park, yet far more commanding, let’s say, than an 1890s row house, were in demand. Though rarely at the corner, a town house was built wider than the 25-foot standard city lot by incorporating more than one row house. Individualistic, like their mansion cousins, town houses were commissioned to an architect from design to completion—always including the materials used, and occasionally the furniture as well. The trend for larger, luxurious, architect-designed town houses continued: The demand for upper-middle-class row houses, meanwhile, disappeared. Soon, town-house construction slowed, eventually vanishing with the specter of another World War.

Flats Building and Apartment Hotel Saga Encapsulated

Although New Yorkers lived in multi-family dwellings early on, the concept was never adapted for the well-heeled. In fits and starts, innovative housing, especially flats buildings, appeared throughout Highlands of New York; these buildings were designed for young families, while some developers had single ladies and gentlemen in mind. To accommodate a burgeoning middle- and working-class migration, real-estate partnerships assembled larger parcels, with plans to develop better multiple-family dwellings—decidedly less cramped than tenements, with somewhat sumptuous moldings and fittings; plus upgraded services, such as a hall porter or concierge (in the old sense), eliminated the bother of an extensive staff.

Furthermore, the Second and Third Avenue El lines delivered the expected northward migration—literally!—depositing hordes of newcomers at their East 86th and 96th Street stations. Catering to this new market, the three-and-basement dumbbell-layout tenement houses was abandoned in favor of six-story flats buildings on 25-foot-wide lots. At the century milestone, the wider (on two or more lots), and seven-story flats building variety, with an elevator, appeared in several architectural styles, though the majority was a Renaissance revival. Luxury flats buildings, advertised as being one- or two-tenant-per-floor layouts—a concept borrowed from London and Edinburgh—included a parlor or reception room, dining room, several chambers or bedrooms, a kitchen, one or two bathrooms, and one or more servants’ rooms, linked along a private corridor.

(1911-15)
New York City Buildings Department refrained from classifying four- to ten-room apartments—minimally with one toilet and bath—in six- or eight-story buildings as second-class-dwelling construction. In fact, a flats building with shops along Madison and Lexington Avenues was no longer labeled a French flats building but simply a flats building. Firstly, there were four precursors, built 20 to 17 years earlier prior to the post-1921 extravagant avenue apartment houses within Carnegie Hill. They are each co-operatively co-owned in close proximity to one another, and they are:

      • The landmark, turn-of-the-century, seven-story—initially 14 units, two tenants per floor—Beaux Arts, 1261 Madison Avenue, at East 90th Street.
      • The turn-of-the-century, Renaissance revival, 61 East 86th Street, at the Madison-to-Park-Avenue-block mid-point—also seven stories, but four apartments per floor.
      • The nine-story, white-glazed ceramic tile, 12 East 87th Street, off Fifth Avenue, with one 14-room apartment on each floor (where Gaetano Ajello, Rosario Candella’s mentor, lived until his death in 1983).
      • The 11-story limestone Gothic revival, 1067 Fifth Avenue, between East 87th and 88th Streets, with one 12-room apartment per floor: boasting two rooms directly on the park.

(1917-32)
At first (according to the 1903 New York City Department of Buildings code), these four buildings were considered flats buildings, or, at any rate, second-class, multiple-family-dwelling variations. However, they became an entity: the luxury apartment house that would define Carnegie Hill as the “silk-stocking district”—a far cry from its not-too-distant-past, rural-district moniker. The transition began on Park Avenue, once re-enforced pillars, with vibration stabilizers and updated noise-abating insulation were installed, and after 15 trying years, for the Fourth Avenue Improvement Committee—a foreshadower of today’s Carnegie Hill Neighborhood Association—finally completed the trademark center-island-mall plantings. The roadway above was now paved for high-rise apartment houses to replace the low-rise tenement apartment houses that had replaced the razed shanties in the 1880s: once-gritty Fourth Avenue was now poised to become Park Avenue.

In a 1921, edition of The New Republic, co-edited by Willard and Dorothy Payne Whitney Straight, owners of the neo-Georgian, 1915 mansion, at 1130 Fifth Avenue, designed by Delano & Aldrich designed, Stuart Chase, a well-respected intellectual economist, proclaimed, “Park Avenue is the end of the American ladder of success,” and gushed: “If America has a heaven, this is it.” But what he could not possible foresee was how far better the luxury apartment house versions to come would be.
Stalling the Fifth-Avenue-apartment-house boom, though, was the 1917 New York Supreme Court Appellate division reversing Fifth Avenue zoning restriction, allowing 75-foot structures. The court’s decision advanced 20-plus 14- or 15-story luxury apartment projects that replaced the remaining six- and seven-story flats on upper Fifth Avenue. It took 20 years from the Carnegie announcement, however, before the multiple-family-dwelling building boom’s blast off—with intensity rarely witnessed before or since.

Ironically, six years later, no less than nine though, half-block apartment houses between East 98th and 86th Streets were designed by the engaging architect, John Carpenter (who brought the suit overturning Fifth Avenue’s height restrictions, by his argument—though a disputable point, with a debatable outcome—The Avenue would be greatly improved in appearance if deluxe apartment houses were to replace the old-style mansions), and each was completed to his designs by builder extraordinaire Anthony Campagna. The duo thereby personified the upper-Fifth-Avenue-apartment-house corridor.

Likewise, a second successful collaboration, the Schwartz & Gross partnership, was mirroring the feat, between East 92nd and 86th Streets on Park Avenue. This duo topped off those at East 93rd Street, atop Carnegie Hill’s summit, with their eighth collaboration: 1185 Park Avenue, a distinctive one-block wide, 1929 central-courtyard apartment house—the Upper East Side’s only. Even today, these two teams’ upper-Park Avenue and upper-Fifth Avenue pre-war apartment houses (at the time, the majority tenant-occupied), are among the Carnegie Hill’s most coveted co-operatively owned residences (increasing in value 500-fold over 70 years, perchance enhances their appeal).

In a decade incalculable 35-year-old multi-family dwellings were demolished, succumbing to this massive development phase. In addition, only four mansions avoided a wrecker’s ball. Every sumptuous mansion—especially an important location, such as at East 92nd Street, 1107 Fifth Avenue, which was a prime target. Here developers Rouse and Goldstone now began coaxing Marjorie Merriweather Post to vacate her family home in exchange for living on the 12th, 13th, and 14th floors of a new tony 1107 Fifth Avenue (where Jacob Ruppert built forty years prior). When the duo’s two powerful points—a penthouse placed above the traffic noise, congestion and soot, affording the city’s most-sought-after view, the reservoir—initially failed to motivate, Mrs. Post did acquiesce with caveats (agreed to begrudgingly for her lifetime), which granted the best of both worlds: Each major room was to be re-created (by proportion, every ceiling molding and wall décor and floor detailing); Two East 92nd Street was to remain her private, footman-attended, porte cochere (covered driveway, in the vernacular), accessing a reception room and private elevator, allowing Mrs. Post to graciously greet family and guests in the city’s ultimate mansion in the sky. (BTW: Each floor now conforms to those below, as a 15- and 14-room unit.)

It would be 20 years after Carnegie moved into his mansion before Highlands of New York saw its big building boom blast off, with intensity rarely witnessed. Lawrence Elliman, then an apartment house manager and rental broker for numerous important, Carnegie Hill buildings, noted in 1910: 10 percent of the city’s richest families live in an apartment, 90 percent in houses; interestingly, 20 years later, throughout Carnegie Hill, Elliman noted that, 10 percent live in single-family houses, 90 percent in apartment houses.

It is true that the same (or a similar) residential housing development scenario occurred all over town. Nowhere, however, as prevalent and as dense as within East 96th to 86th Streets and along the Fifth-to-Lexington-Avenue blocks, these pre-war luxury-apartment houses retain their allure and remain highly sought-after Upper East Side properties today.

Carnegie Hill Historic District

Designated in 1974—incorporated as an expanded historic district in 1998—initially, was far smaller and nowhere contiguous. Greater Carnegie Hill, though, comprises the blocks between East 98th and 86th Streets and stretches from Central Park to Third Avenue, where the land slopes to the East River. Along Fifth Avenue, Greater Carnegie Hill’s northernmost point (once Conservancy Garden, at East 105th Street), extends to East 110th Street, Central Park North. In the south, above the Metropolitan Museum of Art, on East 86th Street, the neighborhood end is punctuated by Neue Gallerie. This important avenue corner, landmark mansion, designed by Carrere and Hastings and completed in 1914, was commissioned by industrialist William Starr Miller, who occupied it only briefly; thereafter, whenever Mrs. Cornelius Vanderbilt III was “at home” and “receiving,” it was New York society’s epicenter and the seat of social power.

The Original Historic Districts consisted of row houses, by esteemed architects, builders, and developers. Curiously, with no Fifth Avenue building included, and they were, as follows:

        • The western portion consisted of noteworthy 1891-94 mid-Fifth-to-Madison-Avenues row houses with significant architectural details, such as stoops and bay windows, exemplified by 1-15 East 92nd, 1-23 East 93rd, and 1-25 East 94th Street.
        • Its eastern portion was a similar, even narrower 1885-1905 mid-block row-house run, exclusively between Madison and Park Avenues. Its southern edge, 55-65 East 90th Street, included the 1902 Carnegie garage designed by Whitefield & King—one of two garages built that year in the city, now the Horace Mann Nursery School—and three brownstone row houses. It continued north to include nine row houses, 53-69 East 91st Street, and three avenue row houses, 1290-94 Madison Avenue as well as 45-65 East 92nd Street.

The expanded Carnegie Hill Historic District now takes into account fine examples of every housing type. Its northwest boundary is Central Park’s rusticated half-wall at East 98th Street, where two sister apartment houses, with wrought-iron marquees, were built under co-operative ownership. From there, each Fifth Avenue building as well as Central Park’s Engineer’s Gate, at 90th Street, which leads to the Jacqueline Kennedy Onassis Reservoir, is included to East 86th Street. The eastern limit is ragged as—along Madison Avenue’s west side to 90th Street, straddling Park Avenue’s east side to East 91st Street, and occludes on Lexington Avenue and East 95th Street.

Highlighting the Historic District Dwelling Bounty

Starting at Fifth Avenue and East 86th Street, the boundary jags north after 9 East 86th Street, a neo-Federal town house, and cuts mid-block between Fifth and Madison Avenues to East 87th Street. Once again, at 11 East 87th Street, a 1920 apartment house, the historic district cuts to 10 East 88th Street, which includes a nine-story neo-Federal apartment house, 4 East 88th Street, and then again continues north at mid-block to 22 East 89th Street, at Madison Avenue’s southwest corner.

        • This 1890 landmark Graham Hotel, now Graham House, which was built by Tomas Graham as the Upper East Side’s first apartment hotel, is now a rental-apartment building owned by St. David’s, a well-respected private school.

Continuing, after that series of mid-block zigzags, along Madison Avenue to East 89th is:

        • Gaetan Ajello’s only Upper East Side innovative apartment house, a rare example of his work incorporating other than a glazed, white-brick and terra-cotta façade.

At East 90th Street, dominating the southeast corner is:

        • The landmark 1901 Beaux Arts building, 1261 Madison Avenue, a flats building designed by Buchman & Fox, with large windows and high ceilings, was an early attempt to rival a private home’s elegance.

Heading east on East 90th Street: the north mid-block was the original historic district’s southeastern limit. One block north on Park Avenue, just west in the mid-Madison-Avenue block is the original historic district eastern portion row houses. (On the northwest corner, note the 1938 Georgian-style Brick Presbyterian Church with its simple columns, classic pediment, and well-proportioned steeple, which was designed by Lewis Ayers of York & Sawyer to harmonize with the urban landscape. And it does!)

Heading east on East 91st Street: the north-side brownstone row houses are intact to Lexington Avenue, where the avenue’s west side becomes the district’s eastern border to East 95th Street. Meanwhile, a worthwhile aside is a mere two blocks continuing down Lexington Avenue. Hardenbergh/Rhinelander Historic District, 1340-50 Lexington Avenue and 121-23 East 89th Street, around the corner, comprising eight (two are lost) are designated landmark row houses.

These three-story black-and-buff brick, terra-cotta-trimmed, Romanesque revival row houses were built from 1886-89 for William C. Rhinelander—the speculative-real-estate builder, an important figure in late 19th-century Manhattan residential development. They were second-class, one-family dwellings, with highly creative designs and carefully matched dormers and balconies, symmetrical arches and doorways, and decorative medallions. Each house has an identical floor plan and a small west-facing rear garden.

        • A further aside across Lexington Avenue (though technically not within a historic district), 146-56 East 89th Street, are remarkable 1887 row houses, also a Rhinelander commission but designed by Hubert, Pirsson & Company. Each of the six 12-and-a-half-foot wide notable bijous is set apart and features early Victorian-era details: a Mansard roof, L-shaped plan, with brick oriel (simply put, bay window).

Returning northward on Lexington Avenue’s west side, at East 91st Street note 1380-82 Lexington Avenue with intact coal bins under their stoops. The historic district dwelling highlights pick up at East 95th Street, where uphill to Park Avenue, once known as Goat Path, are:

        • Queen Anne 1887-92 bow-window-fronted row houses, with stoop heights to accommodate the slope, were built by one group, French & Co., Louis Entzer and Frank Wennemer, as harmonious homes, the largest such development effort on the east side.

From Park Avenue’s northeast corner looking across at 1220 Park Avenue, the Carnegie Hill Historic District excludes this quintessential Rosario Candela, upper-Park Avenue luxury apartment house completed in 1930. A carefully-thought-through family apartment house design, it includes several ground-floor, duplex variations with a private entrance (called, with good reason, Maisonette—a small house).

The 13-room corner apartment, for example, includes:

        • A well-proportioned living room, with a wood-burning fireplace;
        • A library, with a wood-burning fireplace;
        • A 22-by-16 foot dining room;
        • Four large master bedrooms;
        • Three master baths—one bath is also accessed through the library;
        • An oversized kitchen and pantry;
        • A servant’s hall with three small chambers and two baths.

Continuing south on Park Avenue are:

        • East 95th Street, 1217 Park Avenue, a restored 1899 town with an attached garage—converted from a carriage house;
        • East 94th to 93rd Street, 1185 Park Avenue, a block-front apartment house with a triple-arched, ogee-shaped port cochere leading to its unique interior courtyard;
        • East 93rd Street, Carnegie Hill’s geographical highest point, during the early 1800s, the city’s first public country retreat, Prospect Hall, previously an indigenous American village;
        • The northwest corner, a Delano and Aldrich landmark mansion complex, built with a ballroom wing, garage annex, and suitable town house for Mr. George Baker Sr.—since 1954, this is the Synod of Orthodox Bishops Outside Russia’s official headquarters.

Heading west on East 93rd Street, are:

        • Number 56, designed by Walker & Gillette and completed in 1930, as an 80-footer built for Mrs. William G. Lowe (nee Baker)—so she would reside nearby the corner, four-building Baker complex.
        • 1321 Madison Avenue, on the northeast corner, is an avenue row house built for James V.S. Woolley, the prominent real-estate developer, was designed by James E. Ware and completed in 1891, as a one-of-a-kind landmark Queen Anne home.
        • East 93rd and 94th Streets, across the avenue, along both the north and south sides in the Madison-to-Fifth-Avenues mid-block, are the original historic district’s western portion row houses.

Continuing north on Madison Avenue, are:

        • An early flats-building example, 19 East 95th Street, on Madison Avenue was completed in 1900.
        • Immediately north, 1378 and 1379 Madison Avenue, equal French Flats buildings, were built with shops along Madison Avenue.

Heading due west is:

  • The mid-block, landmark, town house, 15 East 96th, designed by Ogden Codman Jr. as the Dahlgren town house which established the city’s social boundary as East 96th Street. And when her time came, Mrs. Dahlgren’s home was sold to Pierre Cartier as his New York residence—since 1915 this has continuously remained the only privately owned residence in the historic district.

Two blocks north, are:

  • At East 98th Street, 1160 and 1170 Fifth Avenue, built as a pair by the Carpenter-Compagna team;
  • And Two East 98th Street, a Carnegie Hill perennial, St. Bernard’s School, is the expanded Carnegie Hill Historic District’s northwest boundary.

Continuing south, upper Fifth Avenue to East 86th Street is a seven-block, luxury-apartment-house corridor, interspersed with four landmark mansions:

  • First, the imposing Dorothy Payne Whitney Straight Federal-style Fifth Avenue mansion at East 94th Street, once the Audubon Society headquarters, then International Photography Center, again, is a hedge-fund owner’s private residence.
  • Second, the French Renaissance Warburg mansion, at East 92nd Street, is the Jewish Museum.
  • Third, on East 91st Street’s northeast corner, built in the Italian renaissance style and completed in 1918, for Otto Kahn, along with his daughter’s town house annex is Convent of the Sacred Heart School.
  • Fourth, Andrew and Louise Carnegie’s 1902 (country-style) Georgian mansion, between East 90th and 91st Streets, is the Smithsonian Institution/Cooper-Hewitt, National Design Museum, and as a coincidental parallel: Nine East 90th Street, the wedding gift Andrew Carnegie bequeathed to his daughter, Margaret, known as McAlpin-Miller House—abutting, no, within his East 90th Street garden—designed by George Keister and completed in 1903, houses the institution’s offices.

The Carnegie Hill Historic District continues down upper Fifth Avenue for four more blocks, passing two remarkable (non-residential) edifices:

  • The Gothic Revival cum Art Moderne Church of the Heavenly Rest, at East 90th Street, a Louise Carnegie gift;
  • And Frank Lloyd Wright’s sole New York City landmark, encompassing the Fifth Avenue block front of East 89th to 88th Streets, Solomon R. Guggenheim Museum.

The remaining dwelling type examples are:

  • Ten-Eighty-Three Fifth Avenue—National Academy Museum and School (of Fine Arts), located south of East 90th Street, the Anna and Archer Huntington mansion.
  • Ten-Eighty Fifth Avenue—an archetypal white-brick, set-back, post-war example, on East 89th Street.
  • Ten-Sixty-Seven Fifth Avenue, mid-block between 88th and 87th Street—a 1916 French Gothic apartment house, designed by C.P.H. Gilbert, where Leopold Stokowski lived with Lucie Hickenlooper from 1911-23, and where they were often seen watching passers-by from the library window, which overlooked Central Park.
  • Ten-Sixty Fifth Avenue, at East 87th Street—the pinnacle of ultra-deluxe, a (1924) John Carpenter-designed apartment house.
  • The East 87th-to-86th-Streets block front—are two quintessential, cream-colored-brick, post-war examples, some units with projected balconies.

The expanded Carnegie Hill Historic District encloses at East 86th Street, where Mrs. Cornelius Vanderbilt III held court. Here ends Carnegie Hill’s dwelling types, and begins Lenox Hill’s housing development, which is another story.

Metropolitan Museum of Art Historic District

With Fifth then Madison Avenues open and Central Park established, some adjacent landholders were already selling their subdivided lots. Then, within Central Park a world-class Metropolitan Museum of Art—incorporated in 1870.as a cultural institution housing masterpieces—opening, in 1880, was an instantaneous magnet for speculators who proceeded to acquire lots nearby. The Metropolitan Museum of Art district is but one enclave within Lenox Hill, which continues to East 70th Streets, encompassing Fifth Avenue and the Lexington-to-Third-Avenues block. The tracts spanning East 86th to 70th Street, from Fifth to Park Avenues (though not perpendicular to the parkland), were held by a handful of individuals:

  • East 86th to 83rd Streets, George McKay;
  • East 83rd to 79th Streets, John P. Schermerhorn;
  • East 79th to 78th Streets, Richard Lee;
  • East 78th to 76th Streets, Martin Hoffman.
  • Adjacent to the south, the Lenox Hill landholders included:
  • East 76th to 74th Streets Henry Post;
  • East 74th to 68th Streets, Robert Lenox.

These owners held their property as an investment; they were not necessarily occupied. Robert Lenox’s residence until his death, for example, remained at 12th Street, on Fifth Avenue; this landholding, purchased from the bankrupt Gracie estate, was leased to tenant farmers. Moreover, third-generation, landed aristocracy intermarriages amalgamated tracts. For instance—a major West Side landowner, Yellis [Yelless] Hopper, married Elizabeth Waldron and thereafter live with his father-in-law Benjamin in the original, William Waldron, stone farmhouse and gardens, at East 86th and Second Avenue.

It wasn’t long (several trades, bearing in mind the Civil War and Panic of 1873 uncertainties) before swank residences: mansions and town houses, without an insignificant row house among them, were built up on the adjacent blocks.

For example, and to pinpoint those remaining on Fifth Avenue:

  • At the museum’s north, on East 84th Street, are three turn-of-the-century Beaux-Arts town houses, built for the Vanderbilt, Pratt, and Milbank families.
  • Opposite the museum entrance steps, on East 82nd Street, is the Seman-Duke town house, another important corner Beaux-Arts residence.

Perhaps, East 79th to 78th Streets, immediately south and speculatively developed by Henry Cook who controlled each lot in the Fifth-to-Madison-Avenue adjoining streets as well, best epitomizes the district: it is both impressive and intact.

  • At East 79th Street, on Fifth Avenue’s southeast corner, stands the 1899 French Renaissance, limestone mansion (better put, palace), build by C.P.H. Gilbert, for Isaac D. Fletcher.
  • Soon purchased by Harry F. Sinclair—the oil robber baron,
  • Then owned by Augustus Van Horn Stuyvesant—a venerable, Colonial-era scion.
  • Mid-block, at the immediate south, are Stanford White-designed, palazzo-style, Italian Renaissance, limestone town houses, built for Coronel Oliver Payne and Payne Whitney, his nephew, and were completed in 1909.
  • The northeast corner of East 78th Street is a free-standing 1909 Horace Trumbauer-designed, quasi-French Renaissance and neo-Classic, limestone mansion. While in residence awaiting a buyer, Mr. Cook referred to his “home” as One East Seventy-Eighth Street, believing that to be more understated—and in better keeping with his modesty—than a Fifth Avenue address sold eventually to James B. Duke—the American Tobacco Duke, father of Doris Duke

(1870)
The nation’s wealthiest-of-the-wealthy aristocrats acquired (from overextended and underfinanced real-estate speculators) the important Fifth Avenue parcel for their new palatial residences. Meanwhile, the adjacent block lots were trading—largely by the same speculators—to Manhattan’s (mere) upper-crust for their new opulent town houses. Likewise, these lots were to be designed by as remarkable architects as their grand counterparts opposite Central Park.

It had all begun at Central Park’s inception. Wholesale land speculation along Fifth Avenue quickly ensued; as park construction started, real estate prices soared. Simultaneously, a financial panic was brewing, and the economy rebounded only shortly after the park’s competition. Substantial land speculators were wiped out. The Civil War building material shortages, then, curbed extensive housing development throughout its duration. Amidst growing post-Civil War commercialization, the ample (30-acre), low East Seventies, tenant farm inherited by James Lenox was sold as standard 25-by-100-foot lots. Likewise, the neighboring Fourth to Third Avenues farmland and estates, running on a sharp southeast diagonal, were undergoing a similar subdivision, which involved:

  • East 84th to 81st Streets, the heirs of Edward Dunscomb;
  • East 81st and 79th Streets, the Sherman family;
  • East 79th and 77th Streets, John Robison;
  • East 77th and 75th Streets, John N. Grenzebach;
  • East 75th and 71st Streets, Nichols Governeur;
  • East 71st and 69th Streets, Martin Hoffman.

Lenox Hill

As the mid-1840s foreign immigration explosions flooded the city’s southern portions, also, in kind, each wave boosted residential housing’s march farther uptown. The Lenox farm blocks began to be sold 20 years later, and were built up with brick town houses in neo-Greco, Queen Anne, Romanesque Revival or suchlike styles. When the first post-Civil War, cyclical financial panic turned into a severe five year economic downturn, land prices plummeted once again. Though for some the “Gilded Age” was just revving up, and lot assemblage for mansion-building ensued on Fifth Avenue, an then Mrs. Caroline Schermerhorn Astor, with her extensive social circle, took up residency, The Avenue’s park-side portion was poised to live up to its destiny: a mansion row. After the financial turmoil resolved itself, and coupled with the delayed but imminent IRT Third and Second Third Avenue El lines arrival, speculative real estate-investment interest renewed throughout the Upper East Side’s western portion.

The area to Madison Avenue‘s east underwent significant development too: especially coveted were the lots encompassing East 78th to 70th Streets, in the blocks west of Third Avenue—nearby the James Lenox landholdings. So, along with mansions and town houses between Fifth and Park Avenues, there remain numerous, architecturally-significant, row house blocks throughout the East Seventies—for example, Henry Armstrong’s 1861 red-brick row homes, 157-165 East 78th Street, between Lexington and Third Avenues; as well as an 1861-65 row house strip, of which six out of the original sixteen have survived, on East 78th Street, east of Third Avenue.

A further glimpse as to the Upper East Side lifestyle 135 years ago, is afforded by the 19th-century carriage-house rows along both north and south sides of East 73rd Street, in the Lexington-to-Third-Avenue blocks. A smattering of equally unique stables are on East 74th and 75th Streets, east of Third Avenue as well as two striking carriage houses, on East 77th Street, in the Park-to-Madison Avenue block. On East 69th Street’s north side, east of Lexington Avenue, there is an additional surviving row whose owners occupied the lavish brownstone town houses on East 70th Street. These two-story buildings permitted the main houses’ major rooms—the living room and master bedroom, in particular—to be south-facing, allowing ample sunlight for the garden separating them, beside by setback from the street they buffered passing horse-drawn carriage wheel noise against the cobblestones as well as the inevitable odor.

By this time, almost every Fifth Avenue lot above East 61st Street was a private mansion—with a few private clubs sprinkled about. Then, Frick’s limestone home was erected on the former Lenox Library site, comprising the East 71st-to-70th-Street block along Fifth Avenue (though purchased in 1906, it was completed in 1914). Without a doubt, though, this free-standing home was the most imposing. Its opulent private gardens, both along Fifth Avenue and at its eastern courtyard—literally—set it apart. There was nothing quite like it until one mile north, except ex-partner (now rival), Carnegie’s mansion at East 91st Street.

However, even as architects Carrere and Hastings designed Henry Clay Frick’s French-inspired palace, the mansion- and town house-building era was coming to a close. Changes were in the air: the opulent mansions would be razed to make way for a slew of deluxe, grand-scale apartment houses. Their development evolved slowly after Fourth Avenue was renamed Park Avenue—but only when Vanderbilt’s prolonged inaction ended 20- years later. Once his New York Central’s Railroad tracks along Park Avenue were submerged completely, eliminating nuisance conditions, and once the through streets were covered by bridges, with the corner traffic signals installed—an apartment house explosion was inevitable (As was the creation of a dedicated accompanying neighborhood improvement alliance, and niceties did ensue.)

So with the avenue’s signature planted malls installed, and with continually modern technology updating the noise and vibration insulation, this was poised to be a prime multiple-family residential address: the Upper East Side had its second imposing boulevard. But: the panic of 1893 (second only to the Great Depression), reeked financial havoc for four years, consequentially, razing the corner Park Avenue mansions and avenue-facing town house rows as well as neighboring streets was staved off, temporarily.

(1900-35)
While initially few Lenox Hill single-family dwelling blocks were destroyed, desire and willingness to pay a premium price continually outpaced the new supply, which escalated land values, furthermore. With the 16th amendment ratified and the Revenue Act of 1913 implementation, Lenox Hill’s single-family-dwelling construction came to a standstill. Contrariwise, the unrelenting social pressure to reside in prime Lenox Hill locations precipitated the ongoing quest for apartment house building sites; soon enough, eight-story, multiple-family buildings took hold of the (side) streets to Lexington Avenue. One by one leading up to the Great Depression, the demand was so acute potential tenants were wait-listed all over the East Seventies.

(1937-50)
Bad times hit hard at most Manhattan neighborhoods, which escalated demand within safe havens such as Lenox Hill. World War II, then, cut short the budding city-wide post-Great Depression, luxury-apartment-house-construction revival for years: worse, a housing shortage ensued. When luxury apartment-house building renewed, East 75th to 71st Streets, Fifth Avenue in Lenox Hill, with exponentially intensive pent-up demand, was developed rapidly: So, interspersed among the statuesque pre-war co-operative are four 21-story, light (definitively not red) brick, post-war apartment houses—Nos. 930, 923, 910, and 900 Fifth Avenues. Park Avenue, having been voraciously built out throughout Lenox Hill allowed only one full-block and four half-block post-war apartment houses. That pattern continued beyond Lenox Hill, throughout the Sociable Sixties.

The Sociable Sixties

Although residential housing types in the East Sixties does not differ substantially from its northern neighbor, telling is that within close proximity are Manhattan’s most prestigious social clubhouses, which underscore a very social nature. The remarkable red-brick, neo-Georgian edifices, designed by Delano & Aldrich, are:

    • Union Club of New York, at East 69th Street, on Park Avenue, was built in 1933.
    • Colony Club, at East 62nd Street, on Park Avenue, was erected in 1916.
    • Knickerbocker Club, at East 62nd Street, on Fifth Avenue, was completed in 1913.

Equally noteworthy are:

      • Metropolitan Club, at East 60th Street, on Fifth Avenue, was designed by McKim, Meade, and White and completed in 1894, for Cornelius and William Vanderbilt, James Roosevelt, Louis L. Lorrilard, J.P. Morgan and their friends.
      • Harmonie Club, Four East 60th Street, off Fifth Avenue, was designed by Stanford White and occupied in 1905, for a decidedly German-Jewish membership.

Additional significant East Sixties clubhouses though social clubs too were thematic-inspired, and they are:

        • Cosmopolitan Club, 122 East 66th Street, at the Park-to-Lexington-Avenue mid-block, was established in 1909, as the first women’s club to include a spa.
        • Lotos Club, Five East 66th Street, off Fifth Avenue, whose credo espouses to expand an appreciation of literature, art, sculpture, music, architecture, journalism, drama, science, and education, appropriately, is housed in a 1900 Beaux-Arts town house.
        • Explorers Club, East 70th Street, off Park Avenue, was completed in 1904, for the adventuresome minded.
        • Asia House, East 64 th Street, off Park Avenue, was designed by Philip Johnson and completed in 1959.

(1865-99)
After the Civil War, East 68th to 66th Streets and comprising Fifth to Third Avenues was a Corporation of the City of New York controlled parcel (specified as Hamilton Square), surrounding Central Park the East Sixties, for the most part too, were primarily open lands, as:

        • East 65th and 64th Streets, the George Grosman tract;
        • East 64th to 62nd Streets, the Peter P. Van Zandt lots;
        • East 62nd to 59th Streets, the heirs of Hugh Gaine.

Even beyond, the Fourth-to-Third-Avenues blocks were vast expanses, dotted with a few homes and their out buildings, as:

        • East 65th to 63rd Streets, a Beekman family holding;
        • East 64th to 60th Streets, Tredwell & Thorn farmlands;
        • East 60th to 59th Streets, the Cheeseborough estate.

When Hunter College moved to East 68th and 69th Streets and Lexington Avenue, its Gothic Thomas Hunter Hall stood alone as the only major structure nearby. Six years later and one-block south, between East 67th and 66th Streets and comprising the entire Lexington-to-Park-Avenue block, the 1880 Seventh Regiment Armory, designed by Charles Clinton, made its presence known. The armory, in many ways, operated as though it were a private club, and instantly was praised for its interior rooms’ ornamental woodwork and marble detailing, with stained glass by Louis B. Tiffany.

Having some effect on the immediate area’s desirability, neither the college nor armory caused their surrounding block lots’ high demand, added to their rapid sale, or aroused instantaneous development. It was not the Third Avenue El opening either—although that did encourage limited nearby speculative row-house building. Although it is true, no doubt, that none of the above were detrimental: The town house construction phenomenon, in fact, was a direct result of the ongoing “Gilded Age” mansion-building due west on Fifth Avenue.

This half-mile was epicenter for Manhattan’s crème-de-la-crème, and Central Park was the “four hundred families” front yard. The ten-block Fifth Avenue span, which began with the Phipps-Dodge mansion on East 61st Street (incidentally, the last Fifth Avenue mansion to be demolished, in the 1960s), ended at the rival Astor sisters-in-laws’ mansions, on East 69th Street—with nothing shabby in between. Not mere mansions, in reality, each was a palace, designed by New York’s preeminent architects and built for the likes of the Vanderbilt patriarch, son, and grandsons; the Plants, whose neo-Renaissance-style residence, designed by C. P. H. Gilbert, set the standard for ensuing mansions and town houses, as well as the Marquands, Burdens, De Lamar, Depew, Fish (represented by several branches), Havemeyer, Kip, Livingston, Schuyler, Sloane, and Van Renssealer families. Society’s enthusiasm to live in the East Sixties spilled all the way to Third Avenue. Although each and every palace or mansion along Fifth Avenue has been demolished, the exceptional town house blocks—off Fifth and extending to Third Avenue, for instance, East 65th to 61st Street, in the Madison-to-Third-Avenues blocks—are intact.

Moreover farther southeast, a renewed interest advanced for the Tredwell & Thorne farm rows, which once dominated Fourth to Second Avenue. For 50 years, the Tredwell family had farmed their East 61st to 62nd Streets portion, the mid-Third-to-Second: post-Civil War, no longer farmed, the heirs sold their undeveloped lots, by Covenant, to be built as modest, four-story, row houses. Twenty years later, now being adjacent to the supra-prime East Sixties drew in Tredwell Farm row houses: updated, the façade revamped and interior refurbished, they traded at a (remarkably) handsome multiple of their 1870s asking price.

Yorkville

With west boundary set as Second Avenue and bounded by the East River, Yorkville now spans the low East Nineties to East 60th Streets and, the riverfront usage varies, to be:

        • East 90th to 79th Streets, the East End Avenue enclave;
        • East 71st to 68th Streets, a healthcare facility swath;
        • East 68th to 63rd Streets comprises the Rockefeller University campus.

The southeastern extremity gradually expanded since Third to Second Avenues was Irishtown; East 86th Street was Germantown’s boulevard; and East 79th Street was the Hungarian grand promenade—all within one working-class neighborhood. Then, as vibrant Czech, Slovak, Albanian, and Polish communities grew, each ethnic group claim-staked gradually as far south as East 59th Street, Ed Koch Queensboro Bridge. Nevertheless, little of that early 20th-century culturally diverse, melting pot remains.

(Colonial Era)
For Native people the northern portion of this outwash plain, near to the river’s loom was cultivated as their veritable breadbasket—and highly prized because it was said the strawberries grew so thick you could lie down and eat them. The surrounding high grasses were a hunting ground. Furthermore, the Konaande Kongh village path from the highlands delivered access to the East River cove oyster and clam beds.

Dutch Colonial demand for the island’s timber—to mill and ship back to Holland—lead to a series of Saw-Kills along the East River. For the most part, the farmland was a vast vegetable garden, traversed by the Boston Post Road and a minimal waterfront district, consisting of tanneries, piano factories, stables, breweries and suchlike commerce. (The preponderance of breweries was convenience delivering produce to taverns along the river.) Cornelius Vanderbilt’s 1837 New York and Harlem Railroad brought additional purveyors at the Upper East Side East 86th Street station, on Lexington Avenue.

(1820-50)
One after another the private villas, estates, and rustic country homes overlooking the East River vanished. Before the mid-19th-century mark, in fact, the small farm tracts were gone—the notable country estate tract exceptions, from north to south, were as follows:

In the East Nineties along the riverbank, the estates included:

        • East 92nd to 91st Streets, William Rhinelander, stretching to East 86th Street and touching Second Avenue;
        • East 91st to 89th Streets, Nathaniel Prime;
        • East 89th Street (a spit only), John Jacob Astor;
        • East 89 and 85th Street, along the riverbank, Archibald Grace.

In the East Eighties:

        • East 86th to 84th Streets (Second Avenue to the East River), Isaac Chauncey;
        • East 85th to 83rd Streets (to Avenue A), Yellis Hopper;
        • East 82nd Street (at the East River), Peter Schermerhorn, four-plus acres were purchased in 1806;
        • East 83rd to 80th Streets (Second Avenue to the East River), Joshua Jones.

In the East Seventies:

  • East 81st to 77th Streets (Third to Second Avenues), The Corporation of the City of New York;
  • East 80th to 77th Streets (Second Avenue to the East River), John Asten;
  • East 79th to 78th and East 77th to 76th Streets (Third to Second Avenue), John Wilkes;
  • East 77th to 76th Streets (Second Avenue to the East River) ,the Lawrence family;
  • East 76th to 75th Streets (Second to the East River), Richard Riker.
  • East 75th to 66th Streets, which was Louvre Farms, John Jones. Peter and Sarah (nee Jones) Schermerhorn built a riverside summer villa at East 67th Street, his wife’s inheritance included the 132 tract. In addition, Peter Shermerhorn purchased the neighboring 20-acre, Hardenbrook Farm, spanning East 66th to 64th Streets and Third Avenue to the East River. The entirety, one-half-mile square, was named Belmont Farms.

In the East Sixties:

  • The heirs of Peter Van Zandt as East 66th to 64th Streets (to Avenue A);
  • The Beekman family as East 64th to 61st Streets (Fourth Avenue to the East River).

Before the 19th-century’s final days, one after another the private domains vanished. Peter Schermerhorn’s heirs had sued, and prevailed. The reversal of the State of New York’s eminent domain edict to become the Central Park site, put the farm’s improvement back in their hands, and they too were clearing their northernmost Louvre Farm lots. (The southwestern-most commercial tracts near along Third Avenue were leased—according to Astor’s principle, “let other’s money improve my properties”—as an amusement park (of sorts), sports fields, picnic area, and public beer garden, which attracted the working-classes.) Besides Gracie’s mansion, one other post-Revolutionary War structure, though a minor one, remains on East 60th Street, off York Avenue. This 1799 carriage house, contiguous to the estate of Colonel William Stephens Smith and his wife, Abigail Adams Smith, daughter of President John Adams, was the sole standing structure when the main house burned to the ground. Briefly, an inn for New Yorkers escaping overcrowded Lower Manhattan, and then, the fieldstone structure became home to one family for three generations.

(Late 1800s)
With the 1878 IRT Third Avenue Elevated Railroad opening (followed two years later by its Second Avenue sister line), the mass transportation link from Upper to Lower Manhattan was complete. Simultaneously, William C. Rhinelander’s heirs aggressively set about a dwelling construction program. The first, at a prominent Yorkville corner plot, on East 86th Street and Second Avenue, conveniently located near to the Second and Third Avenue E l lines. The Manhattan, as it was named—little more than a red-brick box, without decorative details—was designed by George Clinton, seemingly alike his lauded Seventh Armory, and likewise completed in 1880. This is the oldest-known (and surviving) apartment house. A precursor, Stuyvesant Apartments, also along a flats-building design, was razed in the 1930s; both bridged existing working-class tenement apartment houses and the upcoming luxury apartment house. The Manhattan was built one year before the Windemere Apartments, at 400 West 57th Street, the first with an elevator, and four years prior to the Dakota Apartments, at 1 West 72d Street. Even so and more importantly, the overhead tracks would cement the divide—physically and psychologically and materially—between the river-edge modest neighborhoods and its genteel western counterparts: Carnegie and Lenox Hills and the Sociable Sixties.

For twenty years, until banned by the New York State Tenement House Act of 1901, the half-mile-by-two-mile plain (East 100th to 60th Streets, Second to East End Avenue, which is Avenue B actually) was built-out as adjoining slum blocks…one followed by another…then another…and another. Since, these run-down, overcrowded, immigrant-occupied, tenement apartment houses have been upgraded, gut-renovated, or reconfigured and combined as small apartment buildings. Post-World War Two, many more were demolished to make way for—architecturally-speaking, somewhat equally insignificant—rental apartment-house towers, which have come to dominate York, First, and Second Avenues.

Experimental Working-Class Housing

(Early 20th-Century)
Three Progressive-era housing efforts of note are on York Avenue, in the progressives’ backyard, so to speak. The first at East 65th and 66th Streets still seem especially groundbreaking, though tenement-like. It bridges innovative apartment houses, too, by consisting of two H-shaped, six-story wings. The north and south parts are connected by the continuous York Avenue façade and a rear broken façade, creating an open-sided rear courtyard. Four setback exterior planted courts lead to red-brick archway entries with wrought-iron detailing. Other improvements distinguish embraced early apartment house concepts, such as somewhat generous room sizes, and oversized, six-over-six windows, allowing ample light and air, swapped for the customary, narrow, ventilation airshafts. (The H-shaped design, later reproduced throughout New York City, proved uneconomic to heat with so many exterior walls.)

A second, philanthropic-supported complex is quite unique too. The Cherokee Place Apartments, between East 77th and 78th Streets, at York Avenue’s east are adjacent to John Jay Park. The cluster was designed by Henry Atterbury Smith as four cream-color brick, six-story, walkup, tenement apartment houses intended for 448 care-taking families with members carrying tuberculosis. They include glazed-brick and stone, vaulted archway entries, leading to one interior court; its four wings are separated by one 25-foot- and two 16-foot-wide alleyways, providing additional light and ventilation. For public housing their construction was an unheard-of quality, incorporating unprecedented aesthetic integrity, such as slim ironwork balconies serving as awnings partially shielding triple-hung, floor-to-ceiling windows; furthermore, the east-facing units enjoy river views.

City and Suburban Houses, the third compound, was designed by tenement-housing innovator James E. Ware, in collaboration with Philip H. Ohm, and built in stages. The first phase between East 65th and 64th Streets (referred to as Avenue A “estates,” though clearly not) was then repeated, with slight design variations, on East 79th and 78th Streets, encompassing the entire York-Avenue-to-the-East-River block, at Nos. 516-520 and 524-528, 530-534 and 536-540 East 79th Street as well as 541-555 East 78th Street, which included river-facing sleeping porches as rooftop pergolas. Additionally, Nos. 503-509 East 78th Street and Nos. 504-508 East 79th Street is U-shaped that forms a courtyard to take advantage of the light. The series’ investors led by the unassailable, “Granny Vanderbilt herself, voluntarily limit their profits in order to provide “wage-earners” safe and hygienic, comfortable and well-maintained housing at affordable rents.

An East End Enclave Emerges

To the immediate north, across East 79th Street and running to East 90th Street, is Yorkville’s easternmost protuberance into the East River. Therefore, briefly, an Avenue B appears. East End Avenue is a mishmash of post- and pre-war apartment houses—many with a spectacular river view—as well as an exceptional and compact, 1882 single-family-dwelling block, designed by Lamb & Rich. Sited between East 86th and 87th Streets, with six additional mid-block cul-de-sac entrances, these 24 red-brick, Queen Anne-style row houses constitute the entire Henderson Place Historic District, which is opposite Carl Schurz Park, the area’s centerpiece.

The narrow six-block long rectangular park named after a politician and newspaper editor has a formal entrance at East 86th Street, a playground at East 84th Street, and a broad esplanade following the riverbank. The park’s northern section contains the sole Federal-era villa overlooking the East River, Gracie Mansion, which is now the official residence of New York City’s mayor. The original two-story, Federal style house, built for Archibald Gracie, was designed by the architect of New York City Hall, John McComb Jr., according to plans by Ezra Weeks, a prominent builder. It has undergone several updates in order to be the New York City venue for official functions.

As the western and southern Upper East Side building lot values escalated—beyond the means of even Manhattan’s wealthier families—the northeastern-most blocks on and nearby undeveloped East End Avenue became attractive as row house sites. They were suddenly speculatively developed. At the southern park front, along East 84th Street to the river are: One, Seven, and Ten Gracie Square—each a highly regarded, distinctive, pre-war apartment house rivaling those on the best Upper East Side Avenues.

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