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Circa 1903. Circa 1903.
On occasion, diagonal streets such as Broadway slice across New York’s rectilinear street grid creating opportunities for wedge-shaped buildings that seem to sail onto the streetscape with the grace and grandeur of an ocean liner. The Flatiron Building on Madison Square Park is easily the most iconic of the type, yet a century-plus years after the Flatiron rose at Madison Square, scores of acute-angled buildings stand in all boroughs of the city, with more still on the drawing boards.
A visit to the Flatiron Building today may cause a bit of consternation as its ornate terra-cotta facade has been shrouded in scaffolding and construction netting for more than a year. The landmarked 1902 structure, built by the Fuller Company and owned by the Sorgente Group of America is undergoing a $50 million, top-to-bottom 'sustainable' renovation expected to wrap up in 2022.

According to NY1, hundreds of decayed terra cotta pieces are being replaced and window AC units have been removed. There have also been rumors of exterior architectural lighting being added to shapely landmark. Once a hub for book publishers, its nearly-vacant 22 stories will continue its use as offices with ground-floor retail. Interior renovations will bring central air conditioning, a new sprinkler system, upgraded elevators, and a redone lobby. With climate change a front-and-center issue, and buildings topping greenhouse gas emissions, the Flatiron's new sustainable features will include a 21st century HVAC system, rooftop solar panels, and rain reclamation tanks.

22 floors | 1902 | Office

Flatiron placeholder The ften imitated but never duplicated Flatiron Building
Even in the 21st century, few buildings in New York are as iconic and instantly recognizable as the Flatiron, but in 1902, it was a game-changer. The 21-story edifice was designed by Daniel Burnham, the tour-de-force Chicago architect that rose to global fame for his leading role in Chicago’s 1893 Columbian Exposition who once proclaimed: “make no little plans; they have no magic to stir men's blood.”

True to form, the 285-foot edifice at the junction of Fifth Avenue and Broadway was one of the city’s tallest buildings and easily the most dramatic. The structure was at once imposing and graceful, classical and daring, where the ornate opulence of the Beaux-Arts facade was matched by the sheer innovation of the slender steel frame beneath.

Originally known as the Fuller Building, named after its developer-builder, the building’s kinship to a certain household appliance quickly earned it the “Flatiron” moniker, which, in time, extended to define the entire neighborhood south of Madison Square, as well as its spiritual successors around the world, including every “flatiron” listed below.

25 floors | 1904 | Retail, advertisement

Shorpy Manhattan circa 1908.
One Times Square is New York’s great architectural paradox, as it is one of the world’s most famous and exposed buildings that simultaneously stays all but anonymous. Upon its 1904 completion, the stepped wedge stood as the city’s third-tallest building and housed the new headquarters for the New York Times. Though the publisher moved out of the cramped quarters less than a decade later, its name has firmly stuck former Longacre Square, and its tradition of the “ball drop,” originally staged as a promotional stunt for the new building on December 31st, 1903, endures to this day as arguably the most famous New Year’s Eve celebration on Earth.

Despite its starring role at the Crossroads of the World, the building itself maintains a remarkably low profile. In the mid-1960’s, its opulent granite and terra-cotta facade was stripped and “upgraded” with a shabby Modernist makeover, which has since been mostly obstructed by a tapestry of flashing advertisements. Aside from lower-floor retail, the building remains mostly unoccupied, becoming a massive billboard anchoring the country's most popular tourist destination.

A few years ago, plans surfaced for a retrofit that would introduce a Times Square museum and an observatory to the storied building, though little progress has been made on the project since.

38 floors | 133 units | 2021 | Condominium

One-Clinton-03 Rendering of One Clinton courtesy of Marvel Architcts
One Clinton stands at the junction of Clinton Street and Cadman Plaza West, where Downtown Brooklyn meets Brooklyn Heights. The crisp limestone façade soars 38 stories high; neatly-framed, floor-to-ceiling windows that offer observatory-like panoramas thanks to the building’s considerable height, prominent hilltop perch, and exposed location between Cadman Plaza Park and tree-lined brownstone blocks of Brooklyn Heights.

One of Brooklyn’s top-billed condo projects, One Clinton offers apartments with hardwood floors, marble countertops and islands in kitchens, and master bathrooms with soaking tubs, walk-in showers, radiant floor heating and wood and marble finishes. Amenities include a 24-hour attended lobby, a bar-equipped Sky Lounge, a landscaped terrace with grilling stations, a children’s play space with indoor and outdoor areas, a sound-attenuated screening room, a music rehearsal area, a study, and a fitness center with a hot tub, sauna, and yoga studio. One Clinton also offers bike storage, garage parking, a laundry room, and private storage units available for purchase.

From the Listing: Residence 28A at One Clinton is a 2,308sf four-bedroom, three-and-a-half bath home facing north, east and west. Commanding views across New York Harbor, Manhattan and Cadman Plaza Park are framed by nineteen 8-foot windows. Arrive to a lovely foyer with powder room leading to a pillarless, 26-foot living space with open kitchen. Anchoring the western wing of the home is a main bedroom suite complete with a windowed, five-fixture marble clad bath and walk-in-closet. On the opposing end of the apartment you'll find three generously scaled bedrooms and two beautifully appointed full baths. See floor plan and full details here.

15 floors | 126 units | 1904 | Condominium

Cocoa Exchange, which boasts one of the city's finest-looking curves and tastiest-sounding names, marks the convergence of Pearl and Beaver Streets within Downtown’s angled street grid that dates back to the old Dutch days of New Amsterdam. The narrow, triangular building with a rounded, drum-like prow and an ornate, polychromatic pinnacle was built in 1904 and once served as the headquarters for the New York Cocoa Exchange.

More recently, the building gained exposure as the fictional Continental Hotel in the 2019 blockbuster John Wick 3. To potential residents, however, the landmark may be notable for its cozy common areas, fitness center, and a landscaped roof deck that allows for sunbathing whenever the sun passes between the surrounding skyscrapers.

From the Listing: Make your home in the heart of the historic Financial District in this spectacular alcove studio condominium featuring excellent amenities and East River sunrise views.

Thanks to bright east-facing windows, this spectacular studio delivers excellent natural light, a glimpse of the river and an airy ambiance underscored by soaring ceilings. Hardwood floors pave the main living space, providing a generous footprint for sleeping and seating areas. The tiled kitchen dazzles with walnut cabinetry, granite counters and wonderful stainless appliances, including a gas range, dishwasher and built-in microwave. Relax in the spa bathroom featuring decadent floor-to-ceiling marble, a large tub/shower and contemporary fixtures. An extra-large walk-in closet ensures storage will never be a concern in this impeccable Downtown home.
See floor plan and full details here.

37 floors | 476 units | 1928 | Rental

63 Wall Street 63 Wall Street
Across from Cocoa Exchange rises another, much larger “flatiron” that takes up a whole block. The Crest combines two adjacent pre-war office buildings, each angled on one side, creating a massive, 476-unit rental complex with a grand chandelier lounge, a marble-clad elevator lobby, a fitness center, a children’s playroom, and a roof deck that allows for grilling within view of Wall Street gargoyles.

The smaller of the two buildings stands at 67 Wall Street, at the where Beaver and Wall streets meet; its angular, 25-story prow, adorned with nautical reliefs at the base and pinnacle, rises across from the gently-curved Cocoa Exchange next door, making for one of the most dramatic intersections in Downtown. 63 Wall Street, the taller of the pair, greets the crossing of Wall and Hanover streets with a chamfered corner that rises in setbacks to a dramatic crown with a hipped roof, large octagonal windows, and projecting gargoyles.

8 floors | 40 units | 1891 | Rental

Delmonico's Building
Cocoa Exchange may have a more delectable name, but when it comes to culinary delights, it’s 56 Beaver that’s got the goods, as it houses the Delmonico’s Steak House on the ground floor, with a grand entrance at the helm of its rounded prow. The eight-story landmark dates all the way back to 1891, making it a wedge-shaped building that predates even the famed Flatiron.

Architect James Brown Lord’s red-hued, brick-and-stone facade mixes Romanesque and Renaissance motifs, and the building remains one of Downtown’s finest-looking buildings even well more than a century after construction. Today, the former office building is a rental equipped with a fitness center and a roof deck.

14 floors | 74 units | 1929 | Rental

The Shenandoah The Shenandoah (Google streetview)
When the Flatiron Building rose in 1902, skyscrapers remained the exclusive domain of the office worker. By the late 1920’s, on the eve of the 1929 Multiple Dwelling Law that finally updated long-outdated tenement regulations for the skyscraper era, high-rise apartment buildings were already all the rage in the affluent parts of Manhattan, rising to around 15 stories, the maximum height achievable without resorting to loopholes such as the kitchenless “apartment hotel.”

The street gridiron of mid- and upper Manhattan produced canyons of fifteen-story-ish buildings, often whimsical at the top yet nearly always rectilinear in plan. By contrast, the quirky layout of Greenwich Village allowed for eye-catching building forms, such as the rake-angled-plan Shenandoah at 10 Sheridan Square. The building exterior is a romantic flight of medieval fantasy by Emery Roth, arguably the city’s premier architect of pre-war apartment buildings; the units feature spacious pre-war layouts and gridded loft-style windows.

16 floors | 47 units | 1928 | Cooperative

47 Plaza Street West 47 Plaza Street West (via Corcoran)
By the late 1920’s, high-rise apartment buildings rose alongside the Grand Army Plaza, a great oval centered on the Soldiers’ and Sailors’ Memorial Arch at the northern entrance to Prospect Park, and extended for several blocks in either direction. The Plaza’s oblong shape sliced rectangular blocks into concave shapes and gave rise to eye-catching buildings.

Of these, the most notable is the 16-story co-op 47 Park Plaza West, designed in a Gothic-Tudor style by Rosario Candela, the era’s only residential architect arguably more esteemed than Emery Roth. The concave sweep of the facade comes to a one-window-wide point at the tip, a shape that is arguably even more elegant than that of the Flatiron Building.

68 floors | 241 units | 1986 | Condominium

Metropolitan Tower Metropolitan Tower (Credit: Macklowe Properties)
Most “flatirons” on this list respond to their triangular sites; however, Metropolitan Tower’s wedge shape was a deliberate gesture by SLCE Architects, even though the building stands on a rectangular lot. In 1985, the skyscraper stood as the tallest residential building in New York, with a sharp blade of black glass soaring 716 feet and offering spectacular panoramas of Central Park. In addition to creating a dramatic statement on the skyline, the form also allows park views from the building’s broad, east-facing side, which would not face the park if not for the building’s slanted form.

Metropolitan Tower set the precedent for today’s Billionaire’s Row not only with its 57th Street location, record-setting height, and Central Park vistas, but also with an fully-stacked amenity package that includes a full-time doorman, concierge, housekeeping service, a health club with an indoor pool and spa, a roof terrace, a residents-only dining club, a full service garage, and bicycle parking.

From the Listing: Stunning park and city views from the 67th Floor of Metropolitan Tower. Large, renovated 2 bedroom, 2.5 bathroom residence, elegantly designed with beautiful views of Central Park and the City skyline. An exceptional combination of light, space, height and views. Top-of-the-line kitchen, custom closets throughout, luxurious bathrooms. A view from every room! Sorry, no pets. Washer/dryer in apartment. See floor plan and full details here.

16 floors | 19 units | 2015 | Condominium

10 Sullivan Street 10 Sullivan Street exterior (Credit: Corcoran)
Art Moderne is the sleek, streamlined cousin of Art Deco, notable for its machine-line geometries, and there is hardly a better shape for such a building than one that evokes an ocean liner. The 19-story condo at 10 Sullivan Street was completed in 2015, yet its alternating bands of large gridded windows and warm red-orange brick, designed by architect Cary Tamarkin, channel the finest traditions of turn-of-the-century Streamline Moderne.

The rounded, glassed-in rooms in the building’s rounded corner are south-facing, sunlit solariums unlike any other in the city. The building comes with a fitness center, an indoor upper-level pool with panoramic views, a landscaped roof deck, and a garage.

From the Listing: This 2,950-square foot 3-bedroom, 3.5-bath full-floor residence, with 404 square feet of private outdoor space, graces the signature south-facing prow of 10 Sullivan Street, where curved walls of oversized windows offer exceptional southern light, revealing breathtaking Downtown panoramas. The private balcony provides substantial outdoor space with open northern city views. See floor plan and full details here.

12 floors | 43 units | 1900 | Condominium

Varitype Building Varitype Building (Ondel/CityRealty)
The 12-story Varitype Building at the junction of Sixth Avenue and Cornelia Street was built in 1907 as a commercial building and converted to residences in 1982. As is the case with other pre-war loft conversions, apartments benefit from high ceilings, large windows, sturdy industrial-grade construction, and a splendid facade adorned with geometric ornament and projections. The building towers prominently above Greenwich Village, and the roof deck opens onto dramatic skyline panoramas.

From the Listing: Available August 1st -- Embrace voluminous light and air in this stunning, architect renovated one bedroom in a full-service West Village building. This impeccably designed loft-style home has a corner exposure with oversized windows that provide beautiful natural light throughout the day. See floor plan and full details here.

19 floors | 268 units | 1931 | Condominium

230 Riverside Drive 230 Riverside Drive (via CORE Real Estate)
Riverside Drive meanders gently atop the Hudson River-facing bluff of Riverside Park, allowing for angled buildings where the curving promenade meets the rigid street grid. Of these, one of the finest is the 19-story, arch-topped edifice at 230 Riverside Drive, designed by Charles H. Lench and erected at the corner of West 95th Street in 1931. The 2005 condo conversion brought an amenity package that includes a fitness center, a children’s playroom, and more. The building’s lot walls face a large playground, meaning that the freestanding structure offers windows on every side.

From the Listing: Gracious layout includes a grand living room with high beamed ceilings perfect for relaxation with a separate dining area ideal for hosting a dinner party. The high-end windowed kitchen boasts Sub Zero refrigerator, Miele stove-top/oven and dishwasher. Italian white cabinetry and quartz countertops as well. The serene bedroom has two spacious and custom outfitted closets while the "spa-like" white marble bathroom boasts classic chrome finishes, heated floors and a deep-soaking tub. Throughout the unit are 5-inch oak hardwood floors, high beamed ceilings with central heating and air-conditioning. See floor plan and full details here.

28 floors | 108 units | 2007 | Condominium

230 Ashand Place Forte at 230 Ashland Place (Google Streetview)
Downtown Brooklyn offers numerous acutely-angled sites, yet few utilize their footprint as gracefully as the Forte condominium wedged into the askew intersection of Fulton Street and Ashland Place. The tower, designed by FXFowle and completed in 2007, rises almost without setbacks to its 28-story pinnacle and greets the street plaza with a rounded corner that softens the pointed form and creates observatory-like spaces within the apartments. Alternating horizontal bands of tall windows and striped mullions make for a Streamlined Moderne look that makes for a unique presence on the skyline. The condominium offers a full-time doorman, a fitness center, and a roof deck.

From the Listing: Enjoy bright and open views from this spacious two-bedroom, two-bath condominium. This corner unit is flooded with natural sunlight from three exposures and you can watch the sunrise and the sunset. This is an ideal primary residence, pied-a-terre, or investment property. See floor plan and full details here.

15 floors | 167 units | 1926 | Cooperative

173 Riverside Drive 173 Riverside Drive (Corcoran)
173 Riverside Drive is a grand, Gothic-styled pre-war co-op that spans the block between West 89th and 90th streets, with a bright, stone-clad lobby illuminated by pointed, stained-glass windows that create the atmosphere of a medieval cloister. The angle-cornered building comes with a fitness center, a children’s playroom, and a garden.

From the Listing: Off a semi private landing, step into an inviting foyer adorned with a beautiful original staircase and large coat closet. Beyond the foyer through glass paned French doors is the library/fourth bedroom with its own en-suite guest bathroom and walk-in closet. The oversized, 25 foot long living room features a decorative fireplace and a sunny, south facing tree lined exposure looking at the landmarked brownstones of 89th Street. Adjacent to the living room is a large south facing formal dining room perfect for entertaining with a wine refrigerator and extra storage space. The fabulous new windowed eat-in kitchen features a Thermador appliance package including two ovens, two dishwashers and beautiful custom cabinetry, endless counter and storage space, a huge walk in pantry and a large eating area with banquet seating.4 See floor plan and full details here.

16 floors | 169 units | 1929 | Cooperative

NYC corner building apartments 110 Riverside Drive (Google street view)
110 Riverside Drive is a 16-story co-op built in 1929 in a delightful Romanesque style with warm orange brick, twisting colonnettes, and an arched, lanterned entrance. The building, situated between West 83rd and 84th streets, is equipped with a fitness center and a bike room.

From the Listing: Glorious views of Riverside Park and extraordinary western light are just some of the many wonderful features this gracious and large corner classic 6, in one of the premier Riverside Drive co-ops, has to offer. Enter via a semi-private landing to a sprawling gallery which anchors the entertaining rooms. The large principal bedroom, generously sized formal dining room, windowed kitchen and adjacent office or guest-room hang over bucolic Riverside Park - like living in a luxurious tree-house! On the opposite end of the gallery is a huge living room with 2 oversized picture windows providing an attractive northern cityscape. See floor plan and full details here.


Honorable Mentions

16 floors | 133 units | 1929 | Rental

98 Riverside Drive 98 Riverside Drive (Google streetview)

22 floors | 64 units | 2005 | Condominium

2770 Broadway 2770 Broadway (GKV Architects)

From the Listing: SPECTACULAR 6.5 ROOM CONDOMINIUM WITH RIVER VIEWS! Great opportunity to live in a beautiful full service condominium. This flexible 6.5 room home offers 3 bedrooms, den or formal dining room, expansive living room with balcony, top of the line cook's eat in kitchen with stainless steel appliances, 2.5 baths, abundant closets and views of the Hudson River. Both the grand scale living room and master bedroom have multiple exposures offering remarkable views of the area's surrounding architectural landmarks. See floor plan and full details here.

9 floors | 86 units | 2017 | Condominium

"From the Listing: Enjoy immaculate new-construction finishes and private outdoor space in this expansive two-bedroom, two-bathroom condominium in Long Island City.

A bright and airy ambiance welcomes you into this spacious 1,004-square-foot home featuring eastern and western exposures, gorgeous wide-plank oak floors and soaring 10-foot-tall ceilings. Relax and entertain in the open-plan living and dining area, and enjoy a sleek open kitchen featuring custom cabinetry, quartz counters and beautiful backsplashes. The suite of upscale stainless steel appliances includes a gas range, dishwasher and built-in microwave.
See floor plan and full details here.

11 floors | 49 units | Planned for 2021 | Rental

Long Island City rentals Credit: Gerald J. Caliendo Architects

On The Drawing Board

38 floors | 256 units | Planned for 2023 | Residential rental, retail, education

Alloy Development Images credit of Alloy Development
An ambitious mixed-use project in development in Downtown Brooklyn will take the form of one of the city’s most dramatic “flatiron”-style buildings. Alloy Development’s 100 Flatbush Avenue will rise from a sharply-angled site at the meeting point of Flatbush Avenue and State Street, soaring 38 stories as a stepped wedge that bears a certain spirit of the skyscraper slab at 30 Rockefeller Center. The project, designed by Architecture Research Office, is aiming to become the city’s first all-electric, fossil-fuel-independent project, which will consist of two schools, 100,000 square feet of office, 30,000 square feet of retail, and 256 apartments on the upper floors.

24 floors | 84 units | Planned for 2022 | Rental

41-05 29th Street  rendering 41-05 29th Street (SB Development Group)
Jackson Avenue, Long Island City’s main thoroughfare, runs at an angle to the street grid and has already produced several wedge-shaped buildings along its course; none, however, match the height and style of the 24-story, 290-foot-tall high-rise coming to 41-05 29th Street. Foundation work is currently in progress for the 84-unit residential building (likely rental), which will make a bold addition to the northern vanguard of the Long Island City skyline.

10 floors | 112 units | Planned for 2021 | Rental

445 Grand Avenue Credit: Fogarty Finger Architects
The mixed-use condo planned at 445 Grand Avenue in Clinton Hill wedges onto the intersection with an acute corner, yet the building’s angular form is softened via coffered brick mullions and subtle semi-arches dispersed across the facade. Aside from 112 rental units, the building, designed by Fogarty Finger Architects, will also feature ground-level retail and facilities from the adjacent Bethel 7th Day Adventist Church, designed by architect Lawrence B. Valk in Romanesque Revival style and completed in 1882.

115 Broadway

4 floors | Planned for 2023 | Retail, office

115 Broadway 115 Broadway (Cayuga Management Capital)
In recent years, Williamsburg has received a great share of avant-garde architecture, and now it’s getting some of the “flatiron” variety. Cayuga Management Capital LLC is proposing a four-story, wedge-shaped retail and office building at 115 Broadway at the confluence of South 6th Street and Broadway at the foot of the Williamsburg Bridge. A grid of bronze mullions rounds the acute corner in a sleek sweep, complete with floor-to-ceiling curved windows.

Historic Mention

21 floors | 1908 - 1971 | Office

The German American Insurance Building German American Life Insurance Building (demolished)(Credit: Irving Underhill via Library of Congress)
Unfortunately, one of the city’s greatest wedge-shaped buildings no longer stands. In 1908, the German-American Insurance Company erected a 21-story office building at 68 Maiden Lane, deep within the dense tower thickets of Lower Manhattan on a narrow wedge of land at the confluence of Liberty Street and Maiden Lane.

The architecture firm of Hill & Stout composed a less ornate design than that of the similarly-sized Flatiron Building; however, its arched, vaulted, concave cornice of polychrome terra-cotta was among the finest and most unique of the kind in all of New York. The preservation-worthy building bit the dust in 1971 in order to widen the adjacent streets, at a time when bringing more, rather than fewer, cars to Downtown’s alley-like streets still seemed like sound urban planning.

Today, Louise Nevelson Plaza, a small public space in place of the soaring edifice, remains as the city’s consolation prize for the architectural loss, while the closest stylistic kin to the vaulted cornice may be found atop The Adlon in Midtown.

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