How Much of Westchester’s Iconic Architecture Have You Seen?


This eclectic collection of must-see buildings and structures shows off the iconic architecture that anchors our county with a sense of place.
Paul Adler & Nick Brandi

– New Croton Dam, Cortlandt and Kensico Dam Plaza –

Few local structures inspire awe quite like the towering Kensico and New Croton dams. Each unique, both dams serve as points of leisure, exercise, and enjoyment for countless Westchesterites and others. Completed in 1906 (the tallest of its kind on earth at the time), the New Croton Dam (below) stands out for its stepped masonry, towering aqueduct, and popular park sporting biking and nature trails. Another eye-popping feat of county construction, the 307-foot-tall, 1,843-foot-long Kensico Dam was erected in 1917 and was acquired as parkland by the state in 1963. Today, the plaza remains a popular spot to soak in the structure’s soaring face of hand-hewn masonry; the 9/11 memorial, The Rising; and several acres of gorgeous parkland.

– The Armour-Stiner House –

Like some strange treasure tucked away in the forest, the Armour-Stiner House — fondly referred to as The Octagon House — remains one of Westchester’s most oft-discussed architectural icons. To this day, it remains the only known fully domed octagonal home, as well as the only home built to the specifications of Donato Bramante’s 1502 masterpiece, the Tempietto. The Armour-Stiner home was actually modified from a far simpler edifice in the late 1870s, by tea merchant Joseph Stiner. About a century later, in 1976, the singular structure was designated a National Historic Landmark and subsequently sold to the ideal buyer: Joseph Pell Lombardi, a preservation architect specializing in building conservation.

- Advertisement -
Photo by Jessica Norman

– Untermyer Park and Gardens –

Overlooking the Hudson River, this renowned series of gardens and structures founded by attorney Samuel Untermyer fell into disrepair years after its 1916 birth and has been undergoing an incredible restoration since 2011. While the site boasts dozens of moving architectural tableaux, including a Ruin Garden, a staired vista, and even the fantastic Temple of Love, its most iconic architectural achievement is perhaps the Walled Garden, a breathtaking enclosed space inspired by Indo-Persian gardens of antiquity, containing the Temple of the Sky — an impressive semicircle of Corinthian columns — as well as several water features, rare plants, and a Greek-inspired amphitheater.

– Sunnyside –

Boasting equal parts unlikely architecture and fascinating history, Washington Irving’s abode, Sunnyside, remains a popular haunt for curious locals and others. Writer of monumental stories “The Legend of Sleepy Hollow” and “Rip Van Winkle,” Irving, who is said to be America’s first internationally famous author, created a kind of pastoral paradise with his Dutch Colonial revival home, which also borrows elements of Gothic and Tudor architecture. Located on property he purchased in 1835, the fascinating home, boasting stepped gables and a soaring Spanish tower, is situated in Irvington and has since earned a well-deserved spot on the National Registry of Historic Places.

Photo by Jaime Martorano for Historic Hudson Valley

– The Union Church of Pocantico Hills –
Pocantico Hills

Entering this gorgeous stone structure is like being transported to another world. Built in 1921 by John D. Rockefeller, the stone church was revamped after the death of Rockefeller’s wife, Abby, in 1948, when Nelson Rockefeller commissioned the world-renowned French painter Henri Matisse to design the church’s prized rose window. Twelve years later, upon the death of John D., his children again commissioned a legendary artist, this time Marc Chagall, to design a gorgeous stained-glass window in his honor. The alterations have made entering this church like stepping into a jewel box, surrounded by the county’s most exceptional art.

– The Ritz-Carlton, Westchester –
White Plains

Designed by renowned architects Costas Kondylis and Partners, the 44-story twin glass towers of the Ritz-Carlton, Westchester in White Plains are currently the tallest buildings between New York City and Boston (until the 48-story, dual-tower development at 11 Lawton St in New Rochelle opens for business). The gleaming edifices have been spiring majestically through the White Plains skyline since 2007 and have long been sources of pride for the entire region. Though the exigencies of COVID-19 forced the Ritz-Carlton brand to divest itself of the luxury hotel (it will retain control of the buildings’ 365 residential units), the space will be reborn as a five-star Marriott International Autograph Collection hotel.

– Skinny House –

When one ponders Westchester’s many architectural oddities, few stand taller — or slimmer — than the famed Skinny House. A mere 10-feet wide, this utterly unique Mamaroneck structure was built by African American carpenter and contractor Nathan Thomas Seely on an incredibly narrow lot of donated land after he lost his job and prior home to the Great Depression. Seely hardly could have imagined his abode would go down in the history books as both a beloved Mamaroneck Village Landmark and a member of the National Registry of Historic Places.

- Partner Content -

– Sleepy Hollow Country Club –
Briarcliff Manor

Despite its titular implication, Sleepy Hollow Country Club is actually situated in the Scarborough Historic District of Briarcliff Manor. Founded in 1911, Sleepy Hollow Country Club includes its storied clubhouse, Woodlea, designed by the world-famous Stanford White and built between 1892 and 1895. Boasting 140 rooms, Woodlea was one of the famed Beaux-Arts Vanderbilt mansions and is a prime exemplar of Italian Renaissance Revival style, featuring buff-colored Italian brick and symmetrical façades south and west. Its circa 70,000 square feet of interior space makes it tied for No. 15 among America’s 100 largest privately owned houses.

Photo by Alice Gao

– Stone Barns Center –
Pocantico Hills

Hidden amid rolling woodland sits the pleasingly pastoral rock-hewn buildings and agricultural spaces that comprise the Stone Barns Center. A dairy farm for the Rockefeller Family during the 1930s, the center is now home to Dan Barber’s famed James Beard Award-winning restaurant, Blue Hill at Stone Barns, as well an expansive teaching farm, an exceptional bakery/café, and an inviting gift shop.

Photo by Tree Falls Photography/Anthony Moreno

– Usonia –

The Usonia Historic District in Pleasantville was conceived and executed by none other than Frank Lloyd Wright himself, along with a coterie of protégés, on a circular plot of 100 idyllic acres purchased in 1945. The Midcentury Modern community, with its wood-and-stone construction, open floor plans, oversized windows, and flat, overhanging roofs, is quintessential FLW. The community got its name in an homage to Wright, for his ideas on the way Americans should live together. Listed on the National Register of Historic Places in 2012, Usonia was dubbed five years later by Architectural Digest “the best-designed small town in the U.S.”

– The IBM Legacy –
Various locations

Westchester has been the focus of prodigious architectural inspiration over the decades, but one of its corporations, IBM, is itself the recipient of some of the best architectural talent the world has ever seen. In the 1980s, legendary architect I.M. Pei was responsible for the tech giant’s 1.2 million sq. ft. modernist masterpiece in Somers (as well as its former Purchase location, now Mastercard’s global HQ), crowned with its opulent glass-pyramid summits. But it was back in 1961 that none other than Finnish-American virtuoso Eero Saarinen gave Big Blue in Yorktown Heights the crescent-shaped Thomas J. Watson Research Center, which, with its ascending curvilinear overhang perched at the entranceway, evokes the essence of a monolithic spaceship preparing to take flight.

– The Richard H. Mandel House –
Mount Kisco

Four years before the renowned International Style Museum of Modern Art debuted in NYC in 1939, its illustrious architect, Edward Durell Stone, created America’s first significant International Style residence in the form of the 10,000 sq. ft. Richard H. Mandel House in Mount Kisco. Set on 21 acres and boasting a commanding view of the Croton Reservoir, the two-story, concrete-block, steel-and-stucco building is coveted for its clean, smooth, horizontally oriented asymmetrical composition, which includes projecting balconies and wide banks of ribbon windows. The Mandel House is also considered groundbreaking for its use of materials, including cork floors, glass blocks, built-in furniture, and a technically advanced heating system for its time. It was added to the National Register of Historic Places in 1996.

- Advertisement -

– Jackie Gleason’s Round House –
Cortlandt Manor

Known to be fascinated with UFOs, comedy legend Jackie Gleason commissioned the construction of his famous “Mothership” house in 1959, still basking in the glow of his one-season smash-hit sitcom, The Honeymooners. The round, 3,950 sq. ft. modernist house was designed by Frank Lloyd Wright acolyte Robert Sika and built by a shipbuilder in an airplane hangar over a five-year period. The three-building campus on eight acres is replete with natural wood inside and out and is supported by trusses but not crossbeams, as those would have required right angles. Despite the undeniable structural references to his preoccupation with ET mythology, Gleason — a chart-topping composer and producer — is reported to have said that the domicile was circular because he wanted it to be “like a musical note that never ends.”

Photo by Tom Nycz for Historic Hudson Valley

– Philipsburg Manor House –
Sleepy Hollow

Way back in 1693, William and Mary of England granted 52,000 acres of land to Dutch merchant Frederick Philipse, who turned the massive estate into a trading complex, active farm, and mill. Since those days, much of Philipsburg Manor has been restored and/or reconstructed, though the stone exterior of the manor house is mostly original. Named a National Historic Landmark in 1961, the Colonial-style Manor House’s interior furnishings have been painstakingly recreated based on the most expert scholarship, with the reconstructed outbuildings serving as a valuable educational resource about pre-Revolutionary Westchester. Unfortunately, the Philipse family also owns the ignominious distinction of having had one of the largest slave-holdings in the Colonial North.


– Governor Mario M. Cuomo Bridge –

One of Westchester’s newest architectural icons, the Gov. Mario M. Cuomo Bridge, replaced the beloved but aging Tappan Zee Bridge in 2018 after a lengthy construction. With an eye-popping price tag of $4 billion, the brand-new conduit boasts futuristic, safety-forward, and community-centered features, including gleaming, 419-foot chamfered towers along its main span, color-changing LED lights, and a 3.6-mile biking-and-walking path ornamented with impressive sculptures and installations by eight New York-based artists.

AdobeStock/P. Meybruck

– The Lighthouse at Sleepy Hollow –
Sleepy Hollow

Also known as the Tarrytown Lighthouse or the Kingsland Point Lighthouse, this iconic Westchester structure was once situated a full half-mile from the Hudson River shore on which it currently sits. After decades of landfill, thanks to a now-demolished General Motors factory, the lighthouse found itself just a few convenient feet from the beach and has consequently become a popular local site. The lighthouse’s cast-iron tower was erected in 1883, and the lamp inside was automated during the mid-1950s. During the 1970s, the Tappan Zee Bridge rendered the five-story structure’s navigation lights obsolete, and so the lighthouse was taken over by Westchester County, which maintains it to this day.

– Gilded Age Mansions –
Kykuit, Pocantico Hills; Lyndhurst, Tarrytown; Le Chateau, South Salem 

Legendary robber barons and captains of industry epitomized the Gilded Age, and Westchester had some of its own to boast. One is John D. Rockefeller, of course, whose Pocantico Hills mansion, Kykuit, is an excellent example of a Classical Revival-style stone villa, completed in 1913 by architects Chester Holmes Aldrich and William Adams Delano. Meanwhile, tycoon Jay Gould’s Lyndhurst, in Tarrytown, is a Gothic Revival country house, designed in 1838 by Alexander Jackson Davis, that looms on 67 majestic acres overlooking the Hudson River. Not to be outdone, Le Chateau in South Salem is a sprawling Tudor-style mansion of brick and stone that was commissioned in 1907 by legendary banker J.P. Morgan and designed by architects Atterbury & Atterbury. Both Kykuit and Lyndhurst are National Historic Landmarks.

– 800 Westchester Avenue –
Rye Brook

Ensconced in the sleepy, little village of Rye Brook is the magnificent 800 Westchester Avenue complex, a 560,000 sq. ft. behemoth postmodern Class A office building that was once the corporate headquarters of General Foods. Having been described over the years as an “Aztec temple” and “aluminum business palace,” the seven-story, all-white building’s amenities include a semicircular entranceway rotunda, man-made lake with fountains, wooden garden bridges, and an underground parking facility. When commercial real estate developer Robert Weisz acquired the property for $40 million in 2004, it was the county’s largest real estate transaction that year.

Photo courtesy of Westchester County Parks, Recreation & Conservation

– Playland –

The first planned amusement park in the U.S., Rye Playland was created in 1928 by Frank Darling and well-known NYC architectural firm Walker & Gillette, with landscape architect Gilmore D. Clarke. Its 280-acre campus represents a synergistic tour de force of architectural-style integration, with original structures boasting chimerical flourishes in Art Deco, complemented by a Spanish Revival-style bathhouse. This one-of-a-kind amusement attraction was added to the list of National Historical Landmarks in 1987.

– Whitby Castle, Rye; Carrollcliffe, Tarrytown –

Westchester has been a hotspot for mansions and estates for well over a century, but the 914 also boasts its share of castles, including two of the most active, Whitby Castle and Carrollcliffe. Though architect Alexander Jackson Davis’ most famous creation is Tarrytown’s Lyndhurst, he also gave the county Whitby Castle, in Rye. Designed in 1852 and completed two years later, Whitby Castle represents one of Davis’ quintessential Gothic Revival designs. It was created for his friend William Chapman and is said to include stones from its nearly 1,400-year-old inspiration and eponym, Whitney Abbey in North Yorkshire, England. It sits on 126 impeccably manicured acres and is currently the home of Rye Golf Club.

Also referred to as Axe Castle (and formerly the Castle Hotel & Spa), the all-stone Carrollcliffe is rife with redoubtable battlements, including crenellations and merlons. It was constructed in two stages, beginning in 1897, with the intention of resurrecting the essence of Norman castles in Ireland, Scotland, and Wales. Designed by architect Henry Franklin Kilburn for journalist/playwright/businessman General Howard Carroll, Carrollcliffe sits on 10 lush acres perched on one of the highest points in Westchester County.

Photo courtesy of Greenburgh Public Library

Greenburgh Library

A $20 million, 22-month restoration in 2009 transformed the second-busiest library in the county into a true architectural masterpiece. Designed by Salvatore Coco, the library originally built in 1962 is now doubled in space, to 46,000 square feet, and sports a dramatic, cantilevered roof, a 140-foot reading room, and maple library desks. With ash-hued ceilings and soaring glass panels, it all amounts to a truly singular municipal gem.

The Art of Architecture

We round up a handful of stunning buildings that also happen to house many of the county’s most beloved arts organizations.

Caramoor Center for the Arts. Photo by Gabe Palacio

Westchester sports an impressive roster of cultural venues and arts organizations, many of which call some pretty remarkable structures home. Katonah’s Caramoor Center for Music and the Arts comprises lush, park-like grounds; a colonnaded Spanish courtyard; an incredibly expansive Venetian theater; and the center’s architectural triumph: The Rosen House, a Mediterranean-style home on the National Register of Historic Places, built sometime during the 1930s by Walter Rosen, which features unique carved wood, vaulted ceilings, exceptional artwork, and rare Chinese wallpapers, all while serving as a venue for classical music and arts education.

Tarrytown Music Hall. Photo by Bill Foley

For a more rocking respite, the Tarrytown Music Hall has served as a local outpost for good times since its 1885 birth. Built in the Queen Anne style, the structure was designed by renowned architects August Cordes and Thoedore De Lemos — who had also worked on Grand Central Station — for chocolate manufacturer William Wallace. The Hall is considered Westchester’s oldest theater, and during the early 1900s, it hosted everything from silent-film screenings to women’s suffrage gatherings. After making it on the National Register of Historic Places, the Hall fell into disrepair. It was saved from the wrecking ball in 1980 by an area nonprofit and to this day serves as one of the county’s most popular spots to soak in some rock & roll.

The Capitol Theatre. Photo by Scott Harris

The Capitol Theatre in Port Chester is yet another beloved local venue saved from the wrecking ball (and from serving as a catering hall), which now stands proudly as a prime spot to catch a musical act. Opened in 1926 as a dignified playhouse, The Cap, as it is fondly known, morphed into one of the country’s hottest rock venues by the mid-1960s, hosting musical megastars like Janis Joplin, Pink Floyd, and The Grateful Dead. After falling into disrepair during the 1990s and becoming a catering hall, it was given a new lease on life in 2011, boasting a new interior and state-of-the-art-sound system.

ArtsWestchester. Photo by Mary Alice Franklin

An equally impressive structure can be found in Downtown White Plains, towering over Mamaroneck Avenue. Yet this edifice is not home to some billion-dollar firm; it is the abode of ArtsWestchester, one of the county’s most prominent arts organizations. The nine-story structure originated in 1929 as the Peoples National Bank & Trust Company and was immediately commended in local newspapers for its design. The space boasts 40-foot ceilings, a limestone-encased first story, and marble floors. This building also fell into major disrepair and was only saved in 1998, when ArtsWestchester purchased it from Chase Bank for a cool $1.2 million. After an extensive 2003 renovation, the space opened once again as the home of ArtsWestchester’s studios, offices, and exhibition spaces.

Our Best of Westchester Party is July 24!

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.