Bounded by Central Park on the east and the Hudson River on the west, the Upper West Side stretches from 59th Street to 125th Street, including Morningside Heights. Known for its pre-war low rise historic buildings like the Cathedral of St. John the Divine, the Dakota Apartments, Columbia University, Lincoln Center, and several others, the Upper West Sidewas originally home to Dutch immigrants in the early and mid-seventeenth century.

Characteristic of the historic district are its landmarked buildings, which represent the late 19th century and early 20th century architectural styles. Dominated by the Neo-Renaissance, Art Deco, Second Empire, Beaux Arts, and Neoclassical, gothic and Romanesque Revival influences can also be seen, including a few Queen Anne, Art Moderne, and Italianate buildings, that are part of the historic streetscape of the Upper West Side.

Here are our top picks for the most historic landmark buildings, that dot this iconic neighborhood of New York City.

1. Apthorp

We begin our historic trail at West End Avenue on the . One look at the Apthorp, and you'll definitely want to stop and take a moment to appreciate the giant black and ornate gates, that is home to one of the most luxurious, Italian Renaissance Revival architectural masterpiece that is tucked away behind its grand entrance way. Stretching from Broadway and West End Avenue between West 78th and 79th streets, the Apthorp has been often described as “monumental and magnificent”.

Named after Charles Ward Apthorp, the owner of Apthorp Farm, it once stretched over 300 acres around this area. Arched windows, lifesize limestone sculptures, a grand moon shaped courtyard, and of course the stunning architectural structure - the Apthorp condominiums. It is these architectural and historical features that made this a designated New York City Landmark in 1969, and was later added to the National Register of Historic Places in 1978.

The likes of Nora Ephron, Al Pacino, Conan O’Brien, Cyndi Lauper, Rosie O’Donnell, and Steve Kroft, have been on the elite residents list, here at the Apthorp.

2. The Dakota

Constructed between 1880 and 1884, the Dakota Apartments is a co-op located on the northwest corner of 73nd Street and Central Park West on the of Manhattan. Popularly known as the home of the former Beatle John Lennon between 1973 and 1980, it was also sadly the location of his murder.

Considered as one of Manhattan’s iconic, exclusive, and prestigious cooperative residential buildings, the Dakota sells for anything upwards of $4 million. Designed by the architectural firm of Henry Janeway Hardenbergh, the buildings high gables and deep roofs, terracotta spandrels and panels, balconies and balustrades, gives the Dakota a North German Renaissance feel, reflective of a Hanseatic town hall. The Dakotabecame a designated New York City Landmark in 1969, and was on the National Register of Historic Places Inventory in 1976, and was later recognized as a National Historic Landmark.

What was built for the affluent and wealthy, the Dakota was always known for its modern infrastructure and amenities which were second to none back then, like a playroom, a gym, electricity generated by an in-house power plant, central heating, a private garden, a croquet lawn, and tennis court, among others.

Hollywood’s infamous like film producer Jane Rosenthal, actress Rosemary Clooney, singer Sean Lennon, dancer Rudolf Nureyev, and artist Yoko Ono; are just a few among hundreds that have called the Dakota home in the past.

3. San Remo

At a time when new zoning regulations were introduced, architect Emery Roth jumped in to take advantage of it, and proposed to build New York’s first ever twin-towered apartment blocks. Each of the two-ten story towers were topped off with an English Baroque mansion, inspired by the drums of the Choragic Monument of Lysicrates, which was later seen in a number of imitations like The Majestic, The Century, The Eldorado, and most recently the Time Warner Center.

Construction of San Remobegan in 1929, which happened to be weeks before the market crash that set in the Great Depression, and was spread over two years, before it was completed. San Remo was converted into one of the most desirable cooperative residential units in the 1970’s. San Remo became a designated New York City Landmark in 1987. Ever since, San Remo has always been among record Manhattan sale prices, with some units costing as much as $5,400 per square foot.

This luxury tower located between West 74th Street and West 75th Street, was once described by Glen Justice of The New York Times as “a dazzling two-tower building with captivating views of Central Park”. Its marble walls, terrazzo floors, custom light fixtures made of bronze and frosted glass, and the most popular addresses 145 and 146 Central Park West, were designed so that each half structure was served by separate lobbies.

Its past residents list, reads something like this; Stephen Sondheim,Tiger Woods,Steven Spielberg,Donna Karan,Tony Randall,Demi Moore,Glenn Close,Dustin Hoffman,Bono,Steve Martin,Bruce Willis,Trey Parker,Eddie Cantor,Robert Stigwood,Marshall Brickman,Jackie Leo,Don Hewitt,Billy Squier,Dodi Fayed,Andrew Tobias,Aaron Spelling, andHedy Lamarr.Rita Hayworth is known to have spent her last years there, in a unit beside her daughter's, PrincessYasmin Aga Khan. It was also home to Steve Jobs for a while before it was sold to Bono.

4. The Beresford

Located at 211 Central Park West, between 81st and 82nd Streets, is yet another architectural marvel designed by Emery Roth, apart from The El Dorado, The San Remo, and The Ardsley. This luxury 23-floor apartment building, was completed in 1929, has long been one of the most impressive addresses in Manhattan, among the city’s elite coops that line Central Park West.

Designed with architectural details that reflect Georgian houses, the building takes its name from the Hotel Beresford, which once stood in its place since 1889. The Beresford’s exterior boasts of two prominent street-front facades, crowned with distinctive octagonal copper-capped corner towers, one overlooking Central Park, and the other overlooking Theodore Roosevelt Park. Described aptly by author Andrew Alpern in his book “Luxury Apartment Buildings in Manhattan”, An illustrated History, as “a stone symphony”, “there are belt courses, stone balustrades, iron railings, rosettes, and cartouches”, which had him reference the building to a fortress.

Today, this premium slice of real estate sells for anywhere between $3 million to a whopping $23 million. Some of its elite past residents include Jerry Seinfeld, singerDiana Ross, tennis playerJohn McEnroe, Citigroup CEOVikram Pandit, actorTony Randall, fund managerBill Ackman, and musicianLaura Nyro among several others.

That’s a wrap on our little tour of the Upper West Side’s most iconic historic landmarks.