Coolest Homes on America's Poshest Streets

BOSTON ( MainStreet) -- New York's Central Park West, Chicago's Michigan Avenue and other famously upscale U.S. addresses offer people who buy homes there a special cache recognizable around the globe.

"If you're talking to a business associate in South America and you tell them you live on Michigan Avenue, that automatically means something," Chicago real estate broker Phil Skowron says. "It's one of the most prestigious brand names in the entire country -- if not the entire world."

Skowron sells lots of condos on Michigan Avenue, known as the "Magnificent Mile" because it hosts many of Chicago's fanciest residences, shops and restaurants. The famous street not only offers a posh name and great location, but also hosts some of the Windy City's most beautiful condo complexes -- and most powerful people, he says.

"You've got it all here -- good location, beautiful architecture, great views and a virtual who's who of Chicago movers and shakers, " Skowron says. "It's the best of the best in real estate."

Of course, all of those positives don't come cheap.

Posh addresses typically command higher prices than similar properties just a few blocks away do.

For instance, Skowron says Michigan Avenue condos typically cost $1,000 per square foot -- 10% to 20% more than you'd pay if you bought something four or five blocks away.

But the broker thinks the extra price is worth it.

"You'll get you that initial premium back when you sell," Skowron says. "Michigan Avenue is the place where everyone in Chicago wants to live -- and it always will be."

Here's a look at some properties for sale on some of America's most famous upscale streets:

Four-bedroom condo, Central Park West/Broadway, New York
Price: $60 million
Listing agents: Elizabeth Sample and Brenda Powers, Sotheby's International Realty, 212-606-7685
This four-bedroom unit is in Manhattan's prestigious Time Warner Center at Central Park West and Broadway.

The 75th-floor unit features a master bedroom suite, 6.5 bathrooms, two kitchens, a library, a media room and a 40-foot great room overlooking Central Park.

High-end amenities include 14-foot ceilings, motorized window treatments and a whole-house stereo system.

"It's five-star living in a one-of-a-kind apartment," listing agent Elizabeth Sample says.

If the condo's 4,000 square feet of living space aren't enough for you, you can combine them with a 3,450-square-foot duplex that's for sale next door. Price: An additional $25 million.

As for location, the Time Warner ( TWX) Center hosts a hotel, numerous restaurants, a shopping mall and other amenities. You're also just steps Central Park, Lincoln Center and other Manhattan landmarks.

Click here to see the condo's complete listing.

Villa Stella, Star Island Drive, Miami
Price: $20 million
Listing agents: Sylvia Fragos, Great Estate International Realty, 305-904-7847
This Moorish-style home features four bedroom suites, a chef's kitchen, an enclosed rooftop observatory and separate staff quarters.

The one-acre property also has lush gardens, a salt-water pool, 100 feet of ocean frontage and a private dock.

It's on Star Island Drive -- the only street on exclusive Star Island, an enclave of a few dozen homes about a mile off of mainland Miami in Biscayne Bay. Reachable by a single bridge, Star Island counts musician Gloria Estafan, basketball star Shaquille O'Neil and talk-show host Rosie O'Donnell as current or former residents.

You can get more information about Villa Stella here.

Six-bedroom condo, Michigan Avenue, Chicago
Price: $6.3 million
Listing agent: Janet Owen, Prudential Rubloff Properties, 312-268-0700
This condo takes up almost the entire 51st floor of the Park Tower complex at 800 North Michigan Ave. -- generally considered Chicago's most prestigious address.

The 67-story building hosts a Hyatt ( H) hotel on its lower levels, with 117 private residences taking up the top floors. Current or former Park Tower condo owners range from ex-Chicago Mayor Richard Daley Jr. to reality TV star Bill Rancic.

The unit for sale features six bedrooms, 5.5 bathrooms, two terraces, two fireplaces, a chef's kitchen and 30-foot great room. There are also two deeded parking spaces, as well as special access to the Hyatt's spa, pool and other amenities.

The Park Tower is in the heart of the "Magnificent Mile," a short walk from the Chicago Loop, Lake Michigan, Water Tower Place and Chicago Museum of Contemporary Art.

Click here for more information about the condo.

Three-bedroom condo, Michigan Avenue, Chicago
Price: $5.8 million
Listing agent: Phil Skowron, @properties, 312-612-0303
If the previous condo is too big or costly for you, consider this smaller unit on the 26th floor of the same building, the prestigious Park Tower.

This condo features three bedroom suites, two fireplaces, two deeded parking spaces, 3.5 bathrooms, a private terrace and a granite and marble chef's kitchen.

"It's the complete package," broker Phil Skowron says. "Every square inch of the condo is immaculately done with top-of-the-line finishes, and it's hands down in the best location in Chicago."

Check out the unit's listing sheet here.

Three-bedroom condo, Newbury Street, Boston

Price: $2 million
Listing agent: Melinda Sarkis, Hammond Residential Real Estate, 617-587-4609
This condo is in a 123-year-old restored brownstone on Newbury Street, a strip of exclusive homes, shops and restaurants in Boston's posh Back Bay neighborhood.

The 2,100-square-foot unit features three bedrooms, 4.5 bathrooms and one deeded parking space. Upscale amenities include a fireplace, hardwood floors and views of Boston's landmark John Hancock building and Old South Church.

Click here for more details.

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