John Fitzgerald Kennedy was born on May 29, 1917 in this relatively modest home in the Boston suburb of Brookline. Today preserved as the John Fitzgerald Kennedy National Historic Site, and serves as a venue for poetry readings, school visits, and for public tours, during the summer months.

When Jack was a baby, the Kennedy clan summered in Hull, Mass., located on a peninsula that encloses much of Boston Harbor. The Tudor-style house was built for Rose Kennedy by her father, who spent summers in a larger mansion, just uphill.

With Joe Kennedy's growing business success came these larger Brookline digs, where Jack lived from 1920 to 1927. It remains popular with the media, if the camera visible from Google Streetview is anything to go on.

The Kennedys, considered "new money" by Riverdale's high society, soon moved to an even more extravagant estate in Bronxville, where they lived from 1929 to 1938. Known as Crownlands, the columned mansion sat on 5.5 acres at the crest of a prominent hill.

In 1929, Joe and Rose Kennedy purchased the expansive summer home they had been renting in the Cape Cod resort town of Hyannis Port. This house would become the cornerstone of the now-famous "Kennedy Compound."

For 30 years—from 1933 to 1963—JFK spent at least part of his winter in Palm Beach, at the seasonal home of his parents on North Ocean Boulevard. Kept in the family until 1995, the Addison Mizner-designed mansion enjoys 173 feet of direct beachfront.

Following his recuperation from a harrowing experience in the South Pacific, JFK moved into Boston's tony Bellvue Hotel, where his maternal grandfather, John F. Fitzgerald, was living after retiring as U.S. Congressman.

In 1947, John Kennedy rented an apartment in this brick building, just down the block from the Bellevue, to establish residency in Massachusetts. Following his successful election to Congress, Kennedy kept the flat until his death in 1963.

For the first three years of his tenure in the U.S. Congress, Kennedy lived in this stately brick townhouse in Georgetown. The 2,650-square-foot, three-bed, four-bath home sold in January of this year for $1.87M.

With his political star on the rise, JFK moved out on his own again in 1951, renting this historic Georgetown townhouse. He was living here when he first met Jaqueline Bouvier, at a dinner party.

By 1953, Jack and Jaqueline were engaged and living together in this squat Georgetown home. The couple spent less than a year here prior to their nuptials.

Following their wedding, Jack and Jacqueline rented this Georgetown row house, which included a rear carriage house, from Blair Childs. The fickle couple moved again after two years, leaving Georgetown for the first time.

Though frequent guests of his parents at their Cape Cod estate, Jack and Jackie sought a space of their own nearby in 1956. This more modest residence is now owned by Edward Kennedy, Jr.

Finding the country not to their liking, the Kennedys returned to Georgetown in 1957, leasing this clapboard rowhouse. This was the same year that daughter Caroline was born and Jack won a Pulitzer for his book, Profiles in Courage.

With his eye on a national run, Kennedy kept a pair of apartments at New York's 277 Park Avenue. His 1960 campaign offices would later be located in the building, which was replaced by a glassy office tower in 1962.

In 1961, the Kennedy clan moved into the White House, trading in their 4,100-square-foot townhouse for a 55,000-square-foot behemoth. The Kennedy children were often photographed playing with their father in the Oval Office.

With the stress of the presidency a constant companion in D.C., the Kennedys sought solace in the country, leasing the historic Glen Ora estate. The 400-acre spread was centered around a stately main house, which the Kennedys spent $10K to redecorate. The owner would not agree to sell, and so the couple decided to build nearby.

The only home ever designed for Jack and Jackie Kennedy, Wexford was completed in early 1963, but the couple leased the property out until their lease at Glen Ora expired. JFK probably spent just one weekend here prior to his assassination. It was later leased by Ronald Reagan during the 1980 campaign.

With his father quite ill, President Kennedy spent several winter holidays in Palm Beach, at the impressive home of Michael and Josephine Paul, located just a mile from Joe Kennedy's waterfront estate.

With the Secret Service concerned about the close proximity of the Kennedy Compound to its neighbors, the President and his family decamped to nearby Squaw Island in the summer of 1962. They rented a shingled cottage from singing sensation Morton Downey.

For the summer of 1963, JFK's last, the couple moved to Brambletyde, a stately waterfront mansion on the bitter end of Squaw Island, with magnificent views of Nantucket Sound and just one neighbor. Today it is owned by Christopher Kennedy, JFK's nephew and a son of Bobby Kennedy.