A Look at The Obama Family’s Impressive Real Estate Portfolio

From a historic Chicago mansion to a spacious Martha’s Vineyard vacation home, our favorite First Family has called many beautiful properties home.

The White House is one of the most famous homes in the country. And while former President Barack Obama and former First Lady Michelle Obama occupied the historic residence with daughters, Malia and Sasha, for eight years, you may be surprised to learn that they’ve had many other beautiful properties in their impressive real estate portfolio.

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In honor of our Forever President (who just celebrated his 64th birthday on August 4) and our favorite First Family, we’re taking a look at some of the amazing places the Obama family has called home over the years.

Sweet Home Chicago

Screenshot: YouTube

Long before his run for the White House, a then-Senator Obama purchased this 6,000-square-foot home on Chicago’s South Side in the early 2000s.

A Sun-Filled Study

Screenshot: YouTube

It should come as no surprise that the Obamas would have a bright, open study space, perfect for reading while enjoying the view.

The Heart of the Home

Screenshot: YouTube

The kitchen flows beautifully into the dining area, providing a sunny space for the family to enjoy meals together.

D.C. Domain

Screenshot: YouTube

After moving out of the White House in 2017, the Obamas bought this 8,000- square-foot mansion in Washington, D.C., so their youngest daughter Sasha could finish high school.

Beautiful Bedrooms

Screenshot: YouTube

This cozy bedroom with lots of windows and a working fireplace is just one of nine in the home.

Bright, Open Kitchen

Screenshot: YouTube

The home also has not one but two kitchens, including this open space with beautiful white cabinetry, modern appliances and marble countertops.

Cozy Living Space

Screenshot: YouTube

When it’s time to entertain, the home has plenty of living space. We can only imagine the conversations that went down in this spacious living room.

On the Vineyard

Screenshot: YouTube

Martha’s Vineyard has long been one of the Obama family’s favorite places to unwind. So it only makes sense that they would put down roots there, purchasing this nearly 7,000-square-foot home.

Room to Relax

Screenshot: YouTube

There’s no need to fight for shower time. This home includes seven spacious bedrooms and 8.5 bathrooms.

Screened-In Porch

Screenshot: YouTube

The home has a screened-in porch, allowing the family to enjoy a little bit of the outside, even when the weather outside isn’t the best.

Oahu Oasis

Screenshot: YouTube

Now that they can spend more time out of the spotlight, the Obamas have set themselves up in a spacious Hawaiian retreat. According to TMZ, President and Mrs. Obama purchased a three-acre waterfront property on the island of Oahu to build their island oasis back in 2015 for over eight million dollars.

Ties to Television

Screenshot: YouTube

Although the property is tucked away on a beach with plenty of privacy, it does have some ties to Hollywood. The area once included the home used in the 1980s Tom Selleck series “Magnum P.I.,” but the Obamas tore it down to make way for their new crib in 2018, according to TMZ.

A Work in Progress

Screenshot: YouTube

Construction on the Obama’s Hawaiian compound is still ongoing. But according to TMZ, the estate will include a main house, two additional guest properties and two swimming pools.

Winter White House

Screenshot: YouTube/OpenHouse TV

Although we haven’t seen the inside of the new Hawaii home, we can imagine it will be just as fabulous as this Oahu home, which was known as the Winter White House during President Obama’s term. The 7,000-square-foot home has five bedrooms, five-and-a-half bathrooms and a three-car garage.

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