Selling and buying on a regular basis, the rich and famous own some of the most lavish homes in the world. Some properties have managed to rack up an impressive list of celebrity owners, as Hollywood stars flip, swap and sell amazing houses to one another. Alongside pop icon Madonna and Hollywood royalty, Richard Gere, click or scroll on to find out exactly who is selling to who in this game of celebrity house swap... 

This Hollywood actor is no stranger to a blockbuster leading role and VIP lifestyle, and his property portfolio certainly reflects that. Richard Gere and his publicist wife, Alejandra Silva snapped up a 32 acre spread in New Canaan, Connecticut from an equally well known and similarly aged American star.

Alongside a $10 million (£8.26m) 26-acre estate in North Salem and his long term residence at a 49-acre compound in Pound Ridge, Gere reportedly, according to Dirt, snapped up this idyllic estate for $10.8 million (£8.9m) earlier this year. Located in Fairfield County, it is approximately a one hour train ride from Manhattan. Built in 1938, the main house was designed by architect Harold Reeve Sleeper and looks out across rolling hills and its own private pond.

Within the whitewashed brick Georgian facade lies approximately 8,800-square-foot of living space, with a welcoming 30-foot hall foyer ideal for entertaining a wealth of VIP guests. Fresh white walls sing against the hardwood flooring, while a sweeping staircase beckons you upstairs.

Open-plan living areas abound, illuminated via huge arching windows providing picturesque, chocolate box views across the snow capped grounds beyond. We’re sure the A-Lister and his young family enjoy eating dinner with mature trees and walled courtyards in the foreground.

Throughout the three floors of living space you’ll find a 750-square-foot living room, huge lower-level family room, and even an over-sized mud room between the three-car garage and homely eat-in kitchen. In one particularly cosy room a wood-burner awaits, with plentiful shelves for bedtime stories, movie scripts and perhaps a leftover music score from the previous owner…

The six-bedroom spread hosts a private bath with each room, while the primary suite in calming pale blues and cream boasts not one but two bathrooms, a fireplace, seven wardrobes and its own large terrace with stunning Connecticut vistas. From here you may be able to spy the grounds’ own woods.

A distance from the main house awaits a three-bedroom cottage with private gated entrance and garage that sit in the woodlands. Each residence finds access to the estate’s swimming pool, flanked by manicured lawns, formal gardens and picturesque walled courtyards. But who used to enjoy a length or two in the grounds pool?

12 Grammy Award-winning singer-songwriter Paul Simon and his musician wife, Edie Brickell were the previous owners of this beautiful longtime estate. Unfortunately the musical duo, according to Dirt, reportedly lost $5.7 million (£4.7m) in the sale to Gere. While the 'Bridge Over Troubled Water' singer may miss using the cottage as a recording studio, Simon and Brickell still own at least three more expansive homes including a sheltered 30-acre oceanfront compound in the Hamptons as well as a 10-acre spread on the semi-rural outskirts of Dallas.

From the World Class Wreckin’ Cru to NWA star, this Compton based rapper and Beats CEO finally settled in Brentwood, LA having snapped up a stunning castle-esque mansion in 2014. The world renowned record producer might steal the limelight when he takes the mic, but his sprawling estate is hidden away amongst rolling hills and behind its own moat and drawbridge…

Originally on the market for more towards $50 million, but snapped up for $40 million (£33m) the previous megastar owners reportedly spent a whopping $40 million (£33m) building the French-style chateau from scratch. Sitting on almost four acres, the five bedroom ‘castle’ was designed by Richard Landry and received plentiful offers once it hit the market before the 'California Love' star according to the LA Times reportedly snapped it up for $50 million (£41m) and spent no time crossing the cobblestone bridge and raising up the drawbridge.

Should you reach past the winding driveway, cobblestone motor court and moat-meets-koi pond, the limestone chateau welcomes you inside with reclaimed ceiling beams, salvaged tile and antique doors throughout the 18,298-square-foot of living space.

Elsewhere in the five-bedroom spread you’ll find nine bathrooms, a den, a library/study, gym and sauna, as well as multiple loggias, covered terraces and balconies with exquisite views out across the rolling grounds. Complete with well kept lawns and gardens, we’re sure the Beats entrepreneur enjoys surveying his multiple ponds, infinity pool and even waterfalls. But which famous couple constructed the off-season retreat?

Dre’s palatial pad was built by the Buccaneers quarterback Tom Brady and supermodel Gisele Bundchen who bought the estate together in 2008 for $11.75 million (£9.7m). While the power couple offered the property furnished, the NWA icon was said to have no interest in the former furnishings, however we’re sure he enjoys the moat’s koi fish residents and the main suite’s outdoor bath tub.

Hollywood host and producer extraordinaire, Ryan Seacrest has also extended his many talents to real estate over the years. Back in 2012, the reality show producer and radio host invested in a famous duo’s former residence, nestled in the VIP loved area of Beverly Hills worth a whopping $49 million (£40.4m)

TMZ reported that the star paid close to the asking price for the sprawling 2.87 acre abode, the American Idol host is worth a jaw dropping $450 million (£371m). The famous former owners snapped up the main residence on the compound, two additional guest cottages, an extra three-bedroom house as well as snapping up two neighbouring properties. They then set to work on renovations..

Connected via bridge to the main island of Vanua Levue, the lots are lifted above sea level offering dramatic waterfront views with full privacy. The celebrity sellers set to work on renovations themselves, installing a koi pond and scattering dozens of mature trees across the grounds for increased privacy.

According to Trulia, the interiors were toned down by the property flipping former owners to give the reclaimed-wood floors and wooden beams a more relaxed feel inside. While it’s unknown how the Kardashians executive chose to furnish his 15,000 square foot property, the original owners were featured in Architectural Digest with their Californian compound interior choices…

Impressive real estate investors and Hollywood power duo, Ellen Degeneres and Portia de Rossi were the property flippers of this particular compound, having splurged on the Beverly Hills spread for $29 million (£23.9m) before snapping up surrounding properties. Built by the renowned architects Buff & Hensman for actor Laurence Harvey, the designer abode was once home Joan Collins and Will & Grace co-creator Max Mutchnick who reportedly invited the couple over to watch American Idol, funnily enough. Which is when they fell in love with the pad and even bought it furnished.

With an impressive real estate portfolio, Madonna owns homes all over the world including in Portugal, her hometown of London and New York. However, most recently Madonna set her sights on the 'blinding lights' of Hollywood and purchased a mega-mansion that had been on the market for over a year. Previously owned by a fellow pop star, who hails from Canada, can you guess who she snapped up her palatial home from?

In April 2021, Madonna splashed out $19.3 million (£15.9m) on the lavish estate that sits within an ultra-private gated community in the Hidden Hills. It would have been the perfect retreat for the half-time SuperBowl star that she bought it from. With seven bedrooms and 10 bathrooms, there's plenty of space for Madonna and her brood.

Inside, the lavish spread boasts a neutral colour palette that sits alongside hardwood floors and sleek white marble for the ultimate stylish mansion. The double-height hallway leads through to open-plan living spaces that look out over the relaxing outdoor space. Elsewhere a LED-lit wine room, fitness studio and screening room are sure to keep them all entertained. For a bit of privacy, the house also features two master suites that lead out to private balconies with views of the garden below. 

Yet, a little over a year after snapping up the manse the Los Angeles Times reported that the star has listed it for $26 million (£21.4m). While it's unclear how many changes Madonna made to warrant a $6.7 million (£5.5m) price increase, there is one confirmed upgrade, a barn, which the health-conscious singer turned into a gym and Pilates studio. Will another celebrity buy this beautiful abode? Only time will tell. But if Madonna gets her asking price, it’ll be the most expensive home sale in Hidden Hills so far this year. 

The 'Material Girl' bought the sprawling mansion from fellow pop star, The Weeknd. The 'Blinding Lights' singer paid $18.2 million (£15m) for the pad in July 2017, just one year after it was built. He then put it on the market for $25 million (£20.6m), where it languished for a year before the queen of pop decided to buy it. Now living in his huge Bel Air mansion which he snapped up for $70 million (£57.8m), we can't wait to see what the star does next.

The princess of pop, Ariana Grande has lived in a whole host of amazing properties. Having spent her childhood in Florida, the 29-year-old now has a net worth of $180 million (£148m), and a collection of amazing homes to boot. A year before she married realtor Dalton Gomez, she added to her property portfolio with this stunning home in Montecito, which she snapped up from a fellow star and well-known talk show host. 

The 'thank u, next' singer forked out $6.8 million (£5.6m) for this Tudor-style home, which is known as Porter House. Spread over 5,500 square feet it boasts three bathrooms, two bedrooms and not one but two high-tech kitchens, making it the perfect home for Ariana and her new husband to host friends. 

Ariana snapped up her home from frequent house flipper Ellen DeGeneres, who is known for transforming properties into luxury properties, before selling them on for millions. The talk show host bought the property at the beginning of 2020 for $3.6 million (£2.97m), so made quite the profit from the Positions star. 

With a collection of homes worth over $150 million (£123m), Oprah Winfrey is the queen of property. Spending her days in her Promised Land estate in California with her family, she also owns a compound in Hawaii and a ski chalet in Colorado. However, in 2019 she expanded her collection even further with another home in Montecito, which she bought from a legendary American actor. Can you guess who? 

The True Grit actor who previously owned the stunning home, spent time renovating the abode after a landslide caused extensive damage in 2018. Oprah then went on to buy the ranch for the same price as the seller did way back in 2014 for almost $7 million (£5.7m). 

Ever the savvy buyer, Oprah snapped up the home from Hollywood legend Jeff Bridges, but not before she waited for the price to be knocked down from $7.5 million (£6.1m) to the $6.9 million (£5.69m) she paid for it, which is exactly the same price Bridges forked out for it in 2014. In recent years, Bridges has been downsizing his proper portfolio, also selling off his 20-acre estate and some parcels of land in Malibu. 

Also somewhat of a house flipper, Leonardo DiCaprio has an enviable property portfolio. Worth an estimated $260 million (£214m), the Once Upon A Time...In Hollywood star lives in the Bird Streets neighbourhood of Los Angeles, but owns a whole host of properties in the area. Most recently in May this year, he bought a luxury mansion home in the Los Feliz area from a very famous Modern Family actor, who also has a keen eye for interior design. 

On the market for just seven days, before he snapped it up from its previous Hollywood owner, Leo paid a whopping $7.1 million (£5.83m) for his new home. What must have been an easy purchase for the property-loving star, he immediately gifted the mansion to his mother, Irmelin, who can visit the star in his other swanky abode just 30 minutes away. 

Spread over 5,000 square feet, the previous owner knows a thing or two about interior design but also hired Will & Grace set decorator, Peter Gurski, to overhaul the interior. Transformed into an eclectic oasis, the decor boasts beamed ceilings, stone fireplaces and stunning arched windows. 

Previously living in the Spanish Colonial was Jesse Tyler Ferguson, who is known for his role as Mitchell Pritchett in the sitcom Modern Family. The actor bought the home way back in 2013 for just shy of $4.6 million (£3.78m), and after spending time renovating it, put it on the market. A firm favourite for celebrities, the home has previously been home to Gwen Stefani and Robert Pattinson. 

In early 2021, Halsey set about getting things ready for the birth of her first child, Ender Ridley Aydin, who arrived in July. In the process, she snapped up a new home from a famous boyband member and former X Factor contestant. Shall we take a look around? 

Sitting on five acres of secluded land, Halsey's new house has almost 9,7000 square feet of space with five bedrooms and five bathrooms. Spending a huge $10.2 million (£8.4m) on her new luxury home, the property had languished on and of the market for the last three years before finally being chosen by the star as her new family home. 

After initially buying it in 2015 for $10 million (£8.25m), One Direction star, Liam Payne, tried to sell his Calabasas home for three years before finally offloading it to Halsey. Not easy to shift, the star admitted that he thinks the home is haunted by former owner and late aerial film operator Alan Purwin. 

In 2018, American singer John Mayer splashed out $13.5 million (£11.1m) on a home in the Beverly Hills area of California. Sold to him buy a fellow singer and The Voice coach, the single-storey pad would have made the perfect family home for its previous owner. 

Adam Levine and his supermodel wife, Behati Prinsloo, bought the stylish spread in 2012 for $4.8 million (£3.96m) and originally tried to sell the estate for $17.5 million (£14.4m) in 2016. However, unable to find any suitable buyers the superstar pair slashed the price and sold up to John Mayer. 

DJ, record producer, and songwriter, Zedd, is said to be worth a whopping $50 million (£41m) at the young age of just 32, making him one of the wealthiest DJs on the planet. So, it was no surprise when he snapped up a new home in Encino, Los Angeles for $15.2 million (£12.5m) from one of Hollywood's top power couples. Hint, they've just moved to Miami! 

With 15,000 square feet of interior space, the DJ can enjoy grand living spaces, a high-end kitchen and luxury amenities such as the home theatre, which would have been the perfect spot for the previous Game of Thrones actor to watch her work. The previous owners were said to have undertaken a number of upgrades to the home which now includes a spa and a gym. 

Zedd snapped up his swanky new home from Joe Jonas and Sophie Turner. The famous pair have recently located to a mega-mansion in Miami, but not before they put their Encino home on the market for $16.75 million (£13.8m), before slashing the price to finally find a fitting seller in the DJ. 

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