For a small state, Rhode Island has a lot of great real estate.
Playground of the rich and famous in the golden age, the shores are dotted with mansions. Some of them are tourist attractions, but others are still functional (holiday) residences for today’s elite.
From Newport mansions to more laid-back homes in Watch Hill and Warwick, here are five homes owned by well-known celebrities.
$400,000 is the median sale price in RI:But what types of houses is he actually buying?
1. Taylor Swift’s $17 Million Home in Westerly

A big star, with a big reputation, Taylor Swift is arguably Rhode Island’s most well-known celebrity. Dubbed the ‘vacation home’, Swift bought the Watch Hill mansion in 2013, complete with an Olympic-sized swimming pool and a past that links him to the fortunes of Standard Oil. The songwriter told the story of the house’s past – and the divorcee who lived there, Rebekah Harkness – in the song “Great American Dynasty” from his eighth studio album Folklore.
At this time, the house often appears on social networks in the summer. It was the place of his 4 that we talked about a lote July holidays from 2013 to 2017, and last summer, Blake Lively posted photos of herself and visiting Ryan Reynolds.
2. Conan O’Brien’s vacation home in Westerly

It is well known in these parts that comedian Conan O’Brien is a New Englander, with an Irish Catholic education from Boston and a degree from Harvard. Slightly less well known is that his family has a vacation home in Watch Hill, which the Conan host bought in 1997.
In 2014, there was a kerfuffle involving Westerly putting his house up for auction because he owed $8,000 in back taxes, but that was quickly resolved when the taxes were paid. O’Brien’s publicist said this was due to a clerical error. At the time, the house was worth $723,000.
These days, people sometimes see him wandering around Westerly during the summer.
3. Jay Leno’s Gilded Age mansion on Ocean Drive in Newport
![Jay Leno sits behind the wheel of a 1937 Bentley outside Seafair, his Newport mansion. In the background, left to right, is a 1930 Packard Dual-Cowl Phaeton, a 2013 Mercedes-Benz SLS AMG Black Series and a 2014 Bugatti Veyron, all on loan from the Automobile Museum of 'Audrain. [Dave Hansen Photography]](https://www.gannett-cdn.com/authoring/2019/10/21/NPRJ/ghows_image-PJ-b5485316-cb5d-4516-a9a9-6702ef940f4a.jpeg?width=660&height=505&fit=crop&format=pjpg&auto=webp)
Comedian Jay Leno isn’t necessarily known for being a golden mansion guy, but he does have one – Seafair on Ocean Drive in Newport.
Leno lives primarily on the West Coast, but, like Conan, he was born in Massachusetts and has family on the East Coast. During a visit to Newport in 2017, he was driving with his wife along Ocean Drive, saw the house they once admired 30 years ago, stopped, discovered it was at sell and bought it with everything inside for $15 million. Telling this story to a reporter for the USA Today Network in 2019, he said having the house with everything in it was a big selling point because it ensured he wouldn’t have never to spend time thinking about tissue samples, which he described as a nightmare.
He estimated he spent 19 days at Seafair in 2019, but when in town he is often spotted. He’s tested new material at the Firehouse Theatre, attended Audian’s Concours + Motor Week and is known to lunch downtown.
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4. Judge Judy Sheindlin’s Newport Mansion
![Judge Judy Sheindlin and her husband, Jerry Sheindlin, bought the "bird house," at 70 Beacon Hill Road in Newport, for $9 million. [Courtesy of Gustave White Sotheby’s International Realty]](https://www.gannett-cdn.com/authoring/2018/07/30/NPRJ/ghows-PJ-723e393d-b6bb-4841-e053-0100007f505b-0f4943cb.jpeg?width=660&height=440&fit=crop&format=pjpg&auto=webp)
After 25 years of television royalty, Judge Judy Sheindlin bought a home worthy of the title in 2018 for herself and her husband, Judge Jerry Sheindlin. The Newport mansion, called Bird House, on Beacon Hill Road has six bedrooms, six bathrooms and stunning exterior views.
Front and center are the ocean views – of course – but also the garden, which was carefully cultivated by the house’s former owner, the late Campbell Soup heiress Dorrance H. Hamilton, who was known for her love of gardens and helped start the Newport Flower Show.
Sheindlin seems to like the Ocean State. Last year, she received permission from the General Assembly to marry her grandson in the state. While interesting, instead of hosting the affair on her 3.67 acre lot, the wedding took place at the Weekapaug Inn in Westerly.
5. Vanessa Carlton’s Architectural Digest-worthy home in Warwick

It’s not a mansion, but the 223-year-old home Vanessa Carlton bought in Warwick in 2020 is stunning.
The ‘A Thousand Miles’ singer has been posting snapshots of her family’s circa 1803 Federal Colonial home on Instagram since 2021. The singer closed the house in April 2021 after seeing ‘the house on Zillow over the winter and decided to go. “After a year of renovations, she’s created a magazine-worthy home with an article in Architectural Digest to prove it.
The studio space – which she had to ask the town of Warwick to build a gap – is seen as the backdrop for her announcement of her Future Pain 2023 tour which kicks off in March.
6. James Woods compound in Exeter
Originally from Rhode Island, 75-year-old actor James Woods still lives in his home country.
Unlike those who chose an ocean view, Woods lives by Lake Coone in Exeter. Not far from the Arcadia management area, his family has owned the land for decades.
The property has been as controversial as the dual Oscar nominee policy. He put the house up for sale in 2017, but last December got embroiled in a dispute with the city when he challenged his neighbor’s plans to build a house on Lake Boone.