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    The Obamas’ Former Martha’s Vineyard Getaway Hits the Market for $39 Million

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    This iconic Martha’s Vineyard estate—once the Obamas’ go-to summer sanctuary—is back on the market, asking $39 million. Represented by Maggie Gold Seelig of MGS Group Real Estate and Brian Dougherty of Corcoran Property Advisors, the listing has both an architectural pedigree and presidential provenance. 

    Set on nearly 30 private acres in Chilmark, the estate hugs the shoreline of Tisbury Great Pond and delivers serious Vineyard magic: rolling lawns, meadows, and waterfront views. The Obama family rented the home for their summer getaways between 2009 and 2011, reportedly paying $50,000 a week, according to The Wall Street Journal. It’s also where President Barack Obama addressed the nation after Hurricane Irene and honored the late Senator Ted Kennedy, Architectural Digest reported. Years later, the former first family would return to the island to put down more permanent roots, purchasing a $14.85 million estate in nearby Edgartown in 2019.

    At the heart of the property is a gracious 7,000-square-foot main house—classic New England on the outside, tailored luxury inside. Think vaulted ceilings, stone fireplaces, wraparound porches, and a dining room with knockout water views. Arrive via a gated drive, passing a 150-year-old Pennsylvania barn clad in cedar shingles, and it’s hard not to feel like you’ve stumbled into an East Coast fairytale. 

    RELATED: Al Pacino’s Former Beverly Hills Rental Home Is Up for Grabs at $16 Million

    Foster has renovated the property, including the main house, since he bought it over a decade ago.

    Evan Joseph Photography

    But here’s where it gets really interesting: the estate’s current owner is none other than vaunted British architect Norman Foster, the mind behind London’s Gherkin and Wembley Stadium. Foster was struck by the estate’s pastoral approach and the authenticity of its architecture, describing it as a “classic New England house that had grown from historic farming roots,” The WSJ reported. What made it special, he added, was its ability to feel remote and expansive while still sitting in the heart of Martha’s Vineyard. 

    Since acquiring the property in 2011 for $22.4 million, Foster, the founder and chairman of Foster + Partners, has injected his signature style into the compound, most notably with the sleek, contemporary pool and poolhouse he designed to contrast the classic clapboard main home. Modernism meets Martha’s Vineyard? Yes, indeed, and somehow, it works. 

    RELATED: Bill Gates’s Former Waterfront Mansion in Florida Can Be Yours for $23.5 Million

    Vast walls of glass bring the outside to the inside of the Foster-designed poolside pavilion.

    Evan Joseph Photography

    Scattered across the grounds are a five-bedroom guesthouse, a boathouse with a private dock, a design studio, a gym, tennis and basketball courts, an apple orchard, equestrian paddocks, and staff housing. It’s a compound built for both deep relaxation and active living—with just enough gravitas to host a head of state. 

    While Martha’s Vineyard’s luxury market has cooled since the pandemic peak, properties with notable provenance continue to draw interest. Case in point: Diane Sawyer’s waterfront retreat sold for $23.9 million in late 2023 after just two months on the market and for just shy of its $24 million ask. Meanwhile, the island’s median home price dipped to $1.1 million in April, down more than 30 percent from the previous year. 

    Click here to see more photos of Blue Heron Farm.  

    Evan Joseph Photography

    Authors

    Abby Montanez

    Abigail Montanez is a staff writer at Robb Report. She has worked in both print and digital publishing for over half a decade, covering everything from real estate, entertainment, dining, travel to…

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      This $2.2 Million Massachusetts Home Is Where Walt Disney Reportedly Wrote ‘Fantasia’

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      Walt Disney may have settled down in Southern California, but he wrote his hit musical Fantasia at this magical home in Massachusetts. 

      Located in Centerville, a historic village on Cape Cod, the shingled abode is on the market for just shy of $2.2 million. According to the listing, the property originally belonged to a larger estate known as Fernbrook, which dates back to 1881. In its 143-year lifespan, the inn has hosted famous visitors from Audrey Hepburn to the Kennedys and counts Herbert T. Kalmus, the inventor of the Technicolor motion picture process, as its former owner. 

      During Kalmus’s time at Fernbrook, he invited Disney to stay at the estate. The movie and TV producer is believed to have penned the 1940s animated film while holed up in the abode’s water tower, which the house on offer is built around. “The base of the tower is now the primary bedroom,” Gene Orloff of Sotheby’s International Realty—Cape Cod, Osterville Brokerage, told Mansion Global. “The top of the water tower is a wonderful room with a bar and original huge windows that drop into the sills for air and an almost 360-degree view of Centerville and peaks of Nantucket Sound. 

      RELATED: A $14 Million Cape Cod Home Packed With the Charm of a Bygone Era Is Listed for the First Time in 50 Years

      The octagonal water tower where Walt Disney is said to have wrote Fantasia.

      Nauset Media for Sotheby’s International Realty

      The current residence, which was constructed in 1995, last sold in 2017 for a cool $1.13 million. Altogether, the dwelling measures 5,050 square feet and features six bedrooms and four full bathrooms. Another cool feature: legendary landscape architect Frederick Law Olmstead, best known for designing several public parks, starting with Central Park in New York City and Harvard University’s Arnold Arboretum, was tapped to spruce up the roughly one-acre grounds, which include a lily pond and lush gardens. 

      The home features refinished wood floors and a vaulted, wood-clad ceilings.

      Nauset Media for Sotheby’s International Realty

      Set across three floors, the home is decked out with exposed beams and oversized windows that overlook the bucolic landscape. On the first level, you’ll also find the primary suite, a renovated chef’s kitchen, a guest room, and a dining area. Elsewhere, surrounding porches and decks are perfect for soaking in the sun and provide easy access to the heated swimming pool.  

      RELATED: Harry Connick Jr. Is Asking $12.5 Million for His Coastal New England Retreat

      Nestled on Centerville’s Main Street—recognized by the National Register of Historic Places—the house itself is a stone’s throw from Craigville Beach and the beloved Four Seas Ice Cream. Taylor Swift and Adam Sandler have visited the latter. The shop was reportedly put up for sale in February.  

      Click here to see more photos of 489 Main Street.  

      Nauset Media for Sotheby’s International Realty

      Authors

      Abby Montanez

      Abigail Montanez is a staff writer at Robb Report. She has worked in both print and digital publishing for over half a decade, covering everything from real estate, entertainment, dining, travel to…

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      in Luxury

      Celtics Star Jaylen Brown Hopes to Hook a Buyer for His Boston Penthouse

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      Always wanted to sit back and relax in a lofty abode offering picturesque views of South Boston‘s Seaport area—one with an expansive roof deck and easy access to an acclaimed steakhouse, for instance? Well, if you’ve got an extra $4.75 million lying around and are eager to spend it, this industrial-style residence in the Fort Point neighborhood might be the ideal spot to settle down in unique style.

      Records show the condo was last purchased for $5.5 million in October 2021. Its current owner is Celtics star Jaylen Brown, who was named NBA Finals MVP in June after the team snagged its league-record 18th championship. Tailored to suit his personal needs, the corner unit lies on the top floor of the five-story Necco Landing building, which once served as a textile factory.

      The kitchen features an eat-in island and high-end stainless appliances.

      Surette Media Group

      RELATED: Celtics Star Al Horford’s Boston-Area Home Bounces on the Market for $9 Million

      Billed in the listing as a “home for champions,” Brown’s loft features three bedrooms and a matching number of baths in nearly 3,000 square feet of living space adorned throughout with the original exposed brick walls, 12-foot-high wood-beam ceilings, and oversized teal-framed windows providing abundant natural light.

      An open-plan great room holds a living and dining area displaying basketball memorabilia, a wine fridge, a billiard table, and arcade machines, while a sleekly designed kitchen is outfitted with open shelving, an eat-in island, and top-tier stainless appliances. A spacious primary suite boasts two walk-in closets and a bath equipped with dual vanities and a large shower, and elsewhere is an elevator-accessible entry foyer that has a spiral staircase leading up to a 400-square-foot roof deck sporting a fire pit.

      The spacious roof deck comes complete with a fire-pit and city views.

      Surette Media Group

      RELATED: Vladimir Tarasenko Snags Miami Condo, Chris Paul Lists in L.A., and More Sports Celebrity Deals

      The new owner will be required to pay a $1,842 monthly maintenance charge, which includes heat and air-conditioning, water, sewer, master insurance, and trash removal. There’s also a private resident’s entrance to the ground-floor Mooo…. Seaport restaurant.

      Brown, who was drafted as the third overall pick by the Boston Celtics in 2016, agreed to a five-year, $304 million supermax contract extension in 2023, which ranks as the richest contract in NBA history. That means the three-time All-Star will earn an estimated average of $60.8 million per year during the life of the contract.

      The listing is held by George Sarkis and Manny Sarkis of The Sarkis Team at Douglas Elliman.

      Click here for more photos of Jaylen Brown’s Boston penthouse.

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      Harry Connick Jr. Is Asking $12.5 Million for His Coastal New England Retreat

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      You’ll need more than a wink and a smile to pick up this Massachusetts estate! As first reported by The Wall Street Journal, the coastal 1.3-acre spread long owned by award-winning singer, pianist, and actor Harry Connick Jr. has just popped up for sale in the Lower Cape Cod enclave of Chatham, asking $12.5 million. The listing is held by Paul Grover and Matthew de Groot of Berkshire Hathaway HomeServices Robert Paul Properties.

      Records show the New Orleans-born crooner and his wife, former Victoria’s Secret model Jill Goodacre, paid $5.3 million back in early 2006 for the Oyster Pond Lane property. Tucked away behind tall hedges and a lengthy tree-lined driveway, the charming wood-shingled structure boasts five bedrooms and six bathrooms in a tad over 5,300 square feet of two-level living space, all of it accented throughout with the original pine floors, reclaimed wood, and numerous fireplaces.

      The backyard has an inviting freeform pool, an expansive terrace, and a fire-pit conversation area.

      Jack Vatcher Photography

      Built back in the 1960s but extensively renovated during the couple’s tenure, the blufftop structure overlooks Chatham Village and Oyster Pond, a saltwater basin that flows to Nantucket Sound and the Atlantic Ocean. There’s also a staircase and a raised walkway leading down to a boathouse and a private dock, plus an attached two-car garage.

      Other highlights include an entrance hallway displaying a traditional staircase, along with a cozy family room sporting built-in bookcases flanking a wood-burning fireplace. A gourmet kitchen is outfitted with a built-in buffet, an eat-in island, top-tier stainless appliances, and a dining area flaunting two sets of French doors spilling out to the backyard.

      A private balcony in the primary bedroom overlooks picturesque water vistas.

      Jack Vatcher Photography

      Accessed via a private staircase is an upstairs primary suite, which comes complete with a water-view balcony, a walk-in closet, and a luxe bath equipped with dual vanities, a soaking tub, and a glass-encased shower, as well as a study where Connick worked on his tunes. Outdoors, the park-like grounds are dotted with manicured gardens and mature trees and host a fire pit and a freeform swimming pool surrounded by a brick-clad terrace.

      According to WSJ, Connick and Goodacre have decided to let go of the house, which is being sold fully furnished, because they are spending less time on the Cape now that their children are grown.

      In other musician-related real estate news, Kendrick Lamar reportedly just dropped $40 million on a nine-bedroom estate in the Los Angeles neighborhood of Brentwood, while his current arch nemesis Drake wrangled a sprawling Texas ranch for $15 million. Meghan Trainor also scooped up DJ Zedd’s rockstar-worthy mansion in L.A. for $17 million.

      Click here for more photos of Harry Connick Jr.’s Cape Cod house.

      Jack Vatcher Photography More

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      Celtics Star Al Horford’s Boston-Area Home Bounces on the Market for $9 Million

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      After almost three years of ownership, Al Horford is moving on from his Massachusetts estate. The acre-plus spread, tucked away just minutes from downtown Boston in the suburban community of Brookline, is back on the market for a smidge under $9 million. The five-time NBA All-Star and highest-paid Latin American player—who is currently competing in the Eastern Conference Finals with the Boston Celtics—acquired the classic Colonial-inspired home for $7.5 million back in fall 2021, shortly after it was newly built.

      Resting behind wrought-iron gates and fully fenced, the three-level structure is fronted by a spacious motorcourt flanked by an attached three-car garage. Once inside, six bedrooms and eight baths are filtered across a little more than 9,300 square feet of living space that’s been virtually staged by Spotless Agency and boasts caramel-hued hardwood floors, high ceilings, and designer lighting throughout.

      The formal window-lined living room has enough space for a grand piano.

      Surette Media Group

      Glass doors open into a soaring tiled entry foyer displaying a stylish glass-railed staircase and large Pella-brand windows. To one side is the living room, with a dining room on the other. Cloistered in the back of the house is a gourmet kitchen outfitted with sleek white cabinetry, an eat-in island that seats four, a walk-in pantry, and top-tier Miele, Wolf, and Sub-Zero appliances. An adjacent breakfast nook is flanked by a climate-controlled wine cabinet and a family room sporting a chic linear fireplace built into a decorative accent wall, and other main-level highlights include a junior primary suite with its own balcony.

      Elsewhere is an opulent upstairs primary retreat featuring a sitting area warmed by a fireplace, a walk-in closet, a dressing room, and a spa-like bath equipped with dual vanities, a freestanding soaking tub, and a glass-encased shower for two. Four additional en-suite bedrooms and a laundry room can also be found on this floor, while the bottom-most level features a partially finished basement holding a media room, and the woodsy grounds host an expansive rear deck that’s ideal for al fresco lounging and entertaining.

      A fireside family room overlooks the backyard.

      Surette Media Group

      In addition to the for-sale Brookline home, which Horford shares with his longtime actress and former Miss Universe wife Amelia Vega, the 37-year-old Dominican basketball player known to his fans as “Big Al” reportedly still maintains a mansion in the Sandy Springs neighborhood of Atlanta.

      The listing at 100 Cottage St. is held by the Sarkis Team at Douglas Elliman.

      Click here for more photos of Al Horford’s house.

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      in Vacation Homes

      Inside the Most Expensive Summer Rental on Martha’s Vineyard

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      Martha’s Vineyard has long been a popular summer getaway for high-profile vacationers, including Oprah Winfrey, the Obamas, Larry David, and Bill Gates. This year, the most expensive rental to ever hit the island will cost you an eye-watering $1 million per month. 

      Located at 18 Point Inner Way, overlooking the picturesque Menemsha Pond, the roughly five-acre waterfront compound is available to rent for four consecutive weeks between May and July and September and October. Nestled within the pastoral town of Chilmark, one of New England’s priciest ZIP codes, the sprawling contemporary compound has a whopping 11 bedrooms and 13 bathrooms split between the main house and two additional residences, including a writer’s cottage.

      Floor-to-ceiling windows flood the main house with natural light.

      Bob Gothard/ Wallace & Co. Sotheby’s International Realty

      “The lush green surroundings, invigorating coastal breezes, and overall sense of serenity make it an attractive destination for those in search of an escape,” notes the listing, which is held by Tom Wallace of Wallace & Co. Sotheby’s International Realty.

      To justify the hefty price tag, the coastal estate offers a slew of amenities. Inside the main house, which was originally built in 2012, you’ll find two top-of-the-line chef’s kitchens, a home theater with massaging recliners, a sauna and steam room, and a 30-foot indoor pool. There’s also a large water-facing deck with a built-in grill, a pizza oven, a fire pit, a wooden bar, and an outdoor dining area for up to 24 guests. Of course, sweeping views are a given.

      The five-acre compound can be rented for $1 million a month.

      Bob Gothard/ Wallace & Co. Sotheby’s International Realty

      In addition to the residence, the grounds also include an entertainment building, which holds an indoor basketball court with a professional shooting machine as well as a large fitness studio with Technogym and Peloton equipment. Down below, there’s a six-car garage equipped with Porsche and Tesla charging stations.

      Outside, there are plenty of recreational activities to keep everyone busy. The tennis court can also be used for pickleball; there’s a cedar jungle gym for the kids; and seafarers will appreciate the home’s 115-foot private deep-water dock that’s nicely stocked with paddle boards and kayaks. Even better, guests can choose between three boats to cruise around on the pond, including a swanky 55-foot Novamarine BS160 that was custom-made in Italy. Also in the fleet are a Mastercraft X26 ideal for water skiing or wakeboarding and a 26-foot Zodiac Open 7.0 speed boat if you’re in the mood for something quicker to zip around in.

      Click here to see more photos of 18 Point Inner Way.

      Andrew Azoulay/ Wallace & Co. Sotheby’s International Realty

      Authors

      Abby Montanez

      Abigail Montanez is a staff writer at Robb Report. She has worked in both print and digital publishing for over half a decade, covering everything from real estate, dining, travel and topics…

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      in Vacation Homes

      18 Point Inner Way in Photos

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      Published on February 28, 2024

      Andrew Azoulay/ Wallace & Co. Sotheby’s International Realty

      Authors

      Abby Montanez

      Abigail Montanez is a staff writer at Robb Report. She has worked in both print and digital publishing for over half a decade, covering everything from real estate, entertainment, dining, travel to…

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      in Luxury

      Diane Sawyer’s Coastal New England Oasis Sells for Close to Asking

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      Once again Diane Sawyer is associated with breaking news—but this time, the latest juicy tidbit is centered around her own New England home. Barely two months after the TV broadcast journalist’s longtime residence known as “Chip Chop” first hit the market, the sprawling seaside compound has already traded hands for a smidge under the $24 million asking price, as first reported by The Wall Street Journal.

      Records show the speedy buyer is David Malm, managing partner of Webster Equity Partners, who paid $23.9 million for the 20-acre estate resting in the coastal enclave of Martha’s Vineyard. Per WSJ, the investor now lays claim to $100 million worth of luxury homes on the Massachusetts island and neighboring Nantucket, including a historic house on Edgartown’s inner harbor he paid $15 million for earlier this year.

      Designed in the late 1930s by Neoclassical architect Eric Gugler and ultimately completed in the mid-1940s, the property was purchased by the news anchor and her late film director husband Mike Nichols in the mid-1990s for $5.3 million. The couple subsequently undertook an extensive restoration in conjunction with Tate Builders, which included adding dormers, and replicating antique windows and doors.

      Originally built for stage actress Katharine Cornell, and designed by Neoclassical architect Eric Gugler, the New England-style home is topped with 10 chimneys.

      Nestled on two separate parcels of land tucked between Vineyard Sound and Lake Tashmoo, and boasting a combined mile of private shoreline, the seaside spread features a wood-shingled, New England-style main house boasting three bedrooms in nearly 5,000 square feet of living space.

      Numerous additional structures include a two-bedroom caretaker’s cottage and a pair of modern beach cottages affectionately referred to as “The Shacks” because of the fishing shacks they replaced, plus two more detached guest bedroom suites known as the Pond and Ocean pavilions. There’s also a swimming pool and Har-Tru tennis court on the premises.

      Several ancillary structures are scattered across the 20-acre property.

      The 77-year-old anchor known for programs such as ABC World News Tonight, Good Morning America and 20/20, previously told WSJ she is selling this “magic place” because “the rhythms of summer have changed” as her family has grown, and “there is less free time for long visits to the island.”

      The listing was held by Mark Jenkins of Wallace and Co. Sotheby’s International Realty; Malm was repped by Tom Wallace of Wallace & Co. Sotheby’s International Realty.

      Click here for more photos of Diane Sawyer’s New England compound. More

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      Dave Portnoy Drops a Record $42 Million on a Hedge Fund Manager’s Waterfront Nantucket Retreat

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      Earlier this year, prolific property collector Dave Portnoy bought a humble ranch-style house in the Saratoga Springs neighborhood of Upstate New York, just steps from the area’s famed thoroughbred race track.

      Now the veteran sports personality— best known as founder of the Barstool Sports media empire—has added to his prime real estate portfolio yet again, but in a much bigger way, with records showing he paid a whopping $42 million in an off-market deal for a waterfront compound in the Monomoy area of Nantucket. He also shelled out an extra $2 million for furniture and other items.

      Per The Wall Street Journal, which first reported the sale, the deal set a milestone for the most expensive residential real estate transaction ever recorded both on the affluent island and in Portnoy’s native state of Massachusetts—easily topping the $38.1 million transfer of another waterfront compound in Nantucket by venture capitalist Evan Jones and his wildlife photographer wife Cindy this past June.

      The sellers, a pair of trusts known as MAK Daddy and MAK Shack, are both linked to hedge fund manager Mike Colby and his wife Kathi in records. Colby, a longtime executive at Ray Dalio’s Bridgewater Associates, paid a little more than $13 million for two parcels spanning 1.2 acres back in 2016. The couple subsequently razed the existing site structures and engaged architecture and design firm Workshop/APD to create an all-new compound.

      Completed around 2018, the spread is now spotlighted by a four-bedroom main house boasting casual yet elegant interiors highlighted by a double-height entry foyer displaying a sculptural staircase, plus bi-folding glass doors overlooking sweeping views of Nantucket Harbor.

      Other standout features include a living room sporting a freestanding fireplace and pair of sunburst-inspired chandeliers, as well as a dining area, kitchen outfitted with a marble eat-in island, and primary bedroom suite with a private terrace that has an outdoor shower. There’s also a pool area, along with a detached guesthouse hosting a gym and media room.

      Peter Engen of Lee Real Estate acted on behalf of the sellers; the buyer was repped by Shellie Dunlap, also of Lee Real Estate.

      Click here for more photos of Dave Portnoy’s Nantucket house.

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