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Here Now, The Cape & Islands 20 Most Expensive Listings

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Here now, the May edition of the the Cape and Islands 20 most expensive listings. Yes, we're well aware that it's now June, but for whatever reason, we momentarily thought this particular timing made sense. Regardless, there are a number of changes on our map: the priciest listing of them all, that $92 million spread in West Tisbury, has disappeared from the market, and one of the map's old standbys, Fairview in Woods Hole, sold. For those keeping score, Nantucket and Cape Cod are now tied, each with eight properties on the list, and the Vineyard is down to four.

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$47,500,000

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Nantucket's priciest listing hit the market last May for a mindblowing $59M. By September, the pricechopperhad arrived to hack $10M off the ask. After a winter sabbatical, Swain's Neck returned to market in early March with a new broker and a new (slightly) reduced asking price.

$25,000,000

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Although officially a "Price Upon Request," a tipster sent in a copy of the listing from the Wall Street Journal with a $25M asking price. The"Chatham Jewel" hit the market earlier this month and is the Cape's most expensive listing.

$20,000,000

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Built in 1823, "Long Hill" is a 7,211 sq. ft. property located on historic upper Orange Street with panoramic views of the Harbor, Coatue and town. The landscaped grounds include a formal English garden and the entire estate is surrounded by a Privet hedge. Perfect for the "Downton Abbey" fan with deep pockets.

$19,500,000

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Located within Herring Creek Farm is this 25-acre property with views of Edgartown Great Pond and the Atlantic Ocean. The priciest listing in Edgartown has a 5,615 sq. ft. main house with room for a guesthouse as well as an additional vacant parcel. In addition, there's private ownership of the shoreline on Edgartown Great Pond and shared private access to a south shore beach.

$17,900,000

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Built in 2000, this seven bedroom, seven bath waterfront features a deep water dock on Katama Bay and boating access to Edgartown Harbor.

$17,500,000

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"Point of View," designed by Richard Bertman, spent a few weeks off market this winter, before returning in January. The 10,760 sq. ft. estate on 10-acres includes 250-degree oceanfront views, an indoor pool, exercise room with Finlandia sauna, a 700-bottle wine cellar, a miniature golf course, and a six-bay carriage house with guest house.

$16,950,000

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Located "on the prestigious and highly coveted Lincoln Circle," this 5 bedroom with a two bedroom guest cottage hit the market just last week. The .59 acre property is close to Steps Beach and features views of Nantucket Harbor.

$15,999,000

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The "prized properties" of Tom Never Head hit the market in mid-April asking $15,999,000. The two waterfront upside down homes, plus a cottage, feature views of the Atlantic Ocean, Low Beach and Tom Nevers Pond.

$15,950,000

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Built in 1880, this shingle-style manor features seven acres of waterfront privacy, a deep water dock and an additional two acres of Nantucket Sound beachfront. In addition to the three-story main house, there's a guest house, caretaker's cottage and pool pavilion. Once asking $17M, an early January pricechop brought the listing down to $15.95M.

$14,995,000

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Built in 1920, this home was moved to its current site and later renovated in 2011. Surrounded by manicured lawns and gardens, both the main house and guest cottage enjoy views of Nantucket Harbor and town.

$14,750,000

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Here's a Polpis waterfront estate set on ten acres. The property includes a four bedroom main house, a two bedroom guest cottage, swimming pool, media room, wine cellar and access to Polpis Harbor.

$14,500,000

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Built in 2005, this 5,600 sq. ft. four bedroom sits on 2.3 waterfront acres. The property includes private paddocks with a riding arena, in-ground pool and spectacular sandy beach. Asking price is $14,500,000.

$14,250,000

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"Chapeda Hill" on Edgartown Harbor includes a Gambrel-style main residence built in the 1930s with water views from almost every room. Additionally, there are two beachfront outbuildings, a sandy beach and a deep water dock. A March pricechop brought the ask down $500K.

$13,950,000

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This circa 1890 estate has been modernized and now includes an observation tower with a personal workout center and guest quarters. There are also two wine cellars, a five car garage and beach house with a dock extending into East Bay. Asking price is $13,950,000.

$13,900,000

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After a winter break from the market, this listing returned with new brokerbabble, but not a new price - although we're sure the "Stellar views!" remain. Built in 2002, this 5BR, 9BA waterfront estate features an elevator, five fireplaces, in-home home theatre, infinity pool, sauna, steam room, theater, and a private dock.

$13,500,000

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This two-acre waterfront compound overlooking the Eel River and Nantucket Sound hit the market last week for $13,500,000. The property includes an in-ground pool, a deep water dock and a guest house.

$13,000,000

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This 4BR, 4.5BA overlooking the Harbor and Nantucket Sound features interior decor by Bunny Williams (available for an additional $400K) and plans for a three car garage, guest house and swimming pool.

$12,999,000

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"Outlook" features a five bedroom main house, a one bedroom guest cottage both designed by Botticelli and Pohl. The property was on the market in 2012 with a $13.9M price tag. With no takers, the listing went off the market and returned earlier this month asking $12,999,000.

$12,999,000

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This 2.72-acre estate includes over 620 feet of water frontage with a sandy beach. The 7,773 sq. ft. six bedroom main residence features multiple balconies and a central courtyard. There's also a guesthouse and two private deep water docks. A January meeting with the pricechopper brought the listing down $3M.

$12,750,000

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Located in Squibnocket Farm, this 12.2 acre plot of waterfront land includes over 1,300 feet of ocean frontage. There's an existing four bedroom Cape style house with approved plans for a new five bedroom home. Views extend across Squibnocket Beach, the South Shore, the Atlantic, and Nomans Land.

$47,500,000

Nantucket's priciest listing hit the market last May for a mindblowing $59M. By September, the pricechopperhad arrived to hack $10M off the ask. After a winter sabbatical, Swain's Neck returned to market in early March with a new broker and a new (slightly) reduced asking price.

$25,000,000

Although officially a "Price Upon Request," a tipster sent in a copy of the listing from the Wall Street Journal with a $25M asking price. The"Chatham Jewel" hit the market earlier this month and is the Cape's most expensive listing.

$20,000,000

Built in 1823, "Long Hill" is a 7,211 sq. ft. property located on historic upper Orange Street with panoramic views of the Harbor, Coatue and town. The landscaped grounds include a formal English garden and the entire estate is surrounded by a Privet hedge. Perfect for the "Downton Abbey" fan with deep pockets.

$19,500,000

Located within Herring Creek Farm is this 25-acre property with views of Edgartown Great Pond and the Atlantic Ocean. The priciest listing in Edgartown has a 5,615 sq. ft. main house with room for a guesthouse as well as an additional vacant parcel. In addition, there's private ownership of the shoreline on Edgartown Great Pond and shared private access to a south shore beach.

$17,900,000

Built in 2000, this seven bedroom, seven bath waterfront features a deep water dock on Katama Bay and boating access to Edgartown Harbor.

$17,500,000

"Point of View," designed by Richard Bertman, spent a few weeks off market this winter, before returning in January. The 10,760 sq. ft. estate on 10-acres includes 250-degree oceanfront views, an indoor pool, exercise room with Finlandia sauna, a 700-bottle wine cellar, a miniature golf course, and a six-bay carriage house with guest house.

$16,950,000

Located "on the prestigious and highly coveted Lincoln Circle," this 5 bedroom with a two bedroom guest cottage hit the market just last week. The .59 acre property is close to Steps Beach and features views of Nantucket Harbor.

$15,999,000

The "prized properties" of Tom Never Head hit the market in mid-April asking $15,999,000. The two waterfront upside down homes, plus a cottage, feature views of the Atlantic Ocean, Low Beach and Tom Nevers Pond.

$15,950,000

Built in 1880, this shingle-style manor features seven acres of waterfront privacy, a deep water dock and an additional two acres of Nantucket Sound beachfront. In addition to the three-story main house, there's a guest house, caretaker's cottage and pool pavilion. Once asking $17M, an early January pricechop brought the listing down to $15.95M.

$14,995,000

Built in 1920, this home was moved to its current site and later renovated in 2011. Surrounded by manicured lawns and gardens, both the main house and guest cottage enjoy views of Nantucket Harbor and town.

$14,750,000

Here's a Polpis waterfront estate set on ten acres. The property includes a four bedroom main house, a two bedroom guest cottage, swimming pool, media room, wine cellar and access to Polpis Harbor.

$14,500,000

Built in 2005, this 5,600 sq. ft. four bedroom sits on 2.3 waterfront acres. The property includes private paddocks with a riding arena, in-ground pool and spectacular sandy beach. Asking price is $14,500,000.

$14,250,000

"Chapeda Hill" on Edgartown Harbor includes a Gambrel-style main residence built in the 1930s with water views from almost every room. Additionally, there are two beachfront outbuildings, a sandy beach and a deep water dock. A March pricechop brought the ask down $500K.

$13,950,000

This circa 1890 estate has been modernized and now includes an observation tower with a personal workout center and guest quarters. There are also two wine cellars, a five car garage and beach house with a dock extending into East Bay. Asking price is $13,950,000.

$13,900,000

After a winter break from the market, this listing returned with new brokerbabble, but not a new price - although we're sure the "Stellar views!" remain. Built in 2002, this 5BR, 9BA waterfront estate features an elevator, five fireplaces, in-home home theatre, infinity pool, sauna, steam room, theater, and a private dock.

$13,500,000

This two-acre waterfront compound overlooking the Eel River and Nantucket Sound hit the market last week for $13,500,000. The property includes an in-ground pool, a deep water dock and a guest house.

$13,000,000

This 4BR, 4.5BA overlooking the Harbor and Nantucket Sound features interior decor by Bunny Williams (available for an additional $400K) and plans for a three car garage, guest house and swimming pool.

$12,999,000

"Outlook" features a five bedroom main house, a one bedroom guest cottage both designed by Botticelli and Pohl. The property was on the market in 2012 with a $13.9M price tag. With no takers, the listing went off the market and returned earlier this month asking $12,999,000.

$12,999,000

This 2.72-acre estate includes over 620 feet of water frontage with a sandy beach. The 7,773 sq. ft. six bedroom main residence features multiple balconies and a central courtyard. There's also a guesthouse and two private deep water docks. A January meeting with the pricechopper brought the listing down $3M.

$12,750,000

Located in Squibnocket Farm, this 12.2 acre plot of waterfront land includes over 1,300 feet of ocean frontage. There's an existing four bedroom Cape style house with approved plans for a new five bedroom home. Views extend across Squibnocket Beach, the South Shore, the Atlantic, and Nomans Land.