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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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1. $47,500,000

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260 Polpis Road
Nantucket, MA 02554

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.

2. $25,000,000

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97 Tilipi Run Street
Chatham, MA 02633

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.

3. $20,000,000

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30 Orange St
Nantucket, MA 02554

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.

4. $19,500,000

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61 Butler's Cove Rd
Edgartown, MA 02539

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.

5. $17,900,000

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27 Edgartown Bay Road
Edgartown, MA 02539

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

6. $17,500,000

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251 Green Dunes Drive
Barnstable, MA 02601

"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.

7. $16,950,000

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17 Lincoln Avenue
Nantucket, MA 02554

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.

8. $15,999,000

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3 Elliots Way
Nantucket, MA 02554

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.

9. $15,950,000

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52 Ships Eagle Ln
Osterville, MA 02655

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.

10. $14,995,000

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47 Monomoy Rd
Nantucket, MA 02554

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.

11. $14,750,000

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250 Polpis Rd
Nantucket, MA 02554

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.

12. $14,500,000

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959 Sea View Avenue
Osterville, MA 02655

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.

13. $14,250,000

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31 Tower Hill Rd
Edgartown, MA 02539

"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.

14. $13,950,000

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315 Main Street
Osterville, MA 02655

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.

15. $13,900,000

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461 Main Street
Osterville, MA 02655

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.

16. $13,500,000

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74 Garrison Lane
Osterville, MA 02655

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.

17. $13,000,000

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34 Shawkemo Road
Nantucket, MA 02554

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.

18. $12,999,000

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9 Fulling Mill Road
Nantucket, MA 02554

"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.

19. $12,999,000

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986 Sea View Ave
Osterville, MA 02655

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.

20. $12,750,000

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78 Squibnocket Farm Rd
Chilmark, MA 02535

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.

1. $47,500,000

260 Polpis Road, Nantucket, MA 02554

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.

260 Polpis Road
Nantucket, MA 02554

2. $25,000,000

97 Tilipi Run Street, Chatham, MA 02633

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.

97 Tilipi Run Street
Chatham, MA 02633

3. $20,000,000

30 Orange St, Nantucket, MA 02554

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.

30 Orange St
Nantucket, MA 02554

4. $19,500,000

61 Butler's Cove Rd, Edgartown, MA 02539

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.

61 Butler's Cove Rd
Edgartown, MA 02539

5. $17,900,000

27 Edgartown Bay Road, Edgartown, MA 02539

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

27 Edgartown Bay Road
Edgartown, MA 02539

6. $17,500,000

251 Green Dunes Drive, Barnstable, MA 02601

"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.

251 Green Dunes Drive
Barnstable, MA 02601

7. $16,950,000

17 Lincoln Avenue, Nantucket, MA 02554

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.

17 Lincoln Avenue
Nantucket, MA 02554

8. $15,999,000

3 Elliots Way, Nantucket, MA 02554

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.

3 Elliots Way
Nantucket, MA 02554

9. $15,950,000

52 Ships Eagle Ln, Osterville, MA 02655

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.

52 Ships Eagle Ln
Osterville, MA 02655

10. $14,995,000

47 Monomoy Rd, Nantucket, MA 02554

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.

47 Monomoy Rd
Nantucket, MA 02554

11. $14,750,000

250 Polpis Rd, Nantucket, MA 02554

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.

250 Polpis Rd
Nantucket, MA 02554

12. $14,500,000

959 Sea View Avenue, Osterville, MA 02655

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.

959 Sea View Avenue
Osterville, MA 02655

13. $14,250,000

31 Tower Hill Rd, Edgartown, MA 02539

"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.

31 Tower Hill Rd
Edgartown, MA 02539

14. $13,950,000

315 Main Street, Osterville, MA 02655

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.

315 Main Street
Osterville, MA 02655

15. $13,900,000

461 Main Street, Osterville, MA 02655

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.

461 Main Street
Osterville, MA 02655

16. $13,500,000

74 Garrison Lane, Osterville, MA 02655

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.

74 Garrison Lane
Osterville, MA 02655

17. $13,000,000

34 Shawkemo Road, Nantucket, MA 02554

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.

34 Shawkemo Road
Nantucket, MA 02554

18. $12,999,000

9 Fulling Mill Road, Nantucket, MA 02554

"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.

9 Fulling Mill Road
Nantucket, MA 02554

19. $12,999,000

986 Sea View Ave, Osterville, MA 02655

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.

986 Sea View Ave
Osterville, MA 02655

20. $12,750,000

78 Squibnocket Farm Rd, Chilmark, MA 02535

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.

78 Squibnocket Farm Rd
Chilmark, MA 02535