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The Cape & Islands 25 Most Expensive Listings, Sept. '14

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Here now, the September edition of the Cape and Islands 25 most expensive listings. This month, blockbuster asking prices range from $12,500,000 to an incredible $108,000,000. Not surprisingly, tony Nantucket tops the list with 14 of the 25, Cape Cod follows with eight and the Vineyard grabs third place with three ultra-pricey pads for sale. Of course, that nine-figure spread is in West Tisbury, so there's that.

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$108,000,000

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The Cape & Islands' most expensive listing debuted on the market in July 2012 for a mind-blowing $118 million. The place does have 314 acres (!!!) and can be purchased in any number of (buildable) combinations. Case in point, there's an option to grab 50 acres with a 5,600 sq. ft. house, pool and tennis court for "just" $44 million. Alas, the pricechopper visited in March 2014 and brought the ask for whole thing down to $108,000,000. Oddly, the $10 million slice didn't do the trick and the rather epic spread is still available.

$35,000,000

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Nantucket's priciest listing hit the market in May 2012 for a mindblowing $59M. By September, the pricechopper had arrived to hack $10M off the ask. After a winter sabbatical, Swain's Neck returned to market in March 2013 with a new broker and a new (slightly) reduced asking price. As of May 2014, the pricey pad is available for a newly configured $35M.

$27,500,000

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"Amenities abound in this waterfront estate of unparalleled quality." Indeed, 34 & 36 Shawkemo Road is a 15.5 acre spread with a main house, 4-car garage with studio, boat house, pool and cabana, boardwalk to the beach, guest house, and over 100-feet of harbor front. Oh, there are also "permitted plans for a three car garage, guest house and a swimming pool." Yup, a guest house for the guest house. Asking price is $27.5 million.

$25,000,000

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The"Chatham Jewel" hit the market as a price upon request listing, but is now officially the Cape's most expensive listing. "Positioned on the elevated Chatham shoreline, this shingle-clad home presides over the Atlantic Ocean, Monomoy Islands, and Nantucket Sound, and stands as a testament to tranquility." In addition to presiding, the 10,974-square-footer has 6BR, 6BA, and much, much more.

$24,900,000

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Owned by Susan Hilfiger, ex-wife of fashion icon Tommy Hilfiger, this Lincoln Circle area property hit the market in July 2013 for $26,995,000 and is now hoping for "just" $24,900,000.

$22,950,000

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According to the brokerbabble for this Squam Road compound, "...kick off your flip flops and take a short stroll down the sandy pathway to relax on the beach!" Well, for $22,950,000, that is.

$21,999,000

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Set on oceanfront 2.2 acres, this Squam Road compound hit the market for $19,900,000 in September 2013. The seven bedroom, eight and a half bath property with a pool, gardens and a private boardwalk to Squam Beach was then priceupped in May of this year to $21,999,000. So there's that.

$19,500,000

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The brokerbabble assures that this 10,000-square-footer on 2.7 waterfront acres is "Arguably one of Edgartown’s finest Estates..." Regardless, the $19.5M price tag makes this the priciest listing in Edgartown.

$19,500,000

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This "new imagining of the classic beach house" debuted on the market in late May asking a hefty $22 million. The classic, as in "3.74+/- acres, 300 +/-feet of sandy beach, 6 bedroom main house, 5 bedroom guest house, pool and pool house, sweeping lawns, and beach cabana at the water's edge.." quickly reconsidered that ask and is now hoping for $19,500,000.

$18,975,000

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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.

$18,000,000

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Located on Morris Island, this 13-acre waterfront estate features a five bedroom main house, a boathouse with a dock, a children's retreat, and its very own chapel. Asking price is $18 million.

$17,950,000

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Set on one acre, this Cliff Road property with a 1900s main house, 1965 guest cottage and 1986 carriage house hit the market for $19,500,000. In September 2013, a million dollar pricechop brought the ask down to $18,500,000. The chopper returned yet again in July 2014 and discounted the price to $17,950,000.

$17,950,000

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Overlooking Nantucket Harbor, this Monomoy Road property is asking $17,950,000. Per the listing, the 1.18 acre "generational opportunity" comes with a private beach and a total of seven bedrooms in two separate homes.

$17,500,000

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"Point of View" took yet another break from the market, but has returned with the same $17,500,000 asking price - yet again. 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.

$16,500,000

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This 15 acre Quidnet estate features 24 rooms with 8 bedrooms, 9+ baths in 16,000-square-feet. In addition to views galore, there's a pool, pool house with an outdoor kitchen, tennis, and "infrastructure to support many additional possibilities." Asking price is $16.5M.

$15,500,000

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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 in March 2013 for $16,950,000. The .59 acre property is close to Steps Beach and features views of Nantucket Harbor and, after a July 2014 chop, is asking $15,500,000.

$15,500,000

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This Dionis property makes the most of its 7.9 acres with a main house, studio, artist's space, pool with a pool house, five practice golf holes, and a double order of three-car garages. Asking price was $17,995,000, but is now down to $15,500,000.

$15,000,000

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Naturally, Yarmouth's priciest listing is located on Great Island, "one of the most treasured and desirable communities on Cape Cod, known for its privacy, security and amenities..." The 4BR, 5BA is asking an even $15 million.

$14,950,000

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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, and now a December chop has brought the ask to $14,950,000.

$13,750,000

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Built in 2003, this waterfront 10-acre Polpis estate has 22-rooms, "sweeping and endless harbor views", a guest house, pool, a gym, room for tennis, and access to Polpis Harbor. Asking price is $13,750,000.

$13,250,000

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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, but a December slice took $1 million.

$12,999,000

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Here's an Osterville with not one, but two private deep water docks and over 620-feet of water frontage. The house itself was built in 1930 and features 19 rooms in 7,773-square-feet. Asking price is a chopped $12,999,000.

$12,950,000

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When this Wauwinet abode hit the market it April for $12.95M, the brokerbabble left no polished nickel fixture unmentioned. Yup, "Deer Run" is pretty tricked out and even "offers access to a rare deep water dock, two moorings and a storage area for tenders."

$12,500,000

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This Osterville estate overlooking Eel River and Nantucket Sound first hit the market in April 2013 looking for $13.5M, but lost $1 million from the ask in February 2014.

$12,500,000

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Built in 1920, this Monomoy 6BR, 10BA first hit the market in November 2012 for $14,995,000. Alas, no "Downton Abbey" fans came forward and an August 2013 pricechop brought the ask for the renovated 7,500-square-footer down to $12,500,000.

$108,000,000

The Cape & Islands' most expensive listing debuted on the market in July 2012 for a mind-blowing $118 million. The place does have 314 acres (!!!) and can be purchased in any number of (buildable) combinations. Case in point, there's an option to grab 50 acres with a 5,600 sq. ft. house, pool and tennis court for "just" $44 million. Alas, the pricechopper visited in March 2014 and brought the ask for whole thing down to $108,000,000. Oddly, the $10 million slice didn't do the trick and the rather epic spread is still available.

$35,000,000

Nantucket's priciest listing hit the market in May 2012 for a mindblowing $59M. By September, the pricechopper had arrived to hack $10M off the ask. After a winter sabbatical, Swain's Neck returned to market in March 2013 with a new broker and a new (slightly) reduced asking price. As of May 2014, the pricey pad is available for a newly configured $35M.

$27,500,000

"Amenities abound in this waterfront estate of unparalleled quality." Indeed, 34 & 36 Shawkemo Road is a 15.5 acre spread with a main house, 4-car garage with studio, boat house, pool and cabana, boardwalk to the beach, guest house, and over 100-feet of harbor front. Oh, there are also "permitted plans for a three car garage, guest house and a swimming pool." Yup, a guest house for the guest house. Asking price is $27.5 million.

$25,000,000

The"Chatham Jewel" hit the market as a price upon request listing, but is now officially the Cape's most expensive listing. "Positioned on the elevated Chatham shoreline, this shingle-clad home presides over the Atlantic Ocean, Monomoy Islands, and Nantucket Sound, and stands as a testament to tranquility." In addition to presiding, the 10,974-square-footer has 6BR, 6BA, and much, much more.

$24,900,000

Owned by Susan Hilfiger, ex-wife of fashion icon Tommy Hilfiger, this Lincoln Circle area property hit the market in July 2013 for $26,995,000 and is now hoping for "just" $24,900,000.

$22,950,000

According to the brokerbabble for this Squam Road compound, "...kick off your flip flops and take a short stroll down the sandy pathway to relax on the beach!" Well, for $22,950,000, that is.

$21,999,000

Set on oceanfront 2.2 acres, this Squam Road compound hit the market for $19,900,000 in September 2013. The seven bedroom, eight and a half bath property with a pool, gardens and a private boardwalk to Squam Beach was then priceupped in May of this year to $21,999,000. So there's that.

$19,500,000

The brokerbabble assures that this 10,000-square-footer on 2.7 waterfront acres is "Arguably one of Edgartown’s finest Estates..." Regardless, the $19.5M price tag makes this the priciest listing in Edgartown.

$19,500,000

This "new imagining of the classic beach house" debuted on the market in late May asking a hefty $22 million. The classic, as in "3.74+/- acres, 300 +/-feet of sandy beach, 6 bedroom main house, 5 bedroom guest house, pool and pool house, sweeping lawns, and beach cabana at the water's edge.." quickly reconsidered that ask and is now hoping for $19,500,000.

$18,975,000

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.

$18,000,000

Located on Morris Island, this 13-acre waterfront estate features a five bedroom main house, a boathouse with a dock, a children's retreat, and its very own chapel. Asking price is $18 million.

$17,950,000

Set on one acre, this Cliff Road property with a 1900s main house, 1965 guest cottage and 1986 carriage house hit the market for $19,500,000. In September 2013, a million dollar pricechop brought the ask down to $18,500,000. The chopper returned yet again in July 2014 and discounted the price to $17,950,000.

$17,950,000

Overlooking Nantucket Harbor, this Monomoy Road property is asking $17,950,000. Per the listing, the 1.18 acre "generational opportunity" comes with a private beach and a total of seven bedrooms in two separate homes.

$17,500,000

"Point of View" took yet another break from the market, but has returned with the same $17,500,000 asking price - yet again. 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.

$16,500,000

This 15 acre Quidnet estate features 24 rooms with 8 bedrooms, 9+ baths in 16,000-square-feet. In addition to views galore, there's a pool, pool house with an outdoor kitchen, tennis, and "infrastructure to support many additional possibilities." Asking price is $16.5M.

$15,500,000

Located "on the prestigious and highly coveted Lincoln Circle," this 5 bedroom with a two bedroom guest cottage hit the market in March 2013 for $16,950,000. The .59 acre property is close to Steps Beach and features views of Nantucket Harbor and, after a July 2014 chop, is asking $15,500,000.

$15,500,000

This Dionis property makes the most of its 7.9 acres with a main house, studio, artist's space, pool with a pool house, five practice golf holes, and a double order of three-car garages. Asking price was $17,995,000, but is now down to $15,500,000.

$15,000,000

Naturally, Yarmouth's priciest listing is located on Great Island, "one of the most treasured and desirable communities on Cape Cod, known for its privacy, security and amenities..." The 4BR, 5BA is asking an even $15 million.

$14,950,000

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, and now a December chop has brought the ask to $14,950,000.

$13,750,000

Built in 2003, this waterfront 10-acre Polpis estate has 22-rooms, "sweeping and endless harbor views", a guest house, pool, a gym, room for tennis, and access to Polpis Harbor. Asking price is $13,750,000.

$13,250,000

"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, but a December slice took $1 million.

$12,999,000

Here's an Osterville with not one, but two private deep water docks and over 620-feet of water frontage. The house itself was built in 1930 and features 19 rooms in 7,773-square-feet. Asking price is a chopped $12,999,000.

$12,950,000

When this Wauwinet abode hit the market it April for $12.95M, the brokerbabble left no polished nickel fixture unmentioned. Yup, "Deer Run" is pretty tricked out and even "offers access to a rare deep water dock, two moorings and a storage area for tenders."

$12,500,000

This Osterville estate overlooking Eel River and Nantucket Sound first hit the market in April 2013 looking for $13.5M, but lost $1 million from the ask in February 2014.

$12,500,000

Built in 1920, this Monomoy 6BR, 10BA first hit the market in November 2012 for $14,995,000. Alas, no "Downton Abbey" fans came forward and an August 2013 pricechop brought the ask for the renovated 7,500-square-footer down to $12,500,000.