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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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1. $108,000,000

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Pond Road
Vineyard Haven, MA 02568

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.

2. $35,000,000

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260 Polpis Road
Nantucket, MA 02554

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.

3. $27,500,000

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36 Shawkemo Road
Nantucket, MA 02554

"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.

4. $25,000,000

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97 Tilipi Run Street
Chatham, MA 02633

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.

5. $24,900,000

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9 Lincoln Avenue
Nantucket, MA 02554

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.

6. $22,950,000

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33 Squam Road
Nantucket, MA 02554

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.

7. $21,999,000

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13 Squam Road
Nantucket, MA 02554

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.

8. $19,500,000

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295 Katama Road
Edgartown, MA 02539

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.

9. $19,500,000

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861 Sea View Avenue
Osterville, MA 02655

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.

10. $18,975,000

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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.

11. $18,000,000

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157 Wapoos Trail
Chatham, MA 02633

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.

12. $17,950,000

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47 Cliff Road
Nantucket, MA 02554

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.

13. $17,950,000

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68 Monomoy Road
Nantucket, MA 02554

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.

14. $17,500,000

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251 Green Dunes Drive
Marstons Mills, MA 02648

"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.

15. $16,500,000

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30 Quidnet Road
Nantucket, MA 02554

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.

16. $15,500,000

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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 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.

17. $15,500,000

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202 Eel Point Road
Nantucket, MA 02554

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.

18. $15,000,000

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63 Smiths Point Road
West Yarmouth, MA 02673

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.

19. $14,950,000

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

20. $13,750,000

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250 Polpis Road
Nantucket, MA 02554

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.

21. $13,250,000

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31 Tower Hill Road
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, but a December slice took $1 million.

22. $12,999,000

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986 Sea View Avenue
Osterville, MA 02655

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.

23. $12,950,000

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10 Medouie Creek Road
Nantucket, MA 02554

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."

24. $12,500,000

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74 Garrison Lane
Osterville, MA 02655

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.

25. $12,500,000

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47 Monomoy Road
Nantucket, MA 02554

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.

1. $108,000,000

Pond Road, Vineyard Haven, MA 02568

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.

Pond Road
Vineyard Haven, MA 02568

2. $35,000,000

260 Polpis Road, Nantucket, MA 02554

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.

260 Polpis Road
Nantucket, MA 02554

3. $27,500,000

36 Shawkemo Road, Nantucket, MA 02554

"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.

36 Shawkemo Road
Nantucket, MA 02554

4. $25,000,000

97 Tilipi Run Street, Chatham, MA 02633

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.

97 Tilipi Run Street
Chatham, MA 02633

5. $24,900,000

9 Lincoln Avenue, Nantucket, MA 02554

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.

9 Lincoln Avenue
Nantucket, MA 02554

6. $22,950,000

33 Squam Road, Nantucket, MA 02554

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.

33 Squam Road
Nantucket, MA 02554

7. $21,999,000

13 Squam Road, Nantucket, MA 02554

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.

13 Squam Road
Nantucket, MA 02554

8. $19,500,000

295 Katama Road, Edgartown, MA 02539

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.

295 Katama Road
Edgartown, MA 02539

9. $19,500,000

861 Sea View Avenue, Osterville, MA 02655

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.

861 Sea View Avenue
Osterville, MA 02655

10. $18,975,000

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

11. $18,000,000

157 Wapoos Trail, Chatham, MA 02633

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.

157 Wapoos Trail
Chatham, MA 02633

12. $17,950,000

47 Cliff Road, Nantucket, MA 02554

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.

47 Cliff Road
Nantucket, MA 02554

13. $17,950,000

68 Monomoy Road, Nantucket, MA 02554

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.

68 Monomoy Road
Nantucket, MA 02554

14. $17,500,000

251 Green Dunes Drive, Marstons Mills, MA 02648

"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.

251 Green Dunes Drive
Marstons Mills, MA 02648

15. $16,500,000

30 Quidnet Road, Nantucket, MA 02554

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.

30 Quidnet Road
Nantucket, MA 02554

16. $15,500,000

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 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.

17 Lincoln Avenue
Nantucket, MA 02554

17. $15,500,000

202 Eel Point Road, Nantucket, MA 02554

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.

202 Eel Point Road
Nantucket, MA 02554

18. $15,000,000

63 Smiths Point Road, West Yarmouth, MA 02673

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.

63 Smiths Point Road
West Yarmouth, MA 02673

19. $14,950,000

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

52 Ships Eagle Ln
Osterville, MA 02655

20. $13,750,000

250 Polpis Road, Nantucket, MA 02554

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.

250 Polpis Road
Nantucket, MA 02554

21. $13,250,000

31 Tower Hill Road, 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, but a December slice took $1 million.

31 Tower Hill Road
Edgartown, MA 02539

22. $12,999,000

986 Sea View Avenue, Osterville, MA 02655

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.

986 Sea View Avenue
Osterville, MA 02655

23. $12,950,000

10 Medouie Creek Road, Nantucket, MA 02554

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."

10 Medouie Creek Road
Nantucket, MA 02554

24. $12,500,000

74 Garrison Lane, Osterville, MA 02655

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.

74 Garrison Lane
Osterville, MA 02655

25. $12,500,000

47 Monomoy Road, Nantucket, MA 02554

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.

47 Monomoy Road
Nantucket, MA 02554