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The Cape & Islands 20 Most Expensive Listings, Dec. '13

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Here now, the December edition of the Cape and Islands 20 most expensive listings. This month, blockbuster asking prices range from $13,250,000 to $118,000,000. For those keeping score, even with one sale and three pricechops, Nantucket still has 10, Cape Cod has seven and the Vineyard three.

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1. $118,000,000

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Pond Road
West Tisbury, MA 02568

Available with 314 acres for a mind-blowing $118 million or as a 50 acre spread with a 5,600 sq. ft. house with a pool and tennis court for "just" $44 million.

2. $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 pricechopper had 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.

3. $26,995,000

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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 for $26,9995,000.

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.

5. $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.

6. $19,900,000

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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 . The seven bedroom, eight and a half bath property includes a pool, gardens and a private boardwalk to Squam Beach.

7. $18,750,000

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46 Easton Street
Nantucket, MA 02554

Built in 1897, Auburn Cottage is one of only 13 waterfront residences on Easton Street. The property includes sandy beach frontage on Nantucket Harbor and mooring rights. Asking price was $19,999,999 until an August chop brought it down to $18,750,000.

8. $18,500,000

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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, a million dollar pricechop brought the ask down to $18,500,000.

9. $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.

10. $17,995,000

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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 is $17,995,000.

11. $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.

12. $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.

13. $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. 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.

14. $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 for $16,950,000. The .59 acre property is close to Steps Beach and features views of Nantucket Harbor.

15. $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.

16. $14,750,000

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459 Sea View Avenue
Osterville, MA 02655

This waterfront 2.76 acre property features a 7,762 square foot main house with nine bedrooms and eight full and three half baths, a one bedroom carriage house, boat house, beach house, in-ground pool, and over 125' of sandy beach on Nantucket Sound. Asking price is $14,750,000.

17. $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.

18. $13,900,000

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461 Main Street
Osterville, MA 02655

According to the brokerbabble, this oceanfront estate isn't just a home, "It's a lifestyle not to be surpassed." The 14-room 10,279 square footer is amenity packed and asking $13.9 million.

19. $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 and is asking $13,750,000.

20. $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.

1. $118,000,000

Pond Road, West Tisbury, MA 02568

Available with 314 acres for a mind-blowing $118 million or as a 50 acre spread with a 5,600 sq. ft. house with a pool and tennis court for "just" $44 million.

Pond Road
West Tisbury, MA 02568

2. $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 pricechopper had 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

3. $26,995,000

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 for $26,9995,000.

9 Lincoln Avenue
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.

97 Tilipi Run Street
Chatham, MA 02633

5. $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

6. $19,900,000

13 Squam Road, Nantucket, MA 02554

Set on oceanfront 2.2 acres, this Squam Road compound hit the market for $19,900,000 . The seven bedroom, eight and a half bath property includes a pool, gardens and a private boardwalk to Squam Beach.

13 Squam Road
Nantucket, MA 02554

7. $18,750,000

46 Easton Street, Nantucket, MA 02554

Built in 1897, Auburn Cottage is one of only 13 waterfront residences on Easton Street. The property includes sandy beach frontage on Nantucket Harbor and mooring rights. Asking price was $19,999,999 until an August chop brought it down to $18,750,000.

46 Easton Street
Nantucket, MA 02554

8. $18,500,000

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, a million dollar pricechop brought the ask down to $18,500,000.

47 Cliff Road
Nantucket, MA 02554

9. $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

10. $17,995,000

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 is $17,995,000.

202 Eel Point Road
Nantucket, MA 02554

11. $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

12. $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

13. $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. 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

14. $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 for $16,950,000. The .59 acre property is close to Steps Beach and features views of Nantucket Harbor.

17 Lincoln Avenue
Nantucket, MA 02554

15. $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

16. $14,750,000

459 Sea View Avenue, Osterville, MA 02655

This waterfront 2.76 acre property features a 7,762 square foot main house with nine bedrooms and eight full and three half baths, a one bedroom carriage house, boat house, beach house, in-ground pool, and over 125' of sandy beach on Nantucket Sound. Asking price is $14,750,000.

459 Sea View Avenue
Osterville, MA 02655

17. $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

18. $13,900,000

461 Main Street, Osterville, MA 02655

According to the brokerbabble, this oceanfront estate isn't just a home, "It's a lifestyle not to be surpassed." The 14-room 10,279 square footer is amenity packed and asking $13.9 million.

461 Main Street
Osterville, MA 02655

19. $13,750,000

250 Polpis Road, Nantucket, MA 02554

Built in 2003, this waterfront 10-acre Polpis estate has 22-rooms and is asking $13,750,000.

250 Polpis Road
Nantucket, MA 02554

20. $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