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The priciest listing on the Cape & Islands is this $35 million Nantucket estate at 260 Polpis Road. Image via Great Point Properties

Mapping the Cape & Islands 25 Most Expensive Listings

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| The priciest listing on the Cape & Islands is this $35 million Nantucket estate at 260 Polpis Road. Image via Great Point Properties

Here now, our December edition of the Cape and Islands 25 most expensive listings. This month, blockbuster asking prices range from $12,500,000 to a hefty $35,000,000 with a combined ask of $462,588,000. Not surprisingly, tony Nantucket tops the list with 17 of the 25, Cape Cod follows with five, and the Vineyard grabs third place with three ultra-pricey pads for sale.


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1. $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 has been available for a newly configured $35M.

2. $29,750,000

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24 Easton St
Nantucket, MA 02554
The second priciest spread for sale on Nantucket is "perfectly situated on the inner harbor waterfront." The Brant Point listing is currently subdivided as two properties with "120 plus feet of waterfront and one of only three private deep water docks on island."

3. $27,500,000

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28 Easton St
Nantucket, MA 02554
Nantucket's third priciest listing is also in Brant Point, directly on the harbor. "For the avid boatsman, there is a private dock, a rare find on island and certainly in-town. This exceptional home is comprised of a six bedroom main house, two bedroom cottage and carriage house."

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. $22,500,000

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79 Turkeyland Cove Rd
Edgartown, MA 02539
The priciest listing on Martha's Vineyard sits on 29.3 acres overlooking Edgartown Great Pond with "family compound opportunities." Currently, there's a 7BR, 7.5BA main residence, detached barn, and an attached two-car garage.

6. $21,900,000

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9 Lincoln Avenue
Nantucket, MA 02554
Susie Hilfiger, ex-wife of fashion icon Tommy Hilfiger, put her Cliff estate on the market for a whopping $27 million back in July 2013. The ask for the Lincoln Circle 10BR, 8BA was cut in November 2014 to its current $21.9 million.

7. $21,500,000

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119 Eel Point Rd
Nantucket, MA 02554
Located on a "rare portion of the Island undergoing accretion of land rather than erosion," this 7BR Dionis estate features two homes, each sitting on nearly two acres.

8. $20,000,000

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22 Lelands Path
Edgartown, MA 02539
Surrounded by conservation land, this Chappy estate overlooking Katama Bay features a 10,099sf residence on 5.95 acres. Amenities include: "an expansive living room for large family gatherings, 4 fireplaces, screened porch, wine cellar, gym, sauna, steam shower, roof top deck, custom woodwork, arched ceilings, 3 car garage and a top of the line gourmet kitchen with adjacent morning room."

9. $19,999,000

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13 Squam Rd
Nantucket, MA 02554
Built in 2005, this eight-bedroom, nine-full and three-half bath oceanfront compound on Squam Beach has panoramic ocean views and "includes a main house that masterfully wraps around thoughtfully designed outdoor living areas featuring a pool, cabana, decks, gas firepit, tennis court, spacious lawn, exquisite gardens, and a carriage house with a 3 car garage."

10. $19,125,000

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8 Snail Rd
Chilmark, MA 02535
Set 120-feet above the Atlantic Ocean, this stunning six-bedroom served as the 2013 summer White House. In addition to a heated infinity pool and half-basketball court, the secluded 9.5 acre spread features a 2BR guest cottage plus "three private Atlantic Ocean beach lots accessed by boat across Chilmark Pond from your private dock."

11. $18,975,000

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30 Orange St
Nantucket, MA 02554
One of the oldest homes for sale on Nantucket, the circa 1823 beauty known as Long Hill is set on historic Orange Street and features "expansive, panoramic views of the Harbor, Coatue and town." In addition to the 8BR main residence, "the beautifully landscaped grounds include a formal English garden with brick walkway rimmed by manicured boxwood, lovely rose gardens, specimen trees, a two-car garage and a towering privet hedge which surrounds the entire estate."

12. $18,500,000

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251 Green Dunes Dr
Marstons Mills, MA 02648
"Point of View" has been bouncing on and off the market with the same $17,500,000 asking price for a few years, but just recently priceupped a million dollars. 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.

13. $15,895,000

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93 Main St
Nantucket, MA 02554
Nantucket's iconic East Brick mansion hit the market in late August for $17,895,000. As of October, the circa 1837 manse with 8BR, 7.5BA on historic Main Street is now asking $15,895,000.

14. $15,250,000

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72 Monomoy Rd
Nantucket, MA 02554
Owned by the same family for over 50 years, this Monomoy harbor front property comes with a Conservation Commission-approved site plan, "designed by Andrew Kotchen of Workshop/APD, includes a main house overlooking the harbor, a garage/studio, and a guest house, pool, and pool cabana."

15. $15,000,000

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17 Squam Rd
Nantucket, MA 02554
"Exceptional waterfront property of 5.23 acres located in Squam, truly one of the most spectacular, private beaches on Nantucket." So begins the listing for the 1930s bulldozer bait with beachfront compound potential for a "large main house, guest house, attendant buildings, pool and a tennis court."

16. $14,950,000

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12 Lincoln Avenue
Nantucket, MA 02554
"This quintessential 1920s summer home offers water views through the oversized farmhouse windows, high ceilings, a wood burning fireplace and fir floors." The 10-room house sit on .51 acres and "offers a buyer several options to consider including renovation, expansion or potential of subdividing this oversized property."

17. $14,950,000

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30 Quidnet Rd
Nantucket, MA 02554
"Private estate situated on over fourteen acres in a pastoral setting with views of the Atlantic, Sankaty Light House, Sesachacha Pond and the Moors." The eight-bedroom, nine-full and four-half bath Quidnet property also includes a 20-seat movie theater, pool, pool house, and a tennis court that's "well protected from the wind."

18. $14,900,000

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55 Eel Point Rd
Nantucket, MA 02554
This Dionis "oceanside residence with backyard beach path" was built in 1996. The five-bedroom sits on 1.9 acres and is asking $14,900,000.

19. $13,999,000

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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 was asking an even $15 million, but has been sliced down to just under $14 million.

20. $13,900,000

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123 Penzance Rd
Woods Hole, MA 02543
Seven Winds, a private waterfront estate on 1.47 acres in the gated community of Penzance Point, features a 7BR main residence, 2BR beachfront guest house, and a deep water pier on Great Harbor.

21. $13,500,000

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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. First listed in July 2013 for $17,995,000, the spread was chopped to $15,500,000 and is now looking for $13,500,000.

22. $12,995,000

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20 Sankaty Head Rd
Nantucket, MA 02554
Located at "the end of Sankaty Head Road is a spacious custom home with elevations that ensure 360-degree views overlooking the Atlantic, Sankaty Light House and Sesachacha Pond." The 2.91 acre lost includes 5BR, 5.5BA in a main residence and cottage.

23. $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.

24. $12,500,000

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90 Pocomo Rd
Nantucket, MA 02554
Built in 1989, this 7BR Pocomo estate sits on a 4.23 acre elevated waterfront parcel with over 1000 feet of private beach and views galore. "Enjoy the sunrise over Pocomo and the sunsets over Coatue and Tuckernuck."

25. $12,500,000

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79 Squam Rd
Nantucket, MA 02554
"Stunning Squam Compound with spectacular Atlantic Ocean views!" So begins the listing for this six-bedroom, six-full and two-half bath oceanfront estate. Designed by Botticelli and Pohl and completed in 2013, the tricked-out spread hit the market this summer for $12.5 million.

1. $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 has been available for a newly configured $35M.
260 Polpis Road
Nantucket, MA 02554

2. $29,750,000

24 Easton St, Nantucket, MA 02554
The second priciest spread for sale on Nantucket is "perfectly situated on the inner harbor waterfront." The Brant Point listing is currently subdivided as two properties with "120 plus feet of waterfront and one of only three private deep water docks on island."
24 Easton St
Nantucket, MA 02554

3. $27,500,000

28 Easton St, Nantucket, MA 02554
Nantucket's third priciest listing is also in Brant Point, directly on the harbor. "For the avid boatsman, there is a private dock, a rare find on island and certainly in-town. This exceptional home is comprised of a six bedroom main house, two bedroom cottage and carriage house."
28 Easton St
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. $22,500,000

79 Turkeyland Cove Rd, Edgartown, MA 02539
The priciest listing on Martha's Vineyard sits on 29.3 acres overlooking Edgartown Great Pond with "family compound opportunities." Currently, there's a 7BR, 7.5BA main residence, detached barn, and an attached two-car garage.
79 Turkeyland Cove Rd
Edgartown, MA 02539

6. $21,900,000

9 Lincoln Avenue, Nantucket, MA 02554
Susie Hilfiger, ex-wife of fashion icon Tommy Hilfiger, put her Cliff estate on the market for a whopping $27 million back in July 2013. The ask for the Lincoln Circle 10BR, 8BA was cut in November 2014 to its current $21.9 million.
9 Lincoln Avenue
Nantucket, MA 02554

7. $21,500,000

119 Eel Point Rd, Nantucket, MA 02554
Located on a "rare portion of the Island undergoing accretion of land rather than erosion," this 7BR Dionis estate features two homes, each sitting on nearly two acres.
119 Eel Point Rd
Nantucket, MA 02554

8. $20,000,000

22 Lelands Path, Edgartown, MA 02539
Surrounded by conservation land, this Chappy estate overlooking Katama Bay features a 10,099sf residence on 5.95 acres. Amenities include: "an expansive living room for large family gatherings, 4 fireplaces, screened porch, wine cellar, gym, sauna, steam shower, roof top deck, custom woodwork, arched ceilings, 3 car garage and a top of the line gourmet kitchen with adjacent morning room."
22 Lelands Path
Edgartown, MA 02539

9. $19,999,000

13 Squam Rd, Nantucket, MA 02554
Built in 2005, this eight-bedroom, nine-full and three-half bath oceanfront compound on Squam Beach has panoramic ocean views and "includes a main house that masterfully wraps around thoughtfully designed outdoor living areas featuring a pool, cabana, decks, gas firepit, tennis court, spacious lawn, exquisite gardens, and a carriage house with a 3 car garage."
13 Squam Rd
Nantucket, MA 02554

10. $19,125,000

8 Snail Rd, Chilmark, MA 02535
Set 120-feet above the Atlantic Ocean, this stunning six-bedroom served as the 2013 summer White House. In addition to a heated infinity pool and half-basketball court, the secluded 9.5 acre spread features a 2BR guest cottage plus "three private Atlantic Ocean beach lots accessed by boat across Chilmark Pond from your private dock."
8 Snail Rd
Chilmark, MA 02535

11. $18,975,000

30 Orange St, Nantucket, MA 02554
One of the oldest homes for sale on Nantucket, the circa 1823 beauty known as Long Hill is set on historic Orange Street and features "expansive, panoramic views of the Harbor, Coatue and town." In addition to the 8BR main residence, "the beautifully landscaped grounds include a formal English garden with brick walkway rimmed by manicured boxwood, lovely rose gardens, specimen trees, a two-car garage and a towering privet hedge which surrounds the entire estate."
30 Orange St
Nantucket, MA 02554

12. $18,500,000

251 Green Dunes Dr, Marstons Mills, MA 02648
"Point of View" has been bouncing on and off the market with the same $17,500,000 asking price for a few years, but just recently priceupped a million dollars. 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 Dr
Marstons Mills, MA 02648

13. $15,895,000

93 Main St, Nantucket, MA 02554
Nantucket's iconic East Brick mansion hit the market in late August for $17,895,000. As of October, the circa 1837 manse with 8BR, 7.5BA on historic Main Street is now asking $15,895,000.
93 Main St
Nantucket, MA 02554

14. $15,250,000

72 Monomoy Rd, Nantucket, MA 02554
Owned by the same family for over 50 years, this Monomoy harbor front property comes with a Conservation Commission-approved site plan, "designed by Andrew Kotchen of Workshop/APD, includes a main house overlooking the harbor, a garage/studio, and a guest house, pool, and pool cabana."
72 Monomoy Rd
Nantucket, MA 02554

15. $15,000,000

17 Squam Rd, Nantucket, MA 02554
"Exceptional waterfront property of 5.23 acres located in Squam, truly one of the most spectacular, private beaches on Nantucket." So begins the listing for the 1930s bulldozer bait with beachfront compound potential for a "large main house, guest house, attendant buildings, pool and a tennis court."
17 Squam Rd
Nantucket, MA 02554

16. $14,950,000

12 Lincoln Avenue, Nantucket, MA 02554
"This quintessential 1920s summer home offers water views through the oversized farmhouse windows, high ceilings, a wood burning fireplace and fir floors." The 10-room house sit on .51 acres and "offers a buyer several options to consider including renovation, expansion or potential of subdividing this oversized property."
12 Lincoln Avenue
Nantucket, MA 02554

17. $14,950,000

30 Quidnet Rd, Nantucket, MA 02554
"Private estate situated on over fourteen acres in a pastoral setting with views of the Atlantic, Sankaty Light House, Sesachacha Pond and the Moors." The eight-bedroom, nine-full and four-half bath Quidnet property also includes a 20-seat movie theater, pool, pool house, and a tennis court that's "well protected from the wind."
30 Quidnet Rd
Nantucket, MA 02554

18. $14,900,000

55 Eel Point Rd, Nantucket, MA 02554
This Dionis "oceanside residence with backyard beach path" was built in 1996. The five-bedroom sits on 1.9 acres and is asking $14,900,000.
55 Eel Point Rd
Nantucket, MA 02554

19. $13,999,000

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 was asking an even $15 million, but has been sliced down to just under $14 million.
63 Smiths Point Road
West Yarmouth, MA 02673

20. $13,900,000

123 Penzance Rd, Woods Hole, MA 02543
Seven Winds, a private waterfront estate on 1.47 acres in the gated community of Penzance Point, features a 7BR main residence, 2BR beachfront guest house, and a deep water pier on Great Harbor.
123 Penzance Rd
Woods Hole, MA 02543

21. $13,500,000

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. First listed in July 2013 for $17,995,000, the spread was chopped to $15,500,000 and is now looking for $13,500,000.
202 Eel Point Road
Nantucket, MA 02554

22. $12,995,000

20 Sankaty Head Rd, Nantucket, MA 02554
Located at "the end of Sankaty Head Road is a spacious custom home with elevations that ensure 360-degree views overlooking the Atlantic, Sankaty Light House and Sesachacha Pond." The 2.91 acre lost includes 5BR, 5.5BA in a main residence and cottage.
20 Sankaty Head Rd
Nantucket, MA 02554

23. $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

24. $12,500,000

90 Pocomo Rd, Nantucket, MA 02554
Built in 1989, this 7BR Pocomo estate sits on a 4.23 acre elevated waterfront parcel with over 1000 feet of private beach and views galore. "Enjoy the sunrise over Pocomo and the sunsets over Coatue and Tuckernuck."
90 Pocomo Rd
Nantucket, MA 02554

25. $12,500,000

79 Squam Rd, Nantucket, MA 02554
"Stunning Squam Compound with spectacular Atlantic Ocean views!" So begins the listing for this six-bedroom, six-full and two-half bath oceanfront estate. Designed by Botticelli and Pohl and completed in 2013, the tricked-out spread hit the market this summer for $12.5 million.
79 Squam Rd
Nantucket, MA 02554