"> clock menu more-arrow no yes mobile
<a href="http://www.greatpointproperties.com/260-polpis-road-nantucket-massachusetts-79081"></a>
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

View as Map
| 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.


Read More

$35,000,000

Copy Link
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.

$29,750,000

Copy Link
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."

$27,500,000

Copy Link
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."

$25,000,000

Copy Link
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.

$22,500,000

Copy Link
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.

$21,900,000

Copy Link
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.

$21,500,000

Copy Link
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.

$20,000,000

Copy Link
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."

$19,999,000

Copy Link
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."

$19,125,000

Copy Link
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."

$18,975,000

Copy Link
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."

$18,500,000

Copy Link
"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.

$15,895,000

Copy Link
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.

$15,250,000

Copy Link
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."

$15,000,000

Copy Link
"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."

$14,950,000

Copy Link
"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."

$14,950,000

Copy Link
"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."

$14,900,000

Copy Link
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.

$13,999,000

Copy Link
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.

$13,900,000

Copy Link
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.

$13,500,000

Copy Link
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.

$12,995,000

Copy Link
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.

$12,500,000

Copy Link
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

Copy Link
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."

$12,500,000

Copy Link
"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.

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

$29,750,000

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."

$27,500,000

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."

$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.

$22,500,000

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.

$21,900,000

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.

$21,500,000

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.

$20,000,000

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."

$19,999,000

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."

$19,125,000

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."

$18,975,000

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."

$18,500,000

"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.

$15,895,000

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.

$15,250,000

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."

$15,000,000

"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."

$14,950,000

"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."

$14,950,000

"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."

$14,900,000

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.

$13,999,000

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

$13,900,000

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.

$13,500,000

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. 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.

$12,995,000

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.

$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 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."

$12,500,000

"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.