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.

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."

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."

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.

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.

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.

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."

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."

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."

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.

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."

"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."

"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."

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.

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.

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.

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.

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.

"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.