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Updated: The Cape & Islands 20 Most Expensive Listings

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It's been a little over a month since we first published a map of the 20 most expensive listings on the Cape and Islands. Since then, a gazillion dollar Powerball has minted a few new millionaires and Nantucket's priciest listing - last asking $49M - has gone off the market. In place of the Gray Lady listing, we've added an Edgartown property with it's own golf course (above) asking $12.5M. For those keeping score of the top 20, that's Cape Cod and Nantucket tied, each with seven, and the Vineyard close behind with six.


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1. $92,000,000

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Big Home Rd
West Tisbury, MA 02568

The most expensive piece of residential real estate on the market in New England is a plot of vacant land. This 266-acre West Tisbury property includes 1,100' of Atlantic beachfront and is borders a 510-acre preserve. Translation: paradise for a privacy-seeking buyer with deep (very deep) pockets.

2. $28,740,000

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17 Indian Trail
Osterville, MA 02655

Located on a private island, Oyster Harbors, this 26-acre estate includes nearly 1,000 feet of shorefront and views of the Seapuit River, Sampson’s Island and Nantucket Sound. The property features a nearly 7,000 sq. ft. main house, a beach house, detached loft studio, greenhouses, tennis court, and a seasonal dock.

3. $26,500,000

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243 Polpis Rd
Nantucket, MA 02554

"Norwood Farm" is the largest undeveloped, privately owned property on Nantucket. The 243-acre plot is bordered by three large protected parcels. In addition, there are views of Polpis Harbor from the western uplands.

4. $22,500,000

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251 Green Dunes Dr
Barnstable, MA 02601

Designed by Boston architect Richard Bertman, this 10,760 sq. ft. estate on 10-acres includes 250-degree oceanfront views. Amenities include 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.

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.

6. $19,500,000

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61 Butler's Cove Rd
Edgartown, MA 02539

Located within Herring Creek Farm is this 25-acre property with views of Edgartown Great Pond and the Atlantic Ocean. There is a 5,615 sq. ft. main house with room for a guesthouse as well as an additional vacant parcel. In addition, there's private ownership of the shoreline on Edgartown Great Pond and shared private access to a south shore beach.

7. $17,000,000

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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.

8. $16,900,000

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212 Eel Point Rd
Nantucket, MA 02554

This Eeel Point estate includes water views and water access on nearly seven acres. There's a six bedroom main house, two bedroom guest cottage, and a garage/studio. Amenities include a swimming pool, gym and room to add a tennis court or putting green.

9. $15,999,000

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986 Sea View Ave
Osterville, MA 02655

This 2.72-acre estate includes over 620 feet of water frontage with a sandy beach. The 7,773 sq. ft. six bedroom main residence features multiple balconies and a central courtyard. There's also a guesthouse and two private deep water docks.

10. $14,995,000

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47 Monomoy Rd
Nantucket, MA 02554

Built in 1920, this home was moved to its current site and renovated in 2011. Surrounded by manicured lawns and gardens, both the main house and guest cottage enjoy views of Nantucket Harbor and town.

11. $14,995,000

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11 Squam Rd
Nantucket, MA 02554

This oceanfront compound on three-plus acres includes a main residence, guesthouse, carriage house, tennis/guest cottage, four-bay garage, tennis court, gym, swimming pool, and two private boardwalks to the beach.

12. $14,800,000

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41 Dunham Rd
Edgartown, MA 02539

Located in the Tower Hill neighborhood on Edgartown Harbor, this property has been in the same family for over 100 years. The 1.1 acre lot includes a four bedroom main house, a two-story guesthouse, sandy beach, and a new private deep water pier.

13. $14,750,000

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250 Polpis Rd
Nantucket, MA 02554

It's back to Polpis for a waterfront ten acre estate. The property includes a four bedroom main house, a two bedroom guest cottage, swimming pool, media room, wine cellar and access to Polpis Harbor.

14. $14,750,000

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31 Tower Hill Rd
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.

15. $14,000,000

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43 Church St
Woods Hole, MA 02543

"Fairview" is a 7.5 acre waterfront estate with 890 feet of frontage on Little Harbor with views of Vineyard Sound and the Elizabeth Islands. Built in 1918, the 15,078 sq. ft. residence features 11 bedrooms and nine bathrooms. There's also a guest house, carriage house, boat house, greenhouse, and two additional cottages.

16. $13,900,000

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461 Main St
Osterville, MA 02655

Designed by architect Doreve Nicholaeff, this waterfront Osterville estate features "stellar" views, an elevator, four fireplaces, an in-home home theatre, infinity pool, and a private dock.

17. $13,200,000

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79 Eel Point Rd
Nantucket, MA 02554

We're back on Eel Point for this 2.66 acre waterfront property with views of Nantucket Sound. The estate includes a main dwelling, garage with guest quarters, tennis court with attendant tennis house, an a heated in-ground pool.

18. $12,950,000

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60 Harbor Rd
Harwich Port, MA 02646

This 9,400 sq. ft. estate known as "Wychmere Breezes" is located on 3.58 waterfront acres with views across Wychmere Harbor to Nantucket Sound. There's a six bedroom main house, gazebo, heated pool with cabana, boat house, and a private 80-foot dock.

19. $12,750,000

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78 Squibnocket Farm Rd
Chilmark, MA 02535

Located in Squibnocket Farm, this 12.2 acre plot of waterfront land includes over 1,300 feet of ocean frontage. There's an existing four bedroom Cape style house with approved plans for a new five bedroom home. Views extend across Squibnocket Beach, the South Shore, the Atlantic, and Nomans Land.

20. $12,500,000

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35 N Neck Rd
Edgartown, MA 02539

Available for the first time in over 100 years, this waterfront property on 18 acres features a nine hole golf course, multiple residences and 332 feet of sandy beach frontage. There's also a deep water dock and views of Edgartown Harbor, East Chop and Cape Poge.

1. $92,000,000

Big Home Rd, West Tisbury, MA 02568

The most expensive piece of residential real estate on the market in New England is a plot of vacant land. This 266-acre West Tisbury property includes 1,100' of Atlantic beachfront and is borders a 510-acre preserve. Translation: paradise for a privacy-seeking buyer with deep (very deep) pockets.

Big Home Rd
West Tisbury, MA 02568

2. $28,740,000

17 Indian Trail, Osterville, MA 02655

Located on a private island, Oyster Harbors, this 26-acre estate includes nearly 1,000 feet of shorefront and views of the Seapuit River, Sampson’s Island and Nantucket Sound. The property features a nearly 7,000 sq. ft. main house, a beach house, detached loft studio, greenhouses, tennis court, and a seasonal dock.

17 Indian Trail
Osterville, MA 02655

3. $26,500,000

243 Polpis Rd, Nantucket, MA 02554

"Norwood Farm" is the largest undeveloped, privately owned property on Nantucket. The 243-acre plot is bordered by three large protected parcels. In addition, there are views of Polpis Harbor from the western uplands.

243 Polpis Rd
Nantucket, MA 02554

4. $22,500,000

251 Green Dunes Dr, Barnstable, MA 02601

Designed by Boston architect Richard Bertman, this 10,760 sq. ft. estate on 10-acres includes 250-degree oceanfront views. Amenities include 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
Barnstable, MA 02601

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.

30 Orange St
Nantucket, MA 02554

6. $19,500,000

61 Butler's Cove Rd, Edgartown, MA 02539

Located within Herring Creek Farm is this 25-acre property with views of Edgartown Great Pond and the Atlantic Ocean. There is a 5,615 sq. ft. main house with room for a guesthouse as well as an additional vacant parcel. In addition, there's private ownership of the shoreline on Edgartown Great Pond and shared private access to a south shore beach.

61 Butler's Cove Rd
Edgartown, MA 02539

7. $17,000,000

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.

52 Ships Eagle Ln
Osterville, MA 02655

8. $16,900,000

212 Eel Point Rd, Nantucket, MA 02554

This Eeel Point estate includes water views and water access on nearly seven acres. There's a six bedroom main house, two bedroom guest cottage, and a garage/studio. Amenities include a swimming pool, gym and room to add a tennis court or putting green.

212 Eel Point Rd
Nantucket, MA 02554

9. $15,999,000

986 Sea View Ave, Osterville, MA 02655

This 2.72-acre estate includes over 620 feet of water frontage with a sandy beach. The 7,773 sq. ft. six bedroom main residence features multiple balconies and a central courtyard. There's also a guesthouse and two private deep water docks.

986 Sea View Ave
Osterville, MA 02655

10. $14,995,000

47 Monomoy Rd, Nantucket, MA 02554

Built in 1920, this home was moved to its current site and renovated in 2011. Surrounded by manicured lawns and gardens, both the main house and guest cottage enjoy views of Nantucket Harbor and town.

47 Monomoy Rd
Nantucket, MA 02554

11. $14,995,000

11 Squam Rd, Nantucket, MA 02554

This oceanfront compound on three-plus acres includes a main residence, guesthouse, carriage house, tennis/guest cottage, four-bay garage, tennis court, gym, swimming pool, and two private boardwalks to the beach.

11 Squam Rd
Nantucket, MA 02554

12. $14,800,000

41 Dunham Rd, Edgartown, MA 02539

Located in the Tower Hill neighborhood on Edgartown Harbor, this property has been in the same family for over 100 years. The 1.1 acre lot includes a four bedroom main house, a two-story guesthouse, sandy beach, and a new private deep water pier.

41 Dunham Rd
Edgartown, MA 02539

13. $14,750,000

250 Polpis Rd, Nantucket, MA 02554

It's back to Polpis for a waterfront ten acre estate. The property includes a four bedroom main house, a two bedroom guest cottage, swimming pool, media room, wine cellar and access to Polpis Harbor.

250 Polpis Rd
Nantucket, MA 02554

14. $14,750,000

31 Tower Hill Rd, 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.

31 Tower Hill Rd
Edgartown, MA 02539

15. $14,000,000

43 Church St, Woods Hole, MA 02543

"Fairview" is a 7.5 acre waterfront estate with 890 feet of frontage on Little Harbor with views of Vineyard Sound and the Elizabeth Islands. Built in 1918, the 15,078 sq. ft. residence features 11 bedrooms and nine bathrooms. There's also a guest house, carriage house, boat house, greenhouse, and two additional cottages.

43 Church St
Woods Hole, MA 02543

16. $13,900,000

461 Main St, Osterville, MA 02655

Designed by architect Doreve Nicholaeff, this waterfront Osterville estate features "stellar" views, an elevator, four fireplaces, an in-home home theatre, infinity pool, and a private dock.

461 Main St
Osterville, MA 02655

17. $13,200,000

79 Eel Point Rd, Nantucket, MA 02554

We're back on Eel Point for this 2.66 acre waterfront property with views of Nantucket Sound. The estate includes a main dwelling, garage with guest quarters, tennis court with attendant tennis house, an a heated in-ground pool.

79 Eel Point Rd
Nantucket, MA 02554

18. $12,950,000

60 Harbor Rd, Harwich Port, MA 02646

This 9,400 sq. ft. estate known as "Wychmere Breezes" is located on 3.58 waterfront acres with views across Wychmere Harbor to Nantucket Sound. There's a six bedroom main house, gazebo, heated pool with cabana, boat house, and a private 80-foot dock.

60 Harbor Rd
Harwich Port, MA 02646

19. $12,750,000

78 Squibnocket Farm Rd, Chilmark, MA 02535

Located in Squibnocket Farm, this 12.2 acre plot of waterfront land includes over 1,300 feet of ocean frontage. There's an existing four bedroom Cape style house with approved plans for a new five bedroom home. Views extend across Squibnocket Beach, the South Shore, the Atlantic, and Nomans Land.

78 Squibnocket Farm Rd
Chilmark, MA 02535

20. $12,500,000

35 N Neck Rd, Edgartown, MA 02539

Available for the first time in over 100 years, this waterfront property on 18 acres features a nine hole golf course, multiple residences and 332 feet of sandy beach frontage. There's also a deep water dock and views of Edgartown Harbor, East Chop and Cape Poge.

35 N Neck Rd
Edgartown, MA 02539