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31 Tower Hill Road, Edgartown, Wallace & Co. Sotheby's International Realty

The Cape & Islands 20 Most Expensive Listings, August '13

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| 31 Tower Hill Road, Edgartown, Wallace & Co. Sotheby's International Realty

Here now, the August edition of the the Cape and Islands 20 most expensive listings. This month, blockbuster asking prices range from $13,750,000 to $118,000,000. For those keeping score, Nantucket is down to 10, Cape Cod still has seven and the Vineyard is up to 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. $22,995,000

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48 Monomoy Road
Nantucket, MA 02554
Built in 2004, this custom Monomoy waterfront estate was designed by J. Graham Goldsmith Architects and built by Ed Toole. There's a six bedroom main house, cottage with attached garage and pool/spa, all with sweeping views of Nantucket Harbor. Asking price is $22,995,000.

6. $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.

7. $19,500,000

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47 Cliff Road
Nantucket, MA 02554
Set on one acre, this Cliff Road property includes a 1900s main house, 1965 guest cottage and 1986 carriage house for $19,500,000.

8. $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.

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. $17,900,000

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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.

12. $17,000,000

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15 Sherburne Turnpike
Nantucket, MA 02554
Designed by Lyman Perry and built by Winters Construction in 1997, this Cliff waterfront estate is asking $17 million and features views of Nantucket Harbor and the Jetties. There are four bedrooms, six baths and private beach stairs.

13. $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 just last week. The .59 acre property is close to Steps Beach and features views of Nantucket Harbor.

14. $15,950,000

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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.

15. $15,000,000

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177 Seapuit River Road
Osterville, MA 02655
Billionaire Bill Koch, brother to conservative activists Charles and David Koch, has listed this "Yachtsman's Paradise on Nantucket Sound" for $15 million.

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. $14,500,000

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959 Sea View Avenue
Osterville, MA 02655
Built in 2005, this 5,600 sq. ft. four bedroom sits on 2.3 waterfront acres. The property includes private paddocks with a riding arena, in-ground pool and spectacular sandy beach. Asking price is $14,500,000.

18. $14,250,000

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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.

19. $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.

20. $13,750,000

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250 Polpis Rd
Nantucket, MA 02554
Here's a Polpis waterfront estate set on ten acres. The property includes a four bedroom main house, a two bedroom guest cottage, swimming pool, media room, wine cellar and access to Polpis Harbor. An early August pricechop brought the ask down $1 million to $13,750,000.

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. $22,995,000

48 Monomoy Road, Nantucket, MA 02554
Built in 2004, this custom Monomoy waterfront estate was designed by J. Graham Goldsmith Architects and built by Ed Toole. There's a six bedroom main house, cottage with attached garage and pool/spa, all with sweeping views of Nantucket Harbor. Asking price is $22,995,000.
48 Monomoy Road
Nantucket, MA 02554

6. $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

7. $19,500,000

47 Cliff Road, Nantucket, MA 02554
Set on one acre, this Cliff Road property includes a 1900s main house, 1965 guest cottage and 1986 carriage house for $19,500,000.
47 Cliff Road
Nantucket, MA 02554

8. $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

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. $17,900,000

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

12. $17,000,000

15 Sherburne Turnpike, Nantucket, MA 02554
Designed by Lyman Perry and built by Winters Construction in 1997, this Cliff waterfront estate is asking $17 million and features views of Nantucket Harbor and the Jetties. There are four bedrooms, six baths and private beach stairs.
15 Sherburne Turnpike
Nantucket, MA 02554

13. $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 just last week. The .59 acre property is close to Steps Beach and features views of Nantucket Harbor.
17 Lincoln Avenue
Nantucket, MA 02554

14. $15,950,000

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.
52 Ships Eagle Ln
Osterville, MA 02655

15. $15,000,000

177 Seapuit River Road, Osterville, MA 02655
Billionaire Bill Koch, brother to conservative activists Charles and David Koch, has listed this "Yachtsman's Paradise on Nantucket Sound" for $15 million.
177 Seapuit River Road
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. $14,500,000

959 Sea View Avenue, Osterville, MA 02655
Built in 2005, this 5,600 sq. ft. four bedroom sits on 2.3 waterfront acres. The property includes private paddocks with a riding arena, in-ground pool and spectacular sandy beach. Asking price is $14,500,000.
959 Sea View Avenue
Osterville, MA 02655

18. $14,250,000

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.
31 Tower Hill Road
Edgartown, MA 02539

19. $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

20. $13,750,000

250 Polpis Rd, Nantucket, MA 02554
Here's a Polpis waterfront estate set on ten acres. The property includes a four bedroom main house, a two bedroom guest cottage, swimming pool, media room, wine cellar and access to Polpis Harbor. An early August pricechop brought the ask down $1 million to $13,750,000.
250 Polpis Rd
Nantucket, MA 02554