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The 25 Most Expensive Homes For Sale In South Florida

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The most expensive residential listing in South Florida is Pumpkin Key, a 26 acre private island in the Florida Keys, listed for a whopping $110 million. If that doesn't float your boat, are a lot of other very, very expensive listings in this luxury land of ours, including Celine Dion's Jupiter Island compound which is on the market for $62.5 million, water park included.

Or how about another compound, this time in Palm Beach, containing houses by Marion Sims Wyeth and Addison Mizner for $59 million, and a North Bay Road estate formerly home to J-Lo, which has been asking $40 million for almost two years without a budge? Perhaps a sign of our hot market, or just how extreme inequality is in South Florida, all of the 25 most expensive listings are above $25 million.

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1. Pumpkin Key

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Listed for an absolutely mindboggling $110 million, Pumpkin Key was the most expensive new listing of 2014 in the country when it listed earlier this year. Within the exclusive Ocean Reef Club in the Florida Keys, Pumpkin Key comes with a three-bedroom main house, two caretakers cottages, a dock master's office, a twenty slip marina capable of accommodating a megayacht, tennis courts that serve as a helipad, golf cart paths circling the island, and, acreage baby! 26 acres to be exact.

2. 1744 S. Ocean Blvd.

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1744 South Ocean Boulevard
Palm Beach, FL 33480

This $99 million Palm Beach estate stretches from the ocean to Lake Worth, and is totally just down the street from Mar a Lago.

3. 219 S. Beach Rd.

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219 South Beach Road
Hobe Sound, FL 33455

Songstress Celine Dion listed her Bahamian-style compound on Jupiter Island with ocean frontage and private water park for $72 million but, unable to find a buyer, had to price chop it to the current $62.5 million price tag.

4. 89 Middle Road

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89 Middle Road
Palm Beach, FL 33480

An historical twofer in the heart of Palm Beach. A Mizner and a Wyeth for $59 million, with three additional guest houses and a spit of ocean frontage to boot.

5. Palazzo di Richezze

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17749 Collins Avenue
Sunny Isles Beach, FL 33160

The Mansions at Acqualina, currently under construction, originally organized its penthouses as thus: the top two floors were one and the floor below was another. When some richie rich decided they only wanted the very top, and bought that, the would-be lower floor of that penthouse was joined with the single floor penthouse below and re-listed for $50 million. It has been named the 'Palazzo di Rhichezze.'

6. 1545 N. Ocean Way

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1545 North Ocean Way
Palm Beach, FL 33480

This classic Maurice Fatio-designed Palm Beach estate, known as Windansea, is listed for $45 million. Just south of the Palm Beach inlet, the house is on nearly two acres of land and has an "amazingly wide beach."

7. 5800 North Bay Road

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5800 North Bay Road
Miami Beach, FL 33140

J-Lo's old place, this historic North Bay Road house has been on the market for a couple years, and is listed at $40 million. Could it be time for a price adjustment?

8. 40 Star Island Drive

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40 East Star Island Drive
Miami Beach, FL 33139

Another $40 million listing that's been on the market a while, we hear the owner isn't actually trying to sell the place but has it on the market to see if any sucker wants a bite.

9. 800 South Ocean Boulevard

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800 South Ocean Boulevard
Manalapan, FL 33462

This new-build estate in Manalapan has a lot stretching from the ocean to Lake Worth, accoutrements like a 20-car garage, and a tennis court, and, oh yeah, it's listed for $39 million.

10. 5446 North Bay Road

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5446 North Bay Road
Miami Beach, FL 33140

$37 million for a white box on North Bay Road. They're all the rage these days. The house, designed by Cheoff+Levy, replaced a classic Maurice Fatio-designed red brick manor house, and was just recently completed.

11. 3682 Princeton Place

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3682 Princeton Place
Boca Raton, FL 33496

3682 Princeton Place is rather notorious because, despite the rather generically pretty exterior with its lagoon style pool, giant chess board, and palm trees everywhere, portions of the interior are styled after the Star Ship Enterprise from Star Trek. You get all that for $35 million.

12. 17 Indian Creek Drive

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17 Indian Creek Island Road
Indian Creek Village, FL 33154

Oy, this place has been on the market for a while. Built in 2002, this 16,393 square foot house in the exclusive enclave of Indian Creek Village is $35 million. It was featured on Curbed Miami two years ago, listed at $38 million, and it wasn't exactly a fresh rose back then either.

13. 12 Indian Creek Island Road

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12 Indian Creek Island Road
Indian Creek Village, FL 33154

Ditto to #17 Indian Creek, above, except now it's listed for $35 million, a whole $10 million less than last time we mentioned it... a year and a half ago.

14. 110 Arvida Pkwy

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110 Arvida Parkway
Coral Gables, FL 33156

$35 million. The only Coral Gables house to crack the Top 25. Pretty, but kinda blah, and a semi-poor example of Mediterranean Revival architecture. Built in 1993.

15. 13560 Indian Mound Rd.

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13560 Indian Mound Road
Wellington, FL 33414

Lots o' land in Wellington with a house and 72-stall horse barn on it for $34,750,000. Get your ranch on, but maybe get an architect to build yourself something tasteful.

16. 1960 S Ocean Blvd.

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1960 South Ocean Boulevard
Manalapan, FL 33462

$32,500,000. No comment. Oh, here's one: the photographer went a little heavy on the HDR, and it makes this bland pile of stucco even worse.

17. 1102 N Ocean Blvd

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1102 North Ocean Boulevard
Palm Beach, FL 33480

$32 million. Designed by John Volk in 1935. Classy. As. Fuck. Seriously, compared to some of the other schlock on this list, it's worth every penny. Somebody should buy this place. NOW.

18. 1600 Ponce de Leon Drive

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1600 Ponce De Leon Drive
Fort Lauderdale, FL 33316

$32 million. It's been on the market for more than a bit. Maybe nobody wants to spend that much to live in Fort Lauderdale? All insults aside, it is a pretty house.

19. 5 Harborage Isle Dr.

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5 Harborage Isle Drive
Fort Lauderdale, FL 33301

$32 million. Ummm, no. Just no.

20. One Bal Harbour

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10295 Collins Avenue
Bal Harbour, FL 33154

Unit 2604, one of the penthouses, is listed for $30 million. The building went bankrupt recently and was bought by its condo association, just FYI.

21. Continuum South Beach

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100 South Pointe Drive
Miami Beach, FL 33139

Unit 3602, a duplex, is listed for $29,900,000. At the tippy tippy tip of South Beach, wave to the cruise ships as they glide by.

22. 2920 N. Bay Road

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2920 North Bay Road
Miami Beach, FL 33140

Newly constructed, 2920 N. Bay Road was designed to "Feng Shui" specifications by architect Kobi Karp, and is listed for $29,500,000. In case you didn't know, Feng Shui was trendy like ten years ago and is so over. So good luck with that.

23. 9 Harbor Pt.

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9 Harbor Point
Key Biscayne, FL 33149

$27 million. It's 15,000 square feet and is lovely, just lovely. Whoever is selling this place had taste.

24. 4855 Pinetree Drive

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4855 Pinetree Drive
Miami Beach, FL 33140

Build in 1932, this historic Mediterranean Revival estate on Pinetree Drive is listed for $26,770,000. It has lots of original details, including wrought iron balustrades, stone fireplaces, gorgeous wood ceilings, and a tower. Perfect to play fort in.

25. 5930 N. Bay Rd.

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5930 North Bay Road
Miami Beach, FL 33140

$25,995,000. The listing says says this historic 19,600 square foot house was "the former home of royalty" although it sadly doesn't specify which royalty. Short on details, the listing also notes it has "tremendous development potential" if an almost 20,000 square foot house isn't quite enough.

1. Pumpkin Key

Pumpkin Key, Florida 33037

Listed for an absolutely mindboggling $110 million, Pumpkin Key was the most expensive new listing of 2014 in the country when it listed earlier this year. Within the exclusive Ocean Reef Club in the Florida Keys, Pumpkin Key comes with a three-bedroom main house, two caretakers cottages, a dock master's office, a twenty slip marina capable of accommodating a megayacht, tennis courts that serve as a helipad, golf cart paths circling the island, and, acreage baby! 26 acres to be exact.

2. 1744 S. Ocean Blvd.

1744 South Ocean Boulevard, Palm Beach, FL 33480

This $99 million Palm Beach estate stretches from the ocean to Lake Worth, and is totally just down the street from Mar a Lago.

1744 South Ocean Boulevard
Palm Beach, FL 33480

3. 219 S. Beach Rd.

219 South Beach Road, Hobe Sound, FL 33455

Songstress Celine Dion listed her Bahamian-style compound on Jupiter Island with ocean frontage and private water park for $72 million but, unable to find a buyer, had to price chop it to the current $62.5 million price tag.

219 South Beach Road
Hobe Sound, FL 33455

4. 89 Middle Road

89 Middle Road, Palm Beach, FL 33480

An historical twofer in the heart of Palm Beach. A Mizner and a Wyeth for $59 million, with three additional guest houses and a spit of ocean frontage to boot.

89 Middle Road
Palm Beach, FL 33480

5. Palazzo di Richezze

17749 Collins Avenue, Sunny Isles Beach, FL 33160

The Mansions at Acqualina, currently under construction, originally organized its penthouses as thus: the top two floors were one and the floor below was another. When some richie rich decided they only wanted the very top, and bought that, the would-be lower floor of that penthouse was joined with the single floor penthouse below and re-listed for $50 million. It has been named the 'Palazzo di Rhichezze.'

17749 Collins Avenue
Sunny Isles Beach, FL 33160

6. 1545 N. Ocean Way

1545 North Ocean Way, Palm Beach, FL 33480

This classic Maurice Fatio-designed Palm Beach estate, known as Windansea, is listed for $45 million. Just south of the Palm Beach inlet, the house is on nearly two acres of land and has an "amazingly wide beach."

1545 North Ocean Way
Palm Beach, FL 33480

7. 5800 North Bay Road

5800 North Bay Road, Miami Beach, FL 33140

J-Lo's old place, this historic North Bay Road house has been on the market for a couple years, and is listed at $40 million. Could it be time for a price adjustment?

5800 North Bay Road
Miami Beach, FL 33140

8. 40 Star Island Drive

40 East Star Island Drive, Miami Beach, FL 33139

Another $40 million listing that's been on the market a while, we hear the owner isn't actually trying to sell the place but has it on the market to see if any sucker wants a bite.

40 East Star Island Drive
Miami Beach, FL 33139

9. 800 South Ocean Boulevard

800 South Ocean Boulevard, Manalapan, FL 33462

This new-build estate in Manalapan has a lot stretching from the ocean to Lake Worth, accoutrements like a 20-car garage, and a tennis court, and, oh yeah, it's listed for $39 million.

800 South Ocean Boulevard
Manalapan, FL 33462

10. 5446 North Bay Road

5446 North Bay Road, Miami Beach, FL 33140

$37 million for a white box on North Bay Road. They're all the rage these days. The house, designed by Cheoff+Levy, replaced a classic Maurice Fatio-designed red brick manor house, and was just recently completed.

5446 North Bay Road
Miami Beach, FL 33140

11. 3682 Princeton Place

3682 Princeton Place, Boca Raton, FL 33496

3682 Princeton Place is rather notorious because, despite the rather generically pretty exterior with its lagoon style pool, giant chess board, and palm trees everywhere, portions of the interior are styled after the Star Ship Enterprise from Star Trek. You get all that for $35 million.

3682 Princeton Place
Boca Raton, FL 33496

12. 17 Indian Creek Drive

17 Indian Creek Island Road, Indian Creek Village, FL 33154

Oy, this place has been on the market for a while. Built in 2002, this 16,393 square foot house in the exclusive enclave of Indian Creek Village is $35 million. It was featured on Curbed Miami two years ago, listed at $38 million, and it wasn't exactly a fresh rose back then either.

17 Indian Creek Island Road
Indian Creek Village, FL 33154

13. 12 Indian Creek Island Road

12 Indian Creek Island Road, Indian Creek Village, FL 33154

Ditto to #17 Indian Creek, above, except now it's listed for $35 million, a whole $10 million less than last time we mentioned it... a year and a half ago.

12 Indian Creek Island Road
Indian Creek Village, FL 33154

14. 110 Arvida Pkwy

110 Arvida Parkway, Coral Gables, FL 33156

$35 million. The only Coral Gables house to crack the Top 25. Pretty, but kinda blah, and a semi-poor example of Mediterranean Revival architecture. Built in 1993.

110 Arvida Parkway
Coral Gables, FL 33156

15. 13560 Indian Mound Rd.

13560 Indian Mound Road, Wellington, FL 33414

Lots o' land in Wellington with a house and 72-stall horse barn on it for $34,750,000. Get your ranch on, but maybe get an architect to build yourself something tasteful.

13560 Indian Mound Road
Wellington, FL 33414

16. 1960 S Ocean Blvd.

1960 South Ocean Boulevard, Manalapan, FL 33462

$32,500,000. No comment. Oh, here's one: the photographer went a little heavy on the HDR, and it makes this bland pile of stucco even worse.

1960 South Ocean Boulevard
Manalapan, FL 33462

17. 1102 N Ocean Blvd

1102 North Ocean Boulevard, Palm Beach, FL 33480

$32 million. Designed by John Volk in 1935. Classy. As. Fuck. Seriously, compared to some of the other schlock on this list, it's worth every penny. Somebody should buy this place. NOW.

1102 North Ocean Boulevard
Palm Beach, FL 33480

18. 1600 Ponce de Leon Drive

1600 Ponce De Leon Drive, Fort Lauderdale, FL 33316

$32 million. It's been on the market for more than a bit. Maybe nobody wants to spend that much to live in Fort Lauderdale? All insults aside, it is a pretty house.

1600 Ponce De Leon Drive
Fort Lauderdale, FL 33316

19. 5 Harborage Isle Dr.

5 Harborage Isle Drive, Fort Lauderdale, FL 33301

$32 million. Ummm, no. Just no.

5 Harborage Isle Drive
Fort Lauderdale, FL 33301

20. One Bal Harbour

10295 Collins Avenue, Bal Harbour, FL 33154

Unit 2604, one of the penthouses, is listed for $30 million. The building went bankrupt recently and was bought by its condo association, just FYI.

10295 Collins Avenue
Bal Harbour, FL 33154

21. Continuum South Beach

100 South Pointe Drive, Miami Beach, FL 33139

Unit 3602, a duplex, is listed for $29,900,000. At the tippy tippy tip of South Beach, wave to the cruise ships as they glide by.

100 South Pointe Drive
Miami Beach, FL 33139

22. 2920 N. Bay Road

2920 North Bay Road, Miami Beach, FL 33140

Newly constructed, 2920 N. Bay Road was designed to "Feng Shui" specifications by architect Kobi Karp, and is listed for $29,500,000. In case you didn't know, Feng Shui was trendy like ten years ago and is so over. So good luck with that.

2920 North Bay Road
Miami Beach, FL 33140

23. 9 Harbor Pt.

9 Harbor Point, Key Biscayne, FL 33149

$27 million. It's 15,000 square feet and is lovely, just lovely. Whoever is selling this place had taste.

9 Harbor Point
Key Biscayne, FL 33149

24. 4855 Pinetree Drive

4855 Pinetree Drive, Miami Beach, FL 33140

Build in 1932, this historic Mediterranean Revival estate on Pinetree Drive is listed for $26,770,000. It has lots of original details, including wrought iron balustrades, stone fireplaces, gorgeous wood ceilings, and a tower. Perfect to play fort in.

4855 Pinetree Drive
Miami Beach, FL 33140

25. 5930 N. Bay Rd.

5930 North Bay Road, Miami Beach, FL 33140

$25,995,000. The listing says says this historic 19,600 square foot house was "the former home of royalty" although it sadly doesn't specify which royalty. Short on details, the listing also notes it has "tremendous development potential" if an almost 20,000 square foot house isn't quite enough.

5930 North Bay Road
Miami Beach, FL 33140