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Orlando FL Most Expensive Homes for Sale

Orlando is not Hollywood but we also have a good amount of exclusive luxury homes available for sale here in Central Florida. In fact, some of the homes may be very similar to those you see in California, only that your money will get you much further here in sunny Florida. Take a look at the property showcase on the right to preview and browse Orlando’s most expensive homes!

Click on any of the homes to view more pictures, virtual tours and a description of its features.

There are several areas that are considered most expensive within Orlando:

  • Windermere (often referred to as “new money” area): Within Windermere the most expensive subdivisions are Isleworth (Tiger Woods owns a home here), Chain Du Lac and Reserve at Lake Butler Sound. Another popular upscale community is Keene’s Point.
  • Along Markham Woods Road (often referred to as “Millionaire’s Row”): Markham Woods Road extends from Longwood to the West Sanford/Heathrow area. Along this road you will find multiple upscale million dollar and custom home communities. Most famous among these are without a doubt Alaqua and Alaqua Lakes. Other luxury communities along Markham Woods are the new Veramonte and Carisbrooke subdivisions as well as Lake Club that was featured in the Street of Dreams. This is where famous Magic basketball player Dwight Howard bought the most expensive home ever sold in Seminole county at $8 million dollars.
  • Winter Park (often referred to as “old money” area): Since Winter Park is one of the oldest, most established areas in Orlando, there aren’t really a lot of subdivisions in the modern sense. Nevertheless, some of the most expensive and impressive homes of the Orlando area are located in the upscale Park Avenue area of Winter Park, with lakefront properties leading in price. A newer luxury community in Winter Park is Windsong.

Of course, that doesn’t mean those are the only expensive areas in Orlando, just the three you would think of first. Other upscale neighborhoods and subdivisions are among others, Heathrow and Lake Forest in Seminole County and Bay Hill and up and coming Lake Nona in Orange County.

If you have any questions about these areas or are interested in purchasing a home here give us a call at 407-340-6458 or simply send us a quick message and we will be in touch!

Orlando’s Most Expensive Luxury Homes for Sale – Most Recent Listings

  1. 12 beds, 15 baths
    Home size: 31,000 sq ft
    Lot size: 3.94 ac
    Year built: 1990
    Days on market: 154
  2. 11 beds, 14 baths
    Home size: 25,466 sq ft
    Lot size: 3.19 ac
    Year built: 1999
    Days on market: 99
  3. 7 beds, 11 baths
    Home size: 15,063 sq ft
    Lot size: 3.76 ac
    Year built: 2015
    Days on market: 925
  4. 8 beds, 9 baths
    Home size: 13,230 sq ft
    Lot size: 1.03 ac
    Year built: 2004
    Days on market: 171
  5. 6 beds, 9 baths
    Home size: 8,589 sq ft
    Lot size: 17,859 sqft
    Year built: 2019
    Days on market: 254
  6. 7 beds, 10 baths
    Home size: 10,730 sq ft
    Lot size: 5.17 ac
    Year built: 2018
    Days on market: 222
  7. 6 beds, 10 baths
    Home size: 12,128 sq ft
    Lot size: 1.74 ac
    Year built: 2006
    Days on market: 129
  8. 7 beds, 11 baths
    Home size: 10,060 sq ft
    Lot size: 4.67 ac
    Year built: 2012
    Days on market: 14
  9. 6 beds, 10 baths
    Home size: 12,000 sq ft
    Lot size: 33,105 sqft
    Year built: 2014
    Days on market: 255
  10. 6 beds, 9 baths
    Home size: 10,452 sq ft
    Lot size: 2.48 ac
    Year built: 2008
    Days on market: 136
  11. 6 beds, 9 baths
    Home size: 8,049 sq ft
    Lot size: 41,382 sqft
    Year built: 1992
    Days on market: 195
  12. 1 bed, 1 bath
    Home size: 1,088 sq ft
    Lot size: 155.00 ac
    Year built: 2009
    Days on market: 346
  13. 5 beds, 6 baths
    Home size: 9,811 sq ft
    Lot size: 1.18 ac
    Year built: 2002
    Days on market: 132
  14. 7 beds, 10 baths
    Home size: 12,353 sq ft
    Lot size: 29,185 sqft
    Year built: 2008
    Days on market: 789
  15. 7 beds, 9 baths
    Home size: 12,481 sq ft
    Lot size: 2.24 ac
    Year built: 2008
    Days on market: 538
  16. 5 beds, 7 baths
    Home size: 6,389 sq ft
    Lot size: 22,215 sqft
    Year built: 2018
    Days on market: 220
  17. 5 beds, 8 baths
    Home size: 9,621 sq ft
    Lot size: 2.01 ac
    Year built: 2005
    Days on market: 184
  18. 10 beds, 14 baths
    Home size: 21,864 sq ft
    Lot size: 11.31 ac
    Year built: 2006
    Days on market: 206
  19. 5 beds, 9 baths
    Home size: 12,370 sq ft
    Lot size: 4.36 ac
    Year built: 1999
    Days on market: 206
  20. 5 beds, 8 baths
    Home size: 6,956 sq ft
    Lot size: 37,897 sqft
    Year built: 2007
    Days on market: 4

See all Orlando Expensive Homes.
(all data current as of 10/18/2018)

Listing information deemed reliable but not guaranteed. Read full disclaimer.

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