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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. 6 beds, 12 full, 2 half baths
    Home size: 20,333 sq ft
    Lot size: 18.16 ac
    Year built: 2011
    Parking spots: 5
    Days on market: 139
  2. 7 beds, 9 full, 1 half baths
    Home size: 13,519 sq ft
    Lot size: 1.89 ac
    Year built: 1998
    Parking spots: 3
    Days on market: 243
  3. 7 beds, 7 full, 4 half baths
    Home size: 15,063 sq ft
    Lot size: 3.76 ac
    Year built: 2015
    Parking spots: 5
    Days on market: 41
  4. 3 beds, 3 full, 1 half baths
    Home size: 3,746 sq ft
    Year built: 1976
    Parking spots: 2
    Days on market: 1,355
  5. 7 beds, 7 full, 5 half baths
    Home size: 17,649 sq ft
    Lot size: 2.11 ac
    Year built: 2000
    Parking spots: 5
    Days on market: 22
  6. 6 beds, 6 full, 2 half baths
    Home size: 15,332 sq ft
    Lot size: 3.44 ac
    Year built: 2012
    Parking spots: 5
    Days on market: 60
  7. 6 beds, 8 full, 1 half baths
    Home size: 11,182 sq ft
    Lot size: 1.74 ac
    Year built: 2006
    Parking spots: 4
    Days on market: 1
  8. 5 beds, 6 full baths
    Home size: 9,811 sq ft
    Lot size: 1.18 ac
    Year built: 2002
    Parking spots: 5
    Days on market: 187
  9. 5 beds, 7 full, 2 half baths
    Home size: 10,155 sq ft
    Lot size: 40,628 sqft
    Year built: 2006
    Parking spots: 3
    Days on market: 1,300
  10. 5 beds, 7 full, 4 half baths
    Home size: 21,864 sq ft
    Lot size: 9.50 ac
    Year built: 2006
    Parking spots: 5
    Days on market: 251
  11. 7 beds, 6 full, 2 half baths
    Home size: 9,307 sq ft
    Lot size: 39,687 sqft
    Year built: 2000
    Parking spots: 4
    Days on market: 104
  12. 6 beds, 7 full, 2 half baths
    Home size: 10,314 sq ft
    Lot size: 2.20 ac
    Year built: 2005
    Parking spots: 4
    Days on market: 1,091
  13. 7 beds, 10 full, 3 half baths
    Home size: 14,477 sq ft
    Lot size: 2.14 ac
    Year built: 1998
    Parking spots: 5
    Days on market: 95
  14. 5 beds, 7 full, 1 half baths
    Home size: 15,892 sq ft
    Lot size: 1.83 ac
    Year built: 1994
    Parking spots: 5
    Days on market: 916
  15. 5 beds, 5 full, 3 half baths
    Home size: 11,340 sq ft
    Lot size: 1.68 ac
    Year built: 2008
    Parking spots: 4
    Days on market: 48
  16. 6 beds, 7 full, 3 half baths
    Home size: 11,100 sq ft
    Lot size: 26,184 sqft
    Year built: 2004
    Parking spots: 4
    Days on market: 228
  17. 4 beds, 5 full, 1 half baths
    Home size: 7,543 sq ft
    Lot size: 24,927 sqft
    Year built: 2011
    Parking spots: 4
    Days on market: 725
  18. 5 beds, 5 full, 3 half baths
    Home size: 7,800 sq ft
    Lot size: 1.59 ac
    Year built: 1925
    Parking spots: 4
    Days on market: 379
  19. 7 beds, 7 full, 2 half baths
    Home size: 7,940 sq ft
    Lot size: 28,210 sqft
    Year built: 1994
    Parking spots: 4
    Days on market: 167
  20. 3 beds, 2 full baths
    Home size: 1,920 sq ft
    Lot size: 43,560 sqft
    Year built: 1948
    Parking spots: 2
    Days on market: 244

See all Orlando Expensive Homes.
(all data current as of 5/25/2016)

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

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