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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

See all Orlando Expensive Homes.
(all data current as of 8/29/2014)

  1. 3 beds, 3 full, 1 part baths
    Home size: 3,746 sq ft
    Lot size: 17.51 ac
    Year built: 1976
    Parking spots: 2
    Days on market: 721
  2. 9 beds, 11 full, 4 part baths
    Home size: 21,515 sq ft
    Lot size: 3.19 ac
    Year built: 1999
    Parking spots: 5
    Days on market: 310
  3. 4 beds, 5 full, 1 part baths
    Home size: 6,943 sq ft
    Lot size: 24,927 sqft
    Year built: 1989
    Parking spots: 4
    Days on market: 91
  4. 5 beds, 7 full, 2 part baths
    Home size: 10,155 sq ft
    Lot size: 40,628 sqft
    Year built: 2006
    Parking spots: 3
    Days on market: 666
  5. 5 beds, 5 full, 2 part baths
    Home size: 10,307 sq ft
    Lot size: 1.25 ac
    Year built: 2000
    Parking spots: 4
    Days on market: 128
  6. 7 beds, 7 full, 3 part baths
    Home size: 12,353 sq ft
    Lot size: 29,393 sqft
    Year built: 2008
    Parking spots: 5
    Days on market: 18
  7. 6 beds, 5 full, 3 part baths
    Home size: 13,670 sq ft
    Lot size: 1.72 ac
    Year built: 1990
    Parking spots: 5
    Days on market: 86
  8. 7 beds, 10 full, 1 part baths
    Home size: 10,455 sq ft
    Lot size: 38,720 sqft
    Year built: 2012
    Parking spots: 2
    Days on market: 129
  9. 6 beds, 7 full, 2 part baths
    Home size: 10,314 sq ft
    Lot size: 2.20 ac
    Year built: 2005
    Parking spots: 4
    Days on market: 456
  10. 5 beds, 7 full, 1 part baths
    Home size: 15,892 sq ft
    Lot size: 1.83 ac
    Year built: 1994
    Parking spots: 5
    Days on market: 282
  11. 5 beds, 5 full, 2 part baths
    Home size: 8,738 sq ft
    Lot size: 2.13 ac
    Year built: 1925
    Parking spots: 2
    Days on market: 161
  12. 7 beds, 8 full, 1 part baths
    Home size: 10,768 sq ft
    Lot size: 38,161 sqft
    Year built: 2014
    Parking spots: 5
    Days on market: 159
  13. 4 beds, 4 full, 1 part baths
    Home size: 8,662 sq ft
    Lot size: 5.00 ac
    Year built: 1940
    Parking spots: 5
    Days on market: 29
  14. 6 beds, 6 full, 3 part baths
    Home size: 10,190 sq ft
    Lot size: 1.01 ac
    Year built: 2000
    Parking spots: 3
    Days on market: 144
  15. 9 beds, 9 full, 5 part baths
    Home size: 21,864 sq ft
    Lot size: 9.50 ac
    Year built: 2006
    Parking spots: 5
    Days on market: 28
  16. 5 beds, 7 full, 1 part baths
    Home size: 10,646 sq ft
    Lot size: 1.04 ac
    Year built: 2007
    Parking spots: 10
    Days on market: 15
  17. 5 beds, 5 full, 1 part baths
    Home size: 8,207 sq ft
    Lot size: 4.62 ac
    Year built: 2001
    Parking spots: 4
    Days on market: 60
  18. 5 beds, 6 full, 5 part baths
    Home size: 15,917 sq ft
    Lot size: 3.44 ac
    Year built: 2012
    Parking spots: 5
    Days on market: 435
  19. 5 beds, 5 full, 3 part baths
    Home size: 8,581 sq ft
    Lot size: 40,498 sqft
    Year built: 2003
    Parking spots: 4
    Days on market: 142
  20. 5 beds, 5 full, 3 part baths
    Home size: 9,599 sq ft
    Lot size: 1.50 ac
    Year built: 2006
    Parking spots: 4
    Days on market: 228

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

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  1. [...] Status/Destination – If having the best address in town is your thing, then Status/destination neighborhoods are for you. These types of neighborhoods typically feature expansive homes, gated entries and major exclusivity.  Sweetwater Club, Alaqua, or Isleworth (former home to Tiger Woods) are all great Status/Destination neighborhoods in the Orlando area. Others likely to buy in these types of area’s are high powered executives, upper middle class families and even celebrities, so you know you will be in good company. The downside? It is pretty expensive for this fabulous lifestyle and yearly maintenance and membership fees can be exorbitant. Click here is you are interested to learn more about Orlando’s most expensive areas. [...]

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