Homebuyers and sellers are navigating a slow and expensive housing market, with rising prices and stagnant demand keeping many on the sidelines. This comes amid rising economic uncertainty and growing wealth concentration. But luxury homes—multimillion-dollar estates, sleek penthouses, and one-of-a-kind custom builds—are still selling, even as most buyers pull back.
Most people can't afford high-end homes, although they're still fun to dream about. So, to highlight where luxury real estate is commanding the highest prices, Redfin analyzed the most expensive neighborhoods in the Orlando metro area—and showcased a few of the area's standout listings (when possible).
Note: Redfin's analysis focused on metro areas, meaning some neighborhoods fell within smaller nearby cities. Listings and data were gathered on October 15, 2025.
#1. Isleworth (Lake Butler, FL)
Median sale price
: $4,765,000 |
Median days on market
: 243 days
5525 Isleworth Country Club Dr, Windermere, FL 34786
- List price: $14,250,000
- Beds: 5 | Baths: 5.5 | Square feet: 9,511
- See 5525 Isleworth Country Club Dr, Windermere, FL 34786 on Redfin.com
9648 Mccormick Pl, Windermere, FL 34786
- List price: $3,800,000
- Beds: 3 | Baths: 3.5 | Square feet: 4,751
- See 9648 Mccormick Pl, Windermere, FL 34786 on Redfin.com
9731 Chestnut Ridge Dr, Windermere, FL 34786
- List price: $3,400,000
- Beds: 4 | Baths: 4 | Square feet: 4,877
- See 9731 Chestnut Ridge Dr, Windermere, FL 34786 on Redfin.com
9935 Lake Louise Dr, Windermere, FL 34786
- List price: $12,995,000
- Beds: 7 | Baths: 8.5 | Square feet: 16,257
- See 9935 Lake Louise Dr, Windermere, FL 34786 on Redfin.com
#2. Bella Collina (Montverde, FL)
Median sale price
: $2,100,000 |
Median days on market
: 185 days
16300 County Road 455, Montverde, FL 34756
- List price: $449,900
- Beds: 3 | Baths: 3 | Square feet: 1,568
- See 16300 County Road 455, Montverde, FL 34756 on Redfin.com
16300 County Road 455, Montverde, FL 34756
- List price: $380,000
- Beds: 2 | Baths: 2.5 | Square feet: 1,402
- See 16300 County Road 455, Montverde, FL 34756 on Redfin.com
16300 County Road 455, Montverde, FL 34756
- List price: $489,000
- Beds: 3 | Baths: 3 | Square feet: 1,568
- See 16300 County Road 455, Montverde, FL 34756 on Redfin.com
16538 Bolsena Dr, Bella Collina, FL 34756
- List price: $2,095,900
- Beds: 4 | Baths: 5.5 | Square feet: 4,319
- See 16538 Bolsena Dr, Bella Collina, FL 34756 on Redfin.com
#3. Waterside (Winter Garden, FL)
Median sale price
: $1,607,500 |
Median days on market
: 25 days
1559 Bayfront Park Aly, Winter Garden, FL 34787
- List price: $464,999
- Beds: 3 | Baths: 2 | Square feet: 1,692
- See 1559 Bayfront Park Aly, Winter Garden, FL 34787 on Redfin.com
1565 Bayfront Park Aly, Winter Garden, FL 34787
- List price: $625,000
- Beds: 4 | Baths: 3.5 | Square feet: 2,930
- See 1565 Bayfront Park Aly, Winter Garden, FL 34787 on Redfin.com
16761 Broadwater Ave, Winter Garden, FL 34787
- List price: $1,749,000
- Beds: 5 | Baths: 5.5 | Square feet: 3,513
- See 16761 Broadwater Ave, Winter Garden, FL 34787 on Redfin.com
#4. Keenes Pointe (Lake Butler, FL)
Median sale price
: $1,460,000 |
Median days on market
: 65 days
11413 Camden Park Dr, Windermere, FL 34786
- List price: $1,425,000
- Beds: 5 | Baths: 3.5 | Square feet: 3,840
- See 11413 Camden Park Dr, Windermere, FL 34786 on Redfin.com
11524 Claymont Cir, Windermere, FL 34786
- List price: $1,389,000
- Beds: 5 | Baths: 4 | Square feet: 3,358
- See 11524 Claymont Cir, Windermere, FL 34786 on Redfin.com
6161 Blakeford Dr, Windermere, FL 34786
- List price: $1,790,000
- Beds: 5 | Baths: 4.5 | Square feet: 5,704
- See 6161 Blakeford Dr, Windermere, FL 34786 on Redfin.com
9721 Carillon Park Dr, Windermere, FL 34786
- List price: $5,489,000
- Beds: 6 | Baths: 8 | Square feet: 8,305
- See 9721 Carillon Park Dr, Windermere, FL 34786 on Redfin.com
#5. Virginia Heights (Winter Park, FL)
Median sale price
: $1,150,000 |
Median days on market
: 31 days
1221 Richmond Rd, Winter Park, FL 32789
- List price: $5,450,000
- Beds: 5 | Baths: 5.5 | Square feet: 5,164
- See 1221 Richmond Rd, Winter Park, FL 32789 on Redfin.com
1251 Arlington Pl, Winter Park, FL 32789
- List price: $899,000
- Beds: 3 | Baths: 3.5 | Square feet: 2,116
- See 1251 Arlington Pl, Winter Park, FL 32789 on Redfin.com
1661 Hillcrest Ave, Winter Park, FL 32789
- List price: $1,949,999
- Beds: 4 | Baths: 3.5 | Square feet: 3,161
- See 1661 Hillcrest Ave, Winter Park, FL 32789 on Redfin.com
255 Stirling Ave, Winter Park, FL 32789
- List price: $3,299,000
- Beds: 4 | Baths: 3.5 | Square feet: 3,635
- See 255 Stirling Ave, Winter Park, FL 32789 on Redfin.com
This story was produced by Redfin Real Estate and reviewed and distributed by Stacker.
