Top 10 Most Expensive Streets in The Oaks, Kissimmee, FL

The following are the Top 10 most expensive streets in The Oaks. The average price for homes on these streets range from $1,400,000 to $3,300,000.

1. Aquila Loop

Aquila Loop is the 1st most expensive street in Kissimmee. It has single-family homes built in 2006, with an average sale price of $3,300,000.

Average Price: $3,300,000
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2. Siesta Lago Drive

Siesta Lago Drive is the 2nd most expensive street in Kissimmee. It has land with an average sale price of $2,475,000.

Average Price: $2,475,000
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3. Jack Nicklaus Court

Jack Nicklaus Court is the 3rd most expensive street in Kissimmee. It has single-family homes built from 2018 to 2025, ranging in price from $1,375,000 to $4,600,000. It is home to the Bears Den subdivision.

Average Price: $2,338,750
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4. Jacks Club Drive

Jacks Club Drive is the 4th most expensive street in Kissimmee. It has single-family homes built from 2019 to 2023, ranging in price from $1,400,000 to $2,500,000. It is home to the Bears Den subdivision.

Average Price: $1,820,000
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5. Roycroft Avenue

Roycroft Avenue is the 5th most expensive street in Kissimmee. It has single-family homes built in 2004, with an average sale price of $1,700,000.

Average Price: $1,700,000
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6. Jacks Clb Drive

Jacks Clb Drive is the 6th most expensive street in Kissimmee. It has single-family homes built from 2019 to 2022, ranging in price from $1,275,000 to $1,970,000. It is home to the Bears Den subdivision.

Average Price: $1,622,500
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7. Ganesha Loop

Ganesha Loop is the 7th most expensive street in Kissimmee. It has single-family homes built from 2023 to 2024, ranging in price from $1,134,470 to $1,785,000.

Average Price: $1,517,367.50
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8. Golden Noble Street

Golden Noble Street is the 8th most expensive street in Kissimmee. It has single-family homes built in 2023, with an average sale price of $1,449,000.

Average Price: $1,449,000
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9. Rama Drive

Rama Drive is the 9th most expensive street in Kissimmee. It has single-family homes built from 2021 to 2024, ranging in price from $849,380 to $1,580,000. It is home to the Veranda Palms subdivision.

Average Price: $1,421,424.67
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10. Golden Bear Drive

Golden Bear Drive is the 10th most expensive street in Kissimmee. It has single-family homes built from 2007 to 2021, with an average sale price of $1,400,000.

Average Price: $1,400,000
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