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 $1,300,000 to $2,475,000.

The following are the Top 10 most expensive streets in The Oaks. The average price for homes on these streets range from $1,300,000 to $2,475,000.

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1. Siesta Lago Drive

Siesta Lago Drive is the 1st 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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2. Jacks Club Drive

Jacks Club Drive is the 2nd most expensive street in Kissimmee. It has single-family homes built from 2022 to 2023, ranging in price from $1,970,000 to $2,500,000. It is home to the Bears Den subdivision.

Average Price: $2,235,000
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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 2019 to 2024, ranging in price from $1,635,000 to $3,250,000. It is home to the Bears Den subdivision.

Average Price: $2,081,000
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4. Jacks Club Court

Jacks Club Court is the 4th most expensive street in Kissimmee. It has single-family homes built from 2019 to 2022, with an average sale price of $1,967,190. It is home to the Bears Den subdivision.

Average Price: $1,967,190
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5. Gathering Court

Gathering Court is the 5th most expensive street in Kissimmee. It has single-family homes and land with an average sale price of $1,799,999.

Average Price: $1,799,999
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6. Parrot Head Place

Parrot Head Place is the 6th most expensive street in Kissimmee. It has single-family homes built in 2019, with an average sale price of $1,575,000. It is home to the Rolling Oaks subdivision.

Average Price: $1,575,000
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7. Ganesha Loop

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

Average Price: $1,517,368
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8. Sea Pearl Circle

Sea Pearl Circle is the 8th most expensive street in Kissimmee. It has single-family homes built from 2000 to 2003, ranging in price from $700,000 to $2,175,000. It is home to the Formosa Gardens subdivision.

Average Price: $1,437,500
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9. Rama Drive

Rama Drive is the 9th most expensive street in Kissimmee. It has single-family homes built from 2022 to 2024, ranging in price from $849,380 to $1,550,000. It is home to the Veranda Palms subdivision.

Average Price: $1,366,336
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10. Church Street

Church Street is the 10th most expensive street in Kissimmee. It has multi-units built in 1900, with an average sale price of $1,300,000.

Average Price: $1,300,000
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