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 $263,333.33 to $2,449,368.89.

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1. Shiva Loop

Shiva Loop is the 1st most expensive street in Kissimmee. It has single-family homes built from 2016 to 2018, ranging in price from $615,000 to $670,000. It is home to the Veranda Palms subdivision.

Average Price: $645,000
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2. Gobi Drive

Gobi Drive is the 2nd most expensive street in Kissimmee. It has single-family homes built from 2016 to 2019, ranging in price from $525,000 to $670,000. It is home to the Windsor at Westside subdivision.

Average Price: $598,800
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3. Arthur Street

Arthur Street is the 3rd most expensive street in Kissimmee. It has single-family homes built in 1970, with an average sale price of $330,000. It is home to the Orange Gardens subdivision.

Average Price: $330,000
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4. Hemingway House Street

Hemingway House Street is the 4th most expensive street in Kissimmee. It has townhouses built from 2005 to 2006, ranging in price from $215,000 to $292,000. It is home to the Fiesta Key subdivision.

Average Price: $263,333.33
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5. Boggy Creek Road

Boggy Creek Road is the 5th most expensive street in Kissimmee. It has land, manufactured/mobiles, and single-family homes ranging in price from $440,000 to $1,400,000. It is home to the Logans Run, Semoran Farms, and Great Oaks subdivisions.

Average Price: $830,000
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6. Tourmaline Drive

Tourmaline Drive is the 6th most expensive street in Kissimmee. It has single-family homes built from 2007 to 2013, ranging in price from $458,000 to $640,000. It is home to the Crystal Cove Resort subdivision.

Average Price: $527,666.67
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7. Manesty Lane

Manesty Lane is the 7th most expensive street in Kissimmee. It has single-family homes built in 2006, ranging in price from $520,000 to $675,000. It is home to the Windsor Hills subdivision.

Average Price: $597,500
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8. Jack Nicklaus Court

Jack Nicklaus Court is the 8th 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: $2,449,368.89
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9. Ruby Red Lane

Ruby Red Lane is the 9th most expensive street in Kissimmee. It has single-family homes built from 2007 to 2013, ranging in price from $400,000 to $439,900. It is home to the Crystal Cove Resort subdivision.

Average Price: $419,950
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10. Candy Palm Road

Candy Palm Road is the 10th most expensive street in Kissimmee. It has single-family homes, townhouses, and condos built from 2008 to 2013, ranging in price from $340,000 to $495,000. It is home to the Paradise Palms subdivision.

Average Price: $405,083.33
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