Top 10 Most Expensive Streets in Oakland Park, Winter Garden, FL

The following are the Top 10 most expensive streets in Oakland Park. The average price for homes on these streets range from $705,000 to $2,500,000.

1. Lakeview Road

Lakeview Road is the 1st most expensive street in Winter Garden. It has single-family homes built in 2022, with an average sale price of $2,500,000.

Average Price: $2,500,000
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2. Panther Lake Drive

Panther Lake Drive is the 2nd most expensive street in Winter Garden. It has single-family homes built from 2019 to 2020, ranging in price from $1,135,000 to $2,540,000.

Average Price: $1,902,500
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3. Charmed Drive

Charmed Drive is the 3rd most expensive street in Winter Garden. It has single-family homes and townhouses built from 2022 to 2024, ranging in price from $429,740 to $841,871. It is home to the Waterleigh and Storey Grove subdivisions.

Average Price: $733,674.16
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4. Teacup Springs Court

Teacup Springs Court is the 4th most expensive street in Winter Garden. It has single-family homes built from 1972 to 1995, with an average sale price of $705,000.

Average Price: $705,000
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5. Topsail Place

Topsail Place is the 5th most expensive street in Winter Garden. It has single-family homes built from 2017 to 2022, ranging in price from $815,000 to $1,200,000. It is home to the Lakeshore subdivision.

Average Price: $1,016,750
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6. Duff Drive

Duff Drive is the 6th most expensive street in Winter Garden. It has single-family homes built from 2004 to 2005, ranging in price from $780,000 to $949,900. It is home to the Glynwood subdivision.

Average Price: $881,200
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7. Shorebird Lane

Shorebird Lane is the 7th most expensive street in Winter Garden. It has single-family homes built from 2017 to 2021, ranging in price from $758,000 to $2,430,000. It is home to the Lakeshore subdivision.

Average Price: $1,277,200
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8. Wild Blackberry Trail

Wild Blackberry Trail is the 8th most expensive street in Winter Garden. It has single-family homes built from 2013 to 2024, ranging in price from $1,450,000 to $2,159,000. It is home to the Independence subdivision.

Average Price: $1,804,500
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9. Civitas Way

Civitas Way is the 9th most expensive street in Winter Garden. It has single-family homes built from 2020 to 2023, ranging in price from $785,000 to $1,850,000. It is home to the Oakland Park subdivision.

Average Price: $1,260,000
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10. Pawley Way

Pawley Way is the 10th most expensive street in Winter Garden. It has single-family homes built from 2014 to 2016, ranging in price from $775,000 to $1,250,000. It is home to the Oakland Park subdivision.

Average Price: $1,044,625
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