Osceola County · Kissimmee
ZIP 34744 property tax overassessment report
20.7% of homes in Kissimmee ZIP 34744 (4,162 of 20,078 parcels) are assessed more than 10% above what comparable-size homes in the same ZIP typically pay per square foot. Combined annual overpayment: $2,058,877.
★ First 100 FL packets at $49 (62 left, then $79 starting June 1) · 30-day refund · Ownwell takes 25-35%
Your Osceola County deadline
TRIM mailing: Aug 14, 2026 · VAB petition due: Sept 8, 2026
Top 25 most overassessed homes in 34744
Addresses anonymized. Pulled directly from the FL DOR 2025 Final NAL roll. Each home pays significantly more than what a comparable-size home in this ZIP typically pays.
| Address | Sq ft | Year | Just value | Expected | Overage | % over | $/yr |
|---|---|---|---|---|---|---|---|
| 1XXX PINE ISLAND RD | 3,400 | 1928 | $2,762,000 | $513,400 | $2,248,600 | 438% | $19,338 |
| 1XXX SUNSET POINTE PL | 4,934 | 2000 | $1,668,700 | $745,034 | $923,666 | 124% | $7,944 |
| 3XXX GREAT OAKS BLVD | 10,073 | 2007 | $2,326,400 | $1,521,023 | $805,377 | 52.9% | $6,926 |
| 1XXX PINE ISLAND RD | 2,464 | 1997 | $1,109,400 | $372,064 | $737,336 | 198.2% | $6,341 |
| 2XXX SIMPSON RD | 1,823 | 1959 | $941,800 | $275,273 | $666,527 | 242.1% | $5,732 |
| 1XXX SIMMONS RD | 1,368 | 1984 | $854,900 | $206,568 | $648,332 | 313.9% | $5,576 |
| 1XXX SUNSET POINTE PL | 5,717 | 2002 | $1,491,300 | $863,267 | $628,033 | 72.8% | $5,401 |
| 1XXX GRAND OAK DR | 26,259 | 2022 | $4,583,500 | $3,965,109 | $618,391 | 15.6% | $5,318 |
| 1XXX GRAND OAK DR | 26,259 | 2022 | $4,583,500 | $3,965,109 | $618,391 | 15.6% | $5,318 |
| 1XXX HERITAGE KEY BLVD | 26,259 | 2023 | $4,583,500 | $3,965,109 | $618,391 | 15.6% | $5,318 |
| 1XXX HERITAGE KEY BLVD | 26,259 | 2023 | $4,583,500 | $3,965,109 | $618,391 | 15.6% | $5,318 |
| 2XXX MACY ISLAND RD | 2,705 | 1958 | $1,017,800 | $408,455 | $609,345 | 149.2% | $5,240 |
| 2XXX PARTIN SETTLEMENT RD | 4,555 | 2007 | $1,280,600 | $687,805 | $592,795 | 86.2% | $5,098 |
| 1XXX SUNSET POINTE PL | 7,068 | 2001 | $1,654,600 | $1,067,268 | $587,332 | 55% | $5,051 |
| 1XXX SUNSET POINTE PL | 4,796 | 2000 | $1,277,000 | $724,196 | $552,804 | 76.3% | $4,754 |
| 1XXX SUNSET POINTE PL | 5,106 | 1995 | $1,297,400 | $771,006 | $526,394 | 68.3% | $4,527 |
| 3XXX GREAT OAKS BLVD | 3,970 | 2019 | $1,097,800 | $599,470 | $498,330 | 83.1% | $4,286 |
| 1XXX SUNSET POINTE PL | 4,595 | 1998 | $1,191,200 | $693,845 | $497,355 | 71.7% | $4,277 |
| 2XXX FRONTIER DR | 5,883 | 1996 | $1,382,200 | $888,333 | $493,867 | 55.6% | $4,247 |
| 1XXX LEE JANZEN DR | 6,221 | 2008 | $1,428,300 | $939,371 | $488,929 | 52% | $4,205 |
| 1XXX SUNSET POINTE PL | 5,005 | 1995 | $1,234,700 | $755,755 | $478,945 | 63.4% | $4,119 |
| 1XXX GRANDVIEW BLVD | 7,175 | 1987 | $1,562,000 | $1,083,425 | $478,575 | 44.2% | $4,116 |
| 1XXX GRANDVIEW BLVD | 8,688 | 2022 | $1,759,700 | $1,311,888 | $447,812 | 34.1% | $3,851 |
| 3XXX GREAT OAKS BLVD | 4,929 | 2011 | $1,176,900 | $744,279 | $432,621 | 58.1% | $3,721 |
| 2XXX TINDALL ACRES RD | 5,408 | 1991 | $1,244,800 | $816,608 | $428,192 | 52.4% | $3,682 |
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