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%

20,078
Homes in ZIP
4,162
Flagged as overassessed
20.7%
$57,521
Avg overage / home
$337,902
Typical value
~$151/sqft

Your Osceola County deadline

TRIM mailing: Aug 14, 2026 · VAB petition due: Sept 8, 2026

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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.

AddressSq ftYearJust valueExpectedOverage% over$/yr
1XXX PINE ISLAND RD3,4001928$2,762,000$513,400$2,248,600438%$19,338
1XXX SUNSET POINTE PL4,9342000$1,668,700$745,034$923,666124%$7,944
3XXX GREAT OAKS BLVD10,0732007$2,326,400$1,521,023$805,37752.9%$6,926
1XXX PINE ISLAND RD2,4641997$1,109,400$372,064$737,336198.2%$6,341
2XXX SIMPSON RD1,8231959$941,800$275,273$666,527242.1%$5,732
1XXX SIMMONS RD1,3681984$854,900$206,568$648,332313.9%$5,576
1XXX SUNSET POINTE PL5,7172002$1,491,300$863,267$628,03372.8%$5,401
1XXX GRAND OAK DR26,2592022$4,583,500$3,965,109$618,39115.6%$5,318
1XXX GRAND OAK DR26,2592022$4,583,500$3,965,109$618,39115.6%$5,318
1XXX HERITAGE KEY BLVD26,2592023$4,583,500$3,965,109$618,39115.6%$5,318
1XXX HERITAGE KEY BLVD26,2592023$4,583,500$3,965,109$618,39115.6%$5,318
2XXX MACY ISLAND RD2,7051958$1,017,800$408,455$609,345149.2%$5,240
2XXX PARTIN SETTLEMENT RD4,5552007$1,280,600$687,805$592,79586.2%$5,098
1XXX SUNSET POINTE PL7,0682001$1,654,600$1,067,268$587,33255%$5,051
1XXX SUNSET POINTE PL4,7962000$1,277,000$724,196$552,80476.3%$4,754
1XXX SUNSET POINTE PL5,1061995$1,297,400$771,006$526,39468.3%$4,527
3XXX GREAT OAKS BLVD3,9702019$1,097,800$599,470$498,33083.1%$4,286
1XXX SUNSET POINTE PL4,5951998$1,191,200$693,845$497,35571.7%$4,277
2XXX FRONTIER DR5,8831996$1,382,200$888,333$493,86755.6%$4,247
1XXX LEE JANZEN DR6,2212008$1,428,300$939,371$488,92952%$4,205
1XXX SUNSET POINTE PL5,0051995$1,234,700$755,755$478,94563.4%$4,119
1XXX GRANDVIEW BLVD7,1751987$1,562,000$1,083,425$478,57544.2%$4,116
1XXX GRANDVIEW BLVD8,6882022$1,759,700$1,311,888$447,81234.1%$3,851
3XXX GREAT OAKS BLVD4,9292011$1,176,900$744,279$432,62158.1%$3,721
2XXX TINDALL ACRES RD5,4081991$1,244,800$816,608$428,19252.4%$3,682
Data: FL DOR 2025 Final NAL roll, Osceola County, ZIP 34744. Addresses anonymized to protect privacy; full data is public record under Fla. Stat. Ch. 119. Showing top 25 — there are likely more overassessed homes in this ZIP.

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