Howard Dr, Winter Park, FL Property Records

Orange County property records for 59 addresses on Howard Dr, Winter Park, FL · Last verified August 2026

Howard Dr Highlights

Properties 59
Median Sale Price $552,700
Deeds and Mortgages on File 99
Median Price per Sqft $315
Owner Occupied 81%
Median Annual Tax Bill $5,541
Median Year Built 1957
Median Ownership Tenure 10 years

Properties on Howard Dr

Owner names and prior sale amounts shown locked below are available instantly with a free trial.

2004 Howard Dr

3 bd · 2 ba · 1,866 sqft · 0.278 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$4,375Apr 2021 $12,0602025 Amount on Record Nov 2018 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

2005 Howard Dr

3 bd · 2 ba · 1,558 sqft · 0.287 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$9,0172025 2 Names on Record AssessorUpdated May 2026

2011 Howard Dr

3 bd · 2 ba · 1,474 sqft · 0.286 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$464,400Dec 2020 $8,5772025 Amount on Record Jul 2015 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

2012 Howard Dr

3 bd · 2 ba · 2,340 sqft · 0.272 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,031,000Dec 2022 $14,3832025 Amount on Record Jun 2009 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

2016 Howard Dr

4 bd · 3 ba · 2,302 sqft · 0.272 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$106,500Feb 2021 $5,7412025 Amount on Record Jul 2014 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

2017 Howard Dr

5 bd · 4.5 ba · 3,558 sqft · 0.286 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$229,100May 2002 $7,3732025 Amount on Record Dec 2000 2 Names on Record Owner Occupied AssessorUpdated May 2026

2024 Howard Dr

3 bd · 2 ba · 1,673 sqft · 0.272 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$180,000Jul 2020 $8,5302025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

2025 Howard Dr

3 bd · 2 ba · 1,768 sqft · 0.286 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$552,700Apr 2025 $7,1932025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2102 Howard Dr

3 bd · 2 ba · 1,534 sqft · 0.272 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$70,000Feb 1999 $3442025 2 Names on Record Owner Occupied AssessorUpdated May 2026

2103 Howard Dr

5 bd · 3 ba · 2,721 sqft · 0.286 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$368,000Aug 2008 $6,3862025 Amount on Record Jul 2003 2 Names on Record Owner Occupied AssessorUpdated May 2026

2110 Howard Dr

4 bd · 2 ba · 3,201 sqft · Garage

Last Sale Tax Bill Prior Sale Owner Records
$372,000Aug 2010 $7,0672025 Amount on Record Jul 2004 1 Name on Record AssessorUpdated May 2026

2111 Howard Dr

3 bd · 2 ba · 2,299 sqft · 0.286 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$58,000Jan 2021 $5,4622025 Amount on Record Jan 2006 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

2118 Howard Dr

3 bd · 2 ba · 1,606 sqft · 0.272 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$214,800Dec 2002 $8,5892025 2 Names on Record AssessorUpdated May 2026

2119 Howard Dr

4 bd · 2 ba · 2,479 sqft · 0.286 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$841,500Jun 2026 $3,7332025 Amount on Record Nov 1998 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

2126 Howard Dr

3 bd · 2 ba · 1,830 sqft · 0.272 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$595,000Oct 2019 $7,4962025 Amount on Record May 2011 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

2127 Howard Dr

3 bd · 2 ba · 1,896 sqft · 0.285 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$325,000Aug 2014 $5,3932025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2201 Howard Dr

3 bd · 2 ba · 2,087 sqft · 0.285 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$189,000Jul 2000 $4,6302025 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

2202 Howard Dr

3 bd · 2 ba · 2,597 sqft · 0.272 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$367,500Dec 2008 $4,9792025 Amount on Record Jul 1998 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

2208 Howard Dr

3 bd · 2 ba · 2,155 sqft · 0.272 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$845,000Jun 2026 $4,6962025 Amount on Record Jul 2017 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

2209 Howard Dr

3 bd · 2 ba · 2,586 sqft · 0.285 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$385,000Jun 2008 $5,0082025 Amount on Record Jun 2004 2 Names on Record Assessor + 4 DocumentsUpdated Aug 2026

2216 Howard Dr

10 bd · 10.25 ba · 7,940 sqft · 0.272 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$765,000Mar 2013 $12,4252025 Amount on Record Feb 2004 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

2217 Howard Dr

3 bd · 2 ba · 2,387 sqft · 0.285 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,025,000Sep 2024 $13,4912025 Amount on Record Feb 2020 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

2221 Howard Dr

4 bd · 2 ba · 3,861 sqft · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$7,4062025 1 Name on Record AssessorUpdated May 2026

2225 Howard Dr

3 bd · 2 ba · 2,397 sqft · 0.496 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$250,000Jan 2011 $582025 —Jun 2007 1 Name on Record AssessorUpdated May 2026

2227 Howard Dr

3 bd · 2 ba · 2,196 sqft · 0.435 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$825,000Jul 2023 $11,0982025 Amount on Record Jun 2010 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2228 Howard Dr

4 bd · 2 ba · 1,690 sqft · 0.209 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$590,000May 2025 $3,6472025 Amount on Record Feb 2024 1 Name on Record Assessor + 6 DocumentsUpdated Aug 2026

2229 Howard Dr

3 bd · 3 ba · 2,090 sqft · 0.425 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$335,000Jun 2010 $5,2292025 Amount on Record Nov 2003 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2230 Howard Dr

3 bd · 1 ba · 1,485 sqft · 0.208 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$635,000Mar 2023 $8,2842025 Amount on Record Feb 2020 1 Name on Record Owner Occupied Assessor + 7 DocumentsUpdated May 2026

2231 Howard Dr

3 bd · 3.5 ba · 1,838 sqft · 0.413 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$639,000Dec 2016 $8,0652025 Amount on Record May 2006 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

2232 Howard Dr

3 bd · 1.5 ba · 1,345 sqft · 0.2 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$102,000Apr 1997 $1,7482025 Amount on Record Jun 1995 1 Name on Record Owner Occupied AssessorUpdated May 2026

2233 Howard Dr

4 bd · 2 ba · 1,928 sqft · 0.379 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,3872025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2234 Howard Dr

8 bd · 11.25 ba · 6,410 sqft · 0.204 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$152,000Jan 2013 $17,2402025 Amount on Record Jul 2012 2 Names on Record Assessor + 3 DocumentsUpdated Aug 2026

2235 Howard Dr

3 bd · 2 ba · 2,420 sqft · 0.329 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$445,000Dec 2015 $5,5412025 Amount on Record Jun 2006 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2236 Howard Dr

3 bd · 1 ba · 1,307 sqft · 0.175 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,5622025 2 Names on Record AssessorUpdated May 2026

2237 Howard Dr

3 bd · 2 ba · 1,984 sqft · 0.315 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$735,000Mar 2022 $9,4442025 —Dec 2014 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

2238 Howard Dr

3 bd · 2 ba · 1,553 sqft · 0.166 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$87,400Sep 1995 $6,1002025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

2239 Howard Dr

3 bd · 2 ba · 2,235 sqft · 0.271 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,4962025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2240 Howard Dr

10 bd · 7.25 ba · 5,575 sqft · 0.171 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$725,000Nov 2020 $10,0242025 Amount on Record Feb 2019 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

2241 Howard Dr

2 bd · 1.5 ba · 1,826 sqft · 0.347 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$208,000Sep 2000 $4,6772025 1 Name on Record Owner Occupied AssessorUpdated May 2026

2242 Howard Dr

2 bd · 1 ba · 1,320 sqft · 0.161 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$464,000Jun 2026 $7,0882025 Amount on Record May 2013 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

2244 Howard Dr

4 bd · 2 ba · 1,955 sqft · 0.16 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$527,500Aug 2021 $6,9212025 Amount on Record Jan 2011 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2245 Howard Dr

3 bd · 1 ba · 1,053 sqft · 0.237 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,3622025 1 Name on Record Owner Occupied AssessorUpdated May 2026

2246 Howard Dr

3 bd · 2 ba · 1,467 sqft · 0.174 acres

Last Sale Tax Bill Prior Sale Owner Records
$141,000Dec 2014 $6,1712025 Amount on Record Sep 2013 1 Name on Record Assessor + 1 DocumentUpdated May 2026

2247 Howard Dr

3 bd · 2 ba · 1,427 sqft · 0.193 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$241,500Oct 2004 $2,5292025 1 Name on Record Owner Occupied AssessorUpdated May 2026

2248 Howard Dr

3 bd · 2 ba · 1,357 sqft · 0.185 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,3962025 1 Name on Record Owner Occupied AssessorUpdated May 2026

2249 Howard Dr

4 bd · 1 ba · 1,756 sqft · 0.214 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,8782025 2 Names on Record Assessor + 3 DocumentsUpdated May 2026

2250 Howard Dr

3 bd · 3.75 ba · 2,633 sqft · 0.179 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$370,000Sep 2021 $15,9322025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

2252 Howard Dr

3 bd · 2 ba · 1,380 sqft · 0.161 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$350,000Aug 2016 $3,8512025 Amount on Record Jan 2016 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

2255 Howard Dr

4 bd · 2 ba · 1,372 sqft · 0.161 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$300,000May 2018 $4,2302025 Amount on Record Jun 1998 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2257 Howard Dr

4 bd · 2 ba · 1,925 sqft · 0.16 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$500,000Mar 2022 $6,9542025 Amount on Record Aug 2021 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

2258 Howard Dr

5 bd · 3 ba · 2,747 sqft · 0.317 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,255,000Mar 2025 $10,2562025 Amount on Record Nov 2024 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

2259 Howard Dr

3 bd · 1.5 ba · 1,383 sqft · 0.16 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$6992025 1 Name on Record Owner Occupied AssessorUpdated May 2026

2260 Howard Dr

3 bd · 1 ba · 1,157 sqft · 0.175 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,6202025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

2262 Howard Dr

3 bd · 1.5 ba · 1,231 sqft · 0.175 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,2062025 2 Names on Record Owner Occupied AssessorUpdated May 2026

2263 Howard Dr

3 bd · 1.5 ba · 1,361 sqft · 0.17 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,1172025 1 Name on Record Owner Occupied AssessorUpdated May 2026

2264 Howard Dr

3 bd · 2.5 ba · 1,646 sqft · 0.175 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$147,000May 2012 $2,6502025 —May 2010 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2266 Howard Dr

4 bd · 3.75 ba · 3,192 sqft · 0.175 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$410,000Sep 2021 $17,8272025 Amount on Record May 1996 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

2268 Howard Dr

3 bd · 2.5 ba · 1,930 sqft · 0.175 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$228,000May 2016 $3,4932025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2270 Howard Dr

3 bd · 2 ba · 1,457 sqft · 0.175 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$104,000Dec 1997 $1,6722025 2 Names on Record Owner Occupied AssessorUpdated May 2026

Wildfire Risk on Howard Dr

Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020

Wildfire RiskLow
this street's cells rank at the 3rd percentile of exposed land nationally · 3rd in Florida
Wildfire LikelihoodLow — about 1 in 9,211 per year
ExposureDirect
1 of 7 cells directly exposed · 7 adjoin burnable vegetation

Property Records in Nearby Streets