Gregory Dr, Maitland, FL Property Records

Seminole County property records for 18 addresses on Gregory Dr, Maitland, FL · Last verified August 2026

Gregory Dr Highlights

Properties 18
Median Sale Price $510,000
Deeds and Mortgages on File 23
Median Price per Sqft $229
Owner Occupied 94%
Median Annual Tax Bill $3,312
Median Year Built 1966
Median Ownership Tenure 12 years

Properties on Gregory Dr

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

1000 Gregory Dr

3 bd · 2 ba · 1,947 sqft · 0.259 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$280,000Jun 2020 $3,5082025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

1004 Gregory Dr

3 bd · 2 ba · 1,835 sqft · 0.304 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$550,000Oct 2025 $3,3122025 Amount on Record Sep 2019 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

1005 Gregory Dr

3 bd · 2 ba · 1,638 sqft · 0.285 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$240,000Mar 2007 $4,8122025 Amount on Record Nov 2003 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

1010 Gregory Dr

4 bd · 2 ba · 2,431 sqft · 0.284 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$515,000Aug 2026 $4,6522025 Amount on Record May 2020 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

1011 Gregory Dr

3 bd · 2 ba · 1,800 sqft · 0.283 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$288,000Mar 2019 $3,4032025 Amount on Record Jun 1979 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

1020 Gregory Dr

3 bd · 2 ba · 1,998 sqft · 0.284 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$112,000Dec 1997 $1,9312025 Amount on Record Jan 1997 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

1025 Gregory Dr

3 bd · 2 ba · 1,855 sqft · 0.283 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$100Apr 2006 $2,1232025 Amount on Record Oct 1985 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

1030 Gregory Dr

4 bd · 3 ba · 2,289 sqft · 0.275 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$525,000Aug 2025 $6,2532025 Amount on Record Jan 2008 2 Names on Record Owner Occupied AssessorUpdated Dec 2025

1040 Gregory Dr

3 bd · 2 ba · 1,952 sqft · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$280,000Jun 2017 $3,0302025 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Dec 2025

1050 Gregory Dr

3 bd · 2 ba · 1,688 sqft · 0.277 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$90,000Jul 1987 $1,7512025 2 Names on Record Owner Occupied AssessorUpdated Dec 2025

1051 Gregory Dr

3 bd · 2 ba · 1,984 sqft · 0.279 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$460,000Mar 2023 $5,1222025 —Dec 2022 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

1055 Gregory Dr

4 bd · 3 ba · 2,187 sqft · 0.283 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$125,500Sep 2010 $2,3172025 Amount on Record Dec 2009 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1060 Gregory Dr

3 bd · 2 ba · 1,734 sqft · 0.281 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$248,500Mar 2014 $2,4352025 —Sep 2009 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

1061 Gregory Dr

4 bd · 2 ba · 2,341 sqft · 0.276 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$132,000May 1996 $2,0682025 1 Name on Record Owner Occupied AssessorUpdated Dec 2025

1065 Gregory Dr

3 bd · 2 ba · 1,929 sqft · 0.283 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$510,000Aug 2026 $6,0682025 Amount on Record Mar 2018 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

1070 Gregory Dr

4 bd · 2 ba · 1,855 sqft · 0.281 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Oct 1999 $1,7122025 Amount on Record Oct 1993 1 Name on Record Owner Occupied AssessorUpdated Jan 2026

1075 Gregory Dr

3 bd · 2 ba · 2,031 sqft · 0.279 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$250,000Jan 2014 $2,4432025 3 Names on Record Owner Occupied AssessorUpdated Dec 2025

1080 Gregory Dr

3 bd · 3.5 ba · 1,890 sqft · 0.308 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$100Jul 2008 $6,2632025 Amount on Record Oct 2004 1 Name on Record AssessorUpdated Apr 2026

Wildfire Risk on Gregory 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 9th percentile of exposed land nationally · 5th in Florida
Wildfire LikelihoodLow — about 1 in 4,167 per year
ExposureDirect
3 of 3 cells directly exposed · 3 adjoin burnable vegetation

Property Records in Nearby Streets