Roosevelt Dr, Chestertown, MD Property Records

Kent County property records for 25 addresses on Roosevelt Dr, Chestertown, MD · Last verified August 2026

Roosevelt Dr Highlights

Properties 25
Median Sale Price $148,000
Deeds and Mortgages on File 27
Median Price per Sqft $128
Owner Occupied 80%
Median Annual Tax Bill $2,637
Median Year Built 1966
Median Ownership Tenure 8 years

Properties on Roosevelt Dr

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

100 Roosevelt Dr

1.5 ba · 1,152 sqft · built 1968 · 0.427 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,1172025 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

102 Roosevelt Dr

1.5 ba · 1,152 sqft · built 1968 · 0.459 acres

Last Sale Tax Bill Prior Sale Owner Records
—Mar 2000 $2,3232025 Owner on Record Owner Occupied AssessorUpdated Aug 2026

103 Roosevelt Dr

2 ba · 2,220 sqft · built 2016 · 0.509 acres

Last Sale Tax Bill Prior Sale Owner Records
$205,170May 2016 $4,0602025 Amount on Record Sep 2015 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

104 Roosevelt Dr

1.5 ba · 1,152 sqft · built 1968 · 0.491 acres

Last Sale Tax Bill Prior Sale Owner Records
$94,000Jul 2003 $2,6922025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

106 Roosevelt Dr

1.5 ba · 1,152 sqft · built 1968 · 0.516 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,7302025 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

107 Roosevelt Dr

2 ba · 1,568 sqft · built 1989 · 0.436 acres

Last Sale Tax Bill Prior Sale Owner Records
$47,516Jan 2003 $2,9882025 Amount on Record Jun 1988 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

200 Roosevelt Dr

1.5 ba · 1,328 sqft · built 1965 · 0.564 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,000Nov 2021 $2,6552025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

201 Roosevelt Dr

1.5 ba · 1,632 sqft · built 1965 · 0.517 acres

Last Sale Tax Bill Prior Sale Owner Records
—May 2005 $2,9022025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

202 Roosevelt Dr

1.5 ba · 1,152 sqft · built 1965 · 0.467 acres

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

205 Roosevelt Dr

1.5 ba · 1,152 sqft · built 1965 · 0.616 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,000Jul 2019 $2,3632025 Amount on Record Sep 2007 Owner on Record Assessor + 1 DocumentUpdated Aug 2026

300 Roosevelt Dr

1.5 ba · 1,440 sqft · built 1966 · 0.435 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,2392025 Owner on Record AssessorUpdated Aug 2026

302 Roosevelt Dr

1 ba · 960 sqft · built 1966 · 0.487 acres

Last Sale Tax Bill Prior Sale Owner Records
$60,000Jul 1993 $2,4002025 Owner on Record Assessor + 1 DocumentUpdated Aug 2026

303 Roosevelt Dr

2 ba · 960 sqft · built 1966 · 0.672 acres

Last Sale Tax Bill Prior Sale Owner Records
$175,000Sep 2018 $3,4182025 Amount on Record — 2 Owners on Record Owner Occupied Assessor + 6 DocumentsUpdated Aug 2026

305 Roosevelt Dr

2 ba · 1,200 sqft · built 1966 · 0.605 acres

Last Sale Tax Bill Prior Sale Owner Records
$19,500Oct 2018 $6892025 —Nov 2017 Owner on Record Assessor + 2 DocumentsUpdated Aug 2026

306 Roosevelt Dr

1.5 ba · 1,152 sqft · built 1966 · 0.478 acres

Last Sale Tax Bill Prior Sale Owner Records
$250,000Mar 2024 $3,0782025 Amount on Record Jun 2021 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

307 Roosevelt Dr

1 ba · 1,040 sqft · built 1966 · 0.623 acres

Last Sale Tax Bill Prior Sale Owner Records
$60,000Oct 1997 $2,2422025 Owner on Record Owner Occupied AssessorUpdated Aug 2026

309 Roosevelt Dr

1 ba · 1,512 sqft · built 1966 · 0.552 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,2512025 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

311 Roosevelt Dr

1.5 ba · 1,152 sqft · built 1966 · 0.536 acres

Last Sale Tax Bill Prior Sale Owner Records
$148,000Mar 2020 $2,0822025 Amount on Record Aug 1993 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

312 Roosevelt Dr

1.5 ba · 1,152 sqft · built 1966 · 0.737 acres

Last Sale Tax Bill Prior Sale Owner Records
$136,000Mar 2021 $2,4512025 Amount on Record Mar 2016 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

313 Roosevelt Dr

1.5 ba · 1,152 sqft · built 1966 · 0.537 acres

Last Sale Tax Bill Prior Sale Owner Records
$12,000Aug 2019 $2,5562025 —Oct 2001 Owner on Record Assessor + 2 DocumentsUpdated Aug 2026

314 Roosevelt Dr

1.5 ba · 1,152 sqft · built 1966 · 0.753 acres

Last Sale Tax Bill Prior Sale Owner Records
$23,200Nov 1993 $2,4352025 Owner on Record Owner Occupied AssessorUpdated Aug 2026

315 Roosevelt Dr

2 ba · 1,212 sqft · built 1966 · 0.603 acres

Last Sale Tax Bill Prior Sale Owner Records
$224,900May 2022 $3,3712025 Amount on Record Jan 2022 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

316 Roosevelt Dr

1 ba · 960 sqft · built 1966 · 0.674 acres

Last Sale Tax Bill Prior Sale Owner Records
$280,000Feb 2024 $2,6372025 Amount on Record Sep 2023 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

317 Roosevelt Dr

1.5 ba · 1,152 sqft · built 1966 · 0.434 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 2007 $2,3422025 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

318 Roosevelt Dr

1.5 ba · 1,152 sqft · built 1966 · 0.455 acres

Last Sale Tax Bill Prior Sale Owner Records
$26,000May 1994 Amount on Record Mar 1994 Owner on Record Owner Occupied AssessorUpdated Aug 2026

Property Records in Nearby Streets