Oak Leaf Dr, Chestertown, MD Property Records

Kent County property records for 13 addresses on Oak Leaf Dr, Chestertown, MD · Last verified August 2026

Oak Leaf Dr Highlights

Properties 13
Median Sale Price $283,000
Deeds and Mortgages on File 16
Median Price per Sqft $151
Owner Occupied 85%
Median Annual Tax Bill $3,143
Median Year Built 2004
Median Ownership Tenure 5 years

Properties on Oak Leaf Dr

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

100 Oak Leaf Dr

2.5 ba · 1,865 sqft · 0.088 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$290,000Oct 2005 $3,3092025 Amount on Record Dec 2003 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

101 Oak Leaf Dr

2.5 ba · 1,906 sqft · 0.089 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$160,000Jun 2014 $3,4612025 Amount on Record Apr 2004 2 Names on Record AssessorUpdated Aug 2026

102 Oak Leaf Dr

2.5 ba · 1,876 sqft · 0.049 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$254,000Jun 2005 $3,1362025 Amount on Record May 2004 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

103 Oak Leaf Dr

2.5 ba · 1,840 sqft · 0.05 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$204,555Apr 2004 $3,0322025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

104 Oak Leaf Dr

2.5 ba · 1,840 sqft · 0.049 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$283,000Feb 2025 $3,0322025 Amount on Record Jul 2023 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

105 Oak Leaf Dr

2.5 ba · 1,959 sqft · 0.05 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$235,000Nov 2021 $3,5242025 Amount on Record May 2004 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

106 Oak Leaf Dr

2.5 ba · 2,041 sqft · 0.084 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$239,900Jul 2021 $3,6212025 Amount on Record May 2004 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

107 Oak Leaf Dr

2.5 ba · 1,947 sqft · 0.085 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$295,000Apr 2026 $3,5212025 Amount on Record Oct 2021 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

108 Oak Leaf Dr

2.5 ba · 1,867 sqft · 0.084 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$296,500Jun 2026 $3,1262025 Amount on Record Mar 2004 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

110 Oak Leaf Dr

3.5 ba · 1,959 sqft · 0.049 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$190,000Jun 2020 $2,8632025 Amount on Record Jun 2016 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

112 Oak Leaf Dr

2.5 ba · 1,840 sqft · 0.049 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$174,990Feb 2004 $2,9102025 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

114 Oak Leaf Dr

2.5 ba · 1,879 sqft · 0.049 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$250,000Aug 2022 $3,7642025 Amount on Record Aug 2018 2 Names on Record Assessor + 3 DocumentsUpdated Aug 2026

116 Oak Leaf Dr

2.5 ba · 1,867 sqft · 0.096 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$289,500May 2025 $3,1432025 Amount on Record Feb 2004 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

Wildfire Risk on Oak Leaf Dr

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

Wildfire RiskNot rated
no burnable land in reach
Wildfire LikelihoodNegligible
ExposureNone
beyond ember reach

Property Records in Nearby Streets