105 Oak Leaf Dr
Chestertown, MD 21620
3 bd 3 ba 1,959 sqft Built 2004 Lot 2,200 sqft townhomes
Most recent sale
$235,000
Nov 19, 2021
Location
Timeline: Sale, Listing & Tax History
Recorded events
| Date | Event | Price | Source |
|---|---|---|---|
| Nov 19, 2021 | Sold | $235,000 | MLS #MDKE2000546 |
| Sep 30, 2021 | Listed | $229,900 | MLS #MDKE2000546 |
| Dec 31, 2010 | Listing removed | $169,000 | MRIS |
| Aug 27, 2010 | Price changed | $169,000 | MLS #KE7409431 |
| Aug 9, 2010 | Listed | $179,000 | MLS #KE7409431 |
| May 21, 2004 | Sold | $186,500 | Public Record |
Tax assessment history
| Year | Building | Land | Total assessed | Tax paid |
|---|---|---|---|---|
| 2025 | $164,900 | $60,000 | $224,900 | $3,524 |
| 2024 | $164,900 | $60,000 | $224,900 | $3,228 |
| 2022 | $108,300 | $60,000 | $168,300 | $2,620 |
| 2021 | $108,300 | $60,000 | $168,300 | $2,621 |
| 2020 | $108,300 | $60,000 | $168,300 | $2,637 |
| 2019 | $112,700 | $60,000 | $172,700 | $2,701 |
| 2018 | — | — | $167,200 | $2,598 |
| 2017 | — | — | $161,700 | $2,431 |
| 2016 | $96,200 | $60,000 | $156,200 | $2,349 |
| 2015 | $96,200 | $60,000 | $156,200 | $577 |
| 2014 | $96,200 | $60,000 | $156,200 | $2,349 |
| 2013 | $102,500 | $60,000 | $162,500 | $2,444 |
| 2012 | — | — | $162,500 | $2,444 |
| 2011 | — | — | $162,500 | $2,444 |
| 2010 | — | — | $249,040 | $3,621 |
| 2009 | — | — | $229,346 | $3,334 |
| 2008 | — | — | $209,653 | $3,048 |
Property facts
Year built
2004
Property type
townhomes
Stories
3
Beds
3
Baths
3
Living area
1,959 sqft
Lot size
2,200 sqft
ZIP code
21620
City
Chestertown
Street
Oak Leaf Dr
Coordinates
39.22781, -76.06753
Comparable properties nearby
Block-level micro-comps
Same street, ±3 house numbers, sold in the last 24 monthsInvestment analysis
Estimates based on local averages — not personalized adviceEstimated monthly rent
$1,410
Gross rental yield
7.20%
Implied cap rate
4.68%
Trend-extrapolated value
—
Frequently asked questions
When did 105 Oak Leaf Dr last sell?
105 Oak Leaf Dr most recently sold on Nov 19, 2021 for $235,000.
What is the current tax assessment for 105 Oak Leaf Dr?
The most recent total assessment for 105 Oak Leaf Dr (year 2025) is $224,900 with $3,524 in property tax.
How does 105 Oak Leaf Dr's assessment compare to its last sale price?
The current assessment is 4.3% below the last sale price of $235,000.
When was 105 Oak Leaf Dr built?
105 Oak Leaf Dr was built in 2004.
How does 105 Oak Leaf Dr compare to others on Oak Leaf Dr?
We track 8 other properties on Oak Leaf Dr. Browse the list under "Other properties on Oak Leaf Dr" to compare beds, baths, and sale history.
What are the property facts for 105 Oak Leaf Dr?
105 Oak Leaf Dr is a 3 bed, 3 bath, 1,959 sqft, 2,200 sqft lot townhomes.
Is 105 Oak Leaf Dr a flip candidate?
No — 105 Oak Leaf Dr does not appear in our flips dataset.
Is 105 Oak Leaf Dr a tax-appeal candidate?
No — 105 Oak Leaf Dr is not currently flagged as a tax-appeal candidate.
Forecast for this area
ZIP-area linear projection — not a per-property automated valuationQuarterly trend
+1.5%
Implied 1-yr
+6.1%
2026 Q3
$413.1K
2026 Q4
$418.9K
ZIP 21620 — Median Price History + Forecast
Explore nearby
Geography
Other properties on Oak Leaf Dr