Chestertown, MD Investor Insights

Real estate investment activity and market trends in Chestertown, MD, Maryland

482 active investors · 191 acquisitions (last 12 mo)

Data as of May 2026 · Updated monthly

Active Investors482ilast 12 mo
Avg Acquisition$548Kilast 12 mo
Rental Yield5.9%ifrom geo_stats
Acquisitions191ilast 12 mo
Value-Add+81%ipurchase vs value

Most Active Zip Codes in Chestertown, MD

Zip codes with the most investor activity in Chestertown, MD

Zip CodeInvestorsAvg PriceYield
21620482$548K5.9%

Recently Active Investors in Chestertown, MD

Investors with purchases in the last 6 months

#iInvestoriPortfolioiPortfolio ValueiLast PurchaseiLast Addressi
1PECKHAM MATERIALS CORPiLong termi13i$2.1Mi2024-12-12i31 Grandview Rd, Chestertowni
2RED TRUCK INVESTMENTS LLCiLong termi12i$1.0Mi2024-12-15i872 Washington Ave, Chestertowni
3KENT CENTER INCiLong termi11i$1.3Mi2022-09-22i1002 Twin Ct, Chestertowni
4PSR HOLDINGS FOUR LLCiLong termi8i$4.5Mi2023-02-22i79 Dixon Rd, Chestertowni
5CHESTERTOWN AFFILIATED PROPERTIES LLCiLong termi4i$662Ki2024-08-27i21 Pine St, Chestertowni

Investor Value Add

✓ Live Data

Avg Purchase

$548K

i

Avg Value

$993K

i
+81%ivalue appreciation

in Chestertown, MD

Average Rents

✓ Live Data
1 Bedroom$1,720i
2 Bedroom$2,164i
3 Bedroom$2,630i

in Chestertown, MD

Top Recent Sales in Chestertown, MD

Transactions by active real estate investors

423 Calvert St, Chestertown

i

$125K

i
HEALM LLCiLong termi· 2026-03-02i

206 Valley Rd, Chestertown

i

$590K

i
DC PROPERTY GROUP LLCiLong termi· 2026-01-12i

517 High St, Chestertown

i

$362K

i
BLUFF VIEW PROPERTIES LLCiLong termi· 2025-12-19i

23393 Cacaway Farm Ln, Chestertown

i

$1.1M

i
CACAWAY FARM COOPERATIVE HOUSING CORPORATIONiLong termi· 2025-12-10i

131 Flatland Rd, Chestertown

i

$925K

i
VIMI PROPERTIES LLCiLong termi· 2025-05-13i

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