Chestertown, MD Apartments For Rent
615 rentals
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Use arrow keys to navigateSPECIAL OFFERPET FRIENDLY$2,175 - $3,033/mo
3-5 Beds
2-3 BathsPeace River Landing Rental Homes | 24055 Peaceful Brook Loop,
Punta Gorda, FL 33980
Use arrow keys to navigateNEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLY$1,356 - $1,998/moStudio-3 Beds1-2 BathsCharlotte Commons | 24150 Beatrix Blvd,
Pt Charlotte, FL 33954
Use arrow keys to navigateSPECIAL OFFERPET FRIENDLY$1,352 - $1,735/mo1-3 Beds1-2 BathsSwiftwater Apartments | 16325 Franklin Ave,
Pt Charlotte, FL 33953
Use arrow keys to navigateSPECIAL OFFERPET FRIENDLY$1,195 - $1,699/moStudio-1 Bed1 BathSage Grove on Aaron Apartments | 2305 Aaron St,
Pt Charlotte, FL 33952
SPECIAL OFFERPET FRIENDLYTotal price$1,381 - $1,943/mo1-3 Beds1-2 BathsLakes of Tuscana | 24001 Madaca Ln,
Pt Charlotte, FL 33954
NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLY$1,264 - $2,135/moStudio-3 Beds1-2 BathsSprings At Port Charlotte | 24151 Beatrix Blvd,
Pt Charlotte, FL 33954
SPECIAL OFFERPET FRIENDLY
SENIOR HOUSING
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What Locals Say about Chestertown
Average Rent Trends in Chestertown, MD
Rent in Chestertown, MD varies by number of bedrooms and home type. Use these charts to quickly see how rent changes.
Average rent decreased in Aug 2026 compared to the previous month. Rent previously peaked in Sep 2025.
| Month | Average rent |
|---|---|
| Sep 2025 | $2,400 |
| Oct 2025 | $2,100 |
| Nov 2025 | $2,100 |
| Dec 2025 | $2,000 |
| Jan 2026 | $1,575 |
| Feb 2026 | $1,900 |
| Mar 2026 | $2,000 |
| Apr 2026 | $2,000 |
| May 2026 | $1,520 |
| Jun 2026 | $2,050 |
| Jul 2026 | $2,000 |
| Aug 2026 | $1,920 |
Average Rent By Bedroom and Home Type
In August 2026, Apartments and Condos were the most affordable home type to rent compared with Townhomes and Houses.
| 1 bed | 2 beds | 3 beds | 4 beds | All | |
|---|---|---|---|---|---|
| All home types | $1,400 | $1,920 | $1,900 | $2,556 | $1,920 |
| Townhomes | — | — | $2,000 | — | $2,000 |
| Apartments and Condos | $1,400 | $1,820 | — | — | $1,350 |
| Houses | — | $2,400 | $1,900 | $2,556 | $2,000 |
Frequently Asked Questions about Rentals in Chestertown, MD
- What is the average rent of an apartment in Chestertown, MD?The average rent of an apartment in Chestertown, MD is $1,842 per month. This is about 6% lower than the national average.
- When is the average rent cheapest in Chestertown, MD?In the last year, the average rent in Chestertown, MD was lowest in Jan 2025 when it was $1,400 per month.
- When is the average rent most expensive in Chestertown, MD?In the last year, the average rent in Chestertown, MD was highest in Sep 2025 when it was $2,400 per month.
- How does the rent of a 1 bedroom apartment compare to a studio apartment in Chestertown, MD?The average rent of a 1 bedroom apartment in Chestertown, MD is $1,400 per month. That is about $425 more than the cost of a studio apartment.
- How many available rental listings are in Chestertown, MD?There are 7 available rental listings in Chestertown, MD.
- What are some zip codes in Chestertown, MD?
- What are some cities near Chestertown, MD?Some nearby cities include: Worton, Still Pond, Rock Hall, Church Hill, Kennedyville. These cities may have more rental options to explore.
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