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Chestertown
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APARTMENTS
Rent Trends for Apartments in Chestertown
September 2025
| Bedroom count | Chestertown | vs Last Month |
|---|---|---|
| Studio | $1,350 | — |
| 1 Bedroom | $2,200 | — |
| 2 Bedroom | $2,000 |  down 17.53% |
Median rent as of September 7, 2025
This September, we've analyzed our 2 listings in Chestertown to determine the rent trend. We're updating our tables in real time to give you the most up to date Chestertown median apartment rent prices by bedroom count.
Cities Near Chestertown
Apartment Types in Chestertown
Find Your Dream Apartment for Rent in Chestertown
PadMapper has 2 condos, houses, and apartments for rent in Chestertown. Specifically, studio apartments, one-bedroom apartments, 1 two-bedroom apartments, three-bedroom apartments are currently available for rent.
We have options to filter by price, bedroom count, bathroom count, long-term or short-term, housing type, pet friendly, no broker fee, and you can search for an apartment by custom keywords.
Chestertown MD Apartments for Rent
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$3,200
4 Bedrooms · 2 Bathrooms Apartment · Chestertown, MD
2 Days Ago
Brices Mill Rd #0000 is a 4 bedroom, 2 bathrooms apartment for rent. It is located in Chestertown. It has apartment amenities including garage parking, and on-site management. View apartment
$2,500
2 Bedrooms · 1 Bathroom Apartment · Chestertown, MD
5+ Days Ago
202 High St #A is a 2 bedroom, 1 bathroom apartment for rent. It is located in Chestertown. View apartment
New Construction
$2,000
3 Bedrooms · 2 Bathrooms Apartment · Rock Hall, MD
1 Day Ago
5810 Clam Cv is a 3 bedroom, 2 bathrooms apartment for rent. It is located in Rock Hall. It has apartment amenities including on-site laundry. View apartment
$2,600
3 Bedrooms · 2 Bathrooms Apartment · Queenstown, MD
5+ Days Ago
249 Thompson Ave is a 3 bedroom, 2 bathrooms apartment for rent. It is located in Queenstown. It has apartment amenities including garage parking, and outdoor space. Cats and dogs are allowed, making it a pet-friendly apartment. View apartment
$2,400
3 Bedrooms · 2 Bathrooms Apartment · Greensboro, MD
5+ Days Ago
104 Roe St is a 3 bedroom, 2 bathrooms apartment for rent. It is located in Greensboro. It has apartment amenities including outdoor space. View apartment
Online tours
$2,700
2 Bedrooms · 2 Bathrooms Apartment · Chester, MD
5+ Days Ago
54 Queen Caroline Ct is a 2 bedroom, 2 bathrooms apartment for rent. It is located in Chester. It has apartment amenities including outdoor space, swimming pool, and fitness center. View apartment
$3,000
2 Bedrooms · 1 Bathroom Apartment · Stevensville, MD
5+ Days Ago
2620 Love Point Rd is a 2 bedroom, 1 bathroom apartment for rent. It is located in Stevensville. View apartment
$3,500
4 Bedrooms · 3 Bathrooms Apartment · Stevensville, MD
5+ Days Ago
247 Jessica Lyn Ave is a 4 bedroom, 3 bathrooms apartment for rent. It is located in Stevensville. It has apartment amenities including garage parking, swimming pool, and on-site laundry. Cats and dogs are allowed, making it a pet-friendly apartment. View apartment
$600
Studio Apartment · Chester, MD
5+ Days Ago
1712 Main St is a studio, 0 bathrooms apartment for rent. It is located in Chester. View apartment
$5,500
Studio Apartment · Stevensville, MD
5+ Days Ago
102 Saint Claire Pl is a studio, 0 bathrooms apartment for rent. It is located in Stevensville. It has apartment amenities including elevator. View apartment
$1,400
Studio Apartment · Stevensville, MD
5+ Days Ago
203 Romancoke Rd is a studio, 0 bathrooms apartment for rent. It is located in Stevensville. It has apartment amenities including business center. View apartment
Online tours
$2,000
3 Bedrooms · 2 Bathrooms Apartment · Edgewood, Edgewood
4 Hours Ago
703 Cedar Crest Ct is a 3 bedroom, 2 bathrooms apartment for rent. It is located in the Edgewood neighborhood of Edgewood. It has apartment amenities including outdoor space. Cats and dogs are allowed, making it a pet-friendly apartment. View apartment
$1,900
3 Bedrooms · 2 Bathrooms Apartment · Edgewood, Edgewood
13 Hours Ago
1212 Valley Leaf Ct is a 3 bedroom, 2 bathrooms apartment for rent. It is located in the Edgewood neighborhood of Edgewood. It has apartment amenities including on-site laundry, and outdoor space. View apartment
$3,600
6 Bedrooms · 4 Bathrooms Apartment · Stevensville, MD
18 Hours Ago
247 Breeding Blvd is a 6 bedroom, 4 bathrooms apartment for rent. It is located in Stevensville. It has apartment amenities including fitness center, and swimming pool. View apartment
$2,600
3 Bedrooms · 2 Bathrooms Apartment · Middle River, Middle River
1 Day Ago
6 Creek Side Ct is a 3 bedroom, 2 bathrooms apartment for rent. It is located in the Middle River neighborhood of Middle River. It has apartment amenities including garage parking, and on-site laundry. View apartment
$2,400
4 Bedrooms · 2 Bathrooms Apartment · Joppatowne, Joppatowne
2 Days Ago
300 Oakway Ct #NA is a 4 bedroom, 2 bathrooms apartment for rent. It is located in the Joppatowne neighborhood of Joppatowne. It has apartment amenities including outdoor space. View apartment
$2,400
3 Bedrooms · 2 Bathrooms Apartment · Bowleys Quarters, Bowleys Quarters
4 Days Ago
645 Nollmeyer Rd #645 is a 3 bedroom, 2 bathrooms apartment for rent. It is located in the Bowleys Quarters neighborhood of Bowleys Quarters. Cats and dogs are allowed, making it a pet-friendly apartment. View apartment
$3,300
3 Bedrooms · 2 Bathrooms Apartment · Essex, Essex
4 Days Ago
2209 Monocacy Rd is a 3 bedroom, 2 bathrooms apartment for rent. It is located in the Essex neighborhood of Essex. It has apartment amenities including outdoor space. View apartment
$2,600
4 Bedrooms · 2 Bathrooms Apartment · Joppatowne, Joppatowne
5+ Days Ago
301 Stillmeadow Dr is a 4 bedroom, 2 bathrooms apartment for rent. It is located in the Joppatowne neighborhood of Joppatowne. It has apartment amenities including garage parking, outdoor space, and on-site laundry. View apartment
$2,895
4 Bedrooms · 2 Bathrooms Apartment · Edgewood, Edgewood
5+ Days Ago
2605 Maidens Ln is a 4 bedroom, 2 bathrooms apartment for rent. It is located in the Edgewood neighborhood of Edgewood. It has apartment amenities including outdoor space, and garage parking. View apartment
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