425 High St
ChestertownMD21620
Cheap Apartments for Rent in Chestertown, MD from $500 (14 Rentals)
Search the lowest-cost Apartments available for rent right now in Chestertown.
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from $7701 Bedroom Apartments Available Now
Center Park Apartments
38 Center ParkCentreville, MD 21617
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from $875Studio to 2 Bedroom Apartments Available Now
Hartland Village Apartments
1103 Country Terrace RdEssex, MD 21221
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from $940Studio to 2 Bedroom Apartments Available Now
The Greens Apartments and Townhomes
1207 Middleborough RdEssex, MD 21221
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from $9461 to 2 Bedroom Apartments Available Now
Essex Park Apartments and Townhomes
1572 Alconbury RdEssex, MD 21221
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from $9491 to 2 Bedroom Apartments Available Now
Brookside Station Apartments
1618 Swallow Crest DrEdgewood, MD 21040
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from $1,0201 to 2 Bedroom Apartments Available Now
The Village at Slippery Hill Senior Apartments
320 Fallen Horse CirQueenstown, MD 21658
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from $1,1151 to 2 Bedroom Apartments Available Now
Seneca Bay Apartment Homes
3736 White Pine RdMiddle River, MD 21220
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from $1,1351 to 2 Bedroom Apartments Available Now
Merion Village, 62+ Living
904 Edgewood RdEdgewood, MD 21040
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Showing Results 1-14, Page 1 of 1
Chestertown, MD Local Guide
High Street in w:Chestertown, Maryland by Jennifer Schmidt is licensed under Internal
How much does it cost to rent an apartment in Chestertown?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Chestertown Studio Apartments | $1,147 | $875 | $1,760 |
| Chestertown 1 Bedroom Apartments | $1,546 | $770 | $2,199 |
| Chestertown 2 Bedroom Apartments | $1,835 | $1,039 | $2,805 |
| Chestertown 3 Bedroom Apartments | $2,023 | $1,285 | $3,150 |
| Chestertown 4 Bedroom Apartments | $2,137 | $1,899 | $2,225 |
Browse Top Apartments in Chestertown
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Chestertown, MD Local Guide
- Chestertown Neighborhoods
- Nearby Cities
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Cheapest Neighborhoods for Apartments in Chestertown, MD
Pricing Updated: 03/26/2025Current apartment rentals in the Chestertown, MD area range in price from to with an overall median price of . Here is today’s list neighborhoods with the lowest median pricing for Chestertown Apartments for rent:
| Neighborhood | Median Price | Min Price | Available Units |
|---|---|---|---|
| Coventry Farms | $1,900 | $1,000 | 135 |
Cheapest Available Chestertown Apartments for Rent and Nearby
The cheapest available apartment rental in Chestertown, MD is a 1 Bed unit found at Center Park Apartments in the North Brook neighborhood priced from $770. The Village at Slippery Hill II has the second lowest priced unit, which is a 3 Beds apartment currently listed from $799. Here is today’s list of the most affordable Chestertown apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Center Park Apartments | 1 Bed, 1 bath | 1BR,1BA | $770 |
| The Village at Slippery Hill II | C2 - Three Bedroom Townhome | 3BR,2BA | $799 |
| Hartland Village Apartments | Studio | Studio,1BA | $875 |
| The Greens Apartments and Townhomes | Studio | Studio,1BA | $940 |
| The Village at Slippery Hill Senior Apartments | A5 - One Bedroom | 1BR,1BA | $1,020 |
Best Value Apartments for Rent in Chestertown, MD and Nearby
As of March 26, 2025 the best value apartment in the Chestertown area is the $1.39 price per square foot Patriot Village - Freedom Model at Aberdeen Proving Ground on Post Housing in the in the Greenway Farm neighborhood starting from $1,995. The second greatest value Chestertown apartment is the C2 - Three Bedroom Townhome Model at The Village at Slippery Hill II starting at $799 with a $0.60 price per square foot . Here is today’s list of the best values for Chestertown apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| Aberdeen Proving Ground on Post Housing | Patriot Village - Freedom | 3BR,2.5BA | $1.39 |
| The Village at Slippery Hill II | C2 - Three Bedroom Townhome | 3BR,2.5BA | $0.60 |
| Harborside Village Apartments | 2 bedroom, 2 baths (D1, D2, G1, G2) | 2BR,2BA | $1.42 |
| Holly Circle Townhouses | 3 Bedroom 1 Bath Townhouses Ready to Lease! | 3BR,1BA | $1.38 |
| Winston's Choice Family Townhomes | UNIT B | 3BR,2BA | $1.15 |
| Perkins Place | The Garrett | 2BR,1BA | $1.58 |
| The Willows at Cecilton | 2 BEDROOM | 2BR,1BA | $1.10 |
| Brookside Station Apartments | 2 Bedroom 1 Bath | 2BR,1BA | $1.04 |
| Seven Oaks Townhomes | 2 Bedrooms 1.5 Bath | 2BR,1.5BA | $1.42 |
| Essex Park Apartments and Townhomes | Two Bedroom Townhome | 2BR,1BA | $1.45 |
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Walk Score®
47 / 100
Car-Dependent
Most errands require a car
Bike Score®
55 / 100
Bikeable
Some bike infrastructure
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
Frequently Asked Questions about Cheap Chestertown Apartments
What is the Cheapest Studio apartment in Chestertown?
Currently the most affordable Cheap Studio Apartment in Chestertown is at Hartland Village Apartments listed at $875.
How much is rent for a Cheap One Bedroom Chestertown Apartment?
The lowest price for a Cheap One Bedroom Chestertown Apartment is $770 at Center Park Apartments.
What is the lowest price for a Cheap Two Bedroom Chestertown Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Chestertown is starting from $1,039 at Essex Park Apartments and Townhomes.
What is the most affordable Chestertown Three Bedroom Apartment?
The best deal on a cheap Chestertown Three Bedroom Apartment rental is at The Village at Slippery Hill II and starts from $799.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.
Understanding Amenity Fees: Know Where You Might Be Able to Save Money
Written by: Amber Kanuckel
With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.
Renting Smart: Lease Basics Every Renter Needs
Written by: Christine Leonard, Esq.
Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.
Battling the Butts: Your Guide to the Reality of Smoke-Free Renting
Written by: Andrea Lee Negroni, JD
While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.
How Your Move-In Inspection Can Protect Your Security Deposit
Written by: Christine Leonard, Esq.
If you’re anything like most people, housing costs represent a huge chunk of your monthly budget. On top of that, moving can be both a stressful and expensive affair.