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Kent Crossing Apartments
101 Morgnec RdChestertown, MD 21620
1 Bedroom Apartments for Rent in Chestertown, MD (38 Rentals)
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The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
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from $1,2531 Bedroom Apartments Contact Us For Availability
Verona at Middle River
2 Driftwood CtEssex, MD 21221
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from $1,3331 Bedroom Apartments Contact Us For Availability
Seven Oaks Townhomes
802 Kingston CtEdgewood, MD 21040
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from $1,5751 Bedroom Apartments Available Jul 27
ReNew Belcamp
1300 Liriope CtBelcamp, MD 21017
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from $1,0901 Bedroom Apartments Available Now
Seneca Bay Apartment Homes
3736 White Pine RdMiddle River, MD 21220
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from $9401 Bedroom Apartments Available Now
The Greens Apartments and Townhomes
1207 Middleborough RdEssex, MD 21221
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from $9381 Bedroom Apartments Available Jul 26
Hyde Park Apartments
1114 Tace DrEssex, MD 21221
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from $1,0381 Bedroom Apartments Available Now
Kings Mill Apartments and Townhomes
1460 Hadwick DrEssex, MD 21221
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from $8691 Bedroom Apartments Available Now
Hartland Village Apartments
1103 Country Terrace RdEssex, MD 21221
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.
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from $1,3001 Bedroom Apartments Available Aug 18
Beacon Pointe Apartments and Townhomes
7700 Dory LnSparrows Point, MD 21219
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Harborside Village Apartments
610 Towne Center DrJoppa, MD 21085
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from $1,2001 Bedroom Apartments Contact Us For Availability
Hopkins Point by OneWall
37 Alberge LnMiddle River, MD 21220
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Arbors Greenleigh
11550 Crossroads CirBaltimore, MD 21220
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from $1,3771 Bedroom Apartments Available Now
Fox Run Apartments
1600 Ashby Square DrEdgewood, MD 21040
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from $1,2491 Bedroom Apartments Available Now
Annhurst
4600 Annhurst DrBelcamp, MD 21017
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Essex Park Apartments and Townhomes
1572 Alconbury RdEssex, MD 21221
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from $1,3141 Bedroom Apartments Available Now
Perryman Station Senior Apartments, 62+
1222 Perryman RdAberdeen, MD 21001
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
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1 Bedroom Apartments
The Village at Slippery Hill Senior Apartments
320 Fallen Horse CirQueenstown, MD 21658
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Showing Results 1-38, 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 | $1,310 | $869 | $1,699 |
| Chestertown 1 Bedroom Apartments | $1,588 | $946 | $2,282 |
| Chestertown 2 Bedroom Apartments | $1,753 | $1,039 | $4,300 |
| Chestertown 3 Bedroom Apartments | $1,974 | $1,285 | $2,850 |
| Chestertown 4 Bedroom Apartments | $2,095 | $1,929 | $2,245 |
Browse Top Apartments in Chestertown
See all Apartments in ChestertownExplore Chestertown
Chestertown, MD Local Guide
- Chestertown Neighborhoods
- Nearby Cities
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- Local Counties
Largest Available Chestertown and Nearby 1 Bedroom Apartments
The largest available 1 Bedroom apartment unit in Chestertown, MD is found at Riverside in the Holly Woods - Woodfield/Wyngate neighborhood and is 1,098 square feet priced from $1,843. The Berkleigh in the Miramar Landing - Gibson/Taylor neighborhood has the second largest 1 Bedroom, which is sized at 925 square feet and currently listed start at $2,199. Here is today’s list of the largest available 1 Bedroom units in Chestertown:
| Apartment Listing | Model Name | Square Footage | Priced From |
|---|---|---|---|
| Riverside | 1 Bedroom - C (RS2) | 1,098 Sq Ft | $1,843 |
| The Berkleigh | 1 Bed/1 Bath Den-A4-D-Long Point | 925 Sq Ft | $2,199 |
| Arbors Greenleigh | 1 Bed/1 Bath Den-A6-Parkton | 892 Sq Ft | $1,955 |
| Fox Run Apartments | 1 Bedroom 1 Bath Den | 813 Sq Ft | $1,423 |
| Woodsdale Apartments | 1 Bedroom 1 Bath with Den | 770 Sq Ft | $1,295 |
| The Village at Slippery Hill II | A1 - One Bedroom Apartment | 723 Sq Ft | $585 |
| Hartland Village Apartments | One bedroom + den | 704 Sq Ft | $1,113 |
| The Greens Apartments and Townhomes | 1 Bedroom with den | 704 Sq Ft | $1,148 |
| Stansbury Manor | 1 Bedroom Deluxe | 700 Sq Ft | $1,489 |
| Seneca Bay Apartment Homes | One Bedroom - 629 sqft | 460 Sq Ft | $1,215 |
Cheapest Available Chestertown and Nearby 1 Bedroom Apartments
As of June 20, 2025 the lowest priced 1 Bedroom apartment unit in Chestertown, MD is the A1 - One Bedroom Apartment Model starting from $585 at The Village at Slippery Hill II . The second most affordable Chestertown 1 Bedroom is the One bedroom Model at Hartland Village Apartments starting at $986 in the Hopewell Point neighborhood. The average price for all 1 Bedroom apartments in Chestertown is currently $1,588. Here is today’s list of the cheapest available 1 Bedroom options in Chestertown:
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| The Village at Slippery Hill II | A1 - One Bedroom Apartment | $585 |
| Hartland Village Apartments | One bedroom | $986 |
| The Greens Apartments and Townhomes | 1 Bedroom | $1,020 |
| Kings Mill Apartments and Townhomes | One bedroom Apartment | $1,038 |
| Seneca Bay Apartment Homes | One Bedroom | $1,090 |
| Harford Commons | 1 Bedroom | $1,279 |
| Woodsdale Apartments | 1 Bedrooms 1 Bath | $1,295 |
| Annhurst | One Bedroom One Bath | $1,310 |
| Perryman Station Senior Apartments, 62+ | 1 bedroom | $1,314 |
| The Waldon | Myrtle | $1,345 |
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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 1 Bedroom Chestertown Apartments
What is the Cheapest apartment in Chestertown with 1 Bedroom?
Currently the most affordable 1 Bedroom in Chestertown is at The Village at Slippery Hill II listed at $585.
How much is the average rent for a 1 Bedroom Chestertown Apartment?
The average rent for a 1 Bedroom Apartment in Chestertown is $1,588.
What is the largest available 1 Bedroom Chestertown Apartment for rent?
Today's apartment with the most square footage in Chestertown is a 1,098 square feet unit starting from $1,843 at Riverside.
What is the average size for Chestertown 1 Bedroom Apartments for rent?
The average size for a 1 Bedroom rental in Chestertown is currently 738 sq ft.
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.
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.
The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.
Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.
The Freedom of Short-Term Leases: Exploring the Advantages for Renters
Written by: Bobbi Jackson
If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.