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Chestertown Home Report
Average Home
Average Price
$508,009
Avg Bedrooms
2.37 beds
Avg Bathrooms
1.86 baths
Average Price By Bedrooms
1 bedroom
$200,000
2 bedrooms
$281,499
3 bedrooms
$500,764
4 bedrooms
$637,823
5 bedrooms
$927,175
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84+ Homes for Sale in Chestertown
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4
$349,000
126 Char Nor Manor Blvd, Chestertown, MD 21620
*Please join us for our Open Houses Friday, April 24th from 5pm-7pm and Saturday, April 25th from 10...
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3
Beds
2
Baths
1,304
SqFt
Listing Provided By: RE/MAX Executive
20
$265,000
21217 Texas Ave, Chestertown, MD 21620
MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Applianc...
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2
Beds
1
Baths
912
SqFt
Listing Provided By: RE/MAX Leading Edge
1
$296,000
115 Acorn Dr, Chestertown, MD 21620
Welcome to 115 Acorn Drive in the desirable Oak Hollow community of Chestertown, Maryland—an end-uni...
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2
Beds
3
Baths
1,864
SqFt
Listing Provided By: Chesapeake Real Estate Associates
32
$898,000
226 S Water St, Chestertown, MD 21620
Newly constructed three-bedroom townhome with fantastic water views from the living level and bedroo...
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3
Beds
4
Baths
2,172
SqFt
Listing Provided By: Gunther-Mcclary Real Estate
11
$867,000
25475 Turnberry Ct, Chestertown, MD 21620
Coming Soon! Exceptional custom-built 2018 one-level home on 2.28 private acres in the highly sought...
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4
Beds
3
Baths
4,145
SqFt
Listing Provided By: Taylor Properties
53
$550,000
103 Sutton Way, Chestertown, MD 21620
103 Sutton is perfectly situated just a stone’s throw from the vibrant heart of Downtown Chestertown...
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4
Beds
4
Baths
3,816
SqFt
Listing Provided By: Ttr Sotheby's International Realty
42
$369,999
720 Deep Landing Rd, Chestertown, MD 21620
Welcome to Pine Cove. A small peaceful enclave of homes that sits oh so close to the Chester River a...
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3
Beds
2
Baths
1,271
SqFt
Listing Provided By: Coldwell Banker Waterman Realty
37
$295,000
107 Longfellow Dr, Chestertown, MD 21620
There is so much potential for this 3 bedroom, 1 bath ranch, in need of a little updating, with atta...
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3
Beds
1
Baths
n/a
SqFt
Listing Provided By: Doug Ashley Realtors
63
$695,000
10087 John Carvill Rd, Chestertown, MD 21620
Toad Hall, as the current owners affectionately call it, is located in a natural wooded setting on F...
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3
Beds
2
Baths
1,566
SqFt
Listing Provided By: Coldwell Banker Chesapeake Real Estate Company
25
$325,000
217 Philosophers Ter, Chestertown, MD 21620
Charming and full of potential, this 3-bedroom, 1.5-bath Cape Cod home offers a prime in-town Cheste...
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3
Beds
2
Baths
1,404
SqFt
Listing Provided By: Ttr Sotheby's International Realty
20
$319,900
10584 Klamath Rd, Chestertown, MD 21620
View Full Details
2
Beds
2
Baths
n/a
SqFt
Listing Provided By: Real Broker
1
$115,000
108 Pine St, Chestertown, MD 21620
FULL RENOVATION PROJECT - Prime Chestertown Location Priced for Immediate Equity Creation. This 3-be...
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3
Beds
1
Baths
910
SqFt
Listing Provided By: Real Broker
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