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- Any
- $ 100,000
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- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
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121 Properties Available
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
- 1/17 173 Beds 3 Baths 1,964 SqFt$854,000Active
LITTLE HARBOR WAY #20, Chestertown, MD 21620
MLS# MDKE2003934
Listed by Kaitlyn Cole Collins of Benson & Mangold, LLC
Single Family Home, Townhouse
- 1/28 282 Beds 1 Bath 787 SqFt$399,000Active
117 WATER ST N #2A, Chestertown, MD 21620
MLS# MDKE2003742
Listed by John J Burke of Gunther-McClary Real Estate
Condo
- 1/24 241 Bed 1 Bath 652 SqFt$348,000Active
117 N WATER ST N #3B, Chestertown, MD 21620
MLS# MDKE2003722
Listed by John J Burke of Gunther-McClary Real Estate
Condo
- 1/50 503 Beds 4 Baths 4,804 SqFt$3,750,000Price Dropped by $245K
240 ROUND TOP LANDING RD, Chestertown, MD 21620
MLS# MDQA2009012
Listed by Robert D Lacaze of TTR Sotheby's International Realty
Single Family Home
- 1/3 33 Beds 3 Baths 2,400 SqFt$553,500Pending
234 BLAKEFIELD DR, Chestertown, MD 21620
MLS# MDQA2008918
Listed by Chris W Haddaway of Chesapeake Real Estate Associates, LLC
Single Family Home
- 1/32 323 Beds 3 Baths 1,964 SqFt$725,000Active
LANDING LN #37, Chestertown, MD 21620
MLS# MDKE2002800
Listed by Kaitlyn Cole Collins of Benson & Mangold, LLC
Single Family Home
- 1/25 253 Beds 4 Baths 2,315 SqFt$1,449,000Active
LITTLE HARBOR WAY #1, Chestertown, MD 21620
MLS# MDKE2002724
Listed by Kaitlyn Cole Collins of Benson & Mangold, LLC
Single Family Home
- 1/20 204 Beds 4 Baths 2,784 SqFt$949,900Active
LANDING LN #25, Chestertown, MD 21620
MLS# MDKE2002704
Listed by Kaitlyn Cole Collins of Benson & Mangold, LLC
Single Family Home
- 1/77 773 Beds 4 Baths 2,200 SqFt$779,000Active
212 LANDING LN, Chestertown, MD 21620
MLS# MDKE2002650
Listed by Kaitlyn Cole Collins of Benson & Mangold, LLC
Townhouse
- 1/30 303 Beds 4 Baths 2,490 SqFt$995,000Active
230 S WATER ST #1, Chestertown, MD 21620
MLS# MDKE2001598
Listed by John J Burke of Gunther-McClary Real Estate
Townhouse
- 1/24 243 Beds 4 Baths 2,592 Sqft Lot$950,000Active
228 S WATER ST, Chestertown, MD 21620
MLS# MDKE2001612
Listed by John J Burke of Gunther-McClary Real Estate
Townhouse
- 1/27 273 Beds 2 Baths 1,260 SqFt$2,200Coming Soon
Chestertown, MD 21620
MLS# MDKE2004740
Listed by David J. J Moore of RE/MAX Executive
Single Family Home
- 1/15 154 Beds 3 Baths 2,056 SqFt$2,800New
105 FLYING CLOUD DR, Chestertown, MD 21620
MLS# MDKE2004730
Listed by Alicia Gannon Dulin of Benson & Mangold, LLC
Single Family Home
- 1/5 50.99 Acres$49,000Active
22681 WOOD YARD LN, Chestertown, MD 21620
MLS# MDKE2004720
Listed by Maryn J. LeClair of Chesapeake Real Estate Associates, LLC
Vacant Land
- 1/25 252 Beds 2 Baths 1,818 SqFt$1,879Active
224 N KENT ST, Chestertown, MD 21620
MLS# MDKE2004704
Listed by Liddy L Campbell of TTR Sotheby's International Realty
Single Family Home
- 1/5 50.96 Acres$318,500Active
HAACKE DRIVE LOT 3, Chestertown, MD 21620
MLS# MDKE2004648
Listed by Hayley A Norris of Select Land & Homes, LLC
Vacant Land
- 1/7 70.93 Acres$349,999Active
SCHEELER ROAD LOT 2, Chestertown, MD 21620
MLS# MDKE2004650
Listed by William H Norris III of Select Land & Homes, LLC
Vacant Land
- 2.2 Acres$79,900Active
FAIRLEE RD, Chestertown, MD 21620
MLS# MDKE2004652
Listed by William H Norris III of Select Land & Homes, LLC
Vacant Land
- 1/10 102.36 Acres$80,000Active
9020 GEORGETOWN RD, Chestertown, MD 21620
MLS# MDKE2004490
Listed by Jennifer L Mobley of Coldwell Banker Chesapeake Real Estate Company
Vacant Land
- 1/12 122 Beds 1 Bath 624 SqFt$1,400Active
509 CANNON ST, Chestertown, MD 21620
MLS# MDKE2004632
Listed by William Sutton of Coldwell Banker Chesapeake Real Estate Company
Single Family Home
- 1/2 20.09 Acres$5,000Active
TEXAS AVE, Chestertown, MD 21620
MLS# MDKE2004610
Listed by Adam M Shpritz of Ashland Auction Group LLC
Vacant Land
- 1/2 22.85 Acres$9,999Active
831-REAR LOT HIGH ST #REAR LOT, Chestertown, MD 21620
MLS# MDKE2004388
Listed by Daniel R. Lusk of McWilliams/Ballard Inc.
Vacant Land
- 0.35 Acres$29,000Pending
GLENOLA RD, Chestertown, MD 21620
MLS# MDKE2004208
Listed by John J Burke of Gunther-McClary Real Estate
Vacant Land
- 1/3 30.14 Acres$20,000Active
TOLCHESTER BEACH RD, Chestertown, MD 21620
MLS# MDKE2004198
Listed by Maryn J. LeClair of Chesapeake Real Estate Associates, LLC
Vacant Land
- Any
- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
121 Properties Available
- Default
- Baths (Most)
- Beds (Most)
- Newest Listings
- Square Feet (Biggest)
- Price-High To Low
- Price-Low To High
- 1/17 173 Beds 3 Baths 1,964 SqFt$854,000Active
LITTLE HARBOR WAY #20, Chestertown, MD 21620
MLS# MDKE2003934
Listed by Kaitlyn Cole Collins of Benson & Mangold, LLC
Single Family Home, Townhouse
- 1/28 282 Beds 1 Bath 787 SqFt$399,000Active
117 WATER ST N #2A, Chestertown, MD 21620
MLS# MDKE2003742
Listed by John J Burke of Gunther-McClary Real Estate
Condo
- 1/24 241 Bed 1 Bath 652 SqFt$348,000Active
117 N WATER ST N #3B, Chestertown, MD 21620
MLS# MDKE2003722
Listed by John J Burke of Gunther-McClary Real Estate
Condo
- 1/50 503 Beds 4 Baths 4,804 SqFt$3,750,000Price Dropped by $245K
240 ROUND TOP LANDING RD, Chestertown, MD 21620
MLS# MDQA2009012
Listed by Robert D Lacaze of TTR Sotheby's International Realty
Single Family Home
- 1/3 33 Beds 3 Baths 2,400 SqFt$553,500Pending
234 BLAKEFIELD DR, Chestertown, MD 21620
MLS# MDQA2008918
Listed by Chris W Haddaway of Chesapeake Real Estate Associates, LLC
Single Family Home
- 1/32 323 Beds 3 Baths 1,964 SqFt$725,000Active
LANDING LN #37, Chestertown, MD 21620
MLS# MDKE2002800
Listed by Kaitlyn Cole Collins of Benson & Mangold, LLC
Single Family Home
- 1/25 253 Beds 4 Baths 2,315 SqFt$1,449,000Active
LITTLE HARBOR WAY #1, Chestertown, MD 21620
MLS# MDKE2002724
Listed by Kaitlyn Cole Collins of Benson & Mangold, LLC
Single Family Home
- 1/20 204 Beds 4 Baths 2,784 SqFt$949,900Active
LANDING LN #25, Chestertown, MD 21620
MLS# MDKE2002704
Listed by Kaitlyn Cole Collins of Benson & Mangold, LLC
Single Family Home
- 1/77 773 Beds 4 Baths 2,200 SqFt$779,000Active
212 LANDING LN, Chestertown, MD 21620
MLS# MDKE2002650
Listed by Kaitlyn Cole Collins of Benson & Mangold, LLC
Townhouse
- 1/30 303 Beds 4 Baths 2,490 SqFt$995,000Active
230 S WATER ST #1, Chestertown, MD 21620
MLS# MDKE2001598
Listed by John J Burke of Gunther-McClary Real Estate
Townhouse
- 1/24 243 Beds 4 Baths 2,592 Sqft Lot$950,000Active
228 S WATER ST, Chestertown, MD 21620
MLS# MDKE2001612
Listed by John J Burke of Gunther-McClary Real Estate
Townhouse
- 1/27 273 Beds 2 Baths 1,260 SqFt$2,200Coming Soon
Chestertown, MD 21620
MLS# MDKE2004740
Listed by David J. J Moore of RE/MAX Executive
Single Family Home
- 1/15 154 Beds 3 Baths 2,056 SqFt$2,800New
105 FLYING CLOUD DR, Chestertown, MD 21620
MLS# MDKE2004730
Listed by Alicia Gannon Dulin of Benson & Mangold, LLC
Single Family Home
- 1/5 50.99 Acres$49,000Active
22681 WOOD YARD LN, Chestertown, MD 21620
MLS# MDKE2004720
Listed by Maryn J. LeClair of Chesapeake Real Estate Associates, LLC
Vacant Land
- 1/25 252 Beds 2 Baths 1,818 SqFt$1,879Active
224 N KENT ST, Chestertown, MD 21620
MLS# MDKE2004704
Listed by Liddy L Campbell of TTR Sotheby's International Realty
Single Family Home
- 1/5 50.96 Acres$318,500Active
HAACKE DRIVE LOT 3, Chestertown, MD 21620
MLS# MDKE2004648
Listed by Hayley A Norris of Select Land & Homes, LLC
Vacant Land
- 1/7 70.93 Acres$349,999Active
SCHEELER ROAD LOT 2, Chestertown, MD 21620
MLS# MDKE2004650
Listed by William H Norris III of Select Land & Homes, LLC
Vacant Land
- 2.2 Acres$79,900Active
FAIRLEE RD, Chestertown, MD 21620
MLS# MDKE2004652
Listed by William H Norris III of Select Land & Homes, LLC
Vacant Land
- 1/10 102.36 Acres$80,000Active
9020 GEORGETOWN RD, Chestertown, MD 21620
MLS# MDKE2004490
Listed by Jennifer L Mobley of Coldwell Banker Chesapeake Real Estate Company
Vacant Land
- 1/12 122 Beds 1 Bath 624 SqFt$1,400Active
509 CANNON ST, Chestertown, MD 21620
MLS# MDKE2004632
Listed by William Sutton of Coldwell Banker Chesapeake Real Estate Company
Single Family Home
- 1/2 20.09 Acres$5,000Active
TEXAS AVE, Chestertown, MD 21620
MLS# MDKE2004610
Listed by Adam M Shpritz of Ashland Auction Group LLC
Vacant Land
- 1/2 22.85 Acres$9,999Active
831-REAR LOT HIGH ST #REAR LOT, Chestertown, MD 21620
MLS# MDKE2004388
Listed by Daniel R. Lusk of McWilliams/Ballard Inc.
Vacant Land
- 0.35 Acres$29,000Pending
GLENOLA RD, Chestertown, MD 21620
MLS# MDKE2004208
Listed by John J Burke of Gunther-McClary Real Estate
Vacant Land
- 1/3 30.14 Acres$20,000Active
TOLCHESTER BEACH RD, Chestertown, MD 21620
MLS# MDKE2004198
Listed by Maryn J. LeClair of Chesapeake Real Estate Associates, LLC
Vacant Land
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