140 Properties Available
- Price-High To Low
- Newest Listings
- Default
- Price-Low To High
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
- Coming Soon
$275,000
3 Beds3 Baths14,986 SqFt110 TUXEDO RD, Chestertown, MD 21620
Single Family Home
MLS# MDQA2014816
Listed by Cummings & Co. Realtors
- 1/20 20Price Dropped by $15K
$265,000
3 Beds2 Baths3,000 SqFt112 METCALF RD, Chestertown, MD 21620
Single Family Home, Townhouse
MLS# MDKE2005498
Listed by Engel & Volkers Annapolis
- 1/17 17New
$255,000
3 Beds2 Baths5,914 SqFt100 METCALF RD, Chestertown, MD 21620
Townhouse
MLS# MDKE2005634
Listed by Bayside Realty
- 1/7 7Active
$250,000
0.93 AcresSCHEELER ROAD LOT 2, Chestertown, MD 21620
Vacant Land
MLS# MDKE2004650
Listed by Select Land & Homes, LLC
- 1/3 3Active
$240,000
2 Beds1 Bath2,990 SqFt624 HIGH ST, Chestertown, MD 21620
Single Family Home
MLS# MDKE2005274
Listed by Tesla Realty Group, LLC
- 1/5 5Active
$225,000
0.96 AcresHAACKE DRIVE LOT 3, Chestertown, MD 21620
Vacant Land
MLS# MDKE2004648
Listed by Select Land & Homes, LLC
- 1/20 20Under Contract
$220,000
3 Beds3 Baths3,015 SqFt300 HILLTOP LN, Chestertown, MD 21620
Townhouse
MLS# MDKE2005004
Listed by Coldwell Banker Chesapeake Real Estate Company
- 1/31 31Under Contract
$209,900
3 Beds3 Baths2,028 SqFt304 HILLTOP LN, Chestertown, MD 21620
Townhouse
MLS# MDKE2005440
Listed by Doug Ashley Realtors, LLC
- 1/31 31Under Contract
$195,000
2 Beds1 Bath1,269 SqFt21317 PERSIMMON DR, Chestertown, MD 21620
Townhouse
MLS# MDKE2005356
Listed by Doug Ashley Realtors, LLC
- 1/20 20Price Dropped by $27K
$185,000
1.95 AcresLOT 9 PRESTWICK DR, Chestertown, MD 21620
Vacant Land
MLS# MDKE2003918
Listed by Gunther-McClary Real Estate
- 1/25 25New
$179,000
2 Beds1 Bath2,120 SqFt21316 PERSIMMON DR, Chestertown, MD 21620
Townhouse
MLS# MDKE2005624
Listed by Doug Ashley Realtors, LLC
- 1/3 3Price Dropped by $10K
$174,900
2 Beds1 Bath1,296 SqFt234 N COLLEGE AVE, Chestertown, MD 21620
Single Family Home
MLS# MDKE2005434
Listed by Cummings & Co Realtors
- 1/16 16Price Dropped by $8K
$167,000
4 Beds2 Baths7,800 SqFt141 PROSPECT ST, Chestertown, MD 21620
Single Family Home
MLS# MDKE2005504
Listed by Cross Street Realtors LLC
- 1/12 12Active
$165,000
5.34 AcresCHURCH HILL ( LOT 2) RD, Chestertown, MD 21620
Vacant Land
MLS# MDQA2014030
Listed by Coldwell Banker Chesapeake Real Estate Company
- 1/8 8Active
$150,000
2 AcresCAULKS FIELD ROAD, Chestertown, MD 21620
Vacant Land
MLS# MDKE2005120
Listed by RE/MAX Allegiance
- 1/2 2Active
$150,000
2 AcresGEORGETOWN RD SE, Chestertown, MD 21620
Vacant Land
MLS# MDKE2005076
Listed by RE/MAX Allegiance
- 1/5 5Under Contract
$149,900
10.05 AcresHOFFECKER RD, Chestertown, MD 21620
Vacant Land
MLS# MDQA2013914
Listed by Gunther-McClary Real Estate
- 1/7 7Active
$125,000
3 Beds1 Bath87,120 SqFt5700 JOHNSONTOWN RD, Chestertown, MD 21620
Single Family Home
MLS# MDKE2005562
Listed by Tesla Realty Group, LLC
- Active
$120,000
1.8 AcresGEORGETOWN RD & CROSS ROAD, Chestertown, MD 21620
Vacant Land
MLS# MDKE2005074
Listed by Coldwell Banker Chesapeake Real Estate Company
- 1/14 14Pending
$114,000
1 Bed1 Bath22,000 SqFt236 MERGANSER DR, Chestertown, MD 21620
Single Family Home
MLS# MDQA2013084
Listed by Thurston Wyatt Real Estate, LLC
- 1/11 11Active
$103,000
0.48 AcresEAST ST, Chestertown, MD 21620
Vacant Land
MLS# MDQA2013494
Listed by Coldwell Banker Chesapeake Real Estate Company
- New
$89,900
1.49 AcresMCGINNES RD, Chestertown, MD 21620
Vacant Land
MLS# MDQA2014764
Listed by Select Land & Homes, LLC
- 1/7 7Active
$75,000
2.2 AcresFAIRLEE RD, Chestertown, MD 21620
Vacant Land
MLS# MDKE2005204
Listed by EXIT Preferred Realty
- 1/9 9Price Dropped by $5K
$65,000
3 AcresGEORGETOWN RD, Chestertown, MD 21620
Vacant Land
MLS# MDKE2005218
Listed by Doug Ashley Realtors, LLC

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A for-sale-by-owner (FSBO) transaction requires time, know-how and confidence. If you’re not sure that you have all three, enlisting the services of an agent — a professional who knows the ins and outs of listing and selling homes successfully — pays off. * Agents Avoid Emotional Sales
• Agents Weed Out Unqualified Buyers
• Agents Negotiate Price
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