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All Active Listings Near
Chestertown, Maryland in Kent County 
Postal Code: 21620
 Ⓧ USDA 50  Listed by Robert Lacaze at TTR Sotheby's International Realty. Latest property estimate: $725,800 | |
| $3,995,000 240 Round Top Landing Rd | |
 Ⓧ USDA 68 Listed by Robert Davis at Davis Real Estate, Inc. | |
| $1,765,000 22900 Handy Point Road Handy Point Rd | |
Listed by Nancy Mcguire at Maryland Heritage Properties. Latest property estimate: $1,618,500 | |
| $1,725,000 201 N Water St | |
 Ⓧ USDA 82 Listed by Retha Arrabal at Doug Ashley Realtors, LLC. Latest property estimate: $1,469,000 | |
| $1,460,000 22956 Fairgale Farm Ln | |
 Ⓧ USDA 25 ♡ Listed by Kaitlyn Collins at Benson & Mangold Real Estate | |
| $1,449,000 Little Harbor Way Unit 1 | *New Construction* |
 Ⓧ USDA 63 Listed by William Norris at Select Land & Homes, Llc | |
| $1,349,000 9545 Chantilly Farm Ln | |
 Ⓧ USDA 64 Listed by William Norris at Select Land & Homes, Llc | |
| $1,349,000 9545 Chantilly Farm Ln | |
 Ⓧ USDA 22 Listed by Lynn Hilfiker at Gunther-Mcclary Real Estate. Latest property estimate: $273,000 | |
| $1,200,000 9220 N Bayview Ave | *New Listing* |
 Ⓧ USDA 33 Listed by Richard Budden at Coldwell Banker Chesapeake Real Estate. Latest property estimate: $1,141,500 | |
| $1,200,000 331 Park Ln | |
 Ⓧ USDA 12 ♡ Listed by John Burke at Gunther-McClary Real Estate | |
| $995,000 230 S Water St Unit 1 | *New Construction* |
 Ⓧ USDA 14 ♡ Listed by John Burke at Gunther-McClary Real Estate. Latest property estimate: $540,500 | |
| $995,000 226 S Water St | *New Construction* |
 Ⓧ USDA 65 Listed by Lisa Raffetto at Coldwell Banker Chesapeake Real Estate. Latest property estimate: $724,100 | |
| $975,000 7755 Waterview Ln | *New Listing* |
 Ⓧ USDA 11 ♡ Listed by John Burke at Gunther-McClary Real Estate. Latest property estimate: $902,800 | |
| $950,000 228 S Water St | *New Construction* |
 Ⓧ USDA 16 ♡ Listed by Kaitlyn Collins at Benson & Mangold Real Estate | |
| $949,900 Landing Ln Unit 25 | *New Construction* |
 Ⓧ USDA 28 Listed by John Burke at Gunther-McClary Real Estate. Latest property estimate: $422,700 | |
| $848,000 8049 Quaker Neck Rd | |
 Ⓧ USDA 36 ♡ Listed by Kaitlyn Collins at Benson & Mangold Real Estate | |
| $815,000 Landing Ln Unit 12 | *New Construction* |
 Ⓧ USDA 37 ♡ Listed by Kaitlyn Collins at Benson & Mangold Real Estate | |
| $805,000 Landing Ln Unit 11 | *New Construction* |
 👍 USDA Loan 32 Listed by Kaitlyn Collins at Benson & Mangold Real Estate | |
| $725,000 Landing Ln Unit 37 | *New Construction* |
 👍 USDA Loan 41 ♡ Listed by Richard Keaveney at Cross Street Realtors LLC | |
| $695,000 106 Water St N Unit 1/2 | |
 👍 USDA Loan 7 Listed by Lisa Raffetto at Coldwell Banker Chesapeake Real Estate | |
| $650,000 128 N Queen St | *New Listing* |
 👍 USDA Loan 80 ♡ Listed by Thomas Boeshore at Berkshire Hathaway Homeservice Homesale Realty. Latest property estimate: $622,000 | |
| $625,000 118 Westwood Ln | |
 👍 USDA Loan 3 Listed by Chris Haddaway at Chesapeake Real Estate Associates, Llc | |
| $553,500 234 Blakefield Dr | *New Construction* |
 👍 USDA Loan 5 ♡ Listed by Liddy Campbell at TTR Sotheby's International Realty. Latest property estimate: $539,500 | |
| $550,000 193 Westwood Ln | |
Listed by Kenneth Roderick at Chesapeake Real Estate Associates, LLC. Latest property estimate: $524,900 | |
| $529,000 8757 Orchard Dr | |
Listed by Maryn Leclair at Chesapeake Real Estate Associates, LLC | |
| $519,900 Truslow Farm Ln Lot 4 | |
Listed by Maryn Leclair at Chesapeake Real Estate Associates, LLC | |
| $519,900 Truslow Farm Ln Lot 2 | |
Listed by Kenneth Roderick at Chesapeake Real Estate Associates, LLC. Latest property estimate: $439,700 | |
| $499,000 207 Pondview Ct | |
 👍 USDA Loan 34 ♡ Listed by Jennifer Thomas at RE MAX Executive. Latest property estimate: $269,800 | |
| $499,000 9816 Fairlee Rd | |
Listed by Robert Kaetzel at Real Estate Professionals, Inc.. Latest property estimate: $343,500 | |
| $475,000 116 Harlan Loop | |
 👍 USDA Loan 73 ♡ Listed by Lona Todd at Taylor Properties. Latest property estimate: $432,100 | |
| $429,000 134 Char nor Manor Blvd | |
 👍 USDA Loan 47 Listed by Cheryl Hurt at Coldwell Banker Chesapeake Real Estate | |
| $425,000 349 and 351 High St | *New Listing* |
Listed by Maryn Leclair at Chesapeake Real Estate Associates, LLC | |
| $425,000 210 Truslow Farm Ln | |
 👍 USDA Loan 4 Listed by Chris Haddaway at Chesapeake Real Estate Associates, Llc | |
| $422,000 231 Blakefield Dr | *New Construction* |
 👍 USDA Loan 13 Listed by Richard Evans at Cross Street Realtors LLC | |
| $419,900 481 Pear Tree Point Rd | *New Construction* |
 👍 USDA Loan 25 Listed by John Burke at Gunther-McClary Real Estate | |
| $415,000 117 Water St N Unit 2A | |
 👍 USDA Loan 43 ♡ Listed by Peter Heller at Coldwell Banker Chesapeake Real Estate. Latest property estimate: $400,600 | |
| $415,000 105 Sutton Way | |
Listed by Kenneth Roderick at Chesapeake Real Estate Associates, LLC. Latest property estimate: $368,000 | |
| $409,000 109 Coleman Dr | |
 👍 USDA Loan 24 ♡ Listed by John Burke at Gunther-McClary Real Estate | |
| $405,000 117 Water St N Unit 2B | |
Listed by Liddy Campbell at TTR Sotheby's International Realty. Latest property estimate: $392,600 | |
| $399,000 313 River Rd | |
 👍 USDA Loan 23 ♡ Listed by John Burke at Gunther-McClary Real Estate | |
| $395,000 117 N Water St Apt 3A | |
Listed by Sandy Collins at Berkshire Hathaway HomeServices Homesale Realty - Centerville. Latest property estimate: $301,000 | |
| $395,000 116 Riverside Ter Unit 7 | |
 👍 USDA Loan 41 Listed by Douglas Ashley at Doug Ashley Realtors, LLC. Latest property estimate: $326,300 | |
| $385,000 214 Richard Dr | *New Listing* |
 👍 USDA Loan 23 Listed by John Burke at Gunther-McClary Real Estate | |
| $385,000 117 N Water St Apt 3B | |
 👍 USDA Loan 30 ♡ Listed by Michael Oneill at Coldwell Banker Chesapeake Real Estate. Latest property estimate: $171,800 | |
| $385,000 529 Cannon St | |
 👍 USDA Loan 28 ♡ Listed by Joelle Dolch at Cross Street Realtors LLC. Latest property estimate: $409,600 | |
| $380,000 209 Myers Rd | |
 👍 USDA Loan 20 ♡ Listed by Elizabeth Green at Cross Street Realtors LLC. Latest property estimate: $342,100 | |
| $350,000 5772 Johnsontown Rd | |
 👍 USDA Loan 27 ♡ Listed by Lisa Raffetto at Coldwell Banker Chesapeake Real Estate. Latest property estimate: $339,300 | |
| $339,000 21357 Belair Ave | |
 👍 USDA Loan 37 Listed by Brenda Fornos at Taylor Properties. Latest property estimate: $377,100 | |
| $335,500 9062 Fairlee Rd | |
 👍 USDA Loan 28 ♡ Listed by Thomas Boeshore at Berkshire Hathaway Homeservice Homesale Realty. Latest property estimate: $305,700 | |
| $329,000 310 Longfellow Dr | |
 👍 USDA Loan 21 Listed by Mary Fielding at Coldwell Banker Chesapeake Real Estate. Latest property estimate: $316,800 | |
| $325,000 112 Pine Chip Rd | |
Listed by David J. Moore at RE MAX Executive. Latest property estimate: $286,000 | |
| $299,900 10605 Tonopah Rd | |
 👍 USDA Loan 32 ♡ Listed by Deric Beckett at Berkshire Hathaway HomeServices PenFed Realty. Latest property estimate: $303,400 | |
| $299,900 103 Trafford Dr | |
 👍 USDA Loan 48 ♡ Listed by Peter Heller at Coldwell Banker Chesapeake Real Estate. Latest property estimate: $285,000 | |
| $297,000 9020 Cumberland St | |
 👍 USDA Loan 24 Listed by John Carroll at Village Real Estate Company Llc. Latest property estimate: $179,800 | |
| $289,000 235 Burchard Sawmill Rd | *New Listing* |
 👍 USDA Loan 22 ♡ Listed by Jody Baker at Cross Street Realtors LLC. Latest property estimate: $276,500 | |
| $285,000 870 Washington Ave | |
 👍 USDA Loan 29 Listed by James Blackwell at Blackwell Real Estate. Latest property estimate: $292,200 | |
| $284,900 332 Truslow Rd | |
 👍 USDA Loan 17 ♡ Listed by Kaitlyn Collins at Benson & Mangold Real Estate. Latest property estimate: $283,700 | |
| $265,000 305 Pine Tree Rd | |
 👍 USDA Loan 33 ♡ Listed by Lisa Raffetto at Coldwell Banker Chesapeake Real Estate. Latest property estimate: $256,900 | |
| $259,000 23315 Sandpiper Rd | |
Listed by Maryn Leclair at Chesapeake Real Estate Associates, LLC | |
| $249,000 510 Truslow Rd | |
 👍 USDA Loan 28 Listed by Lisa Raffetto at Coldwell Banker Chesapeake Real Estate. Latest property estimate: $242,800 | |
| $242,000 124 Edmore Rd | *New Listing* |
 👍 USDA Loan 23 ♡ Listed by Jordan Larigan at Berkshire Hathaway HomeServices Homesale Realty - Canton. Latest property estimate: $187,000 | |
| $234,900 104 Conley Dr | |
 👍 USDA Loan 17 Listed by Roger Boyce at Chesapeake Real Estate Associates, Llc. Latest property estimate: $150,300 | |
| $158,000 21345 Persimmon Dr | *New Listing* |
 👍 USDA Loan 5 ♡ Listed by Michael Oneill at Coldwell Banker Chesapeake Real Estate | |
| $149,000 24581 Willow Oak Ln | |
 👍 USDA Loan 4 ♡ Listed by Lisa Raffetto at Coldwell Banker Chesapeake Real Estate | |
| $148,500 Muirfield Dr | |
 👍 USDA Loan 8 ♡ Listed by Joseph Ciganek at Coldwell Banker Chesapeake Real Estate | |
| $139,000 Annie Crow Rd | |
 👍 USDA Loan 6 ♡ Listed by Alexandra Burrell-hodges at Cottage Street Realty LLC | |
| $100,000 Gateway Dr | |
 👍 USDA Loan 1 ♡ Listed by William Norris at Select Land & Homes, Llc | |
| $92,500 Fairlee Rd | |
 👍 USDA Loan 2 ♡ Listed by Theresa Michel at Long & Foster Frederick | |
| $75,000 Caulks Field Rd | |
 👍 USDA Loan 7 Listed by Julia Hilfiker at Gunther-McClary Real Estate. Latest property estimate: $141,200 | |
| $70,000 23060 Old Fairlee Rd | *New Listing* |
 👍 USDA Loan 2 Listed by William Norris at Select Land & Homes, Llc | |
| $68,500 113 Pine Cove Ln | *New Listing* |
 👍 USDA Loan 1 ♡ Listed by Theresa Michel at Long & Foster Frederick | |
| $60,000 Georgetown Rd SE | |
 👍 USDA Loan 3 Listed by Andrew Meikle at Doug Ashley Realtors, LLC | |
| $55,000 Map 36 Watertower Rd Parcel 80 | |
 👍 USDA Loan 2 ♡ Listed by Beverly Sloane at Benson & Mangold Real Estate | |
| $50,000 9048 Georgetown Rd | |
 👍 USDA Loan 13 Listed by Kristina Hyland at Coldwell Banker Chesapeake Real Estate | |
| $47,500 Georgetown Rd | |
 👍 USDA Loan 5 ♡ Listed by Christopher Mcclary at Gunther-McClary Real Estate | |
| $45,000 23628 Canvasback Rd | |
 👍 USDA Loan 19 ♡ Listed by Lisa Raffetto at Coldwell Banker Chesapeake Real Estate | |
| $41,500 Elm Rd | |
 👍 USDA Loan 1 ♡ Listed by Vaughn Hogans at The Hogans Agency | |
| $40,000 Elm Rd | |
 👍 USDA Loan 2 ♡ Listed by Vaughn Hogans at The Hogans Agency | |
| $40,000 Montgomery Ave | |
 👍 USDA Loan 2 ♡ Listed by Deanna Miller at Long & Foster Severna Park | |
| $38,000 Redfield Rd | |
 👍 USDA Loan 2 ♡ Listed by Deanna Miller at Long & Foster Severna Park | |
| $38,000 Spinnaker Rd | |
 👍 USDA Loan 2 ♡ Listed by Deanna Miller at Long & Foster Severna Park | |
| $37,000 Fish Hatchery Rd | |
 👍 USDA Loan 7 ♡ Listed by Vincent Raimond at Doug Ashley Realtors, LLC | |
| $30,000 Caulks Field Rd | |
 👍 USDA Loan 1 ♡ Listed by Samantha Powell at Keller Williams Real Estate - Media | |
| $30,000 147 Char nor Manor Blvd | |
 👍 USDA Loan 1 ♡ Listed by Jo Edwards at The Hogans Agency | |
| $30,000 Melitota Ln | |
 👍 USDA Loan 2 ♡ Listed by Deanna Miller at Long & Foster Severna Park | |
| $28,000 Caulks Field Rd | |
 👍 USDA Loan 3 ♡ Listed by Willie Johnson at Keller Williams Flagship of Maryland | |
| $25,000 23690 L Rd | |
 👍 USDA Loan 3 ♡ Listed by Brian Morris at The Land Group | |
| $25,000 23683 L Rd | |
 👍 USDA Loan 2 ♡ Listed by Deanna Miller at Long & Foster Severna Park | |
| $24,000 23710 L Rd | |
 👍 USDA Loan 1 ♡ Listed by Deanna Miller at Long & Foster Severna Park. Latest property estimate: $76,200 | |
| $23,000 23693 L Rd | |
 👍 USDA Loan 4 Listed by Maryn Leclair at Chesapeake Real Estate Associates, LLC | |
| $22,000 Millbrook Dr | |
 👍 USDA Loan 3 ♡ Listed by Cheryl Hurt at Coldwell Banker Chesapeake Real Estate | |
| $20,000 Elm Rd | |
 👍 USDA Loan 3 Listed by Adam Shpritz at Ashland Auction Group Llc | |
| $15,000 Neck Ldg Rd Parcel Buck | *New Listing* |
 👍 USDA Loan 2 Listed by Adam Shpritz at Ashland Auction Group Llc | |
| $15,000 Sandpiper Rd | *New Listing* |
 👍 USDA Loan 2 ♡ Listed by Peter Heller at Coldwell Banker Chesapeake Real Estate | |
| $15,000 Sheldrake Dr | |
 👍 USDA Loan 2 Listed by Hayley Norris at Select Land & Homes, Llc | |
| $12,500 Buck Neck Rd | *New Listing* |
 👍 USDA Loan 3 ♡ Listed by Debra Meikle at Doug Ashley Realtors, LLC | |
| $12,000 Carimon Rd Lot 253-254 | |
 👍 USDA Loan 6 Listed by Jody Baker at Cross Street Realtors LLC | |
| $9,500 Kinglet Rd | *New Listing* |
 👍 USDA Loan 6 ♡ Listed by Andrew Meikle at Doug Ashley Realtors, LLC | |
| $8,000 Buck Neck Rd Lots 24 & 25 | |
 👍 USDA Loan 1 ♡ Listed by Jo Edwards at The Hogans Agency | |
| $4,000 Clarissa Lots 233 & 234 | |
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