CHESTERTOWN, MD - Most Valuable Residential Properties in 2025
Updated on November 25, 2025.
According to data from official Maryland government agencies, among residential properties in CHESTERTOWN, MD, the following were the most valuable residential properties by Appraised Full Value in 2025. The most valuable residential property was 240 ROUND TOP LANDING RD ($1.81M), followed by 400 RIVER RD ($1.76M), 430 TRUSLOW RD ($1.67M), and 208 RIVER RD ($1.58M).
The chart below shows the top 10 valuable residential properties, and the table below shows the top 200.
You can see similar information for other Maryland cities.
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Data Source: Official Government Sites.
CHESTERTOWN, MD - Most Valuable Residential Properties in 2025
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| Address | Appraised Full Value ($) |
|---|---|
| 240 ROUND TOP LANDING RD, CHESTERTOWN, MD 21620 | 1809300 |
| 400 RIVER RD, CHESTERTOWN, MD 21620 | 1754500 |
| 430 TRUSLOW RD, CHESTERTOWN, MD 21620 | 1666500 |
| 208 RIVER RD, CHESTERTOWN, MD 21620 | 1579300 |
| 116 HOFFMAN LN, CHESTERTOWN, MD 21620 | 1523900 |
| 111 RIVERVIEW POINT LN, CHESTERTOWN, MD 21620 | 1438000 |
| 407 FEY RD, CHESTERTOWN, MD 21620 | 1424800 |
| 1201 TRUSLOW RD, CHESTERTOWN, MD 21620 | 1257500 |
| 140 SUMMERFIELD LN, CHESTERTOWN, MD 21620 | 1229000 |
| 416 PEAR TREE POINT RD, CHESTERTOWN, MD 21620 | 1223800 |
| 516 PEAR TREE POINT RD, CHESTERTOWN, MD 21620 | 1202500 |
| 200 TRUSLOW RUN, CHESTERTOWN, MD 21620 | 1183500 |
| 1001 ROLPHS WHARF RD, CHESTERTOWN, MD 21620 | 1106500 |
| 351 PARK LN, CHESTERTOWN, MD 21620 | 1088100 |
| 414 RIVER RD, CHESTERTOWN, MD 21620 | 1076400 |
| 410 RIVER RD, CHESTERTOWN, MD 21620 | 1057900 |
| 201 GRASSLANDS DR, CHESTERTOWN, MD 21620 | 1046700 |
| 417 FEY RD, CHESTERTOWN, MD 21620 | 1046200 |
| 300 RIVER RD, CHESTERTOWN, MD 21620 | 997300 |
| 421 FEY RD, CHESTERTOWN, MD 21620 | 987100 |
| 101 CHESTER VW, CHESTERTOWN, MD 21620 | 981400 |
| 120 RIVER RD, CHESTERTOWN, MD 21620 | 962000 |
| 201 RIVERVIEW RD, CHESTERTOWN, MD 21620 | 948400 |
| 205 FEY RD, CHESTERTOWN, MD 21620 | 932700 |
| 232 RIVER RD, CHESTERTOWN, MD 21620 | 923000 |
| 244 RIVER RD, CHESTERTOWN, MD 21620 | 922200 |
| 330 RIVER RD, CHESTERTOWN, MD 21620 | 919500 |
| 116 HICKORY LN, CHESTERTOWN, MD 21620 | 917400 |
| 305 FEY RD, CHESTERTOWN, MD 21620 | 912900 |
| 413 FEY RD, CHESTERTOWN, MD 21620 | 912200 |
| 238 RIVER RD, CHESTERTOWN, MD 21620 | 906200 |
| 216 RIVER RD, CHESTERTOWN, MD 21620 | 899700 |
| 228 RIVER RD, CHESTERTOWN, MD 21620 | 886800 |
| 336 RIVER RD, CHESTERTOWN, MD 21620 | 884400 |
| 306 RIVER RD, CHESTERTOWN, MD 21620 | 867500 |
| 557 FEY RD, CHESTERTOWN, MD 21620 | 844900 |
| 408 PEAR TREE POINT RD, CHESTERTOWN, MD 21620 | 843000 |
| 424 PEAR TREE POINT RD, CHESTERTOWN, MD 21620 | 838000 |
| 200 TRUSLOW FARM LN, CHESTERTOWN, MD 21620 | 827100 |
| 545 FEY RD, CHESTERTOWN, MD 21620 | 815800 |
| 509 FEY RD, CHESTERTOWN, MD 21620 | 811700 |
| 205 GREEN HERON WAY, CHESTERTOWN, MD 21620 | 805800 |
| 108 RIVERVIEW RD, CHESTERTOWN, MD 21620 | 803700 |
| 115 BASS TRACK CT, CHESTERTOWN, MD 21620 | 803100 |
| 118 GOOSE ROOST LN, CHESTERTOWN, MD 21620 | 803000 |
| 117 HOFFMAN LN, CHESTERTOWN, MD 21620 | 791100 |
| 498 PEAR TREE POINT RD, CHESTERTOWN, MD 21620 | 788300 |
| 200 RIVER RD, CHESTERTOWN, MD 21620 | 784200 |
| 510 PEAR TREE POINT RD, CHESTERTOWN, MD 21620 | 775200 |
| 549 FEY RD, CHESTERTOWN, MD 21620 | 775200 |
| 128 BASS TRACK CT, CHESTERTOWN, MD 21620 | 768800 |
| 240 RIVER RD, CHESTERTOWN, MD 21620 | 767100 |
| 432 PEAR TREE POINT RD, CHESTERTOWN, MD 21620 | 762000 |
| 154 ROYSTON SHORES RD, CHESTERTOWN, MD 21620 | 757000 |
| 331 PARK LN, CHESTERTOWN, MD 21620 | 749800 |
| 209 LARSON LN, CHESTERTOWN, MD 21620 | 743700 |
| 216 ROYSTON SHORES RD, CHESTERTOWN, MD 21620 | 739800 |
| 472 PEAR TREE POINT RD, CHESTERTOWN, MD 21620 | 730700 |
| 234 ROYSTON SHORES RD, CHESTERTOWN, MD 21620 | 725800 |
| 108 ROYSTON SHORES RD, CHESTERTOWN, MD 21620 | 725700 |
| 115 ROYSTON SHORES CT, CHESTERTOWN, MD 21620 | 716700 |
| 209 RIVERVIEW RD, CHESTERTOWN, MD 21620 | 710100 |
| 104 RIVERVIEW PL, CHESTERTOWN, MD 21620 | 706200 |
| 492 PEAR TREE POINT RD, CHESTERTOWN, MD 21620 | 699600 |
| 2810 MCGINNES RD, CHESTERTOWN, MD 21620 | 699000 |
| 112 GOOSE ROOST LN, CHESTERTOWN, MD 21620 | 687400 |
| 208 ROYSTON SHORES RD, CHESTERTOWN, MD 21620 | 687400 |
| 529 FEY RD, CHESTERTOWN, MD 21620 | 684500 |
| 471 ROLPHS WHARF RD, CHESTERTOWN, MD 21620 | 683900 |
| 204 TRUSLOW FARM LN, CHESTERTOWN, MD 21620 | 683000 |
| 456 PEAR TREE POINT RD, CHESTERTOWN, MD 21620 | 680300 |
| 112 RIVERVIEW RD, CHESTERTOWN, MD 21620 | 668400 |
| 730 ROSIN DR, CHESTERTOWN, MD 21620 | 658000 |
| 144 ROYSTON SHORES RD, CHESTERTOWN, MD 21620 | 651800 |
| 214 RIVERVIEW RD, CHESTERTOWN, MD 21620 | 650100 |
| 104 CHURCH MEADOW CT, CHESTERTOWN, MD 21620 | 649200 |
| 116 BASS TRACK CT, CHESTERTOWN, MD 21620 | 648000 |
| 226 ROYSTON SHORES RD, CHESTERTOWN, MD 21620 | 647600 |
| 302 UNION CHURCH RD, CHESTERTOWN, MD 21620 | 647400 |
| 440 PEAR TREE POINT RD, CHESTERTOWN, MD 21620 | 643200 |
| 202 ROYSTON SHORES RD, CHESTERTOWN, MD 21620 | 637500 |
| 118 CHESTER VW, CHESTERTOWN, MD 21620 | 612200 |
| 150 ROYSTON SHORES RD, CHESTERTOWN, MD 21620 | 609100 |
| 133 CHAR NOR MANOR BLVD, CHESTERTOWN, MD 21620 | 606400 |
| 306 HICKORY LN, CHESTERTOWN, MD 21620 | 604500 |
| 120 BASS TRACK CT, CHESTERTOWN, MD 21620 | 602900 |
| 436 PEAR TREE POINT RD, CHESTERTOWN, MD 21620 | 594500 |
| 106 GOOSE ROOST LN, CHESTERTOWN, MD 21620 | 592700 |
| 114 CHESTER VW, CHESTERTOWN, MD 21620 | 591600 |
| 121 LYONS LN, CHESTERTOWN, MD 21620 | 589000 |
| 103 BASS TRACK CT, CHESTERTOWN, MD 21620 | 586100 |
| 143 CHAR NOR MANOR BLVD, CHESTERTOWN, MD 21620 | 576800 |
| 309 ANTHONY RD, CHESTERTOWN, MD 21620 | 576300 |
| 220 ROYSTON SHORES RD, CHESTERTOWN, MD 21620 | 571600 |
| 116 ROYSTON SHORES RD, CHESTERTOWN, MD 21620 | 571100 |
| 127 BASS TRACK CT, CHESTERTOWN, MD 21620 | 561600 |
| 329 TRUSLOW RD, CHESTERTOWN, MD 21620 | 555400 |
| 236 UNION CHURCH RD, CHESTERTOWN, MD 21620 | 555200 |
| 109 GANDER WAY, CHESTERTOWN, MD 21620 | 549700 |
| 207 FEY RD, CHESTERTOWN, MD 21620 | 546000 |
| 105 HOFFMAN LN, CHESTERTOWN, MD 21620 | 545600 |
| 121 BASS TRACK CT, CHESTERTOWN, MD 21620 | 540100 |
| 102 BASS TRACK CT, CHESTERTOWN, MD 21620 | 539100 |
| 132 ROYSTON SHORES RD, CHESTERTOWN, MD 21620 | 535400 |
| 108 HILLTOP DR, CHESTERTOWN, MD 21620 | 532400 |
| 103 GOOSE ROOST LN, CHESTERTOWN, MD 21620 | 532300 |
| 317 UNION CHURCH RD, CHESTERTOWN, MD 21620 | 526700 |
| 413 MERGANSER DR, CHESTERTOWN, MD 21620 | 525000 |
| 108 GARLAND AVE, CHESTERTOWN, MD 21620 | 524700 |
| 305 HICKORY LN, CHESTERTOWN, MD 21620 | 522100 |
| 124 ROYSTON SHORES RD, CHESTERTOWN, MD 21620 | 518300 |
| 210 TRUSLOW FARM LN, CHESTERTOWN, MD 21620 | 517300 |
| 217 FEY RD, CHESTERTOWN, MD 21620 | 513100 |
| 318 RIVER RD, CHESTERTOWN, MD 21620 | 512400 |
| 212 ROYSTON SHORES RD, CHESTERTOWN, MD 21620 | 511900 |
| 309 UNION CHURCH RD, CHESTERTOWN, MD 21620 | 510000 |
| 101 HOFFMAN LN, CHESTERTOWN, MD 21620 | 504200 |
| 230 ROYSTON SHORES RD, CHESTERTOWN, MD 21620 | 500000 |
| 321 UNION CHURCH RD, CHESTERTOWN, MD 21620 | 498500 |
| 227 HOFFECKER RD, CHESTERTOWN, MD 21620 | 498200 |
| 1530 MCGINNES RD, CHESTERTOWN, MD 21620 | 497600 |
| 200 RIVERVIEW RD, CHESTERTOWN, MD 21620 | 495700 |
| 302 ROSIN DR, CHESTERTOWN, MD 21620 | 494400 |
| 428 PEAR TREE POINT RD, CHESTERTOWN, MD 21620 | 493900 |
| 220 MARCUS LN, CHESTERTOWN, MD 21620 | 493500 |
| 448 PEAR TREE POINT RD, CHESTERTOWN, MD 21620 | 492200 |
| 345 BURCHARD SAWMILL RD, CHESTERTOWN, MD 21620 | 485000 |
| 124 BASS TRACK CT, CHESTERTOWN, MD 21620 | 482700 |
| 211 FEY RD, CHESTERTOWN, MD 21620 | 480400 |
| 131 HOFFECKER RD, CHESTERTOWN, MD 21620 | 475100 |
| 148 CHURCH MEADOW CT, CHESTERTOWN, MD 21620 | 469200 |
| 156 CHURCH MEADOW CT, CHESTERTOWN, MD 21620 | 468600 |
| 110 NENTEGO ACRES, CHESTERTOWN, MD 21620 | 467300 |
| 115 CHAR NOR MANOR BLVD, CHESTERTOWN, MD 21620 | 466100 |
| 464 PEAR TREE POINT RD, CHESTERTOWN, MD 21620 | 465900 |
| 468 PEAR TREE POINT RD, CHESTERTOWN, MD 21620 | 465100 |
| 313 UNION CHURCH RD, CHESTERTOWN, MD 21620 | 459900 |
| 126 PINE TREE RD, CHESTERTOWN, MD 21620 | 453600 |
| 112 PRIMROSE RD, CHESTERTOWN, MD 21620 | 452700 |
| 405 RIVER RD, CHESTERTOWN, MD 21620 | 451200 |
| 133 CHURCH MEADOW CT, CHESTERTOWN, MD 21620 | 447400 |
| 112 SHEAFFER RD, CHESTERTOWN, MD 21620 | 447100 |
| 234 BLAKEFIELD DR, CHESTERTOWN, MD 21620 | 446700 |
| 220 PINE TREE RD, CHESTERTOWN, MD 21620 | 444800 |
| 141 CHAR NOR MANOR BLVD, CHESTERTOWN, MD 21620 | 444600 |
| 603 DEEP LANDING RD, CHESTERTOWN, MD 21620 | 441900 |
| 109 RIVER RD, CHESTERTOWN, MD 21620 | 441400 |
| 109 MYERS RD, CHESTERTOWN, MD 21620 | 440600 |
| 5645 CHURCH HILL RD, CHESTERTOWN, MD 21620 | 440600 |
| 226 BLAKEFIELD DR, CHESTERTOWN, MD 21620 | 440100 |
| 204 DOUBLE CREEK RD, CHESTERTOWN, MD 21620 | 439100 |
| 106 RYAN CT, CHESTERTOWN, MD 21620 | 438900 |
| 1432 MCGINNES RD, CHESTERTOWN, MD 21620 | 438800 |
| 227 FLYWAY LN, CHESTERTOWN, MD 21620 | 437200 |
| 734 ROSIN DR, CHESTERTOWN, MD 21620 | 435000 |
| 100 PRINCESS ANNE DR, CHESTERTOWN, MD 21620 | 434300 |
| 115 PINTAIL RD, CHESTERTOWN, MD 21620 | 433800 |
| 316 SCHRADER RD, CHESTERTOWN, MD 21620 | 433400 |
| 310 NENTEGO ACRES, CHESTERTOWN, MD 21620 | 432700 |
| 136 GARLAND AVE, CHESTERTOWN, MD 21620 | 431400 |
| 257 BLAKEFIELD DR, CHESTERTOWN, MD 21620 | 431200 |
| 109 SHEAFFER RD, CHESTERTOWN, MD 21620 | 429300 |
| 139 CHURCH MEADOW CT, CHESTERTOWN, MD 21620 | 429200 |
| 209 FLYWAY LN, CHESTERTOWN, MD 21620 | 429100 |
| 600 HOFFECKER RD, CHESTERTOWN, MD 21620 | 428300 |
| 310 ROSIN DR, CHESTERTOWN, MD 21620 | 427700 |
| 120 PINE TREE RD, CHESTERTOWN, MD 21620 | 425500 |
| 107 CHAR NOR MANOR BLVD, CHESTERTOWN, MD 21620 | 424800 |
| 1200 EWINGTOWN RD, CHESTERTOWN, MD 21620 | 424800 |
| 126 HILLTOP DR, CHESTERTOWN, MD 21620 | 424000 |
| 242 UNION CHURCH RD, CHESTERTOWN, MD 21620 | 423400 |
| 112 CHURCH MEADOW CT, CHESTERTOWN, MD 21620 | 422100 |
| 117 KLINEFELLAR LN, CHESTERTOWN, MD 21620 | 421400 |
| 128 ROUND TOP VIEW RD, CHESTERTOWN, MD 21620 | 418500 |
| 1710 PONDTOWN RD, CHESTERTOWN, MD 21620 | 418500 |
| 105 HOLLY CT, CHESTERTOWN, MD 21620 | 416400 |
| 120 FEY RD, CHESTERTOWN, MD 21620 | 416100 |
| 329 UNION CHURCH RD, CHESTERTOWN, MD 21620 | 415900 |
| 108 LAUREL CT, CHESTERTOWN, MD 21620 | 414700 |
| 314 ROSIN DR, CHESTERTOWN, MD 21620 | 414700 |
| 105 LAUREL CT, CHESTERTOWN, MD 21620 | 412100 |
| 120 RIVERVIEW RD, CHESTERTOWN, MD 21620 | 412100 |
| 2205 PONDTOWN RD, CHESTERTOWN, MD 21620 | 412100 |
| 101 PINE TREE RD, CHESTERTOWN, MD 21620 | 408700 |
| 253 BLAKEFIELD DR, CHESTERTOWN, MD 21620 | 407900 |
| 209 DUKE OF KENT ST, CHESTERTOWN, MD 21620 | 407500 |
| 200 FLYWAY LN, CHESTERTOWN, MD 21620 | 407400 |
| 141 HILLTOP DR, CHESTERTOWN, MD 21620 | 405000 |
| 118 WESTWOOD LN, CHESTERTOWN, MD 21620 | 403700 |
| 120 CHURCH MEADOW CT, CHESTERTOWN, MD 21620 | 402400 |
| 1933 MCGINNES RD, CHESTERTOWN, MD 21620 | 401300 |
| 1316 EWINGTOWN RD, CHESTERTOWN, MD 21620 | 400800 |
| 809 TRUSLOW RD, CHESTERTOWN, MD 21620 | 400000 |
| 307 FAIRVIEW DR, CHESTERTOWN, MD 21620 | 397200 |
| 208 ORIOLE RD, CHESTERTOWN, MD 21620 | 392300 |
| 100 FLYWAY LN, CHESTERTOWN, MD 21620 | 391600 |
| 125 CHURCH MEADOW CT, CHESTERTOWN, MD 21620 | 390500 |
| 201 OLD BRIDGE RD, CHESTERTOWN, MD 21620 | 390400 |
| 1104 ROUND TOP RD, CHESTERTOWN, MD 21620 | 390300 |
| 217 PEAR TREE POINT RD, CHESTERTOWN, MD 21620 | 390200 |