Woodbury, CT - Most Valuable Residential Properties in 2025
Updated on November 25, 2025.
According to data from official Connecticut government agencies, among residential properties in Woodbury, CT, the following were the most valuable residential properties by Appraised Total Value in 2025. The most valuable residential property was 15 WOODSIDE CIRCLE ($3.58M), followed by 14 TOMLINSON RD ($2.39M), 245 PLUMB BROOK RD ($2.21M), and 59 HILLSIDE RD EXT ($2.07M).
The chart below shows the top 10 valuable residential properties, and the table below shows the top 200.
You can see similar information for other Connecticut cities.
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Data Source: Official Government Sites.
Woodbury, CT - Most Valuable Residential Properties in 2025
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| Address | Appraised Total Value ($) |
|---|---|
| 15 WOODSIDE CIRCLE, Woodbury, CT 06798 | 3582700 |
| 14 TOMLINSON RD, Woodbury, CT 06798 | 2389800 |
| 245 PLUMB BROOK RD, Woodbury, CT 06798 | 2209000 |
| 59 HILLSIDE RD EXT, Woodbury, CT 06798 | 2068800 |
| 37 ROWLEY RD, Woodbury, CT 06798 | 1988900 |
| 401 HOOP POLE HILL RD, Woodbury, CT 06798 | 1968800 |
| 86 CAT SWAMP RD, Woodbury, CT 06798 | 1943100 |
| 1692 MAIN ST NORTH, Woodbury, CT 06798 | 1846200 |
| 241 FLANDERS RD, Woodbury, CT 06798 | 1787700 |
| 66 RUCUUM RD EXT, Woodbury, CT 06798 | 1780700 |
| 49 POND VALLEY RD, Woodbury, CT 06798 | 1768100 |
| 380 TRANSYLVANIA RD, Woodbury, CT 06798 | 1655000 |
| 79 OWL RIDGE, Woodbury, CT 06798 | 1636400 |
| 350 WHITE DEER ROCKS RD, Woodbury, CT 06798 | 1616600 |
| 920 MAIN ST SOUTH, Woodbury, CT 06798 | 1606100 |
| 505 UPPER GRASSY HILL RD, Woodbury, CT 06798 | 1599500 |
| 237 PLUMB BROOK RD, Woodbury, CT 06798 | 1571900 |
| 346 MAIN ST SOUTH, Woodbury, CT 06798 | 1563300 |
| 212 GRASSY HILL RD, Woodbury, CT 06798 | 1559900 |
| 98 OWL RIDGE, Woodbury, CT 06798 | 1548600 |
| 59 SYCAMORE AVE, Woodbury, CT 06798 | 1530500 |
| 100 WEEKEEPEEMEE RD, Woodbury, CT 06798 | 1529700 |
| 72 WOODLAND LANE, Woodbury, CT 06798 | 1514600 |
| 49 OWL RIDGE, Woodbury, CT 06798 | 1435300 |
| 36 EAST HILL RD, Woodbury, CT 06798 | 1427800 |
| 119 ROWLEY RD, Woodbury, CT 06798 | 1421200 |
| 63 JUDSON AVE, Woodbury, CT 06798 | 1396600 |
| 208 TUTTLE RD, Woodbury, CT 06798 | 1377900 |
| 39 QUANOPAUG TRAIL, Woodbury, CT 06798 | 1372900 |
| 21 TERRELL RD, Woodbury, CT 06798 | 1366700 |
| 105 OLD GRASSY HILL RD, Woodbury, CT 06798 | 1337500 |
| 215 PLUMB BROOK RD, Woodbury, CT 06798 | 1335700 |
| 29 ORTON LANE, Woodbury, CT 06798 | 1297900 |
| 362 TRANSYLVANIA RD, Woodbury, CT 06798 | 1248300 |
| 449 MIDDLE RD TPKE, Woodbury, CT 06798 | 1245900 |
| 93 PETER RD, Woodbury, CT 06798 | 1244300 |
| 161 CHOHEES TRAIL, Woodbury, CT 06798 | 1242700 |
| 35 GATE POST LANE, Woodbury, CT 06798 | 1238800 |
| 352 TRANSYLVANIA RD, Woodbury, CT 06798 | 1236200 |
| 17 GATE POST LANE, Woodbury, CT 06798 | 1228100 |
| 226 SCUPPO RD, Woodbury, CT 06798 | 1212100 |
| 117 PAINTER HILL RD, Woodbury, CT 06798 | 1205100 |
| 162 MIDDLE RD TPKE, Woodbury, CT 06798 | 1160900 |
| 426 MIDDLE RD TPKE, Woodbury, CT 06798 | 1159100 |
| 188 HOOP POLE HILL RD, Woodbury, CT 06798 | 1157500 |
| 225 OLD SHERMAN HILL RD, Woodbury, CT 06798 | 1156600 |
| 28 LEAVENWORTH RD, Woodbury, CT 06798 | 1151400 |
| 1488 MAIN ST NORTH, Woodbury, CT 06798 | 1149900 |
| 868 WASHINGTON RD, Woodbury, CT 06798 | 1144500 |
| 68 GOOD HILL RD, Woodbury, CT 06798 | 1138900 |
| 218 OLD SHERMAN HILL RD, Woodbury, CT 06798 | 1138400 |
| 87 COACH LIGHT DRIVE, Woodbury, CT 06798 | 1138200 |
| 595 MIDDLE RD TPKE, Woodbury, CT 06798 | 1134900 |
| 138 MINORTOWN RD, Woodbury, CT 06798 | 1132300 |
| 283 SAW PIT HILL RD, Woodbury, CT 06798 | 1121200 |
| 138 SCUPPO RD, Woodbury, CT 06798 | 1118000 |
| 348 WEEKEEPEEMEE RD, Woodbury, CT 06798 | 1114300 |
| 97 OWL RIDGE, Woodbury, CT 06798 | 1113900 |
| 156 JOSHUA HILL RD, Woodbury, CT 06798 | 1113300 |
| 452 MIDDLE RD TPKE, Woodbury, CT 06798 | 1113100 |
| 274 GRASSY HILL RD, Woodbury, CT 06798 | 1098600 |
| 267 GOOD HILL RD, Woodbury, CT 06798 | 1083800 |
| 132 STONE PIT RD, Woodbury, CT 06798 | 1079800 |
| 717 FLANDERS RD, Woodbury, CT 06798 | 1079400 |
| 121 TOWN LINE RD, Woodbury, CT 06798 | 1079200 |
| 8 STONE HOLLOW RD, Woodbury, CT 06798 | 1077600 |
| 264 GOOD HILL RD, Woodbury, CT 06798 | 1068600 |
| 47 BEAR HILL RD, Woodbury, CT 06798 | 1066400 |
| 5 FOX RD, Woodbury, CT 06798 | 1065700 |
| 26 GATE POST LANE, Woodbury, CT 06798 | 1057700 |
| 247 UPPER GRASSY HILL RD, Woodbury, CT 06798 | 1057300 |
| 168 UPPER GRASSY HILL RD, Woodbury, CT 06798 | 1056100 |
| 354 WEEKEEPEEMEE RD, Woodbury, CT 06798 | 1049400 |
| 226 PLUMB BROOK RD, Woodbury, CT 06798 | 1048100 |
| 509 MAIN ST NORTH, Woodbury, CT 06798 | 1040900 |
| 112 WEST SIDE RD, Woodbury, CT 06798 | 1040800 |
| 59 CAT SWAMP RD, Woodbury, CT 06798 | 1038000 |
| 136 SYCAMORE AVE, Woodbury, CT 06798 | 1033800 |
| 200 MINORTOWN RD, Woodbury, CT 06798 | 1033800 |
| 935 WASHINGTON RD, Woodbury, CT 06798 | 1031400 |
| 46 TIMBER LANE, Woodbury, CT 06798 | 1029700 |
| 981 WASHINGTON RD, Woodbury, CT 06798 | 1028100 |
| 156 WEEKEEPEEMEE RD, Woodbury, CT 06798 | 1022300 |
| 11 OWL RIDGE, Woodbury, CT 06798 | 1021600 |
| 31 STONE HOLLOW RD, Woodbury, CT 06798 | 1014900 |
| 64 HILLSIDE RD EXT, Woodbury, CT 06798 | 1014500 |
| 45 BIRCHWOOD LANE, Woodbury, CT 06798 | 1013700 |
| 40 PETER RD, Woodbury, CT 06798 | 1012600 |
| 144 GOOD HILL RD, Woodbury, CT 06798 | 994400 |
| 344 WEEKEEPEEMEE RD, Woodbury, CT 06798 | 989000 |
| 20 SILVER BROOK LANE, Woodbury, CT 06798 | 987400 |
| 99 OWL RIDGE, Woodbury, CT 06798 | 983700 |
| 104 COWLES RD, Woodbury, CT 06798 | 979400 |
| 100 MAIN ST SOUTH, Woodbury, CT 06798 | 978100 |
| 135 MINORTOWN RD, Woodbury, CT 06798 | 969800 |
| 66 OWL RIDGE, Woodbury, CT 06798 | 965700 |
| 200 QUASSUK RD, Woodbury, CT 06798 | 960600 |
| 362 WEEKEEPEEMEE RD, Woodbury, CT 06798 | 953900 |
| 198 PLUMB BROOK RD, Woodbury, CT 06798 | 953000 |
| 49 SOUCY RD, Woodbury, CT 06798 | 952800 |
| 86 CURTISS MEADOWS, Woodbury, CT 06798 | 952200 |
| 41 OWL RIDGE, Woodbury, CT 06798 | 948400 |
| 41 RIVER BEND DRIVE, Woodbury, CT 06798 | 946800 |
| 85 OWL RIDGE, Woodbury, CT 06798 | 941700 |
| 73 OWL RIDGE, Woodbury, CT 06798 | 940800 |
| 272 GOOD HILL RD, Woodbury, CT 06798 | 938900 |
| 48 GATE POST LANE, Woodbury, CT 06798 | 938300 |
| 36 ASH SWAMP RD, Woodbury, CT 06798 | 936600 |
| 144 CURTISS RD EXT, Woodbury, CT 06798 | 936200 |
| 177 PLUMB BROOK RD, Woodbury, CT 06798 | 935300 |
| 35 OLD MEADOW RD, Woodbury, CT 06798 | 934800 |
| 5 GATE POST LANE, Woodbury, CT 06798 | 933600 |
| 234 FLANDERS RD, Woodbury, CT 06798 | 931900 |
| 157 WESTWOOD RD, Woodbury, CT 06798 | 931000 |
| 26 COACH LIGHT DRIVE, Woodbury, CT 06798 | 931000 |
| 43 OLD MEADOW RD, Woodbury, CT 06798 | 930400 |
| 33 NORTH FORTY RD, Woodbury, CT 06798 | 928100 |
| 121 CROSS BROOK RD, Woodbury, CT 06798 | 927300 |
| 49 NORTH FORTY RD, Woodbury, CT 06798 | 927100 |
| 137 MINORTOWN RD, Woodbury, CT 06798 | 926600 |
| 362 RAIL TREE HILL RD, Woodbury, CT 06798 | 926400 |
| 7 OWL RIDGE, Woodbury, CT 06798 | 923100 |
| 43 BIRCHWOOD LANE, Woodbury, CT 06798 | 921400 |
| 56 SILVER BROOK LANE, Woodbury, CT 06798 | 918700 |
| 57 OWL RIDGE, Woodbury, CT 06798 | 916000 |
| 36 HAZEL WOODS DR, Woodbury, CT 06798 | 909800 |
| 6 OWL RIDGE, Woodbury, CT 06798 | 908500 |
| 50 OWL RIDGE, Woodbury, CT 06798 | 908400 |
| 115 BARN HILL RD, Woodbury, CT 06798 | 907500 |
| 92 TUTTLE RD, Woodbury, CT 06798 | 907400 |
| 230 PLUMB BROOK RD, Woodbury, CT 06798 | 907200 |
| 48 COACH LIGHT DRIVE, Woodbury, CT 06798 | 905000 |
| 165 HOOP POLE HILL RD, Woodbury, CT 06798 | 903600 |
| 2 GATE POST LANE, Woodbury, CT 06798 | 903000 |
| 124 JOSHUA HILL RD, Woodbury, CT 06798 | 901500 |
| 90 CROSS BROOK RD, Woodbury, CT 06798 | 896600 |
| 167 SYCAMORE AVE, Woodbury, CT 06798 | 895600 |
| 76 COWLES RD, Woodbury, CT 06798 | 891600 |
| 619 MIDDLE RD TPKE, Woodbury, CT 06798 | 890800 |
| 23 STEEPLEVIEW LANE, Woodbury, CT 06798 | 890600 |
| 38 BIRCHWOOD LANE, Woodbury, CT 06798 | 890200 |
| 36 MOUNTAIN LAUREL RD, Woodbury, CT 06798 | 889500 |
| 155 HURDS HILL RD, Woodbury, CT 06798 | 889000 |
| 89 NORTH GATE RD, Woodbury, CT 06798 | 885700 |
| 101 OLD GRASSY HILL RD, Woodbury, CT 06798 | 884700 |
| 41 STEEPLEVIEW LANE, Woodbury, CT 06798 | 884100 |
| 235 WHITE DEER ROCKS RD, Woodbury, CT 06798 | 883600 |
| 245 HOOP POLE HILL RD, Woodbury, CT 06798 | 881700 |
| 556 FLANDERS RD, Woodbury, CT 06798 | 879600 |
| 881 MAIN ST SOUTH, Woodbury, CT 06798 | 877900 |
| 31 SILVER BROOK LANE, Woodbury, CT 06798 | 877000 |
| 335 MIDDLE RD TPKE, Woodbury, CT 06798 | 875100 |
| 555 OLD SHERMAN HILL RD, Woodbury, CT 06798 | 875100 |
| 232 SCUPPO RD, Woodbury, CT 06798 | 873300 |
| 29 STEEPLEVIEW LANE, Woodbury, CT 06798 | 872600 |
| 92 GREY FOX TRAIL, Woodbury, CT 06798 | 872100 |
| 798 MAIN ST NORTH, Woodbury, CT 06798 | 871500 |
| 420 UPPER GRASSY HILL RD, Woodbury, CT 06798 | 871300 |
| 38 OWL RIDGE, Woodbury, CT 06798 | 868500 |
| 246 TUTTLE RD, Woodbury, CT 06798 | 867100 |
| 43 RIVER BEND DRIVE, Woodbury, CT 06798 | 866800 |
| 84 GRASSY HILL RD, Woodbury, CT 06798 | 862900 |
| 161 SPRAIN BROOK RD, Woodbury, CT 06798 | 862600 |
| 120 HURDS HILL RD, Woodbury, CT 06798 | 861800 |
| 45 OLD MEADOW RD, Woodbury, CT 06798 | 859500 |
| 9 SILVER BROOK LANE, Woodbury, CT 06798 | 858100 |
| 726 FLANDERS RD, Woodbury, CT 06798 | 856900 |
| 543 UPPER GRASSY HILL RD, Woodbury, CT 06798 | 855600 |
| 45 GATE POST LANE, Woodbury, CT 06798 | 853800 |
| 212 PLUMB BROOK RD, Woodbury, CT 06798 | 853000 |
| 392 RAIL TREE HILL RD, Woodbury, CT 06798 | 852200 |
| 7 OLD MEADOW RD, Woodbury, CT 06798 | 849900 |
| 24 SCUPPO RD, Woodbury, CT 06798 | 849500 |
| 15 BLUEBERRY LANE, Woodbury, CT 06798 | 849300 |
| 30 TIMBER LANE, Woodbury, CT 06798 | 848300 |
| 203 SPRAIN BROOK RD, Woodbury, CT 06798 | 847700 |
| 5 STONE HOLLOW RD, Woodbury, CT 06798 | 846500 |
| 60 STONE PIT RD, Woodbury, CT 06798 | 844800 |
| 34 WOODLAND LANE, Woodbury, CT 06798 | 843900 |
| 260 MIDDLE RD TPKE, Woodbury, CT 06798 | 843100 |
| 35 EAST HILL RD, Woodbury, CT 06798 | 841900 |
| 67 SILVER BROOK LANE, Woodbury, CT 06798 | 841300 |
| 26 OWL RIDGE, Woodbury, CT 06798 | 841000 |
| 393 WEEKEEPEEMEE RD, Woodbury, CT 06798 | 840500 |
| 43 TIMBER LANE, Woodbury, CT 06798 | 839800 |
| 15 SILVER BROOK LANE, Woodbury, CT 06798 | 839200 |
| 48 NORTH FORTY RD, Woodbury, CT 06798 | 837600 |
| 94 CROSS BROOK RD, Woodbury, CT 06798 | 836400 |
| 138 QUANOPAUG TRAIL, Woodbury, CT 06798 | 836200 |
| 9 BIRCHWOOD LANE, Woodbury, CT 06798 | 833800 |
| 12 OWL RIDGE, Woodbury, CT 06798 | 833600 |
| 88 CURTISS MEADOWS, Woodbury, CT 06798 | 832700 |
| 56 HILLSIDE RD EXT, Woodbury, CT 06798 | 832100 |
| 19 SILVER BROOK LANE, Woodbury, CT 06798 | 830200 |
| 68 WHITTLESEY ROAD, Woodbury, CT 06798 | 830200 |
| 100 CAT SWAMP RD, Woodbury, CT 06798 | 830100 |
| 20 OLD MEADOW RD, Woodbury, CT 06798 | 829800 |
| 87 CARMEL HILL RD, Woodbury, CT 06798 | 829700 |
| 76 CROSS BROOK RD, Woodbury, CT 06798 | 829400 |
| 220 CHURCH HILL RD, Woodbury, CT 06798 | 828500 |