Chester, CT - Most Valuable Residential Properties in 2025

Updated on November 25, 2025.

According to data from official Connecticut government agencies, among residential properties in Chester, CT, the following were the most valuable residential properties by Appraised Total Value in 2025. The most valuable residential property was 49&51 FERRY RD ($3.40M), followed by 35 PARKERS PT RD ($2.09M), 45 PARKERS PT RD ($1.93M), and 49 PARKERS PT RD ($1.90M).

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.

Data Source: Official Government Sites.
Chester, CT - Most Valuable Residential Properties in 2025
49&51 FERRY RD
35 PARKERS PT RD
45 PARKERS PT RD
49 PARKERS PT RD
7 PARKERS PT RD
25 PARKERS PT RD
31 PARKERS PT RD
19 PARKERS PT RD
286 MIDDLESEX AVE
226-8 MIDDLESEX AVE
Chester, CT - Most Valuable Residential Properties in 2025
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Address Appraised Total Value ($)
49&51 FERRY RD, Chester, CT 06412 3398200
35 PARKERS PT RD, Chester, CT 06412 2093000
45 PARKERS PT RD, Chester, CT 06412 1926400
49 PARKERS PT RD, Chester, CT 06412 1903400
7 PARKERS PT RD, Chester, CT 06412 1864000
25 PARKERS PT RD, Chester, CT 06412 1833300
31 PARKERS PT RD, Chester, CT 06412 1812600
19 PARKERS PT RD, Chester, CT 06412 1600700
286 MIDDLESEX AVE, Chester, CT 06412 1518600
226-8 MIDDLESEX AVE, Chester, CT 06412 1494600
23 PARKERS PT RD, Chester, CT 06412 1325200
27 PARKERS PT RD, Chester, CT 06412 1312900
288 MIDDLESEX AVE, Chester, CT 06412 1304300
65 DOCK RD, Chester, CT 06412 1278100
18 E LIBERTY ST, Chester, CT 06412 1276800
46 DEEP HOLLOW RD, Chester, CT 06412 1271700
134 PINNACLE LN, Chester, CT 06412 1226700
88 GOOSE HILL RD, Chester, CT 06412 1207200
75 CEDAR LAKE RD, Chester, CT 06412 1192400
9 PARKERS PT RD, Chester, CT 06412 1178200
20 LIBERTY ST, Chester, CT 06412 1120000
153 W MAIN ST, Chester, CT 06412 1085000
11 BARTKIEWICZ RD, Chester, CT 06412 1062500
35-20 CASTLE VIEW DR, Chester, CT 06412 1048700
18 WATERHOUSE LN, Chester, CT 06412 1040100
35-18 CASTLE VIEW DR, Chester, CT 06412 1033500
35-14 CASTLE VIEW DR, Chester, CT 06412 1029900
81 TURKEY HILL RD, Chester, CT 06412 1017600
16 WATERHOUSE LN, Chester, CT 06412 1008000
35-16 CASTLE VIEW DR, Chester, CT 06412 1006300
39-1 GILBERT HILL RD, Chester, CT 06412 1002700
51 DOCK RD, Chester, CT 06412 992800
35-10 CASTLE VIEW DR, Chester, CT 06412 987900
20 PRATT ST, Chester, CT 06412 982500
71 DOCK RD, Chester, CT 06412 979000
260 MIDDLESEX AVE, Chester, CT 06412 974400
44 SPRING ST, Chester, CT 06412 958000
248 MIDDLESEX AVE, Chester, CT 06412 953400
95 CEDAR SWAMP RD, Chester, CT 06412 924100
41 E LIBERTY ST, Chester, CT 06412 917700
32 DEEP HOLLOW RD, Chester, CT 06412 913100
41A HOOP POLE HILL RD, Chester, CT 06412 910400
25 GILBERT HILL RD, Chester, CT 06412 898200
123 MAIN ST, Chester, CT 06412 877900
32 GILBERT HILL RD, Chester, CT 06412 870400
82 CEDAR LAKE RD, Chester, CT 06412 870200
72 W MAIN ST, Chester, CT 06412 866600
19 W MAIN ST, Chester, CT 06412 862000
209 MIDDLESEX AVE, Chester, CT 06412 861200
179 PINNACLE LN, Chester, CT 06412 860800
47 FERRY RD, Chester, CT 06412 858400
34 LIBERTY ST, Chester, CT 06412 844100
67-2 WIG HILL RD, Chester, CT 06412 841000
31-33 STRAITS RD, Chester, CT 06412 836200
9 OLD COUNTY RD, Chester, CT 06412 834000
10 HIGH FIELD LN, Chester, CT 06412 826800
87 SPRING ST, Chester, CT 06412 823500
322 W MAIN ST, Chester, CT 06412 822100
1 WINTHROP RD, Chester, CT 06412 819700
15 SUNSET AVE, Chester, CT 06412 816100
5 PATTACONK DR, Chester, CT 06412 811200
112 MIDDLESEX AVE, Chester, CT 06412 804800
69 CEDAR LAKE RD, Chester, CT 06412 792400
80 GOOSE HILL RD, Chester, CT 06412 785700
252 MIDDLESEX AVE, Chester, CT 06412 778000
78 PINNACLE LN, Chester, CT 06412 777000
14 LIBERTY ST, Chester, CT 06412 775500
23 GILBERT HILL RD, Chester, CT 06412 775500
167 PINNACLE LN, Chester, CT 06412 775100
35 GILBERT HILL RD, Chester, CT 06412 772300
91 GOOSE HILL RD, Chester, CT 06412 771700
22 OLD COUNTY RD, Chester, CT 06412 770000
65 BOKUM RD, Chester, CT 06412 769900
213 MIDDLESEX AVE, Chester, CT 06412 762300
61-17 GOOSE HILL RD, Chester, CT 06412 760100
22 WATERHOUSE LN, Chester, CT 06412 757600
7 E LIBERTY ST, Chester, CT 06412 756400
82 GOOSE HILL RD, Chester, CT 06412 753600
68 E KINGS HWY, Chester, CT 06412 750000
94 CEDAR LAKE RD, Chester, CT 06412 737100
83 TURKEY HILL RD, Chester, CT 06412 735700
12 WINTHROP RD, Chester, CT 06412 734300
147 PINNACLE LN, Chester, CT 06412 734200
68 W MAIN ST, Chester, CT 06412 733800
18 FERRY RD, Chester, CT 06412 733400
31 GILBERT HILL RD, Chester, CT 06412 733000
37 S WIG HILL RD, Chester, CT 06412 732700
47 E KINGS HWY, Chester, CT 06412 732100
83 MAIN ST, Chester, CT 06412 729100
19 KINGS HWY, Chester, CT 06412 726100
99 PINNACLE LN, Chester, CT 06412 718300
6 WATERHOUSE LN, Chester, CT 06412 718200
119 PINNACLE LN, Chester, CT 06412 717300
24 OLD COUNTY RD, Chester, CT 06412 715600
45 PINNACLE LN, Chester, CT 06412 713400
3 STRAITS RD, Chester, CT 06412 713200
16 SPRING ST, Chester, CT 06412 712900
34 DEEP HOLLOW RD, Chester, CT 06412 712800
158 MIDDLESEX AVE, Chester, CT 06412 711800
4 PINE KNOLL DR, Chester, CT 06412 711600
10 OLD DEPOT RD, Chester, CT 06412 709900
15 WATERHOUSE LN, Chester, CT 06412 708600
15 OLD COUNTY RD, Chester, CT 06412 708300
33 E LIBERTY ST, Chester, CT 06412 707600
20 SPRING ST, Chester, CT 06412 706400
11 SUNSET AVE, Chester, CT 06412 702000
76 GOOSE HILL RD, Chester, CT 06412 700500
9 JOHNSON RD, Chester, CT 06412 699200
22 GILBERT HILL RD, Chester, CT 06412 697900
36 E LIBERTY ST, Chester, CT 06412 697800
7 OLD DEPOT RD, Chester, CT 06412 697400
14 BOKUM RD, Chester, CT 06412 696600
45-2 GOOSE HILL RD, Chester, CT 06412 696100
15 HIGH FIELD LN, Chester, CT 06412 692200
75 PINNACLE LN, Chester, CT 06412 691300
95 GOOSE HILL RD, Chester, CT 06412 689000
24 WATERHOUSE LN, Chester, CT 06412 688700
246 MIDDLESEX AVE, Chester, CT 06412 688000
11 PINE KNOLL DR, Chester, CT 06412 687400
9 STORY HILL RD, Chester, CT 06412 686000
193 W MAIN ST, Chester, CT 06412 685000
8-10 N MAIN ST, Chester, CT 06412 684100
127 PINNACLE LN, Chester, CT 06412 683700
49 BISHOP RD, Chester, CT 06412 680300
27 GILBERT HILL RD, Chester, CT 06412 671800
280 W MAIN ST, Chester, CT 06412 668500
79 CEDAR LAKE RD, Chester, CT 06412 666900
10 SPRING ST, Chester, CT 06412 665500
6 HIGH FIELD LN, Chester, CT 06412 664700
3 PARKERS PT RD, Chester, CT 06412 664300
37 GILBERT HILL RD, Chester, CT 06412 661300
19 HOOP POLE HILL RD, Chester, CT 06412 660000
5 GILBERT HILL RD, Chester, CT 06412 656600
13 BARTKIEWICZ RD, Chester, CT 06412 655000
11 WATERHOUSE LN, Chester, CT 06412 652200
1 KINGS HWY, Chester, CT 06412 651900
2 WINTHROP RD, Chester, CT 06412 651600
9 BAKER RD, Chester, CT 06412 651500
53 MAPLE ST, Chester, CT 06412 646800
45-1 GOOSE HILL RD, Chester, CT 06412 645900
10 HIGH ST, Chester, CT 06412 644400
8 WATERHOUSE LN, Chester, CT 06412 644400
162 W MAIN ST, Chester, CT 06412 642300
30 STORY HILL RD, Chester, CT 06412 642000
6 OLD COUNTY RD, Chester, CT 06412 640500
15 W MAIN ST, Chester, CT 06412 640200
10 WATERHOUSE LN, Chester, CT 06412 640000
96 WINTHROP RD, Chester, CT 06412 638500
11 OLD COUNTY RD, Chester, CT 06412 637600
46 STRAITS RD, Chester, CT 06412 637600
20 E KINGS HWY, Chester, CT 06412 636900
45 TURKEY HILL RD, Chester, CT 06412 635200
16 GILBERT HILL RD, Chester, CT 06412 632700
19 BOKUM RD, Chester, CT 06412 632400
87 WIG HILL RD, Chester, CT 06412 632300
39 HOOP POLE HILL RD, Chester, CT 06412 631600
74 HOOP POLE HILL RD, Chester, CT 06412 631500
17 WATERHOUSE LN, Chester, CT 06412 630300
7 HIGH FIELD LN, Chester, CT 06412 629500
3 PATTACONK DR, Chester, CT 06412 629300
98 - 102 GOOSE HILL RD, Chester, CT 06412 629300
19 WATERHOUSE LN, Chester, CT 06412 627700
19 CEDAR LAKE RD, Chester, CT 06412 627300
30 LIBERTY ST, Chester, CT 06412 626900
108 MIDDLESEX AVE, Chester, CT 06412 626700
27 MAPLE ST, Chester, CT 06412 624300
134 GOOSE HILL RD, Chester, CT 06412 624100
13 OLD COUNTY RD, Chester, CT 06412 623800
254 W MAIN ST, Chester, CT 06412 619200
324 W MAIN ST, Chester, CT 06412 619100
17 WIG HILL RD, Chester, CT 06412 618800
101 MAIN ST, Chester, CT 06412 618700
11 CEDAR LAKE RD, Chester, CT 06412 618200
43-47 MAIN ST, Chester, CT 06412 618200
5 PINE KNOLL DR, Chester, CT 06412 618200
23 OLD DEPOT RD, Chester, CT 06412 618000
42 KINGS HWY, Chester, CT 06412 616700
109 CEDAR LAKE RD, Chester, CT 06412 616500
43 LIBERTY ST, Chester, CT 06412 615900
32 STRAITS RD, Chester, CT 06412 615700
9 PINE KNOLL DR, Chester, CT 06412 615500
88 WINTHROP RD, Chester, CT 06412 614600
23 STORY HILL RD, Chester, CT 06412 612900
12 WATERHOUSE LN, Chester, CT 06412 611700
4 WATERHOUSE LN, Chester, CT 06412 610900
35 SPRING ST, Chester, CT 06412 610200
23 BATES RD, Chester, CT 06412 609800
232 W MAIN ST, Chester, CT 06412 609800
107 W MAIN ST, Chester, CT 06412 609600
26 STRAITS RD, Chester, CT 06412 609600
6 DOCK RD, Chester, CT 06412 608500
15 GILBERT HILL RD, Chester, CT 06412 608100
38 GILBERT HILL RD, Chester, CT 06412 607500
99 MAPLE ST, Chester, CT 06412 606000
19 GILBERT HILL RD, Chester, CT 06412 604900
3 PINE KNOLL DR, Chester, CT 06412 604800
36 RAILROAD AVE, Chester, CT 06412 604700
11 HIGH FIELD LN, Chester, CT 06412 604000
28 HOOP POLE HILL RD, Chester, CT 06412 601500
59&61 WIG HILL RD, Chester, CT 06412 601400