Cheshire Town property records for 38 addresses on Pleasant Dr, Cheshire, CT · Last verified October 2026
| Properties | 38 |
|---|---|
| Median Sale Price | $406,000 |
| Deeds and Mortgages on File | 42 |
| Median Price per Sqft | $235 |
| Owner Occupied | 92% |
| Median Annual Tax Bill | $8,639 |
| Median Year Built | 1965 |
| Median Ownership Tenure | 15 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9 Pleasant Dr |
1.5 ba · 2,549 sqft built 1968 · 0.519 acres | $375,000 May 2022 | $7,494 2025 | Assessor + 1 Document Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
18 Pleasant Dr |
3 bd · 3.5 ba · 2,869 sqft built 1985 · 0.5 acres | $11,402 2026 | Assessor + 1 Document Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
19 Pleasant Dr |
3 bd · 2.5 ba · 1,512 sqft built 1968 · 0.46 acres | $192,000 Oct 1997 | $8,150 2025 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
28 Pleasant Dr |
3 bd · 2 ba · 1,184 sqft built 1979 · 0.519 acres | $287,000 May 2011 | $8,210 2026 | Assessor + 4 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
29 Pleasant Dr |
3 bd · 2.5 ba · 1,876 sqft built 1969 · 0.46 acres | $260,000 Mar 2025 | $8,109 2025 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
38 Pleasant Dr |
3 bd · 2 ba · 1,224 sqft built 1963 · 0.439 acres | $285,000 Aug 2013 | $9,018 2026 | Assessor + 1 Document Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
39 Pleasant Dr |
4 bd · 2.5 ba · 1,876 sqft built 1970 · 0.46 acres | $380,100 Jul 2011 | $8,369 2025 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
48 Pleasant Dr |
3 bd · 2.5 ba · 1,752 sqft built 1964 · 0.55 acres | $9,130 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
49 Pleasant Dr |
3 bd · 2 ba · 1,236 sqft built 1962 · 0.469 acres | — Jun 2014 | $7,896 2025 | Assessor + 2 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
58 Pleasant Dr |
3 bd · 2.5 ba · 1,803 sqft built 1963 · 0.55 acres | $278,500 Mar 2002 | $7,920 2026 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
59 Pleasant Dr |
3 bd · 2 ba · 1,420 sqft built 1963 · 0.469 acres | $440,000 Sep 2022 | $8,223 2025 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
68 Pleasant Dr |
4 bd · 3 ba · 1,478 sqft built 1964 · 0.56 acres | $170,900 Mar 1996 | $7,890 2026 | Assessor + 2 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
69 Pleasant Dr |
3 bd · 2 ba · 1,298 sqft built 1963 · 0.469 acres | $342,000 Sep 2007 | $7,091 2025 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
78 Pleasant Dr |
4 bd · 2 ba · 1,242 sqft built 1963 · 0.6 acres | $169,500 Sep 1995 | $8,162 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
79 Pleasant Dr |
4 bd · 2.5 ba · 2,176 sqft built 1964 · 0.469 acres | $328,600 May 2012 | $8,694 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
88 Pleasant Dr |
3 bd · 2.5 ba · 1,966 sqft built 1964 · 0.639 acres | $372,000 May 2007 | $10,585 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
89 Pleasant Dr |
4 bd · 3.5 ba · 2,310 sqft built 1964 · 0.46 acres | $8,546 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
98 Pleasant Dr |
4 bd · 2.5 ba · 2,108 sqft built 1967 · 0.63 acres | $164,000 Nov 1995 | $8,748 2026 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
99 Pleasant Dr |
4 bd · 2.5 ba · 2,206 sqft built 1967 · 0.46 acres | $377,000 Sep 2008 | $8,639 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
108 Pleasant Dr |
5 bd · 4 ba · 3,120 sqft built 1964 · 0.439 acres | $385,000 Jul 2018 | $11,964 2026 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
109 Pleasant Dr |
3 bd · 2.5 ba · 1,657 sqft built 1962 · 0.46 acres | $369,900 Oct 2005 | $8,061 2025 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
118 Pleasant Dr |
3 bd · 2 ba · 2,441 sqft built 1968 · 0.45 acres | $9,360 2026 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
119 Pleasant Dr |
3 bd · 2 ba · 1,759 sqft built 1957 · 0.469 acres | $415,000 Apr 2024 | $8,192 2025 | Assessor + 2 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
128 Pleasant Dr |
4 bd · 2.5 ba · 2,042 sqft built 1968 · 0.469 acres | $350,000 Oct 2009 | $9,288 2026 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
129 Pleasant Dr |
3 bd · 2 ba · 1,663 sqft built 1968 · 0.469 acres | $406,000 Jul 2026 | $6,984 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
138 Pleasant Dr |
4 bd · 2.5 ba · 1,740 sqft built 1968 · 0.51 acres | $312,000 Nov 2010 | $9,646 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
139 Pleasant Dr |
3 bd · 2.5 ba · 1,904 sqft built 1966 · 0.489 acres | $320,000 Feb 2004 | $7,490 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
148 Pleasant Dr |
4 bd · 3 ba · 1,662 sqft built 1965 · 0.51 acres | $8,981 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
149 Pleasant Dr |
4 bd · 2.5 ba · 1,840 sqft built 1964 · 0.489 acres | $184,600 Sep 1995 | $7,463 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
158 Pleasant Dr |
4 bd · 2.5 ba · 2,096 sqft built 1963 · 0.519 acres | $9,169 2026 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
159 Pleasant Dr |
3 bd · 2 ba · 1,953 sqft built 1967 · 0.489 acres | $8,875 2025 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
168 Pleasant Dr |
3 bd · 3 ba · 2,212 sqft built 1963 · 0.55 acres | $550,000 Sep 2025 | $9,848 2026 | Assessor + 3 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
169 Pleasant Dr |
4 bd · 3 ba · 1,538 sqft built 1964 · 0.489 acres | $225,000 Mar 2016 | $7,859 2025 | Assessor + 6 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
178 Pleasant Dr |
4 bd · 3 ba · 2,683 sqft built 1968 · 0.869 acres | $370,000 Dec 2017 | $10,704 2026 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
179 Pleasant Dr |
4 bd · 2.5 ba · 3,724 sqft built 1963 · 0.639 acres | $218,000 Jun 1990 | $12,318 2025 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
188 Pleasant Dr |
4 bd · 3.5 ba · 2,752 sqft built 1976 · 1.88 acres | $385,000 Aug 2013 | $11,529 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
198 Pleasant Dr |
4 bd · 2.5 ba · 2,215 sqft built 1972 · 1.43 acres | $9,753 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
208 Pleasant Dr |
3 bd · 2.5 ba · 1,758 sqft built 1979 · 0.78 acres | $257,500 Sep 1987 | $8,173 2025 | Assessor Updated Oct 2026 | 2 Owners on File |