Essex County and Gloucester City property records for 30 addresses on Sleepy Hollow Rd, Gloucester, MA · Last verified October 2026
| Properties | 30 |
|---|---|
| Median Sale Price | $750,000 |
| Deeds and Mortgages on File | 35 |
| Median Price per Sqft | $593 |
| Owner Occupied | 17% |
| Median Annual Tax Bill | $16,631 |
| Median Year Built | 1962 |
| Median Ownership Tenure | 12 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1 Sleepy Hollow Rd |
3 bd · 1 ba · 936 sqft built 1953 · 0.153 acres | $440,000 Aug 2003 | $10,091 2026 | Assessor Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4 Sleepy Hollow Rd |
3 bd · 3 ba · 2,574 sqft built 1961 · 0.23 acres | $17,033 2026 | Assessor Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5 Sleepy Hollow Rd |
2 bd · 2 ba · 1,144 sqft built 1962 · 0.116 acres | $678,600 Jul 2016 | $11,038 2026 | Assessor Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
6 Sleepy Hollow Rd |
4 bd · 3 ba · 2,368 sqft built 1957 · 0.231 acres | $1,600,000 May 2021 | $15,518 2026 | Assessor + 3 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
7 Sleepy Hollow Rd |
2 bd · 2.5 ba · 1,994 sqft built 1956 · 0.165 acres | $655,000 May 2014 | $15,033 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
8 Sleepy Hollow Rd |
2 bd · 2 ba · 1,248 sqft built 1972 · 0.231 acres | $650,000 Dec 2014 | $13,554 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9 Sleepy Hollow Rd |
3 bd · 4 ba · 3,036 sqft built 2020 · 0.196 acres | $17,546 2026 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
10 Sleepy Hollow Rd |
3 bd · 1.5 ba · 1,558 sqft built 1955 · 0.231 acres | $430,000 Feb 2017 | $13,796 2026 | Assessor + 4 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
11 Sleepy Hollow Rd |
5 bd · 2.5 ba · 1,893 sqft built 1956 · 0.289 acres | $16,576 2026 | Assessor Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
11R Sleepy Hollow Rd |
5 bd · 2 ba · 1,352 sqft built 1962 · 0.289 acres | — Nov 2008 | $13,500 2026 | Assessor Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
12 Sleepy Hollow Rd |
0.072 acres | $430,000 Feb 2017 | $306 2026 | Assessor + 4 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
13 Sleepy Hollow Rd |
0.289 acres | $750,000 Aug 2018 | $1,527 2026 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
13R Sleepy Hollow Rd |
4 bd · 3 ba · 3,234 sqft built 1991 · 0.289 acres | $901,875 Jun 2010 | $20,865 2026 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
14 Sleepy Hollow Rd |
0.159 acres | $370 2026 | Assessor Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15 Sleepy Hollow Rd |
4 bd · 5 ba · 3,792 sqft built 2017 · 0.289 acres | $727,500 May 2014 | $27,550 2026 | Assessor + 2 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15R Sleepy Hollow Rd |
2 bd · 2 ba · 1,242 sqft built 1952 · 0.289 acres | $21,000 Nov 1994 | $15,774 2026 | Assessor + 2 Documents Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
16 Sleepy Hollow Rd |
3 bd · 1.5 ba · 1,102 sqft built 1954 · 0.15 acres | — Nov 2013 | $14,072 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
17 Sleepy Hollow Rd |
4 bd · 3.5 ba · 2,900 sqft built 2017 · 0.289 acres | $1,000,000 Sep 2021 | $22,429 2026 | Assessor + 1 Document Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
17R Sleepy Hollow Rd |
3 bd · 1.5 ba · 1,324 sqft built 1952 · 0.289 acres | $350,000 Sep 2018 | $14,565 2026 | Assessor Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
18 Sleepy Hollow Rd |
2 bd · 2.5 ba · 1,261 sqft built 1997 · 0.313 acres | $16,914 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
19 Sleepy Hollow Rd |
6 bd · 4.5 ba · 3,034 sqft built 1999 · 0.289 acres | $20,311 2026 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21 Sleepy Hollow Rd |
7 bd · 5 ba · 3,688 sqft built 1988 · 0.289 acres | $1,650,000 Aug 2015 | $27,190 2026 | Assessor + 2 Documents Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
22 Sleepy Hollow Rd |
3 bd · 1.5 ba · 1,854 sqft built 1955 · 0.231 acres | $230,000 Nov 1995 | $15,297 2026 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24 Sleepy Hollow Rd |
3 bd · 4.5 ba · 3,306 sqft built 1998 · 0.231 acres | $1,650,000 Nov 2005 | $25,160 2026 | Assessor Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26 Sleepy Hollow Rd |
5 bd · 3.5 ba · 1,772 sqft built 1949 · 0.231 acres | $16,631 2026 | Assessor Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
28 Sleepy Hollow Rd |
4 bd · 3 ba · 3,109 sqft built 1963 · 0.239 acres | $670,000 Dec 1997 | $36,250 2026 | Assessor + 1 Document Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
28R Sleepy Hollow Rd |
4 bd · 3 ba · 3,423 sqft built 1997 · 0.239 acres | $4,000,000 Sep 2021 | $39,959 2026 | Assessor + 4 Documents Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
30 Sleepy Hollow Rd |
4 bd · 3.5 ba · 2,463 sqft built 2013 · 0.315 acres | — Oct 2014 | $37,277 2026 | Assessor Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
32 Sleepy Hollow Rd |
6 bd · 2 ba · 2,600 sqft built 1950 · 0.314 acres | $31,011 2026 | Assessor Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
34 Sleepy Hollow Rd |
5 bd · 3 ba · 3,767 sqft built 1990 · 0.314 acres | $1,725,000 Jun 2006 | $37,293 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File |