Chestnut Dr, Orleans, MA Property Records

Barnstable County and Orleans Town property records for 8 addresses on Chestnut Dr, Orleans, MA · Last verified August 2026

Chestnut Dr Highlights

Properties 8
Median Sale Price $1,325,000
Deeds and Mortgages on File 13
Median Price per Sqft $478
Owner Occupied 13%
Median Annual Tax Bill $14,942
Median Year Built 1998
Median Ownership Tenure 8 years

Properties on Chestnut Dr

Owner names and prior sale amounts shown locked below are available instantly with a free trial.

24 Chestnut Dr

4 bd · 3 ba · 1,568 sqft · built 1998 · 1.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$750,000May 2013 $7,1222025 2 Names on Record Assessor + 1 DocumentUpdated Jul 2026

30 Chestnut Dr

4 bd · 3.5 ba · 3,677 sqft · built 1998 · 2.09 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,170,000Mar 2015 $11,6862025 Amount on Record Feb 2011 1 Name on Record Assessor + 2 DocumentsUpdated Jul 2026

40 Chestnut Dr

4 bd · 3.5 ba · 2,239 sqft · built 1995 · 0.969 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,325,000May 2021 $11,1882025 2 Names on Record Assessor + 1 DocumentUpdated Jul 2026

41 Chestnut Dr

4 bd · 4.5 ba · 4,303 sqft · built 2021 · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,525,000Jun 2018 $26,3902025 —Mar 2017 1 Name on Record Assessor + 4 DocumentsUpdated Aug 2026

43 Chestnut Dr

2 bd · 1 ba · 1,146 sqft · built 1960 · 1.05 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jun 2017 $14,9422025 —Dec 2013 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

46 Chestnut Dr

3 bd · 2 ba · 2,932 sqft · built 1975 · 0.969 acres

Last Sale Tax Bill Prior Sale Owner Records
$790,000Feb 2016 $8,9412025 2 Names on Record AssessorUpdated Jul 2026

49 Chestnut Dr

4 bd · 2.5 ba · 2,145 sqft · built 2002 · 1.51 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,140,000Nov 2020 $17,1132025 Amount on Record Aug 1995 2 Names on Record Assessor + 1 DocumentUpdated Jun 2026

50 Chestnut Dr

6 bd · 5.5 ba · 5,758 sqft · built 2019 · 2.31 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,625,000Jan 2021 $31,0752025 Amount on Record Sep 2017 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

Wildfire Risk on Chestnut Dr

Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020

Wildfire RiskLow
this street's cells rank above 11% of the US · above 28% of Massachusetts
Wildfire LikelihoodLess than 1 in 10,000 per year
ExposureDirect
3 of 3 cells directly exposed · 3 adjoin burnable vegetation

Property Records in Nearby Streets