Chester Dr, Rye, NY Property Records

Westchester County and Rye City property records for 26 addresses on Chester Dr, Rye, NY · Last verified July 2026

Chester Dr Highlights

Properties 26
Median Sale Price $2,055,000
Deeds and Mortgages on File 32
Median Price per Sqft $691
Owner Occupied 85%
Median Annual Tax Bill $48,775
Median Year Built 1958
Median Ownership Tenure 9 years

Properties on Chester Dr

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

1 Chester Dr

5 bd · 5 ba · 6,112 sqft · 0.769 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,350,000Jan 2007 $103,8362025 2 Names on Record Owner Occupied AssessorUpdated May 2026

2 Chester Dr

3 bd · 3.5 ba · 2,173 sqft · 0.65 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,302,750Apr 2017 $41,0652025 Amount on Record Jul 2005 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

3 Chester Dr

5 bd · 4 ba · 4,965 sqft · 0.939 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,357,770Dec 2019 $26,3152025 Amount on Record Apr 2018 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

4 Chester Dr

4 bd · 3 ba · 2,700 sqft · 0.63 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,100,000Apr 2017 $19,6102025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5 Chester Dr

4 bd · 3 ba · 3,336 sqft · 1.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,307,000Jul 2023 $60,0892025 Amount on Record Sep 2015 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

6 Chester Dr

4 bd · 2 ba · 2,488 sqft · 0.48 acres

Last Sale Tax Bill Prior Sale Owner Records
$49,6972025 1 Name on Record Owner Occupied AssessorUpdated May 2026

7 Chester Dr

4 bd · 3.5 ba · 2,270 sqft · 0.88 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,055,000Jul 2024 $56,3182025 Amount on Record Mar 2010 2 Names on Record AssessorUpdated May 2026

8 Chester Dr

5 bd · 3 ba · 3,726 sqft · 0.53 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,075,000Jun 2018 $38,5512025 Amount on Record Aug 2015 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

9 Chester Dr

2 bd · 2 ba · 2,912 sqft · 0.589 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,400,000Jul 2024 $61,6812025 Amount on Record Oct 2000 2 Names on Record Assessor + 1 DocumentUpdated May 2026

10 Chester Dr

4 bd · 3 ba · 2,822 sqft · 0.469 acres

Last Sale Tax Bill Prior Sale Owner Records
$51,0382025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

11 Chester Dr

4 bd · 4.5 ba · 4,334 sqft · 0.56 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,260,000Jul 2012 $69,7272025 Amount on Record Sep 2010 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

14 Chester Dr

3 bd · 2.5 ba · 2,583 sqft · 0.53 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,285,100Feb 2022 $43,5372025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

15 Chester Dr

3 bd · 2 ba · 2,609 sqft · 0.48 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,065,000Oct 2012 $48,7752025 Amount on Record Dec 2007 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

16 Chester Dr

6 bd · 3 ba · 3,417 sqft · 0.51 acres

Last Sale Tax Bill Prior Sale Owner Records
$51,4742025 1 Name on Record Owner Occupied AssessorUpdated May 2026

17 Chester Dr

5 bd · 4 ba · 3,652 sqft · 0.469 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,584,000Aug 2016 $45,4232025 Amount on Record Jul 2014 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

18 Chester Dr

2 bd · 2 ba · 2,990 sqft · 0.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$680,000Jul 1998 $49,6132025 Amount on Record Jan 1994 1 Name on Record Owner Occupied AssessorUpdated May 2026

19 Chester Dr

5 bd · 5 ba · 3,471 sqft · 0.489 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$2,750,000Jul 2023 $45,5902025 Amount on Record Jun 2011 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

20 Chester Dr

6 bd · 4.5 ba · 2,885 sqft · 0.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$730,000Mar 2000 $47,0152025 2 Names on Record Owner Occupied AssessorUpdated May 2026

21 Chester Dr

5 bd · 4 ba · 3,810 sqft · 0.48 acres

Last Sale Tax Bill Prior Sale Owner Records
$735,000Oct 2000 $49,9482025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

22 Chester Dr

2 bd · 2 ba · 3,445 sqft · 0.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,190,500Aug 2003 $40,2272025 1 Name on Record Owner Occupied AssessorUpdated May 2026

23 Chester Dr

5 bd · 5 ba · 4,518 sqft · 0.5 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,732,000Jul 2013 $43,2442025 Amount on Record May 2004 2 Names on Record Owner Occupied AssessorUpdated May 2026

24 Chester Dr

5 bd · 4 ba · 3,926 sqft · 0.519 acres

Last Sale Tax Bill Prior Sale Owner Records
$950,000May 2004 $12,6542025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

25 Chester Dr

6 bd · 3 ba · 2,712 sqft · 0.48 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$46,7642025 1 Name on Record AssessorUpdated May 2026

27 Chester Dr

4 bd · 3 ba · 4,772 sqft · 0.48 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,145,000Feb 2005 $49,5292025 2 Names on Record Owner Occupied AssessorUpdated May 2026

29 Chester Dr

4 bd · 3 ba · 3,072 sqft · 0.55 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,300,000Sep 2019 $46,5962025 Amount on Record Sep 2014 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

31 Chester Dr

3 bd · 2 ba · 2,946 sqft · 0.5 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,100,000Nov 2021 $80,7892025 2 Names on Record Assessor + 1 DocumentUpdated May 2026

Wildfire Risk on Chester Dr

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

Wildfire RiskNot rated
no burnable land in reach
Wildfire LikelihoodNegligible
ExposureNone
beyond ember reach of burnable land

Property Records in Nearby Streets