Chesham Dr, Middlebury, CT Property Records

Middlebury Town property records for 12 addresses on Chesham Dr, Middlebury, CT · Last verified July 2026

Chesham Dr Highlights

Properties 12
Median Sale Price $450,000
Deeds and Mortgages on File 14
Median Price per Sqft $202
Owner Occupied 67%
Median Annual Tax Bill $11,389
Median Year Built 1955
Median Ownership Tenure 10 years

Properties on Chesham Dr

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

36 Chesham Dr

3 bd · 3.5 ba · 2,692 sqft · built 1956 · 7.58 acres

Last Sale Tax Bill Prior Sale Owner Records
$713,350Jan 2020 $12,5492025 —Dec 2018 2 Names on Record Assessor + 2 DocumentsUpdated Jul 2026

49 Chesham Dr

2 bd · 1.5 ba · 1,296 sqft · built 1950 · 2 acres

Last Sale Tax Bill Prior Sale Owner Records
$160,000Sep 1998 $8,0362025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

58 Chesham Dr

1.88 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,000Jun 2025 $3,2592025 2 Names on Record Assessor + 2 DocumentsUpdated Jul 2026

92 Chesham Dr

3 bd · 3.5 ba · 3,069 sqft · built 2009 · 3.78 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,250,000Dec 2023 $23,0632025 Amount on Record Jun 1994 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

109 Chesham Dr

5 bd · 4 ba · 4,552 sqft · built 1957 · 3.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$450,000Jun 2016 $11,2842025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

114 Chesham Dr

3 bd · 3 ba · 2,738 sqft · built 1952 · 3.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$206,946Dec 2021 $4,1012025 Amount on Record Apr 2021 2 Names on Record Assessor + 3 DocumentsUpdated Jul 2026

150 Chesham Dr

4 bd · 3.5 ba · 2,185 sqft · built 1955 · 1.98 acres

Last Sale Tax Bill Prior Sale Owner Records
$295,000Sep 2016 $11,3892025 2 Names on Record AssessorUpdated Jul 2026

161 Chesham Dr

2 bd · 3 ba · 2,024 sqft · built 1955 · 3.98 acres

Last Sale Tax Bill Prior Sale Owner Records
$410,000Jul 2016 $11,0182025 Amount on Record May 1998 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

180 Chesham Dr

3 bd · 2.5 ba · 2,622 sqft · built 1965 · 4.31 acres

Last Sale Tax Bill Prior Sale Owner Records
$17,121Nov 1998 $14,2992025 Amount on Record Jul 1996 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

182 Chesham Dr

2 bd · 1 ba · 1,277 sqft · built 1913 · 2.08 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,6472025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

195 Chesham Dr

3 bd · 3 ba · 2,185 sqft · built 1955 · 3.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$580,000Jun 2021 $12,7322025 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

197 Chesham Dr

4 bd · 4 ba · 5,164 sqft · built 1915 · 4.41 acres

Last Sale Tax Bill Prior Sale Owner Records
$500,000Dec 1998 $15,0862025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

Wildfire Risk on Chesham Dr

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

Wildfire RiskLow
this street's cells rank above 20% of the US · above 55% of Connecticut
Wildfire LikelihoodAbout 1 in 5,000 per year
ExposureDirect
3 of 3 cells directly exposed · 3 adjoin burnable vegetation

Property Records in Nearby Streets