Highland Dr, Middlebury, CT Property Records

Middlebury Town property records for 7 addresses on Highland Dr, Middlebury, CT · Last verified October 2026

Highland Dr Highlights

Properties 7
Median Sale Price $285,000
Deeds and Mortgages on File 5
Median Price per Sqft $230
Owner Occupied 86%
Median Annual Tax Bill $5,782
Median Year Built 1980
Median Ownership Tenure 8 years

Properties on Highland Dr

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

15 Highland Dr

3 bd · 2 ba · 1,130 sqft · built 1980 · 0.919 acres

Last Sale Tax Bill Prior Sale Owner Records
$285,000Jun 2018 $5,2712025 Amount on Record Jan 1992 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

30 Highland Dr

4 bd · 2.5 ba · 2,832 sqft · built 1979 · 0.939 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,6422025 2 Owners on Record AssessorUpdated Oct 2026

37 Highland Dr

3 bd · 2 ba · 1,564 sqft · built 1980 · 0.85 acres

Last Sale Tax Bill Prior Sale Owner Records
$360,000Jul 2022 $6,2052025 Amount on Record Jul 2002 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

50 Highland Dr

2 bd · 1 ba · 1,312 sqft · built 1979 · 1.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,6412025 Owner on Record Owner Occupied AssessorUpdated Oct 2026

55 Highland Dr

3 bd · 1.5 ba · 1,288 sqft · built 1980 · 0.96 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,7822025 2 Owners on Record Owner Occupied AssessorUpdated Oct 2026

63 Highland Dr

3 bd · 1.5 ba · 1,044 sqft · built 1980 · 1.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$235,000Dec 2015 $5,4992025 —Oct 2005 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

64 Highland Dr

3 bd · 2 ba · 1,044 sqft · built 1980 · 0.919 acres

Last Sale Tax Bill Prior Sale Owner Records
$159,800Jun 1998 $5,2032025 Amount on Record Mar 1988 Owner on Record Owner Occupied AssessorUpdated Oct 2026

Property Records in Nearby Streets