Benson Rd, Middlebury, CT Property Records

Middlebury Town property records for 22 addresses on Benson Rd, Middlebury, CT · Last verified August 2026

Benson Rd Highlights

Properties 22
Median Sale Price $457,000
Deeds and Mortgages on File 22
Median Price per Sqft $211
Owner Occupied 50%
Median Annual Tax Bill $7,938
Median Year Built 1978
Median Ownership Tenure 9 years

Properties on Benson Rd

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

86 Benson Rd

59,400 sqft · Built 1966 · 28.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,000Jul 2011 $43,6222025 1 Name on Record AssessorUpdated Jul 2026

99 Benson Rd

4.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$150,000May 2007 $2,5722025 2 Names on Record AssessorUpdated Jul 2026

149 Benson Rd

2 bd · 1 ba · 1,260 sqft · 5.55 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$6,3772025 1 Name on Record AssessorUpdated Jul 2026

199 Benson Rd

40.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,409,000Apr 2017 $322,3322025 Amount on Record Mar 2004 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

200 Benson Rd

3 ba · 7,100 sqft · 33.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$30,7762025 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

270 Benson Rd

1,360 sqft · Built 1971 · 0.239 acres

Last Sale Tax Bill Prior Sale Owner Records
$75,925Jun 2014 1 Name on Record AssessorUpdated Jul 2026

354 Benson Rd

3 bd · 2.5 ba · 3,598 sqft · 2.85 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$12,1462025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

368 Benson Rd

4 bd · 3.5 ba · 3,164 sqft · 1.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$110,000May 2021 $13,6582025 1 Name on Record Assessor + 5 DocumentsUpdated Aug 2026

384 Benson Rd

3 bd · 2 ba · 1,540 sqft · 0.919 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$326,000Dec 2005 $7,3692025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

394 Benson Rd

3 bd · 2.5 ba · 1,927 sqft · 2.28 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$290,000Oct 2016 $7,1642025 Amount on Record Aug 2015 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

406 Benson Rd

3 bd · 1.5 ba · 1,322 sqft · 3.3 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$280,000Apr 2024 $7,1382025 2 Names on Record Assessor + 1 DocumentUpdated Jul 2026

428 Benson Rd

5 bd · 4 ba · 3,106 sqft · 1.43 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$66,261Mar 2026 $10,4102025 Amount on Record Mar 2025 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

438 Benson Rd

3 bd · 2.5 ba · 1,710 sqft · 2.6 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$175,000Dec 1992 $6,9332025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

443 Benson Rd

4 bd · 2 ba · 1,766 sqft · 5.98 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$7,0602025 1 Name on Record AssessorUpdated Aug 2026

444 Benson Rd

4 bd · 2.5 ba · 1,800 sqft · 4.18 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$175,000Feb 1991 $8,5922025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

452 Benson Rd

3 bd · 2.5 ba · 1,584 sqft · 1.53 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$207,000Jul 2016 $7,9382025 —Jan 2015 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

470 Benson Rd

4 bd · 1 ba · 1,498 sqft · 1.01 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$125,000May 2004 $6,6472025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

513 Benson Rd

3 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jun 2018 $10,7932025 2 Names on Record AssessorUpdated Jul 2026

541 Benson Rd

0.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$465,000Jun 2026 $10,0492025 Amount on Record Feb 2007 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

566 Benson Rd

4 bd · 2.5 ba · 2,020 sqft · 2.48 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$520,000Jul 2026 $8,7932025 Amount on Record Sep 2001 2 Names on Record Assessor + 1 DocumentUpdated Aug 2026

576 Benson Rd

4 bd · 2 ba · 1,294 sqft · 2.48 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$265,000Jun 2017 $6,5332025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

592 Benson Rd

4 bd · 2 ba · 1,518 sqft · 2.16 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$457,000Jul 2023 $7,4802025 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

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