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Middlebury Dr, Sunnyvale, CA Property Records

Santa Clara County property records for 34 addresses on Middlebury Dr, Sunnyvale, CA · Last verified October 2026

Middlebury Dr Highlights

Properties 34
Median Sale Price $2,739,000
Deeds and Mortgages on File 50
Median Price per Sqft $1,030
Owner Occupied 91%
Median Annual Tax Bill $18,407
Median Year Built 2001
Median Ownership Tenure 20 years

Properties on Middlebury Dr

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

524 Middlebury Dr

5 bd · 3 ba · 2,945 sqft · built 2001 · 0.153 acres

Last Sale Tax Bill Prior Sale Owner Records
$979,000Jan 2002 $17,2042025 —Jan 2002 Owner on Record Assessor + 1 DocumentUpdated Oct 2026

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528 Middlebury Dr

5 bd · 3 ba · 2,945 sqft · built 2001 · 0.153 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,739,000Apr 2019 $36,0462025 Amount on Record Oct 2003 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

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529 Middlebury Dr

4 bd · 3 ba · 3,157 sqft · built 2001 · 0.153 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,700,000Apr 2025 $10,5792025 Amount on Record Aug 2006 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

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532 Middlebury Dr

5 bd · 3 ba · 2,805 sqft · built 2001 · 0.153 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,050,000Dec 2011 $15,6302025 Amount on Record Jun 2001 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

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533 Middlebury Dr

5 bd · 3 ba · 2,945 sqft · built 2001 · 0.153 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,200,000Nov 2009 $18,4072025 Amount on Record Nov 2001 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

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536 Middlebury Dr

4 bd · 3 ba · 3,157 sqft · built 2001 · 0.153 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,100,000Nov 2001 $19,2162025 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

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537 Middlebury Dr

5 bd · 3 ba · 2,805 sqft · built 2001 · 0.153 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,500,000Sep 2007 $23,2582025 Amount on Record May 2001 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

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540 Middlebury Dr

5 bd · 3 ba · 2,945 sqft · built 2001 · 0.153 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,130,000Sep 2003 $19,0002025 —Sep 2003 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

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541 Middlebury Dr

4 bd · 3 ba · 3,157 sqft · built 2001 · 0.153 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,250,000Jul 2021 $40,5742025 Amount on Record Jun 2021 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Oct 2026

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544 Middlebury Dr

5 bd · 3 ba · 2,805 sqft · built 2001 · 0.153 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,268,000Mar 2001 $22,5612025 2 Owners on Record Owner Occupied AssessorUpdated Oct 2026

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545 Middlebury Dr

5 bd · 3 ba · 2,945 sqft · built 2001 · 0.153 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,446,000May 2001 $41,7262025 —Jul 2020 Owner on Record Owner Occupied Assessor + 7 DocumentsUpdated Oct 2026

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548 Middlebury Dr

5 bd · 3 ba · 3,157 sqft · built 2001 · 0.153 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,466,000May 2001 $26,1362025 —May 2012 Owner on Record AssessorUpdated Oct 2026

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549 Middlebury Dr

5 bd · 3 ba · 2,805 sqft · built 2001 · 0.153 acres

Last Sale Tax Bill Prior Sale Owner Records
—Dec 2002 $18,1602025 Owner on Record Owner Occupied AssessorUpdated Aug 2026

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551 Middlebury Dr

4 bd · 3 ba · 3,157 sqft · built 2001 · 0.153 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,500,000Aug 2017 $33,4972025 Amount on Record Apr 2001 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

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552 Middlebury Dr

5 bd · 3 ba · 2,945 sqft · built 2001 · 0.153 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,280,000Jun 2010 $19,6432025 Amount on Record Jan 2002 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Oct 2026

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556 Middlebury Dr

5 bd · 3 ba · 2,805 sqft · built 2001 · 0.153 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,328,000Jun 2004 $22,2972025 —Apr 2001 2 Owners on Record Owner Occupied AssessorUpdated Oct 2026

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559 Middlebury Dr

5 bd · 3 ba · 2,639 sqft · built 2001 · 0.153 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,183,000Apr 2001 $21,0612025 2 Owners on Record Owner Occupied AssessorUpdated Oct 2026

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560 Middlebury Dr

2 bd · 2.5 ba · 2,079 sqft · built 1968 · 0.152 acres

Last Sale Tax Bill Prior Sale Owner Records
$280,000Jul 2005 $11,7832025 —Jul 2005 Owner on Record Owner Occupied AssessorUpdated Aug 2026

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561 Middlebury Dr

4 bd · 2 ba · 1,856 sqft · built 1968 · 0.162 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,680,000Oct 2023 $32,2792025 —Jul 2022 2 Owners on Record Owner Occupied Assessor + 11 DocumentsUpdated Aug 2026

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564 Middlebury Dr

5 bd · 2.5 ba · 2,250 sqft · built 1968 · 0.148 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,032,000Mar 2001 $18,4782025 —Jun 2000 2 Owners on Record Owner Occupied AssessorUpdated Oct 2026

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565 Middlebury Dr

3 bd · 2 ba · 1,699 sqft · built 1968 · 0.139 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,2102025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

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568 Middlebury Dr

3 bd · 2.5 ba · 2,079 sqft · built 1966 · 0.143 acres

Last Sale Tax Bill Prior Sale Owner Records
$449,000Jul 1989 $9,7622025 —Jan 2013 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

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569 Middlebury Dr

4 bd · 2.5 ba · 3,186 sqft · built 1968 · 0.166 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,050,000Aug 2001 $18,3512025 —Oct 2003 Owner on Record Owner Occupied AssessorUpdated Oct 2026

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572 Middlebury Dr

4 bd · 4.5 ba · 2,178 sqft · built 1968 · 0.139 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,700,000Aug 2021 $33,8212025 Amount on Record Nov 2012 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

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573 Middlebury Dr

6 bd · 2.5 ba · 2,388 sqft · built 1967 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 2006 $1,9092025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

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576 Middlebury Dr

6 bd · 2.5 ba · 2,388 sqft · built 1967 · 0.141 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,9092025 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

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580 Middlebury Dr

4 bd · 2.5 ba · 2,178 sqft · built 1968 · 0.141 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,200,000Aug 2020 $28,0562025 —Jul 2008 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

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584 Middlebury Dr

3 bd · 2 ba · 1,699 sqft · built 1968 · 0.141 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,6202025 2 Owners on Record AssessorUpdated Aug 2026

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587 Middlebury Dr

4 bd · 2.5 ba · 2,178 sqft · built 1968 · 0.123 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,205,000Oct 2012 $17,6442025 Amount on Record Jul 2012 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

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588 Middlebury Dr

4 bd · 2.5 ba · 2,149 sqft · built 1968 · 0.141 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,8832025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

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591 Middlebury Dr

3 bd · 2.5 ba · 2,079 sqft · built 1968 · 0.149 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,6692025 —May 1998 Owner on Record Owner Occupied AssessorUpdated Aug 2026

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592 Middlebury Dr

4 bd · 2.5 ba · 2,178 sqft · built 1968 · 0.141 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,8232025 Owner on Record Owner Occupied AssessorUpdated Aug 2026

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595 Middlebury Dr

3 bd · 2 ba · 1,699 sqft · built 1968 · 0.123 acres

Last Sale Tax Bill Prior Sale Owner Records
$750,000Jul 2003 $12,6732025 —Oct 2005 2 Owners on Record Owner Occupied AssessorUpdated Oct 2026

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596 Middlebury Dr

3 bd · 2.5 ba · 2,322 sqft · built 1966 · 0.148 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,2862025 —Jul 2009 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

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Property Records in Nearby Streets