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Douglas Way, Winter Garden, FL Property Records

Orange County property records for 42 addresses on Douglas Way, Winter Garden, FL · Last verified October 2026

Douglas Way Highlights

Properties 42
Median Sale Price $210,000
Deeds and Mortgages on File 50
Median Price per Sqft $225
Owner Occupied 21%
Median Annual Tax Bill $2,408
Median Year Built 1988
Median Ownership Tenure 8 years

Properties on Douglas Way

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

302 Douglas Way, #91

2 bd · 2.25 ba · 930 sqft · built 1989 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$47,000May 1997 $2432025 Amount on Record Jul 1993 2 Owners on Record AssessorUpdated May 2026

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306 Douglas Way, #92

2 bd · 2.25 ba · 930 sqft · built 1989 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$59,000Mar 2003 $1042025 Amount on Record Jun 1994 Owner on Record AssessorUpdated May 2026

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310 Douglas Way, #89

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$115,000Mar 2018 $3,0452025 Amount on Record Sep 2011 Owner on Record Assessor + 2 DocumentsUpdated Sep 2026

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314 Douglas Way, #90

2 bd · 2.25 ba · 930 sqft · built 1989 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$34,500Sep 2009 $2,4082025 Amount on Record Jul 2009 Owner on Record Owner Occupied AssessorUpdated Sep 2026

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318 Douglas Way, Unit 87

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$210,000Jul 2023 $3,2242025 Amount on Record Apr 2016 2 Owners on Record AssessorUpdated May 2026

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322 Douglas Way, #88

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,000Apr 2024 $2,1852025 Amount on Record Jul 2015 Owner on Record Assessor + 2 DocumentsUpdated May 2026

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326 Douglas Way, #86

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,4082025 2 Owners on Record AssessorUpdated May 2026

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330 Douglas Way, #85

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$195,000Sep 2021 $3,1382025 Amount on Record Jan 2020 2 Owners on Record Assessor + 3 DocumentsUpdated May 2026

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338 Douglas Way, #83

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$200,000Mar 2022 $3,2242025 Amount on Record Apr 2007 2 Owners on Record Assessor + 1 DocumentUpdated May 2026

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340 Douglas Way, #84

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$210,000Feb 2024 $3,3102025 2 Owners on Record Assessor + 1 DocumentUpdated May 2026

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342 Douglas Way, #82

2 bd · 2.25 ba · 930 sqft · built 1989 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$32,500Feb 2017 $2432025 —Jul 1993 Owner on Record Assessor + 1 DocumentUpdated May 2026

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346 Douglas Way, #81

2 bd · 2.25 ba · 930 sqft · built 1989 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$58,000Feb 2002 $2432025 Owner on Record AssessorUpdated May 2026

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347 Douglas Way, #51

2 bd · 2.25 ba · 930 sqft · built 1987 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$69,000Jan 2016 $2,6492025 Amount on Record Jan 2016 2 Owners on Record AssessorUpdated May 2026

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350 Douglas Way, #80

2 bd · 2.25 ba · 930 sqft · built 1989 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$225,000Mar 2023 $2,3022025 Amount on Record Jun 2000 Owner on Record Assessor + 1 DocumentUpdated May 2026

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351 Douglas Way, #52

2 bd · 2.25 ba · 930 sqft · built 1987 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$2432025 2 Owners on Record AssessorUpdated May 2026

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354 Douglas Way, #79

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$49,000Jan 1999 $2432025 Owner on Record Assessor + 3 DocumentsUpdated May 2026

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355 Douglas Way, Apt 53

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$210,000Dec 2025 $3,2242025 Amount on Record Sep 2022 Owner on Record Assessor + 3 DocumentsUpdated May 2026

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358 Douglas Way, #78

2 bd · 2.25 ba · 930 sqft · built 1989 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$187,000Sep 2025 $2432025 Amount on Record Mar 1996 2 Owners on Record Assessor + 1 DocumentUpdated May 2026

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359 Douglas Way, #54

2 bd · 2.25 ba · 930 sqft · built 1989 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$245,000Mar 2024 $3,3102025 Amount on Record Dec 2018 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

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362 Douglas Way, #77

2 bd · 2.25 ba · 930 sqft · built 1989 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$151,000Nov 2020 $3,1202025 Amount on Record May 2008 Owner on Record Assessor + 2 DocumentsUpdated Oct 2026

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363 Douglas Way, #55

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$110,000May 2017 $2,6492025 Amount on Record Jan 2014 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

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366 Douglas Way, #76

2 bd · 2.25 ba · 930 sqft · built 1989 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$55,900Sep 2000 $2432025 Amount on Record Jul 2000 Owner on Record AssessorUpdated May 2026

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367 Douglas Way, #56

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$156,000Jul 2020 $1,6402025 Amount on Record Oct 2005 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

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370 Douglas Way, #75

2 bd · 2.25 ba · 930 sqft · built 1989 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$52,000Jan 2000 $2432025 —Nov 1994 2 Owners on Record AssessorUpdated May 2026

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371 Douglas Way, #58

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$165,000Sep 2021 $3,1382025 Amount on Record Jun 2015 Owner on Record Assessor + 1 DocumentUpdated May 2026

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375 Douglas Way, #57

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$239,400Apr 2023 $2,3022025 Amount on Record Feb 2023 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

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376 Douglas Way, #73

2 bd · 2.25 ba · 930 sqft · built 1989 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$40,000Dec 2011 $3,1202025 —Nov 2011 Owner on Record Assessor + 1 DocumentUpdated Sep 2026

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378 Douglas Way, #74

2 bd · 2.25 ba · 930 sqft · built 1989 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$42,400Jun 2012 $3,1202025 Amount on Record Feb 2012 Owner on Record Assessor + 1 DocumentUpdated Sep 2026

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379 Douglas Way, #60

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$63,000Dec 2002 $2432025 Owner on Record AssessorUpdated May 2026

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383 Douglas Way, #59

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$117,500Sep 2018 $1,2302025 Amount on Record Oct 1994 Owner on Record Assessor + 2 DocumentsUpdated May 2026

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387 Douglas Way, #62

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$100Dec 1995 $3,2242025 Amount on Record Feb 1995 2 Owners on Record AssessorUpdated Sep 2026

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389 Douglas Way, #61

2 bd · 2.25 ba · 930 sqft · built 1987 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$130,000Nov 2018 $1,2302025 Amount on Record Jan 2010 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

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390 Douglas Way, #71

2 bd · 2.25 ba · 930 sqft · built 1989 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$125,000May 2019 $3,0492025 2 Owners on Record Assessor + 1 DocumentUpdated May 2026

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394 Douglas Way, #72

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$232,000Oct 2022 $2,3022025 Amount on Record Jan 2014 Owner on Record Assessor + 1 DocumentUpdated May 2026

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395 Douglas Way, #64

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$235,000Jun 2023 $2,3022025 Amount on Record Aug 1996 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

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398 Douglas Way, #69

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$250,000Mar 2024 $3,3102025 Amount on Record Sep 2021 2 Owners on Record Assessor + 3 DocumentsUpdated May 2026

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399 Douglas Way, #63

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$250,000May 2022 $2,3022025 Amount on Record Jan 2021 Owner on Record Owner Occupied Assessor + 6 DocumentsUpdated May 2026

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402 Douglas Way, #70

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$91,000Apr 2005 $2,4082025 Amount on Record Jun 2001 2 Owners on Record AssessorUpdated May 2026

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403 Douglas Way, #65

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$100Mar 2017 $2,4812025 —Oct 2015 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

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406 Douglas Way, #67

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$2432025 Owner on Record AssessorUpdated May 2026

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407 Douglas Way, #66

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$44,000Apr 2013 $2,4812025 Amount on Record Dec 2005 Owner on Record Assessor + 1 DocumentUpdated Oct 2026

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410 Douglas Way, #68

2 bd · 2.25 ba · 930 sqft · built 1988 · 0.021 acres

Last Sale Tax Bill Prior Sale Owner Records
$15,000Sep 2007 $2432025 Amount on Record Jun 2003 Owner on Record Assessor + 1 DocumentUpdated May 2026

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Property Records in Nearby Streets