Orange County property records for 63 addresses on Chestnut Ave, Winter Park, FL · Last verified August 2026
| Properties | 63 |
|---|---|
| Median Sale Price | $1,040,000 |
| Deeds and Mortgages on File | 98 |
| Median Price per Sqft | $460 |
| Owner Occupied | 62% |
| Median Annual Tax Bill | $8,348 |
| Median Year Built | 1970 |
| Median Ownership Tenure | 5 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
5 bd · 4.5 ba · 3,692 sqft · 0.254 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,200,000Sep 2023 | $30,1182025 | Amount on Record Aug 2015 | 1 Name on Record | Assessor + 4 DocumentsUpdated Aug 2026 |
3 bd · 3 ba · 2,169 sqft · 0.228 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $610,000Jul 2006 | $6,4102025 | Amount on Record May 2002 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
8 bd · 6.25 ba · 5,707 sqft · 0.228 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $100,000Apr 1994 | $11,8202025 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
4 bd · 3 ba · 2,462 sqft · 0.317 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $675,000Jul 2017 | $9,5292025 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
8 bd · 7.25 ba · 6,781 sqft · 0.411 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $305,000Jul 2012 | $16,3022025 | Amount on Record Mar 2012 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
5 bd · 5 ba · 3,425 sqft · 0.225 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $800,000Feb 2011 | $14,6052025 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 1 ba · 1,325 sqft · 0.17 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,8812025 | 1 Name on Record Owner Occupied | AssessorUpdated May 2026 |
2 bd · 1 ba · 1,090 sqft · 0.17 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $560,000Oct 2023 | $8,2622025 | Amount on Record Jul 2023 | 1 Name on Record | Assessor + 1 DocumentUpdated May 2026 |
2 bd · 1.5 ba · 947 sqft · 0.098 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $299,000Jul 2019 | $3,9032025 | Amount on Record Dec 1999 | 1 Name on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
8 bd · 6.25 ba · 7,262 sqft · 0.257 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $750,000Dec 2009 | $10,0892025 | Amount on Record Feb 2007 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 3.5 ba · 1,845 sqft · 0.129 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,095,000Dec 2025 | $7,3092025 | Amount on Record Jun 2017 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated Aug 2026 |
3 bd · 1.5 ba · 1,022 sqft · 0.255 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $348,000May 2008 | $6,2932025 | Amount on Record May 2005 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 1.5 ba · 1,188 sqft · 0.228 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,3782025 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |
2 bd · 1 ba · 1,012 sqft · 0.171 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,7112025 | 1 Name on Record Owner Occupied | AssessorUpdated May 2026 |
5 bd · 4.5 ba · 3,237 sqft · 0.208 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,500,000Mar 2025 | $19,5282025 | Amount on Record Mar 2003 | 1 Name on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
4 bd · 2.5 ba · 2,173 sqft · 0.199 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $750,000Apr 2019 | $10,9182025 | Amount on Record Oct 2017 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
2 bd · 2 ba · 1,275 sqft · 0.171 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $661,000Nov 2025 | $7,1742025 | Amount on Record Jul 2025 | 2 Names on Record | Assessor + 2 DocumentsUpdated May 2026 |
4 bd · 3.5 ba · 2,516 sqft · 0.171 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $327,500May 2019 | $21,6872025 | 1 Name on Record | Assessor + 2 DocumentsUpdated Jul 2026 |
2 bd · 2 ba · 1,209 sqft · 0.149 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $160,000May 2011 | $8,1412025 | 1 Name on Record | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,199 sqft · 0.171 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $160,000Apr 2014 | $7,4572025 | Amount on Record Oct 1997 | 2 Names on Record | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,120 sqft · 0.149 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $104,000Apr 1997 | $8,1722025 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |
8 bd · 6.25 ba · 5,565 sqft · 0.171 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,607,160Aug 2025 | $16,3912025 | Amount on Record Aug 2021 | 2 Names on Record Owner Occupied | Assessor + 5 DocumentsUpdated Jul 2026 |
2 bd · 2 ba · 1,155 sqft · 0.149 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $392,500Feb 2021 | $8,5392025 | Amount on Record Oct 2002 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,298 sqft · 0.257 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $8,1052025 | 2 Names on Record | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,120 sqft · 0.149 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $230,000Feb 2014 | $8,4082025 | Amount on Record Jul 2010 | 2 Names on Record | AssessorUpdated May 2026 |
4 bd · 3 ba · 2,244 sqft · 0.257 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $805,000Aug 2023 | $6,4542025 | Amount on Record Aug 2002 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2 ba · 1,155 sqft · 0.149 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $260,000May 2005 | $8,1452025 | Amount on Record Mar 2005 | 1 Name on Record | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,410 sqft · 0.149 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $606,000Oct 2024 | $9,0392025 | Amount on Record Sep 2021 | 1 Name on Record | Assessor + 2 DocumentsUpdated May 2026 |
4 bd · 2.5 ba · 2,220 sqft · 0.171 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $987,500Jun 2025 | $13,9862025 | Amount on Record Jun 2023 | 1 Name on Record Owner Occupied | Assessor + 3 DocumentsUpdated Jun 2026 |
2 bd · 2.5 ba · 1,804 sqft · 0.149 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $450,000Nov 2015 | $4,6302025 | Amount on Record Jun 2001 | 1 Name on Record Owner Occupied | AssessorUpdated May 2026 |
4 bd · 3 ba · 2,683 sqft · 0.172 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,295,000Apr 2025 | $18,4182025 | Amount on Record Oct 2024 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2.5 ba · 1,878 sqft · 0.149 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $980,000Aug 2025 | $12,4042025 | Amount on Record Apr 2022 | 2 Names on Record Owner Occupied | Assessor + 4 DocumentsUpdated May 2026 |
3 bd · 2 ba · 2,822 sqft · 0.172 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3,5892025 | 2 Names on Record Owner Occupied | AssessorUpdated Jun 2026 |
3 bd · 2 ba · 1,755 sqft · 0.149 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,7212025 | 1 Name on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 2,022 sqft · 0.172 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $190,000Jun 2000 | $3,3112025 | 2 Names on Record | AssessorUpdated May 2026 |
3 bd · 3.5 ba · 2,475 sqft · 0.149 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,690,000Mar 2026 | $17,2622025 | Amount on Record Jun 2021 | 2 Names on Record Owner Occupied | Assessor + 4 DocumentsUpdated May 2026 |
3 bd · 2.5 ba · 1,870 sqft · 0.172 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $350,000Apr 2016 | $8,7892025 | Amount on Record Jul 2013 | 1 Name on Record | AssessorUpdated May 2026 |
3 bd · 4 ba · 2,215 sqft · 0.149 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,360,000Jun 2022 | $20,1832025 | Amount on Record Aug 2019 | 1 Name on Record Owner Occupied | Assessor + 4 DocumentsUpdated May 2026 |
3 bd · 3 ba · 1,750 sqft · 0.172 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $287,550Jun 2026 | $4,2072025 | Amount on Record Aug 2013 | 2 Names on Record | Assessor + 2 DocumentsUpdated Jul 2026 |
3 bd · 2 ba · 2,026 sqft · 0.149 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $189,000Jul 2003 | $4,8532025 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
2 bd · 1 ba · 1,000 sqft · 0.172 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $150,600May 2011 | $7,4912025 | Amount on Record Mar 1994 | 1 Name on Record | AssessorUpdated May 2026 |
8 bd · 7.25 ba · 5,957 sqft · 0.209 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,192,634Jun 2020 | $23,1312025 | Amount on Record Aug 2018 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
4 bd · 4.5 ba · 3,466 sqft · 0.224 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,666,300Aug 2021 | $26,2132025 | Amount on Record Sep 2020 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
5 bd · 2.5 ba · 2,946 sqft · 0.207 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,000,000May 2021 | $14,6302025 | Amount on Record Nov 2007 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 4.5 ba · 2,784 sqft · 0.427 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,600,000Mar 2022 | $16,8882025 | Amount on Record Feb 2020 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
4 bd · 3.5 ba · 2,971 sqft · 0.207 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $90,000Jun 2023 | $8,1162025 | Amount on Record Aug 2013 | 1 Name on Record Owner Occupied | Assessor + 4 DocumentsUpdated May 2026 |
8 bd · 8.25 ba · 6,447 sqft · 0.207 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,075,000Apr 2018 | $22,3052025 | Amount on Record May 2016 | 1 Name on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
12 bd · 9 ba · 8,920 sqft · 0.422 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $4,100,000Apr 2025 | $32,4252025 | 2 Names on Record | Assessor + 2 DocumentsUpdated May 2026 |
4 bd · 2 ba · 1,707 sqft · 0.282 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $8,3482025 | 2 Names on Record | AssessorUpdated May 2026 |
4 bd · 2 ba · 2,288 sqft · 0.363 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,040,000Dec 2025 | $4,3122025 | Amount on Record Jun 1995 | 1 Name on Record | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2 ba · 1,680 sqft · 0.216 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3,0472025 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2.5 ba · 2,608 sqft · 0.265 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,201,000Jun 2026 | $4,8792025 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Jul 2026 |
3 bd · 2 ba · 1,438 sqft · 0.216 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,2922025 | 1 Name on Record Owner Occupied | AssessorUpdated May 2026 |
5 bd · 6 ba · 3,834 sqft · 0.265 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $500,000May 2021 | $25,7162025 | Amount on Record Aug 2019 | 1 Name on Record Owner Occupied | Assessor + 5 DocumentsUpdated May 2026 |
4 bd · 2 ba · 1,501 sqft · 0.216 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $680,000Feb 2024 | $7,6832025 | Amount on Record Jun 2020 | 1 Name on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2 ba · 1,386 sqft · 0.265 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $149,000May 1997 | $7,7982025 | Amount on Record Feb 1994 | 2 Names on Record | AssessorUpdated May 2026 |
4 bd · 4.5 ba · 3,090 sqft · 0.216 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,875,000Dec 2025 | $18,5672025 | Amount on Record Dec 2021 | 2 Names on Record Owner Occupied | Assessor + 5 DocumentsUpdated May 2026 |
3 bd · 2 ba · 1,544 sqft · 0.265 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,6472025 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2 ba · 1,760 sqft · 0.216 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $899,000Dec 2024 | $4002025 | Amount on Record May 2023 | 1 Name on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
3 bd · 3 ba · 1,969 sqft · 0.261 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $835,000Apr 2024 | $11,8522025 | 1 Name on Record | Assessor + 1 DocumentUpdated May 2026 |
5 bd · 4.75 ba · 3,591 sqft · 0.216 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,150,000Sep 2023 | $24,8492025 | Amount on Record Sep 2021 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated Jul 2026 |
4 bd · 6.25 ba · 4,490 sqft · 0.293 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $500,000Mar 2022 | $31,1772025 | —Jul 2021 | 2 Names on Record | Assessor + 3 DocumentsUpdated May 2026 |
4 bd · 3.5 ba · 2,838 sqft · 0.213 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $462,500Nov 2017 | $8,5862025 | Amount on Record Aug 2005 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020
| Wildfire Risk | Low this street's cells rank above 5% of the US · above 4% of Florida |
|---|---|
| Wildfire Likelihood | About 1 in 4,202 per year |
| Exposure | Direct 1 of 5 cells directly exposed · 5 adjoin burnable vegetation |