Roxbury Rd, Winter Park, FL Property Records

Orange County property records for 73 addresses on Roxbury Rd, Winter Park, FL · Last verified August 2026

Roxbury Rd Highlights

Properties 73
Median Sale Price $350,000
Deeds and Mortgages on File 65
Median Price per Sqft $271
Owner Occupied 56%
Median Annual Tax Bill $3,786
Median Year Built 1953
Median Ownership Tenure 9 years

Properties on Roxbury Rd

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

2299 Roxbury Rd

0.159 acres

Last Sale Tax Bill Prior Sale Owner Records
2 Names on Record AssessorUpdated May 2026

2300 Roxbury Rd

3 bd · 2.5 ba · 2,292 sqft · 0.323 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$6,2452025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

2321 Roxbury Rd

3 bd · 2 ba · 1,956 sqft · 0.224 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$100Dec 1996 $3,6142025 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

2332 Roxbury Rd

3 bd · 2 ba · 1,538 sqft · 0.323 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$169,000Mar 2001 $5,7662025 1 Name on Record AssessorUpdated May 2026

2336 Roxbury Rd

0.257 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,4752025 1 Name on Record AssessorUpdated May 2026

2340 Roxbury Rd

2 bd · 2 ba · 1,582 sqft · 0.545 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$108,800Nov 2013 $3,7342025 1 Name on Record AssessorUpdated May 2026

2341 Roxbury Rd

6 bd · 4.25 ba · 3,874 sqft · 0.237 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$6,6142025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2346 Roxbury Rd

2 bd · 1 ba · 1,248 sqft · 0.257 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,5572025 1 Name on Record AssessorUpdated May 2026

2352 Roxbury Rd

2 bd · 1 ba · 1,176 sqft · 0.381 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$275,000Jul 2017 $2,8752025 Amount on Record Feb 2014 1 Name on Record Assessor + 3 DocumentsUpdated May 2026

2358 Roxbury Rd

2 bd · 2 ba · 1,564 sqft · 0.381 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$90,300Apr 2012 $4,2212025 1 Name on Record AssessorUpdated May 2026

2361 Roxbury Rd

3 bd · 2 ba · 1,723 sqft · 0.275 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$115,500Aug 1997 $2,1842025 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

2381 Roxbury Rd

3 bd · 1.5 ba · 1,476 sqft · 0.275 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$470,000Dec 2025 $2,1622025 —Aug 2002 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

2400 Roxbury Rd

4 bd · 3.5 ba · 3,093 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$997,500Jan 2024 $11,2282025 2 Names on Record Assessor + 1 DocumentUpdated May 2026

2401 Roxbury Rd

3 bd · 1 ba · 1,066 sqft · 0.275 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,4562025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2421 Roxbury Rd

3 bd · 2 ba · 1,082 sqft · 0.275 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$4,6692025 2 Names on Record AssessorUpdated May 2026

2430 Roxbury Rd

4 bd · 3 ba · 3,089 sqft · 0.467 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$969,000Feb 2024 $14,4122025 Amount on Record Dec 2013 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

2440 Roxbury Rd

3 bd · 2 ba · 1,456 sqft · 0.325 acres

Last Sale Tax Bill Prior Sale Owner Records
$350,000Nov 2021 $5,9752025 Amount on Record Apr 2015 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2441 Roxbury Rd

2 bd · 1 ba · 1,253 sqft · 0.275 acres

Last Sale Tax Bill Prior Sale Owner Records
—May 2016 $2,2472025 Amount on Record May 2016 2 Names on Record AssessorUpdated Aug 2026

2450 Roxbury Rd

2 bd · 1 ba · 986 sqft · 0.239 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$265,000Jun 2022 $3,7552025 Amount on Record Dec 2001 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2461 Roxbury Rd

5 bd · 2 ba · 1,910 sqft · 0.275 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$132,000May 2011 $3,8302025 Amount on Record May 2006 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

2481 Roxbury Rd

4 bd · 2 ba · 1,253 sqft · 0.275 acres

Last Sale Tax Bill Prior Sale Owner Records
$24,200Jan 2004 $4,7242025 —Aug 2003 1 Name on Record AssessorUpdated May 2026

2482 Roxbury Rd

2 bd · 1 ba · 873 sqft · 0.239 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$130,100Jun 2010 $5,4832025 Amount on Record Sep 2001 2 Names on Record AssessorUpdated Aug 2026

2500 Roxbury Rd

3 bd · 1.5 ba · 1,413 sqft · 0.31 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$5,0672025 1 Name on Record AssessorUpdated May 2026

2501 Roxbury Rd

2 bd · 1 ba · 813 sqft · 0.197 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$180,000Sep 2019 $4,1132025 Amount on Record Jan 1996 2 Names on Record Assessor + 2 DocumentsUpdated May 2026

2512 Roxbury Rd

4 bd · 2 ba · 2,393 sqft · 0.285 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$421,000Mar 2021 $9,2382025 Amount on Record Oct 1995 2 Names on Record Assessor + 1 DocumentUpdated May 2026

2519 Roxbury Rd

2 bd · 1 ba · 805 sqft · 0.197 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$21,900Apr 1996 $1,7142025 Amount on Record — 1 Name on Record Owner Occupied AssessorUpdated May 2026

2520 Roxbury Rd

2 bd · 1 ba · 825 sqft · 0.298 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$320,000Apr 2024 $4,7862025 1 Name on Record AssessorUpdated May 2026

2521 Roxbury Rd

2 bd · 1 ba · 1,079 sqft · 0.197 acres

Last Sale Tax Bill Prior Sale Owner Records
$335,000Apr 2022 $4,2402025 Amount on Record Mar 2005 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2524 Roxbury Rd

4 bd · 2.5 ba · 3,257 sqft · 0.298 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$453,100Jun 2018 $7,7832025 Amount on Record May 2002 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Jun 2026

2526 Roxbury Rd

2 bd · 1 ba · 1,276 sqft · 0.199 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$300,000Sep 2023 $4,1412025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

2531 Roxbury Rd

2 bd · 1 ba · 935 sqft · 0.197 acres

Last Sale Tax Bill Prior Sale Owner Records
$50,000Jun 2013 $3,5902025 2 Names on Record Owner Occupied AssessorUpdated May 2026

2541 Roxbury Rd

3 bd · 2 ba · 1,210 sqft · 0.197 acres

Last Sale Tax Bill Prior Sale Owner Records
$375,000Aug 2024 $4,9882025 Amount on Record Jul 2018 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

2551 Roxbury Rd

3 bd · 1 ba · 977 sqft · 0.197 acres

Last Sale Tax Bill Prior Sale Owner Records
$239,000Jun 2018 $4,8912025 Amount on Record Sep 2013 1 Name on Record Assessor + 1 DocumentUpdated May 2026

2561 Roxbury Rd

2 bd · 1 ba · 890 sqft · 0.197 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$305,000Aug 2022 $4,4532025 Amount on Record Jan 2013 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

2601 Roxbury Rd

4 bd · 2 ba · 1,964 sqft · 0.197 acres

Last Sale Tax Bill Prior Sale Owner Records
$140,000May 2012 $2,4172025 Amount on Record Jan 2004 2 Names on Record Owner Occupied AssessorUpdated May 2026

2611 Roxbury Rd

3 bd · 2 ba · 2,116 sqft · 0.197 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Aug 2011 $4,8542025 Amount on Record Oct 2010 2 Names on Record AssessorUpdated May 2026

2612 Roxbury Rd

3 bd · 2 ba · 2,472 sqft · 0.199 acres

Last Sale Tax Bill Prior Sale Owner Records
$425,000Jan 2024 $6,7242025 1 Name on Record Assessor + 3 DocumentsUpdated May 2026

2618 Roxbury Rd

4 bd · 2 ba · 2,184 sqft · 0.199 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$5,4502025 2 Names on Record AssessorUpdated May 2026

2631 Roxbury Rd

3 bd · 2 ba · 1,742 sqft · 0.197 acres

Last Sale Tax Bill Prior Sale Owner Records
$425,000Dec 2021 $8,0782025 Amount on Record May 2015 1 Name on Record Assessor + 1 DocumentUpdated May 2026

2641 Roxbury Rd

2 bd · 1 ba · 1,518 sqft · 0.197 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$78,800Sep 1999 $1,8832025 1 Name on Record Owner Occupied AssessorUpdated May 2026

2646 Roxbury Rd

2 bd · 1 ba · 1,030 sqft · 0.199 acres

Last Sale Tax Bill Prior Sale Owner Records
$189,000Jul 2005 Amount on Record Jan 2005 1 Name on Record AssessorUpdated May 2026

2654 Roxbury Rd

2 bd · 2 ba · 625 sqft · 0.199 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$170,000Feb 2021 $3,6912025 Amount on Record Feb 2010 1 Name on Record Assessor + 2 DocumentsUpdated May 2026

2658 Roxbury Rd

2 bd · 1 ba · 1,148 sqft · 0.199 acres

Last Sale Tax Bill Prior Sale Owner Records
$135,000Mar 2003 Amount on Record Dec 2002 1 Name on Record AssessorUpdated May 2026

2659 Roxbury Rd

2 bd · 1 ba · 1,174 sqft · 0.215 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,3672025 1 Name on Record Owner Occupied AssessorUpdated May 2026

2660 Roxbury Rd

3 bd · 1 ba · 1,298 sqft · 0.254 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
1 Name on Record AssessorUpdated May 2026

2667 Roxbury Rd

3 bd · 1 ba · 1,008 sqft · 0.173 acres

Last Sale Tax Bill Prior Sale Owner Records
1 Name on Record AssessorUpdated May 2026

2816 Roxbury Rd

3 bd · 1 ba · 1,075 sqft · 0.212 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,7862025 1 Name on Record Assessor + 1 DocumentUpdated May 2026

2819 Roxbury Rd

3 bd · 1 ba · 1,207 sqft · 0.254 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$33,800May 2002 $1,0862025 Amount on Record Feb 1999 1 Name on Record Owner Occupied AssessorUpdated May 2026

2822 Roxbury Rd

3 bd · 2 ba · 1,595 sqft · 0.223 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$133,800Oct 2003 $1,5672025 Amount on Record Feb 1996 1 Name on Record Owner Occupied AssessorUpdated May 2026

2825 Roxbury Rd

2 bd · 1.5 ba · 1,261 sqft · 0.194 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$265,000May 2021 $4,0002025 Amount on Record Jun 2009 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2826 Roxbury Rd

3 bd · 1 ba · 1,675 sqft · 0.184 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$215,000May 2005 $1,3982025 Amount on Record Mar 2004 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2828 Roxbury Rd

4 bd · 2 ba · 2,189 sqft · 0.184 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,9772025 1 Name on Record Owner Occupied AssessorUpdated May 2026

2831 Roxbury Rd

3 bd · 2 ba · 1,535 sqft · 0.194 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,5802025 1 Name on Record Owner Occupied AssessorUpdated May 2026

2834 Roxbury Rd

2 bd · 1 ba · 1,332 sqft · 0.214 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$355,000Aug 2022 $4,1272025 Amount on Record Apr 2021 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

2837 Roxbury Rd

3 bd · 1.5 ba · 1,530 sqft · 0.194 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,4322025 1 Name on Record Owner Occupied AssessorUpdated May 2026

2843 Roxbury Rd

3 bd · 2.5 ba · 1,405 sqft · 0.194 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,3112025 2 Names on Record Owner Occupied AssessorUpdated May 2026

2844 Roxbury Rd

2 bd · 2 ba · 1,333 sqft · 0.208 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$90,000Nov 1998 $1,4402025 Amount on Record Oct 1995 1 Name on Record Owner Occupied AssessorUpdated May 2026

2849 Roxbury Rd

3 bd · 1.5 ba · 1,468 sqft · 0.194 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,2492025 1 Name on Record Owner Occupied AssessorUpdated May 2026

2850 Roxbury Rd

3 bd · 2 ba · 1,206 sqft · 0.208 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$8552025 2 Names on Record AssessorUpdated May 2026

2855 Roxbury Rd

3 bd · 1 ba · 1,139 sqft · 0.194 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$38,700Dec 2002 $1,1162025 Amount on Record Oct 1999 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2856 Roxbury Rd

3 bd · 2.5 ba · 1,235 sqft · 0.21 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,0542025 1 Name on Record Owner Occupied AssessorUpdated May 2026

2861 Roxbury Rd

3 bd · 2 ba · 1,850 sqft · 0.194 acres

Last Sale Tax Bill Prior Sale Owner Records
$257,000Oct 2017 $4,2652025 Amount on Record Apr 2017 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated May 2026

2862 Roxbury Rd

2 bd · 1 ba · 1,384 sqft · 0.244 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,2742025 1 Name on Record AssessorUpdated May 2026

2867 Roxbury Rd

3 bd · 2 ba · 1,465 sqft · 0.194 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Feb 2002 $4,9912025 1 Name on Record AssessorUpdated May 2026

2868 Roxbury Rd

4 bd · 2.5 ba · 1,572 sqft · 0.244 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$132,000Apr 2015 $1,1692025 Amount on Record Jan 2003 2 Names on Record Owner Occupied AssessorUpdated May 2026

2873 Roxbury Rd

4 bd · 3 ba · 2,073 sqft · 0.194 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,9772025 1 Name on Record Owner Occupied AssessorUpdated May 2026

2874 Roxbury Rd

3 bd · 2 ba · 1,328 sqft · 0.244 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,1242025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2879 Roxbury Rd

3 bd · 2 ba · 1,231 sqft · 0.194 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$78,500Jan 1998 $1,2292025 2 Names on Record Owner Occupied AssessorUpdated May 2026

2880 Roxbury Rd

2 bd · 1 ba · 1,288 sqft · 0.244 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$283,500Mar 2021 $4,1412025 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

2885 Roxbury Rd

3 bd · 1 ba · 1,460 sqft · 0.194 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$310,000Feb 2020 $2,3792025 Amount on Record Jul 2019 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated May 2026

2886 Roxbury Rd

3 bd · 1 ba · 1,162 sqft · 0.244 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$316,000Feb 2025 $4,8832025 Amount on Record Jan 2021 1 Name on Record Assessor + 2 DocumentsUpdated May 2026

2891 Roxbury Rd

3 bd · 1.5 ba · 1,375 sqft · 0.221 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$400,000May 2024 $4,7952025 —Oct 2014 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

2892 Roxbury Rd

3 bd · 1.5 ba · 1,456 sqft · 0.28 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$257,500Mar 2006 $1,5862025 Amount on Record Jun 2001 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

Wildfire Risk on Roxbury Rd

Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020

Wildfire RiskLow
this street's cells rank above 2% of the US · above 2% of Florida
Wildfire LikelihoodLess than 1 in 10,000 per year
ExposureDirect
2 of 7 cells directly exposed · 6 adjoin burnable vegetation

Property Records in Nearby Streets