Wintergreen Dr, Chesapeake, VA Property Records

Chesapeake City property records for 29 addresses on Wintergreen Dr, Chesapeake, VA · Last verified August 2026

Wintergreen Dr Highlights

Properties 29
Median Sale Price $245,000
Deeds and Mortgages on File 36
Median Price per Sqft $197
Owner Occupied 97%
Median Annual Tax Bill $2,727
Median Year Built 1954
Median Ownership Tenure 10 years

Properties on Wintergreen Dr

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

2100 Wintergreen Dr

4 bd · 2 ba · 1,596 sqft · 0.408 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$341,000Jul 2024 $3,2942025 Amount on Record Nov 2021 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

2101 Wintergreen Dr

3 bd · 1.5 ba · 1,544 sqft · 0.371 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$109,500May 2002 $2,7372025 —Oct 2017 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jun 2026

2205 Wintergreen Dr

3 bd · 2.5 ba · 1,150 sqft · 0.289 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$207,000Jun 2016 $2,7512025 Amount on Record Dec 2015 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

2208 Wintergreen Dr

3 bd · 1.5 ba · 1,464 sqft · 0.276 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$70,000Mar 1989 $2,7272025 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

2209 Wintergreen Dr

2 bd · 1 ba · 975 sqft · 0.266 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$247,000Jun 2026 $7062025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

2212 Wintergreen Dr

3 bd · 1 ba · 936 sqft · 0.253 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$82,000Sep 2003 $2,1572025 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

2213 Wintergreen Dr

3 bd · 1 ba · 1,048 sqft · 0.266 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$144,000Jun 2014 $2,2952025 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

2216 Wintergreen Dr

3 bd · 1 ba · 1,104 sqft · 0.267 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$114,000Dec 2002 $2,2922025 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

2217 Wintergreen Dr

3 bd · 1.5 ba · 1,222 sqft · 0.275 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$192,500Dec 2016 $2,6942025 Amount on Record Jan 2014 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

2220 Wintergreen Dr

4 bd · 2 ba · 1,767 sqft · 0.223 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$226,557Oct 2019 $3,3002025 Amount on Record May 2017 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

2221 Wintergreen Dr

3 bd · 1 ba · 1,344 sqft · 0.271 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$150,000May 2011 $2,4022025 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

2224 Wintergreen Dr

4 bd · 1 ba · 1,984 sqft · 0.339 acres

Last Sale Tax Bill Prior Sale Owner Records
$14,600Jun 1969 $2,8062025 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

2225 Wintergreen Dr

3 bd · 1 ba · 1,112 sqft · 0.287 acres

Last Sale Tax Bill Prior Sale Owner Records
$239,000Apr 2025 $2,3472025 Amount on Record Jan 2022 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

2300 Wintergreen Dr

4 bd · 2 ba · 2,059 sqft · 0.332 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$88,500Dec 2000 $2,9422025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

2301 Wintergreen Dr

4 bd · 1 ba · 1,528 sqft · 0.407 acres

Last Sale Tax Bill Prior Sale Owner Records
$19,000Jun 1979 $1,3112025 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

2304 Wintergreen Dr

3 bd · 2.5 ba · 1,408 sqft · 0.269 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$295,000Apr 2021 $3,2742025 Amount on Record Jul 2017 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

2305 Wintergreen Dr

3 bd · 2 ba · 1,664 sqft · 0.264 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$175,000Nov 2018 $2,8122025 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jun 2026

2308 Wintergreen Dr

3 bd · 1 ba · 1,529 sqft · 0.257 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,000Apr 2021 $2,8752025 Amount on Record Mar 2009 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

2309 Wintergreen Dr

2 bd · 1.5 ba · 1,552 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$155,000Aug 2023 $3,0112025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

2312 Wintergreen Dr

4 bd · 2 ba · 2,246 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Feb 1974 $3,0892025 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

2313 Wintergreen Dr

3 bd · 1.5 ba · 1,482 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$169,900Jun 2020 $2,7052025 Amount on Record Nov 2019 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jun 2026

2316 Wintergreen Dr

4 bd · 2 ba · 1,503 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$245,000Sep 2021 $6222022 Amount on Record Feb 2014 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

2317 Wintergreen Dr

3 bd · 1.5 ba · 1,362 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,6502025 2 Names on Record AssessorUpdated Jun 2026

2320 Wintergreen Dr

4 bd · 2.5 ba · 1,863 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Aug 2020 $3,5642025 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

2321 Wintergreen Dr

3 bd · 1 ba · 1,416 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Mar 2004 $2,6332025 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

2324 Wintergreen Dr

4 bd · 3 ba · 2,419 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Jun 1993 $3,3292025 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

2325 Wintergreen Dr

3 bd · 1 ba · 1,296 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Jun 1975 $2,4722025 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

2328 Wintergreen Dr

3 bd · 1.5 ba · 1,164 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$182,000Nov 2016 $2,5842025 Amount on Record Aug 2003 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

2329 Wintergreen Dr

4 bd · 2 ba · 1,597 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$316,000Oct 2025 $3,0272025 Amount on Record Nov 2019 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Jun 2026

Wildfire Risk on Wintergreen Dr

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

Wildfire RiskLow
this street's cells rank at the 3rd percentile of exposed land nationally · 1st in Virginia
Wildfire LikelihoodLow — less than 1 in 10,000 per year
ExposureDirect
1 of 4 cells directly exposed · 2 adjoin burnable vegetation

Property Records in Nearby Streets