NOT LISTED FOR SALE

1029 Windswept Cir Chesapeake, VA 23320

Greenbrier East Neighborhood

Estimated Value: $546,000 - $603,740

5 Beds
3 Baths
2,736 Sq Ft
$208/Sq Ft Est. Value

About This Home

This home is located at 1029 Windswept Cir, Chesapeake, VA 23320 and is currently estimated at $570,185, approximately $208 per square foot. 1029 Windswept Cir is a home located in Chesapeake City with nearby schools including Greenbrier Primary School, Greenbrier Intermediate School, and Greenbrier Middle.

Range of Values:

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Value Increase
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Percent Increase
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Adjusted for Inflation
Collateral Analytics

Collateral Analytics Collateral Analytics AVMs (Automated Valuation Model) employ a number of statistical approaches combined with neighborhood-specific comparable selection guarantees the most up-to-date and precise valuations.

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ICE

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First American

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Quantarium

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Average Value
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List Price
Sold Price
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Ownership History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Name Owned For Owner Type

Purchase Details

Closed on
Feb 3, 2026
Sold by
Willis Larry and Willis Patricia P
Current Estimated Value
$559,790
Source: Public Records

Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Agents Specializing in Greenbrier East, VA

  • Jessica Lewis Real Estate Agent - Iron Valley Real Estate Hampton Roads

    Jessica Lewis

    Iron Valley Real Estate Hampton Roads

    (757) 255-5771

    339 Total Sales

    2 in Greenbrier East

    $363K - $370K Price Range

    Jessica Lewis
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  • Troye Levin-Whiting Real Estate Agent - Iron Valley Real Est Norfolk

    Troye Levin-Whiting

    Iron Valley Real Est Norfolk

    (757) 982-3709

    124 Total Sales

    3 in Greenbrier East

    $305K - $865K Price Range

    Troye Levin-Whiting
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  • Jason Dunaway Real Estate Agent - Howard Hanna Real Estate Svcs.

    Jason Dunaway

    Responds Quickly

    Howard Hanna Real Estate Svcs.

    (757) 908-6859

    131 Total Sales

    5 in Greenbrier East

    $235K - $420K Price Range

    Jason Dunaway
     Section Image
  • Courtney Myers Real Estate Agent - Own Real Estate LLC

    Courtney Myers

    Own Real Estate LLC

    (757) 702-5370

    37 Total Sales

    2 in Greenbrier East

    $295K - $330K Price Range

    Courtney Myers
     Section Image
  • Jake Maines Real Estate Agent - Iron Valley Real Estate HR

    Jake Maines

    Iron Valley Real Estate HR

    (864) 387-8519

    155 Total Sales

    2 in Greenbrier East

    $341K - $475K Price Range

    Jake Maines
     Section Image
  • Kathy Keene Real Estate Agent - CHJ Realty

    Kathy Keene

    CHJ Realty

    (757) 981-0481

    73 Total Sales

    1 in Greenbrier East

    $641,450 Price

    Kathy Keene
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Purchase History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Buyer Sale Price Title Company
-- -- None Listed On Document
Source: Public Records

Mortgage History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Status Borrower Loan Amount
Previous Owner -- $2,000,000
Source: Public Records

Tax History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $5,252 $520,000 $165,000 $355,000
2024 $5,127 $507,600 $150,000 $357,600
2023 $4,740 $469,300 $130,000 $339,300
2022 $4,332 $428,900 $120,000 $308,900
2021 $3,994 $380,400 $110,000 $270,400
2020 $3,805 $362,400 $105,000 $257,400
2019 $3,723 $354,600 $100,000 $254,600
2018 $3,648 $298,400 $103,000 $195,400
2017 $3,406 $324,400 $99,800 $224,600
2016 $3,387 $322,600 $98,000 $224,600
2015 $3,065 $312,500 $98,000 $214,500
2014 $3,182 $303,000 $98,000 $205,000
Source: Public Records

Map

Virginia Chesapeake County Chesapeake 23320 Greenbrier East

1029 Windswept Cir, Chesapeake, VA

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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