527 Windward DR Chesapeake, VA ^$ 498,000

527 Windward DR

^$ 498,000

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527 Windward DR

Chesapeake, VA, 23320

^$ 498,000

Bedrooms4 Baths2.1 Sq 2,100

Monthly Estimate*

^$ 3,440

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Single Family Home for sale in Chesapeake, VA

for $498,000 with 4 bedrooms and 2 full baths, 1 half bath. This 2,100 square foot home was built in 1997.

Come check out this amazing well kept two story home in the heart of Greenbrier. Conveniently located to shopping, restaurants, parks, military bases and major interstates. Roof was replaced in 2015, HVAC in 016, gutter and vinyl wrap in 2017, master shower replaced in 2022. Home features a huge master bedroom sitting area as a bonus complete with an additional fireplace! Outside folks will love the proximity to the Chesapeake City Park!Romantic gas fireplace in primary suite and more!

Single Family Active

Price

^$ 498,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 4,251

Style

Traditional

Year Built

1997

Town/City

Chesapeake

County/Region

Chesapeake City

MLS | Web ID

10641660

Features

Interior

Interior Features Fireplace Gas-natural Pull Down Attic Stairs Skylights

Other Rooms Attic Breakfast Area Foyer PBR with Bath Porch Utility Closet

Fireplaces 2

Equipment Cable Hookup Ceiling Fan Gar Door Opener Security Sys

General

Heating Forced Hot Air Nat Gas

Water Type City/County

Cooling Central Air

Ownership Type Simple

Waterfront Description Not Waterfront

Roof Composite

Appliances 220 V Elec Dishwasher Disposal Dryer Hookup Elec Range Washer Hookup

Amenities Ground Maint

Parking Garage Att 1 Car Multi Car Off Street Street

Style Traditional

Property Type Residential

Area 32 - South Chesapeake

Subdivision Name ESTATES OF GREENBRIER

HOA Y/N 1

Sub Type Detached

New Construction Y/N 0

Elementary School Greenbrier Primary

High School Indian River

Middle School Greenbrier Middle

Fees HOA/POA Monthly 23

Fees Condo Monthly 0

Non Non Contingent

Exterior

Waterfront 0

Exterior Features Irrigation Control

Siding Brick Vinyl

Fence? 1

Foundation Slab

Pool No Pool

Garage Y/N 1

* Excluded Features

List By

Janice Hollowell

Listing Agent

World Class Realty

Broker

Affordability Calculator

$3,794

Per Month

Monthly Principal & Interest: $3,440
Monthly Property Taxes: $354
Monthly Home Insurance: --

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Loan Term

Interest Rate

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Yearly Home Insurance

Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends
Schools

Single family listings in Chesapeake, VA

Average List Price ^$563,565

Percent of Sale Price 13%

About Chesapeake, VA

244,523 Population

23% Since 2002

^$70,156 Median Income

38.59 Median Age

33% Households with Children

View more area information

Trends Information provided by ATTOM Data Solutions.

239155 Elementary School

239190 Middle School

Indian River High School High School

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527 Windward DR, Chesapeake, VA, 23320 is a Single Family Home for sale at $498,000 with 2,100 sqft. 527 Windward DR has 4 bedrooms, 2.1 baths, and was built in 1997. The property's zip code is 23320 which is in Chesapeake, VA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

The listings data displayed on this medium comes in part from the Real Estate Information Network, Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.

©2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.

Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.

This application does not include information on all of the properties available for sale at this time.

REIN updates its listings on a daily basis. Data last updated 10/18/2026.

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527 Windward DR

Single Family Home for sale in Chesapeake, VA

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