# 527 Windward Drive, Chesapeake, VA 23320

> **TL;DR:** 4bd/3ba single family, $498,000 ($237/sqft), built 1997, 2,100 sqft.
> Fireplace, A/C. Est. $2,663/mo. Listed 86 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $498,000 |
| Price/sqft | $237 |
| Bedrooms | 4 |
| Bathrooms | 2 full, 1 half |
| Square Feet | 2,100 |
| Year Built | 1997 |
| Property Type | Single Family (Other) |
| Status | Active |
| Days on Market | 86 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $2,518 |
| Estimated Insurance | $145 |
| **Total** | **$2,663** |

## Nearby Schools

- **Elementary:** Greenbrier Primary
- **Middle:** Greenbrier Middle

## Key Amenities

- Fireplace
- A/C

## Property Highlights

- Built in 1997
- Fireplace

## Description

### Agent Description
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!

## Location

- **Address:** 527 Windward Drive, Chesapeake, VA 23320
- **County:** Chesapeake VA
- **Neighborhood:** ESTATES OF GREENBRIER
- **Coordinates:** 36.749056, -76.224565
- **Google Maps:** https://www.google.com/maps?q=36.749056,-76.224565

## Listing Agent

- **Name:** Janice Hollowell
- **Brokerage:** World Class Realty
- **Phone:** (757) 288-7773
- **Broker Phone:** (757) 288-7773
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/527-Windward-Dr_Chesapeake_VA_23320_M60643-18778?f=listhub&s=REINVA&m=10641660&c=propsimple)

## Photos

![527 Windward Drive - Photo 1](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f3912313241r.jpg)

![527 Windward Drive - Photo 2](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f385953203r.jpg)

![527 Windward Drive - Photo 3](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f93402920r.jpg)

![527 Windward Drive - Photo 4](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f3831924407r.jpg)

![527 Windward Drive - Photo 5](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f2120453879r.jpg)

![527 Windward Drive - Photo 6](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f3867853681r.jpg)

![527 Windward Drive - Photo 7](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f2646250821r.jpg)

![527 Windward Drive - Photo 8](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f2887078385r.jpg)

![527 Windward Drive - Photo 9](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f186745470r.jpg)

![527 Windward Drive - Photo 10](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f3469120536r.jpg)

![527 Windward Drive - Photo 11](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f66759946r.jpg)

![527 Windward Drive - Photo 12](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f3011856553r.jpg)

![527 Windward Drive - Photo 13](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f990092802r.jpg)

![527 Windward Drive - Photo 14](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f2568539943r.jpg)

![527 Windward Drive - Photo 15](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f1112366781r.jpg)

![527 Windward Drive - Photo 16](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f5420230r.jpg)

![527 Windward Drive - Photo 17](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f951658653r.jpg)

![527 Windward Drive - Photo 18](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f4078667788r.jpg)

![527 Windward Drive - Photo 19](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f1544657385r.jpg)

![527 Windward Drive - Photo 20](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f1963021228r.jpg)

![527 Windward Drive - Photo 21](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f2514655481r.jpg)

![527 Windward Drive - Photo 22](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f901596760r.jpg)

![527 Windward Drive - Photo 23](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f3376482972r.jpg)

![527 Windward Drive - Photo 24](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f3223439029r.jpg)

![527 Windward Drive - Photo 25](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f1633043394r.jpg)

![527 Windward Drive - Photo 26](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f3008077474r.jpg)

![527 Windward Drive - Photo 27](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f3908582500r.jpg)

![527 Windward Drive - Photo 28](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f4155760288r.jpg)

![527 Windward Drive - Photo 29](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f576437386r.jpg)

![527 Windward Drive - Photo 30](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f1789438787r.jpg)

![527 Windward Drive - Photo 31](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f3171250261r.jpg)

![527 Windward Drive - Photo 32](http://lh.rdcpix.com/f61cda1daa104d390c0401055c36dea3l-f2266576300r.jpg)

---

**MLS#:** 10641660 | **Updated:** 2026-08-25
**Source:** listhub

*Copyright © 2026 Real Estate Information Network, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.ai/listing/527-windward-drive-chesapeake-va-23320-10641660)

---

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