• Primary Photo - 500 Windward Dr
  • Building Photo - 500 Windward Dr
    Building Photo - 500 Windward Dr
  • Building Photo - 500 Windward Dr
    Building Photo - 500 Windward Dr
$2,250 Total Monthly Price

500 Windward Dr

,

Chesapeake, VA 23320

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757-517-2345

  • Bedrooms

    3

  • Bathrooms

    2

  • Square Feet

    1,332 sq ft

  • Available

    Available Aug 14

500 Windward Dr
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About This Home

$2,250 deposit, Available Aug 14

This 1330 plus square foot home has 3 bedrooms and 2 baths. Living room has vaulted ceilings. Large kitchen with plenty of cabinet space and new appliances. Spacious primary bedroom and walk in closets. Large laundry room with washer/dryer included. One car garage, and plenty of off street parking.Fenced in yard with additional storage building. Pets are welcome. This home will be available August 14th. HOA documentation can be provided as requested, if applicable. Please visit our direct website to be added to the waitlist, to review qualifications, or to apply. Minimum 1 year lease agreement is required.

500 Windward Dr is a house located in Chesapeake County and the 23320 ZIP Code. This area is served by the Chesapeake Public Schools attendance zone.

* Price shown is total price based on community-supplied monthly required fees. Excludes user-selected optional fees and variable or usage-based fees and required charges due at or prior to move-in or at move-out. Price, availability, fees, and any applicable rent special are subject to change without notice.
* Square footage definitions vary. Displayed square footage is approximate.

Fees and Policies

The fees listed below are community-provided and may exclude utilities or add-ons. All payments are made directly to the property and are non-refundable unless otherwise specified.

  • Dogs Allowed
  • Fees not specified
  • Cats Allowed
  • Fees not specified

Contact

  • Listed by RedSail Property Management
  • Phone Number
  • Contact
Location Get Directions
| Edit
Edit Commute

Under 30 minutes

Commute Time is calculated at rush hour.
Neighborhood

Located 20 miles south of Norfolk and 14 miles east of Downtown Chesapeake, Greenbrier East is a centrally located neighborhood with a lot to offer. The southeastern corner of town is made up of lush, wooded areas while the northwestern parts of town are full of convenient amenities and residential areas. Head to Greenbrier Parkway to find premier shopping destinations like the Greenbrier Mall and surrounding shopping centers. More amenities in this area include hotels, skating rinks, and several office complexes. The city’s rental options are conveniently situated near the town’s amenities in the north of town. Rentals include moderately priced mid-rise apartments in a range of styles.

Learn more about living in Greenbrier East 
Education
Colleges & Universities Distance
Colleges & Universities Distance
Regent University
Drive: 12 min 5.5 mi
Tidewater C.C., Chesapeake
Drive: 13 min 6.8 mi
ECPI University
Drive: 14 min 8.6 mi
Norfolk State University
Drive: 17 min 9.3 mi
500 Windward Dr is within 12 minutes or 5.5 miles from Regent University. It is also near Tidewater C.C., Chesapeake and Norfolk State University.
Schools
Greenbrier Primary School
Public Elementary School
Grades PK-5
679 Students
Attendance Zone
GreatSchools rating: 6 out of 10
Greenbrier Intermediate School
Public Elementary School
Grades K-5
608 Students
Attendance Zone
GreatSchools rating: 6 out of 10
Greenbrier Middle School
Public Middle School
Grades 6-8
827 Students
Attendance Zone
GreatSchools rating: 6 out of 10
Indian River High School
Public High School
Grades 9-12
1,643 Students
Attendance Zone
GreatSchools rating: 4 out of 10
Greenbrier Enrichment Center
Private Elementary School
Grades PK-5
92 Students
Nearby
Oxford Day School
Private Elementary, Middle & High School
Grades K-12
25 Students
Nearby
School data provided by GreatSchools The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.

View GreatSchools Rating Methodology

Data provided by GreatSchools.org © 2026. All rights reserved.
Transportation

Transportation options available in Chesapeake include Military Highway, located 7.4 miles from 500 Windward Dr. 500 Windward Dr is near Norfolk International, located 12.9 miles or 21 minutes away, and Newport News/Williamsburg International, located 38.4 miles or 56 minutes away.

Transit / Subway Distance
Transit / Subway Distance
Military Highway
Drive: 13 min 7.4 mi
Newtown Road
Drive: 14 min 8.5 mi
Nsu
Drive: 15 min 8.7 mi
Ballentine / Broad Creek
Drive: 16 min 10.0 mi
Ingleside Road
Drive: 19 min 10.8 mi
Commuter Rail Distance
Commuter Rail Distance
Norfolk
Drive: 16 min 9.2 mi
Newport News
Drive: 62 min 46.4 mi
Airports Distance
Airports Distance
Norfolk International
 Drive: 21 min 12.9 mi
Newport News/Williamsburg International
 Drive: 56 min 38.4 mi
Getting Around
Fairly Walkable
Walkability
50 / 100
Minimal Public Transit
Transit
0 / 100
Exceptionally Drivable
Drivability
90 / 100
Moderately Bikeable
Bikeability
60 / 100

Scores provided by

What do Walkability, Transit, Drivability, and Bikeability mean? Walkability measures the walking distance to day-to-day needs. Transit measures access to public transportation. Drivability measures congestion, parking availability, and access to major roads. Bikeability measures the suitability for cycling. How It Works
Active
Soundscore™
72 / 100

Traffic

Busy

Airport

Calm

Businesses

Calm

Scores provided by

HowLoud What is a Sound Score Rating? A Sound Score Rating aggregates noise caused by vehicle traffic, airplane traffic and local sources. How It Works
Points of Interest

Time and distance from 500 Windward Dr.

Shopping Centers Distance
Shopping Centers Distance
Greenbrier Shoppes
Walk: 13 min 0.7 mi
Green Tree Marketplace
Walk: 14 min 0.8 mi
Green Tree Commons
Drive: 2 min 1.1 mi
500 Windward Dr has 3 shopping centers within 1.1 miles, which is about a 2-minute drive. The miles and minutes will be for the farthest away property.
Parks and Recreation Distance
Parks and Recreation Distance
Chesapeake Arboretum
 Drive: 5 min 2.1 mi
Chesapeake Planetarium
 Drive: 7 min 3.7 mi
Stumpy Lake
 Drive: 12 min 7.0 mi
Nauticus
 Drive: 18 min 12.0 mi
Children's Museum of Virginia
 Drive: 18 min 12.1 mi
500 Windward Dr has 5 parks within 12.1 miles, including Chesapeake Arboretum, Chesapeake Planetarium, and Stumpy Lake.
Hospitals Distance
Hospitals Distance
Chesapeake Regional Medical Center
Drive: 6 min 2.6 mi
Sentara Leigh Hospital
Drive: 15 min 9.0 mi
Sentara Princess Anne Hospital
Drive: 17 min 9.6 mi
500 Windward Dr has 3 hospitals within 9.6 miles, the nearest is Chesapeake Regional Medical Center which is 2.6 miles away and a 6 minute drive.
Military Bases Distance
Military Bases Distance
US Naval Saint Helena Annex
Drive: 17 min 8.6 mi
Norfolk Naval Shipyard
Drive: 18 min 11.2 mi
Fentress NALF
Drive: 29 min 15.0 mi
500 Windward Dr has 3 military bases within 15.0 miles, the nearest is US Naval Saint Helena Annex which is 8.6 miles away and a 17 minute drive.

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