
500 Windward Dr, Chesapeake, VA 23320
What This House Offers
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.
Unit
- $2,250
Total Monthly Price - 3 Beds
- 2 Baths
- 1332 sq. ft.
- Available Aug 14
500 Windward Dr is a single-family home for rent in Chesapeake, VA
Fees and Policies
The fees below are based on community-supplied data and may exclude additional fees and utilities.
Cats Allowed
- Fee Not Specified
Dogs Allowed
- Fee Not Specified
Property Fee Disclaimer Based on community-supplied data and independent market research. Subject to change without notice. May exclude fees for mandatory or optional services and usage-based utilities.
Explore Commute Options
- Drive Time--
- Walk Time--
- Bike Ride Time--
- Public Transit--
Get In Touch
Chesapeake, VA 23320
Area Scores
Walkability
Fairly walkable50 / 100
Driveability
Exceptionally drivable90 / 100
Bikeability
Moderately bikeable60 / 100
Soundscore ™
Active72 / 100
Travel and Transit


Local Education
Primary and Secondary Schools
Greenbrier Intermediate School
Grades K-5
Public
Greenbrier Primary School
Grades PK-5
Public
Greenbrier Enrichment Center
Grades PK-5
Private
Greenbrier Middle School
Grades 6-8
Public
Indian River High School
Grades 9-12
Public
Oxford Day School
Grades K-12
Private
Data provided by GreatSchools.org © 2026. All rights reserved.
Colleges and Universities
School
Commute Time (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)
Discover Greenbrier East, Chesapeake, VA
Shopping Centers
Shoppers will appreciate 500 Windward Dr proximity to Greenbrier Shoppes, Green Tree Marketplace, and Green Tree Commons. Greenbrier Shoppes is 0.7 miles away, and Green Tree Marketplace is within a 14 minute walk.
Parks and Recreation
Recreational activities near 500 Windward Dr are plentiful. Discover 2 parks within 3.7 miles, including Chesapeake Arboretum and Chesapeake Planetarium.
Airports
Living in Greenbrier East provides easy access to Norfolk International, located just 21 minutes from 500 Windward Dr. Another nearby airport is Newport News/Williamsburg International, located 38.4 miles away.
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