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!
For sale
$504,500
527 Windward Dr, Chesapeake, VA 23320
4beds
2,100sqft
Single Family Residence
Built in 1997
-- sqft lot
$505,300 Zestimate®
$240/sqft
$23/mo HOA
What's special
Additional fireplace
- 18 days |
- 713 |
- 31 |
Zillow last checked:
Listing updated:
Listed by:
Janice Hollowell,
World Class Realty 757-228-7773
Source: REIN Inc.,MLS#: 10641660
Loading...
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Rooms
- Room types: Attic, Breakfast Area, PBR with Bath, Utility Closet
Utility room
- Level: Second
Heating
- Forced Air, Natural Gas
Cooling
- Central Air
Appliances
- Included: 220 V Elec, Dishwasher, Disposal, Electric Range, Electric Water Heater
- Laundry: Dryer Hookup, Washer Hookup
Features
- Ceiling Fan(s), Entrance Foyer
- Flooring: Carpet, Ceramic Tile, Laminate/LVP
- Windows: Skylight(s)
- Attic: Pull Down Stairs
- Number of fireplaces: 2
- Fireplace features: Fireplace Gas-natural
Interior area
- Total interior livable area: 2,100 sqft
Property
Parking
- Total spaces: 1
- Parking features: Garage Att 1 Car, Multi Car, Off Street, On Street, Garage Door Opener
- Attached garage spaces: 1
- Has uncovered spaces: Yes
Features
- Stories: 2
- Patio & porch: Porch
- Exterior features: Irrigation Control
- Pool features: None
- Fencing: Back Yard,Rail,Fenced
- Waterfront features: Not Waterfront
Details
- Parcel number: 0376004000790
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
Materials
- Brick, Vinyl Siding
- Foundation: Slab
- Roof: Composition
Condition
- New construction: No
- Year built: 1997
Utilities & green energy
- Sewer: City/County
- Water: City/County
- Utilities for property: Cable Hookup
Community & HOA
Community
- Security: Security System
- Subdivision: Estates Of Greenbrier
HOA
- Has HOA: Yes
- Amenities included: Landscaping
- HOA fee: $23 monthly
Location
- Region: Chesapeake
Financial & listing details
- Price per square foot: $240/sqft
- Tax assessed value: $420,900
- Annual tax amount: $4,251
- Date on market: 6/26/2026
Estimated market value
$505,300
$480,000 - $531,000
$2,789/mo
Price history
Price history is unavailable.
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $4,251 +2.9% | $420,900 +2.9% |
| 2024 | $4,131 +4.9% | $409,000 +4.9% |
| 2023 | $3,938 +5.4% | $389,900 +9.6% |
| 2022 | $3,737 +20% | $355,900 +20% |
| 2021 | $3,114 | $296,600 +0.3% |
| 2020 | -- | $295,700 +1.5% |
| 2019 | $3,058 | $291,200 |
| 2018 | $3,058 +2.8% | $291,200 +2.8% |
| 2017 | $2,976 +3.3% | $283,400 +3.3% |
| 2016 | $2,881 +3.2% | $274,400 +3.2% |
| 2015 | $2,792 | $265,900 |
| 2014 | $2,792 +0% | $265,900 |
| 2013 | $2,792 +3.3% | $265,900 +3.3% |
| 2012 | $2,702 -3.7% | $257,300 -3.7% |
| 2011 | $2,807 -3.6% | $267,300 -3.6% |
| 2010 | $2,913 -6.3% | $277,400 -6.3% |
| 2009 | $3,108 -2.9% | $296,000 -2.9% |
| 2008 | $3,200 -4.2% | $304,800 -3.2% |
| 2007 | $3,339 +11.7% | $315,000 +17% |
| 2006 | $2,989 +27.5% | $269,300 +47% |
| 2004 | $2,345 +13.8% | $183,200 +13.8% |
| 2003 | $2,061 +8.4% | $161,000 +8.4% |
| 2002 | $1,901 +2.9% | $148,500 +2.9% |
| 2001 | $1,847 | $144,300 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: Greenbrier East
Nearby schools
GreatSchools rating
- 6/10Greenbrier Primary SchoolGrades: PK-2Distance: 1.3 mi
- 7/10Greenbrier Middle SchoolGrades: 6-8Distance: 0.8 mi
- 4/10Indian River High SchoolGrades: 9-12Distance: 3.5 mi
Schools provided by the listing agent
- Elementary: Greenbrier Primary
- Middle: Greenbrier Middle
- High: Indian River
Source: REIN Inc.. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
- $478,1003 bd2 ba2.4k sqft525 Windward Dr, Chesapeake, VA 23320Off Market
- $467,9004 bd2 ba2k sqft529 Windward Dr, Chesapeake, VA 23320Off Market
- $513,0004 bd3 ba2.4k sqft921 Lee Shore Ct, Chesapeake, VA 23320Off Market
- $467,3004 bd3 ba1.9k sqft523 Windward Dr, Chesapeake, VA 23320Off Market
- $481,3003 bd2 ba2.2k sqft917 Lee Shore Ct, Chesapeake, VA 23320Off Market
- $505,4004 bd3 ba2.3k sqft808 Broad Reach Rd, Chesapeake, VA 23320Off Market
- $398,9003 bd2 ba1.5k sqft806 Broad Reach Rd, Chesapeake, VA 23320Off Market
- $478,9003 bd3 ba2.3k sqft521 Windward Dr, Chesapeake, VA 23320Off Market
A local agent can set up tours, give advice and negotiate with sellers.
Similar homes
- $499,0004 bd3 ba2.3k sqft1028 Austin Dr, Chesapeake, VA 23320For Sale
MLS ID #10642093, Jillian Walter. REIN Inc. - $490,0004 bd3 ba2.5k sqft1124 Kilby Dr, Chesapeake, VA 23320For Sale
MLS ID #10639866, Courtney Gonzales. REIN Inc. - $509,0004 bd3 ba2.1k sqft405 S Monterey Dr, Chesapeake, VA 23320For Sale
MLS ID #10642834, Jackie Feagin. REIN Inc. - $440,0004 bd3 ba2.1k sqft909 Long Beeches Ave, Chesapeake, VA 23320For Sale
MLS ID #10640661, Christopher Russell. REIN Inc. - $520,0003 bd3 ba2.6k sqft533 Broad Bend Cir, Chesapeake, VA 23320For SaleMLS ID #10637145, Allen Boone. REIN Inc.
- $560,0004 bd3 ba2.3k sqft424 Pines Of Warrick Dr, Chesapeake, VA 23322For SaleMLS ID #10643841, Laura Daugherty. REIN Inc.
- $574,9004 bd3 ba2.3k sqft716 Tallahassee Dr, Chesapeake, VA 23322For SaleMLS ID #10643678, Karen Powell. REIN Inc.
- $585,0004 bd3 ba2.5k sqft1412 Flyfisher Ct, Virginia Beach, VA 23456For SaleMLS ID #10643621, Jerome Caddell. REIN Inc.
- $449,9005 bd3 ba2.2k sqft2040 Miller Ave, Chesapeake, VA 23320For SaleMLS ID #10639322, John Leu. REIN Inc.
- $550,0004 bd3 ba2.6k sqft2213 Eagle Ridge Ct, Virginia Beach, VA 23456For SaleMLS ID #10643527, Valentina Lee. REIN Inc.
- $475,0003 bd2 ba1.9k sqft717 Greenwing Dr, Chesapeake, VA 23323For SaleMLS ID #10638652, Sherry Snyder. REIN Inc.
- $539,9004 bd3 ba2.4k sqft936 Saddleback Trail Rd, Chesapeake, VA 23322For SaleMLS ID #10636555, Erin Ward. REIN Inc.
- $525,0005 bd3 ba2.6k sqft3248 Galberry Rd, Chesapeake, VA 23323For SaleMLS ID #10636774, Bessie Ostrander. REIN Inc.
- $585,0003 bd3 ba2.4k sqft1251 Veranda Way, Chesapeake, VA 23320For SaleMLS ID #10635941, Tom Pullen. REIN Inc.
- $599,9904 bd3 ba2.6k sqft805 Dolph Cir, Chesapeake, VA 23322For SaleMLS ID #10640214, Kimberly Field. REIN Inc.
- $529,0004 bd3 ba2.1k sqft3849 Whitley Park Dr, Virginia Beach, VA 23456For SaleMLS ID #10643183, Nina Olander. REIN Inc.
- $500,0004 bd3 ba2.2k sqft5453 Wingate Way, Virginia Beach, VA 23464For SaleMLS ID #10640209, Kris Weaver. REIN Inc.
- $609,9004 bd3 ba2.6k sqft829 Donnington Dr, Chesapeake, VA 23322For SaleMLS ID #10643428, Sarah Wood Bigler. REIN Inc.
- $560,0004 bd3 ba2.8k sqft208 Robinhood Rd, Chesapeake, VA 23322For SaleMLS ID #10641154, Joy Catalano. REIN Inc.
- $500,0004 bd3 ba2.3k sqft3614 Elkton Dr, Chesapeake, VA 23321For SaleMLS ID #10641167, Jennifer Brickhouse. REIN Inc.
