For sale

Price cut: $6.5K (8/5)

$498,000

527 Windward Dr, Chesapeake, VA 23320

4beds

2,100sqft

$3,160/mo

Get pre-qualified

Single Family Residence

Built in 1997

-- sqft lot

$497,800 Zestimate^®

$237/sqft

$23/mo HOA

What's special

Additional fireplace

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!

64 days
509
32

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: $237/sqft
Tax assessed value: $420,900
Annual tax amount: $4,251
Date on market: 6/26/2026

Estimated market value

$497,800

$473,000 - $523,000

$2,898/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