519 Windward Dr, Chesapeake, VA 23320
UNDER CONTRACT

519 Windward Dr
Chesapeake, VA 23320

Greenbrier East
  • 4 Beds
  • 3.5 Baths
  • 2,595 sqft

$400,000

Est. Mortgage $2,363/mo*
Get Pre-Qualified

$400,000

Est. Mortgage $2,363/mo*
Get Pre-Qualified
4 Beds
3.5 Baths
2,595 sqft
We estimate this home will sell faster than 98% nearby.

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Priced to Sell in Chesapeake! Don't miss this opportunity to own a spacious 4-bedroom, 3.5-bath home offering approximately 2,596 square feet of living space. Features include a 2-car garage, an eat-in kitchen, and a gas fireplace. This home needs some TLC and updating, but offers tremendous potential for buyers looking to build equity and make it their own. Located in an established neighborhood near shopping, dining, schools, and commuter routes. Property is being sold strictly as-is. Seller to make no repairs.
We estimate this home will sell faster than 98% nearby.

Home Highlights

Parking
2 Car Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
$28/Monthly
Price/Sqft
$154
Listed
12 days ago

Home Details for 519 Windward Dr

Interior Features

Interior Details
Number of Rooms: 9Types of Rooms: Primary Bedroom, Bedroom, Full Bathroom, Dining Room, Family Room, Great Room, Kitchen, Living Room, Utility Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2595 Square Feet
Appliances & Utilities
Utilities: Cable HookupAppliances: Dishwasher, Microwave, Gas Range, Refrigerator, Gas Water HeaterDishwasherLaundry: Dryer Hookup,Washer HookupMicrowaveRefrigerator
Heating & Cooling
Heating: Forced Air,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Fireplace Gas-naturalSpa: BathHas a FireplaceHas a Spa
Windows, Doors, Floors & Walls
Flooring: Laminate/LVP, VinylCommon Walls: No Common Walls
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: Main Floor LaundryFloors: Laminate LVP, Vinyl
View
Has a ViewView: City

Exterior Features

Exterior Home Features
Roof: Asphalt ShingleFencing: Back Yard, FencedFoundation: Slab
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Garage Att 2 Car,2 Space,Off Street,Driveway
Pool
Pool: None
Frontage
Waterfront: Not WaterfrontNot on Waterfront
Water & Sewer
Sewer: City/County
Farm & Range
Not Allowed to Raise Horses

Days on Market

Days on Market: 12

Property Information

Year Built
Year Built: 1997
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Traditional
Building
Construction Materials: Vinyl SidingNot a New ConstructionNot Attached Property

Price & Status

Price
List Price: $400,000Price Per Sqft: $154
Status Change & Dates
Off Market Date: Mon Jun 01 2026Possession Timing: @closing

Active Status

MLS Status: Under Contract

Location

Direction & Address
City: ChesapeakeCommunity: Estates Of Greenbrier
School Information
Elementary School: Greenbrier IntermediateJr High / Middle School: Greenbrier MiddleHigh School: Indian River

Agent Information

Listing Agent
Listing ID: 10636623

HOA

Has an HOAHOA Fee: $28/Monthly

Offer

Contingencies: Non Contingent

Miscellaneous

Mls Number: 10636623Zillow Contingency Status: Under ContractAttic: Pull Down Stairs

Additional Information

HOA Amenities: Landscaping
Last check for updates: about 5 hours ago
Listing courtesy of Patricia Lobo
KW Coastal Virginia Chesapeake, (757) 361-0106
Source: REIN Inc., MLS#10636623

Market trends in Greenbrier East

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$395K
$20.97KMoM
Sale-to-List Price
100.0%
Price per sq ft
$212
$5MoM
Available listings
105
21MoM

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Property Tax and Assessment

Year2025
Tax$4,635
Assessment$458,900
Home facts updated by county records

Comparable Sales for 519 Windward Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
900 Lee Shore Ct, Chesapeake, VA
0.12
Single-Family Home
$538,097
04/14/26
4
2.5
2,226
717 Gulfwind Rd, Chesapeake, VA
0.14
Single-Family Home
$452,500
12/12/25
4
2.5
2,162
903 Lee Shore Ct, Chesapeake, VA
0.11
Single-Family Home
$509,000
12/16/25
3
2.5
2,184
709 Gulfwind Rd, Chesapeake, VA
0.15
Single-Family Home
$470,000
09/12/25
3
2.5
2,108
1005 Fairway Dr, Chesapeake, VA
0.24
Single-Family Home
$565,000
09/12/25
5
2.5
3,000
828 Cranston Dr, Chesapeake, VA
0.27
Single-Family Home
$485,000
05/22/26
4
3
1,664
1816 Tristan Rd, Chesapeake, VA
0.42
Single-Family Home
$675,000
12/08/25
4
3
2,619

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 519 Windward Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Greenbrier East
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Greenbrier East

At least 321 Trulia users voted on each feature.

  • 94 % Say it's dog friendly

  • 88 % Say car is needed

  • 88 % Say parking is easy

  • 78 % Say there are sidewalks

  • 74 % Say it's quiet

  • 73 % Say people would walk alone at night

  • 73 % Say streets are well-lit

  • 73 % Say there's holiday spirit

  • 70 % Say yards are well-kept

  • 68 % Say kids play outside

  • 56 % Say they plan to stay for at least 5 years

  • 53 % Say it's walkable to restaurants

  • 52 % Say neighbors are friendly

  • 49 % Say it's walkable to grocery stores

  • 40 % Say there's wildlife

  • 28 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Sophia.anne.molina
    "Some days there is bad traffic and others it’s smooth. I find that compared to other cities it’s decent. I would describe my commute as fair compared to living in Portsmouth or Norfolk or Virginia Beacb. My commute is anywhere from 5 minutes to 35 minutes from my place of residence. That’s all I would say. "
    0
    Flag
  • Shirley Belue
    " The is a family oriented community. There are schools and parks to get walks for health. Many neighbors have dogs and cats. There are no sidewalks, just a two lane road. "
    1
    Flag
  • stampwithsharon
    "Excellent book club! Neighbors are very friendly. Quiet neighbors,nice pool. Walkable to grocery, restaurants and library. "
    0
    Flag
  • M2jfr2k9vs
    "Motor vehicles are the ultimate way to travel, they’re so convenient! I highly recommend getting or having a vehicle!!!"
    1
    Flag
  • 94zw848pdw
    "Not too bad. I get to work within 20 minutes with minimal traffic. Not sure what else to say about it"
    2
    Flag
  • Kclynncarlisle
    "Pizza party’s, barbecues, trick or treating, thanksgiving potlucks, back porch hang outs, pool party’s. "
    0
    Flag
  • Colpotitoli
    "Nice safe clean friendly close to all shopping center urgent care and other hospitals are very close "
    1
    Flag
  • Trulia User
    "There are always dogs being walked and playing in the field by my apartment with their owners. It is a very dog friendly area and the owners are polite and kind and courteous of other dogs as well as people who live around here without dogs. "
    1
    Flag
  • Trulia User
    "Great community, Friendly , quiet , kid friendly. Lived here all of my life and have never had issues or problems. "
    0
    Flag
  • Trulia User
    "I've lived here and love it I would recommend everyone to live here .I'm so ready To live in this area again "
    2
    Flag
  • Trulia User
    "There are no events at our apartment complex or the 2 next to ours. The mall is dieing. I do love the craft fair at the park. I hope next year it is bigger with more information on what our city has to offer. I miss the pow wows the park had. it is a good reminder of the Native American heritage. "
    0
    Flag
  • Trulia User
    "They would definitely not like people not picking up after their dogs They’ll love walking their dog around the neighborhood "
    0
    Flag
  • Rachelrb
    "This neighborhood is the perfect place to raise a family.It’s beautiful, safe, and extremely fun for kids! "
    13
    Flag
  • Ken L.
    "Close to everything. Very friendly people, and nice area. Schools are great. I went to Oscar Smith for a year, and while there teachers truly pushed me."
    5
    Flag
  • Sharlene R.
    "As there many dog owners in the neighbor. A lot of dog lovers within the communities. Must be careful as Bishopstokes is a race trap "
    7
    Flag
  • Littlesugarmom
    "Great area to raise kids, family oriented area. Great parks and trails. Lots to do and close proximity to everything necessary "
    1
    Flag
  • Stephaniestout94
    "Quiet neighborhood. A lot of families. Close to everything. Food entertainment , shopping, dog parks. "
    2
    Flag
  • Katelyn W.
    "There’s plenty of areas to walk your dog. Sidewalks, parks, lots of trees. Most places have fences and yards or are pet friendly apartments. "
    0
    Flag
  • Carrie J.
    "it's nice and quite yet close to anything you could possibly need or want. I have lived here for 2 years and love the area."
    4
    Flag
  • Ashley D.
    "Quiet and safe. Right next to a school and a mall which is hard to find. The cops monitor the neighbor and make sure speeding is kept to a minimum."
    12
    Flag
  • Karena P.
    "It’s a great place to live, especially if you have a young family! Great schools, and great for pets! "
    0
    Flag
  • Ash M.
    "Great neighborhood with great restaurants and shopping within 5 miles radius. Very safe with sidewalks pretty much everywhere."
    3
    Flag
  • Ahagenbucher182
    "I love this area so much. It’s such a great place to raise of family!!! :) Greenbrier East is the best! "
    0
    Flag
  • A.brown2134
    "It’s a great place to raise your family. I would recommend this area to anyone looking for a nice, friendly, quiet atmosphere "
    1
    Flag
  • Rebecca B.
    "Although there are areas to play between our patios and the white sticks indicating the golf course property, children do not play back there. The only time I’ve ever seen children play in the area that is available and allowed is wintertime when snow is on the grounds."
    0
    Flag
  • Brittany B.
    "Been around this neighborhood for a while. Very family friendly. Love the area in general. Great place to raise a family."
    3
    Flag
  • Fw
    "I love it here! Neighborhood is nice and quiet. Streets are always clean, very convenient to shopping, I always feel safe here. "
    0
    Flag
  • Don7likeu
    "This is a great place to live. There are many shops nearby and great schools. I have been here for two years and don't plan on moving to a different area any time soon."
    0
    Flag
  • Lpierce4511
    "I've loved in this neighborhood for 4 years. It's close to shopping and interstates making it easy to travel. I've always felt very safe in this area. I love the lake and walking path!"
    4
    Flag
  • Rebekah MO
    "This is a wonderful neighborhood, everyone is so friendly and close to everything! I would highly recommend this area to anyone! "
    0
    Flag
  • Rosario36@yahoo.com
    "Cooks outs, sharing info, schools, friends, scenery, hospitality, clean, pool, fun, picnics, and parties "
    0
    Flag
  • Fabian O.
    "Great area to live in. Everything you could ever need is within 10 to 15 minutes driving would recommend to anyone"
    0
    Flag
  • Marlena S.
    "Dog owners would love that 4 Paws, PetSmart, Barker and open dog parks are literally down the street"
    0
    Flag
  • Amy B.
    "My neighborhood is 100% dog friendly. People are always out walking their dogs. There is also a dog park around the corner at Chesapeake City Park "
    0
    Flag
  • KC
    "I’ve lived here for six months now, the area is great for going on runs and walks, my neighbors are friendly and the area is clean. There’s a lake nearby and plenty of shopping for anything you need within minutes of your house."
    9
    Flag
  • Gellinabaez
    "Dogs in the Greenbrier area seem to be friendly and well-trained; I never hear loud, constant barking. "
    0
    Flag

LGBTQ Local Legal Protections

Patricia Lobo, KW Coastal Virginia Chesapeake, (757) 361-0106
The listings data displayed on this medium comes in part from the Real Estate Information Network, Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
Copyright 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW. REIN updates its listings on a daily basis. Data last updated: 2026-06-07 23:58:35 PDT.
Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.
This application does not include information on all of the properties available for sale at this time.
519 Windward Dr, Chesapeake, VA 23320 is a 4 bedroom, 4 bathroom, 2,595 sqft single-family home built in 1997. 519 Windward Dr is located in Greenbrier East, Chesapeake. This property is currently available for sale and was listed by REIN Inc. on May 27, 2026. The MLS # for this home is MLS# 10636623.