301 Windlesham Dr, Chesapeake, VA 23322
OFF MARKET

$658,000

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 2,590 sqft (on 2.05 acres)

301 Windlesham Dr, Chesapeake, VA 23322

Great Bridge East
Est. Refi. Payment $3,906/mo*
Refinance Your Home

Home Value

Trulia Estimate
$658K
Since last month
Increased$2K (+0.3%)
Since last year
Increased$58K (+9.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +78% in the last 10 years
MonthEstimated value
2026
August 2026$658K
August 2026$658K
July 2026$656K
June 2026$654K
May 2026$619K
April 2026$622K
March 2026$616K
February 2026$608K
January 2026$604K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
201 Kendra Ct, Chesapeake, VA
0.10
Single-Family Home
$659,000
08/19/26
5
3
2,600
300 Windlesham Dr, Chesapeake, VA
0.03
Single-Family Home
$620,000
02/04/26
4
3
3,532
900 Brookedale Ct, Chesapeake, VA
0.20
Single-Family Home
$714,000
10/10/25
4
3
2,490
304 Jule Dr, Chesapeake, VA
0.34
Single-Family Home
$1,100,000
06/01/26
5
4.5
4,319
1024 Wymers Ct, Chesapeake, VA
0.33
Single-Family Home
$550,000
02/20/26
4
2.5
2,780
204 Castleberry Dr, Chesapeake, VA
0.28
Single-Family Home
$695,000
07/23/26
5
3.5
3,074
313 Sweetbay Dr, Chesapeake, VA
0.18
Single-Family Home
$775,000
04/24/26
5
3
3,328
309 Sweetbay Dr, Chesapeake, VA
0.17
Single-Family Home
$808,000
06/17/26
5
3.5
3,600

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
300 Windlesham Dr, Chesapeake, VA 23322
0.03
$620,000
4
3
3,532
Recently Sold
201 Kendra Ct, Chesapeake, VA 23322
0.10
$659,000
5
3
2,600
Recently Sold
901 Bernard Ln, Chesapeake, VA 23322
0.18
$545,900
3
3.5
2,200
For Sale
903 Bernard Ln, Chesapeake, VA 23322
0.18
$525,900
4
3.5
2,200
For Sale
309 Sweetbay Dr, Chesapeake, VA 23322
0.17
$808,000
5
3.5
3,600
Recently Sold
313 Sweetbay Dr, Chesapeake, VA 23322
0.18
$775,000
5
3
3,328
Recently Sold
900 Brookedale Ct, Chesapeake, VA 23322
0.20
$738,800
4
3
2,490
Off Market
401 White Egret Cv, Chesapeake, VA 23322
0.24
$729,000
4
3.5
3,596
For Sale
201 Hodges Rd, Chesapeake, VA 23322
0.25
$619,165
3
3.5
2,500
Recently Sold
203 Hodges Rd, Chesapeake, VA 23322
0.25
$639,155
3
3.5
2,500
Recently Sold
925 Calhoun Way, Chesapeake, VA 23322
0.27
$635,375
3
3.5
2,500
Recently Sold

Local Information

  • Map ViewExplore the area around 301 Windlesham Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1983
2.05 acre lot
2,590 sqft
$254/sqft
Garage

About this House

Move-in ready and perfectly positioned in the highly sought-after Great Bridge School District, this rare 2-acre property offers exceptional space, privacy, and versatility. In addition to the attached 2-car garage, the standout feature is the impressive 2700+sqft detached garage — ideal for car enthusiasts, hobbyists, storage, or future expansion possibilities. Thoughtful updates include vinyl siding (2015), vinyl windows (2016), HVAC replacement (2017 & 2021), a 50-gallon water heater and architectural roof (2018), plus a full interior refresh in 2026 with new lighting and plumbing fixtures, fresh paint, new carpet, and updated hardware throughout. Hard-surface flooring flows through all main living areas and a relaxing hot tub conveys. Enjoy outdoor living on the long front porch with swing or the screened back porch overlooking the spacious yard. All kitchen and laundry appliances convey. A truly unique opportunity — come see it today!
301 Windlesham Dr, Chesapeake, VA 23322 is a 4 bedroom, 4 bathroom, 2,590 sqft single-family home in Great Bridge East, built in 1983. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $658,000, with a rent estimate of $3,632/month.
Last check for updates: about 2 hours ago
Listed by Madonna Bossa
World Class Realty, (757) 228-7773
Bought with: Paul Morreira, Iron Valley Real Estate HR, (757) 645-9700
Source: REIN Inc., MLS#10635700

Home Details for 301 Windlesham Dr

Interior Features

Interior Details
Basement: Crawl SpaceNumber of Rooms: 11Types 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): 4
Dimensions and Layout
Living Area: 2590 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Disposal, Dryer, Microwave, Electric Range, Refrigerator, Washer, Electric Water HeaterDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Heat Pump,ZonedHas CoolingAir Conditioning: Heat Pump,ZonedHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Wood BurningSpa: Hot TubHas a FireplaceHas a Spa
Windows, Doors, Floors & Walls
Window: Window TreatmentsDoor: Storm Door(s)Flooring: Carpet, Laminate/LVP, VinylCommon Walls: No Common Walls
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: Front-mounted Range Controls, Main Floor LaundryFloors: Carpet, Laminate LVP, Vinyl
View
Has a ViewView: Trees/Woods

Exterior Features

Exterior Home Features
Roof: Asphalt ShinglePatio / Porch: Deck, Porch, Screened PorchFencing: None
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 5No CarportHas a GarageNo Attached GarageNo Open ParkingParking Spaces: 5Parking: Garage Att 2 Car,Garage Det 3+ Car,Oversized,Garage Door Opener
Pool
Pool: None
Frontage
Waterfront: Not WaterfrontNot on Waterfront
Water & Sewer
Sewer: City/County
Farm & Range
Not Allowed to Raise Horses

Property Information

Year Built
Year Built: 1983
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Transitional
Building
Construction Materials: Vinyl SidingNot a New ConstructionNot Attached Property

Price & Status

Price
List Price: $652,500
Status Change & Dates
Off Market Date: Sat May 23 2026Possession Timing: Settlement

Active Status

MLS Status: Sold

Location

Direction & Address
City: ChesapeakeCommunity: All Others Area 32
School Information
Elementary School: Southeastern ElementaryJr High / Middle School: Great Bridge MiddleHigh School: Great Bridge

HOA

No HOA

Lot Information

Lot Area: 2.05 Acres

Offer

Contingencies: Non Contingent

Miscellaneous

Mls Number: 10635700Attic: Walk-In

Price and Tax history

YearProperty taxTax assessment
2025
$5,318
$526,500
Home facts updated by county records

Market trends in Great Bridge East

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$518K
Sale-to-List Price
100.0%
Price per sq ft
$247
Available listings
65
6MoM

Around this home

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

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

What Locals Say about Great Bridge East

At least 103 Trulia users voted on each feature.

  • 97 % Say yards are well-kept

  • 94 % Say car is needed

  • 93 % Say parking is easy

  • 90 % Say people would walk alone at night

  • 89 % Say it's dog friendly

  • 86 % Say it's quiet

  • 81 % Say kids play outside

  • 80 % Say there's holiday spirit

  • 66 % Say streets are well-lit

  • 62 % Say neighbors are friendly

  • 58 % Say they plan to stay for at least 5 years

  • 50 % Say there are sidewalks

  • 40 % Say there's wildlife

  • 40 % Say there are community events

  • 35 % Say it's walkable to grocery stores

  • 21 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Trevor Jacob Upson
    "Peace and quiet is the most special thing about Chesapeake, never wanna move. It’s nice and very subtle here. Very cozy half city, half country. It’s really nice! Visit sometime and you’ll see exactly what I’m talking about."
    0
    Flag
  • Trevor Jacob Upson
    "Honestly walking your dog around here would be great, many people do it at all times of the day. I’m sure anyone would be happy here or near here, specifically in Chesapeake "
    0
    Flag
  • Trevor Jacob Upson
    "Very comfortable and easy living with quiet neighbors. Very southern living, makes it comfortable to most people. Very friendly as well!"
    0
    Flag
  • Trulia User
    "I have lived in the neighborhood for almost six years. Many of the neighbors are friendly and we've always felt welcomed. Our next door neighbors have always looked put for us and we've had several new families with children move into the neighborhood over the past several years, which has been great! We would love to see a new family scoop up this house and join the neighborhood!"
    3
    Flag
  • Trulia User
    "That it’s a safe neighborhood for Children and very low crime … great neighborhood to live in and attend school"
    0
    Flag
  • Trulia User
    "That the neighborhood is very safe for small children and it’s a family oriented neighborhood .. great place to live work and play "
    0
    Flag
  • Trulia User
    "Beautiful community to live in quiet neighborhood great place to raise kids everything is close by beach is minutes away"
    0
    Flag
  • Pgmjulie
    "Long commutes, heavy traffic. Traffic heavy on weekend too.. yards must be well maintained. Lots of golf carts roam the neighborhood. Be prepared to share yard and common area with neighbors but not the work or expense."
    9
    Flag
  • CHERYL L.
    "No sidewalks, main thoroughfare to bypass And sometimes the cars go to quickly. Just another typical great Bridge neighborhood"
    1
    Flag
  • Devan W.
    "This neighborhood is safe, friendly and clean. Dog-friendly as well. There are farms maybe 5 or 6 miles from here and they have awesome food/produce. "
    2
    Flag
  • Tlmaynard
    "The schools are top notch and kids are able to play and bicycle in the neighborhood safely. Shopping and restaurants are very convenient and plentiful. "
    1
    Flag
  • Jim M.
    "Commute can be long when bridge is shut down. Rush hour can be a nightmare. Other commuters may not be as welcoming to let you into traffic. "
    2
    Flag
  • Kjcoolong
    "There are many dogs in this area, so most seem to be pet lovers. We do not own a pet, but are ok with them. My only complaint is some are left out barking to long. Super annoying!"
    0
    Flag
  • Andrew
    "Great schools, quite neighborhood, nice mature neighbors, kids are safe to play outside. Nonsense, anyone looking to live in a safe peaceful neighborhood needs to buy their home in Etheridge Lakes."
    0
    Flag
  • jjs
    "you see dog walkers all the time . This is a very pet friendly neighborhood. we all have pets. ,,,......................"
    1
    Flag
  • Tlmaynard
    "Above average schools as well as a Great place to live and raise a family. Peaceful and mostly very nice neighbors. Easy access to lots of local community events. "
    9
    Flag
  • Kim
    "Great Area! Awesome place to raise children. Kids love it so many friends. Amazing Schools in Hickory District."
    4
    Flag
  • Peggy h. p.
    "Family friendly area, safe and comfortable. Great place to call home. We have loved it here for over 30 years, since our son was one."
    2
    Flag
  • Huber k.
    "We just moved to this area 3 years ago. The neighborhood is a perfect place for a family--great schools, safe, quiet, friendly, and close to everything."
    2
    Flag
  • Jennifer
    "Sought-after school district - Hickory! Beautiful/established neighborhood - Etheridge area. "
    2
    Flag
  • cielostellato1013
    "I have lived within a one mile radius of this home for over thirty years. During this time I have lived in four different homes as my family grew, then grew up and left home. It is an amazing community with lovely homes, well-groomed yards, excellent schools and friendly neighbors."
    2
    Flag

LGBTQ Local Legal Protections

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. © 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: 2026-09-08 17:08:48 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.
Some or all of the listings (or Listing Data) represented in this application have been enhanced with information not provided by REIN. Such enhancements may include information obtained from Zillow Inc. and other third-party or publicly available sources and are not part of the Listing Data provided by REIN.

Frequently asked questions about 301 Windlesham Dr

  • What is 301 Windlesham Dr estimated to be worth?
    Trulia's estimated value for 301 Windlesham Dr in Chesapeake, VA is $658,000.
  • Is Chesapeake a buyer's or seller's market?
    Chesapeake is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Chesapeake?
    The median sale price in Chesapeake is $518K.
  • What do residents say about the Great Bridge East neighborhood?
    Residents describe the Great Bridge East neighborhood in Chesapeake, VA as well-kept, easy to park in, and dog-friendly. Most residents say you need a car. See recently sold homes in Great Bridge East, Chesapeake.
  • Does 301 Windlesham Dr have air conditioning?
    Yes, 301 Windlesham Dr in Chesapeake, VA has air conditioning.
  • Does 301 Windlesham Dr have laundry facilities?
    Yes, 301 Windlesham Dr in Chesapeake, VA has in-unit laundry.

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