2 days on market
$610,000
301 Windlesham Dr
Chesapeake, Virginia 23322
MLS# 10635700 · ALL OTHERS AREA 32 · Chesapeake VA
Updated May 29, 2026 · Source: REIN MLS
Est. payment
$3,786/mo
Edit below
Price / sq ft
$236
2,590 sq ft
Days on market
2
New listing
HOA
None
Year built
1983
43 yrs old
Beds
4
Full Baths
4
Half Baths
0
Sq Ft
2,590
Garage
Yes
About this home
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 w…
Listed by Madonna Bossa · World Class Realty
VaHome Team property overview
301 Windlesham Drive is a four-bedroom, four-bath home in Chesapeake, Virginia 23322, offering 2,590 square feet of space built in 1983. Groceries, coffee, and fitness studios are all within a short walk, and two military installations are a quick commute away.
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Why this home stands out
What sets 301 Windlesham Drive apart is the rare combination of walkable daily convenience and genuine square footage. Four full bathrooms across 2,590 square feet means no morning traffic jams in the hallway, and the 1983 build era typically delivers solid construction with larger room proportions than many newer tract homes. Add a sub-ten-minute drive to USCG Finance Center Chesapeake and you have a home that works hard on every front.
ALL OTHERS AREA 32 and the Chesapeake real estate market
Windlesham Drive sits in the southern reaches of Chesapeake, Virginia — one of the largest cities by land area on the East Coast and a place that consistently draws buyers who want suburban breathing room without sacrificing urban access. The surrounding zip code, 23322, is a well-established pocket of the city where mature trees line the streets and neighbors tend to stay put for years. Chesapeake carries a reputation for lower crime rates relative to the broader Hampton Roads region, and that sense of stability shows in the streetscape around this address. If you're working with chesapeake real estate agents to compare neighborhoods across the city, this corridor stands out for its walkability score — unusual for Chesapeake — and its proximity to both commercial corridors and quieter residential streets. Virginia Beach is a short drive east, Norfolk is accessible to the north, and Interstate 64 keeps the entire Hampton Roads metro within reasonable reach.
What's nearby
Daily errands from 301 Windlesham Drive are genuinely easy. Harris Teeter is just 0.3 miles away for a full grocery run, and Food Lion is a mile out for a second option. Your morning coffee is practically at the front door — Starbucks Coffee Company is 0.2 miles away, and Millers is 0.3 miles for a local alternative. China Sun handles weeknight dinners when cooking isn't on the agenda. Fitness is equally convenient: Club Pilates, The Little Gym of Chesapeake, and CrossFit Krypton are all within 0.4 miles, covering everything from recovery sessions to high-intensity training to kids' classes.
For different buyers
For military families relocating
USCG Finance Center Chesapeake is nine minutes from the front door, and Norfolk Naval Shipyard is a 21-minute drive — manageable even on a busy duty day. A VA loan can make ownership here straightforward, and four bedrooms give you the flexibility to host family during PCS transitions or set up a proper home office during remote-work stretches.
For families upgrading
Four bedrooms and four full bathrooms give a growing family real room to breathe. The Little Gym of Chesapeake is 0.3 miles away for the younger kids, Club Pilates and CrossFit Krypton are close for the adults, and Harris Teeter is a short walk when the week's groceries need restocking. This is the kind of layout and location that makes the upgrade feel worth it.
Frequently asked questions
How far is 301 Windlesham Drive from Norfolk Naval Shipyard?
Norfolk Naval Shipyard is approximately 21 minutes from 301 Windlesham Drive under typical traffic conditions. The route connects via Interstate 64 and surface roads through Portsmouth.
How far is 301 Windlesham Drive from USCG Finance Center Chesapeake?
USCG Finance Center Chesapeake is about nine minutes away, making it one of the closest military installations to this address in the Hampton Roads area.
What grocery stores are near 301 Windlesham Drive?
Harris Teeter is 0.3 miles away, making it the closest full-service grocery option. Food Lion is about a mile out, giving you a second choice for everyday staples.
Is 301 Windlesham Drive in a flood zone?
Flood zone information for this address is displayed in the dedicated FloodRisk tile on this page, which pulls current FEMA map data for the most accurate and up-to-date designation.
Does 301 Windlesham Drive have an HOA?
HOA status for this property is confirmed in the listing details section — check there for the most current information on whether a homeowners association governs this address.
Ready to walk through 301 Windlesham Drive? Reach out to Tom and Dariya Milan at LPT Realty — they know Chesapeake inside and out and can get you in the door.
Summary generated by AI from public records and publicly available information.
Location & Neighborhood
Places within ~1 mile, ordered by distance from this property. Powered by Google Places.
Flood Risk
Property Details
Bedrooms
4
Full Baths
4
Half Baths
0
Approx Sq Ft
2,590
Stories
2
Fireplaces
0
Flooring
Carpet, Laminate/LVP, Vinyl
Heating
Cooling
Laundry
Interior Features
N/A
Appliances
Dishwasher, Disposal, Dryer, Microwave, Elec Range, Refrigerator, Washer
Sale & Tax History
List Price
$610,000
Price / Sq Ft
$236
Annual Taxes
$5,318
Monthly Tax
$443
HOA
None
Tax Rate (effective)
0.87%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | May 27, 2026 | $610,000 | — |
| Currently listed | — | $610,000 | — |
Looking for multi-year tax assessments or prior sales? REIN MLS only ships data for the current listing. For full property history, check the city assessor record:
Tax data above from REIN public-records sync. Sale timeline tracked from this listing's first appearance in our feed forward; prior owner sales are not included.
Comparable Properties
Comps are selected by city, bed count, square footage and price proximity. Composite similarity score weights bed match, sqft variance, price variance, and straight-line distance.
About buying in Chesapeake
Homes for sale in Chesapeake, VA appeal to buyers who want suburban space, top-rated schools, and easy access to Virginia Beach and Norfolk. The city's geography splits roughly into five corridors: Greenbrier (23320) with newer construction and shopping near the mall; Great Bridge (23320, 23322) with the historic Battlefield district and excellent schools; Hickory (23322) with large-lot family homes and Hickory High; Western Branch (23321) near the Portsmouth border with mature trees and starter homes; and Deep Creek / South Norfolk (23323, 23324) with affordable inventory and waterfront access. Buyer demand is anchored by Chesapeake Public Schools — among the highest-rated in Hampton Roads — including Hickory High, Grassfield High, Great Bridge High, and Western Branch High. Median home prices range from $300K starter homes in Deep Creek to $600K+ Great Bridge family homes and $1M+ luxury estates in Hickory's gated communities. Chesapeake's commute is excellent for buyers working in Virginia Beach, Norfolk Naval Shipyard, or Newport News Shipbuilding via the I-664 and I-64 corridors. Below you'll find every active Chesapeake MLS listing pulled every 5 minutes from the REIN feed.
Military Commute
Drive times to nearest basesDrive times via Google Maps with current traffic patterns. Times are typical and may vary by time of day. Use the "Analyze" button up top to see live drive time to your saved base.
Estimate your monthly payment
$3,786/moPrincipal & interest
$3,165
Property tax
$443
Home insurance
$178
PMI
None
HOA
None
Estimate only. Insurance assumed at 0.35% of home value annually. Actual taxes, insurance, and rate will vary by lender, credit, and property. Contact a lender for a personalized quote.
Listed by World Class Realty · MLS# 10635700
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$610,000
301 Windlesham DR, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
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