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Chesapeake › ALL OTHERS AREA 32 › 301 Windlesham Dr✓ Source: REIN MLS #10635700 · record updated Jun 16, 2026 · synced every 2 min · your inquiry is never resold
301 Windlesham DR, CHESAPEAKE VA 23322 - Main photo
$652,500
$252 / sqft · est. $4,019/mo →
4beds
4baths
2,590sqft
2days on market

301 Windlesham Dr, Chesapeake, VA 23322

SoldResidential · built 1983 · ALL OTHERS AREA 32

About this home

The listing, in the seller's words

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!

Listing courtesy of Madonna Bossa · World Class Realty · REIN MLS #10635700

VaHome team overview

Our read on this home

At a glance

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.

Read the full overview ↓

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.

More buyer 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.

Schools

Info provided by GreatSchools

Facts & features

The record, sourced

Type

Residential

Year built

1983

Price / sqft

$252

HOA

None

Taxes

$5,318/yr

County

Chesapeake VA

Waterfront

Yes

MLS #

10635700

Interior

Bedrooms
4
Full baths
4
Approx. sqft
2,590
Stories
2
Flooring
Carpet, Laminate/LVP, Vinyl
Ensuite bedrooms
1
First-floor bed & full bath
Yes
Total rooms
11
Other rooms
1st Floor Primary BR, Attic, Breakfast Area, Fin. Rm Over Gar, Foyer, PBR with Bath, Pantry, Porch, Screened Porch, Workshop
Appliances
Dishwasher, Disposal, Dryer, Microwave, Elec Range, Refrigerator, Washer
Equipment
Ceiling Fan, Central Vac, Gar Door Opener, Hot Tub
Accessibility
Front-mounted Range Controls, Main Floor Laundry

Construction & exterior

Style
Transitional
Subtype
Detached
Foundation
Crawl
Roof
Asphalt Shingle
Exterior
Vinyl
Pool
No Pool
Waterfront
Not Waterfront

Utilities & systems

Heating
Heat Pump, Zoned
Cooling
Heat Pump, Zoned
Water heater
Electric
Water
City/County
Sewer
City/County

Lot, parking & ownership

Lot size
2.0500
Subdivision
ALL OTHERS AREA 32
Zoning
R15S
Ownership
Fee Simple
Garage
Yes
Parking
Garage Att 2 Car, Garage Det 3+ Car, Oversized Gar
Possession
SETTLEMENT
Disclosures
Disclosure Statement

Sources: REIN MLS record · null fields are suppressed, never faked

Flood & environment

FEMA flood zone X · outside the high-risk area · FIRM 510034

Flood Risk

Looking up FEMA flood zone…

Hurricane Evacuation Zone

Evacuation Zone C

Source: Virginia Dept. of Emergency Management — Know Your Zone

Explore this neighborhood

Hanbury

Hanbury is an established pocket of Chesapeake centered on the Hanbury Road corridor in the Great Bridge area.

1

For sale now

$131K

HH income

76.5%

Owner-occupied

U.S. Census ACS 2024 5-year

Explore Hanbury →
Map of Hanbury with neighborhood boundaryNeighborhood

Chesapeake houses for sale →

Location intelligence

Minutes to real places, not a score

Location & Neighborhood

Places within ~1 mile, ordered by distance from this property. Powered by Google Places.

Military Commute

Drive times to nearest bases

Drive 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.

The numbers

Run the real carrying cost

Estimates only — taxes come from the public record; confirm rates with your lender. VA-eligible buyers: $0-down financing may apply.

Estimate your monthly payment

$4,019/mo

Principal & interest

$3,386

Property tax

$443

Home insurance

$190

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.

Value & history

Judge value on real ground

Why we show no algorithmic estimate.

National AVMs misprice homes whose value drivers they can't see. Instead: the sourced assessment above, the carrying cost, real price history, and honest comparables below.

Price context — similar nearby homes

$520,000 – $660,000

The 6 most similar homes nearby (same city, within ~20% of this size, ~2.5 mi; 6 sold). Context for judging the asking price — not an appraisal or an estimate of this home's value.

928 Jodi Lynn TRL · 0.6 mi · 2,491 sqft$660,000 sold 2026-06
909 Douglas Eley LN · 0.3 mi · 2,300 sqft$558,500 sold 2026-07
1113 Edinburgh PW · 0.6 mi · 2,416 sqft$619,000 sold 2026-01

Sale & Tax History

List Price

$652,500

Price / Sq Ft

$252

Annual Taxes

$5,318

Monthly Tax

$443

HOA

None

Tax Rate (effective)

0.82%

Sale Timeline (this listing)

EventDatePriceDetail
ListedJun 14, 2026$652,500—
Price increasedJun 16, 2026$652,500+$42,500
SoldJun 12, 2026$652,500—

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:

Chesapeake Real Estate Assessor

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.

Questions buyers ask

Real questions, answered from the record

Is 301 Windlesham Dr in a good school zone?+
The assigned zones on the listing record are Southeastern Elementary (GreatSchools 6/10), Great Bridge Middle (GreatSchools 7/10), Great Bridge (GreatSchools 7/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 301 Windlesham Dr in a flood zone?+
FEMA maps this parcel in Zone X, outside the high-risk Special Flood Hazard Area. See the flood section on this page for details and sources.
Does 301 Windlesham Dr have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 301 Windlesham Dr built?+
It was built in 1983, per the listing record.

Answers generated from the listing record, verified school zones, FEMA data, and cached nearby-places data — never invented.

The people

You'll talk to a person, not a lead queue

TD

Tom & Dariya Milan

LPT Realty · Hampton Roads · answer their own phone

✓ Your inquiry goes to Tom & Dariya — never sold to strangers

Listing courtesy of Madonna Bossa · World Class Realty · REIN MLS #10635700

Call or text (757) 777-7577

Ask Dariya — instant answers

Schools, flood, drive times, what it really costs to own — answered from this page's data, by chat or voice.

This home has sold

Curious what it means for your own plans? Ask about similar homes nearby, or what your home might sell for in this market.

🏡 Similar homes for saleWhat's my home worth?
301 Windlesham Dr, Chesapeake — photo

This one's sold — the next one doesn't have to be.

🏡 Homes for sale in ChesapeakeCall or text (757) 777-7577

301 Windlesham Dr, Chesapeake, Virginia 23322 · MLS #10635700 · Source: REIN MLS + public record. Information deemed reliable but not guaranteed — verify independently. School zones subject to change; confirm with the local school division. All locations are described by neutral geographic fact. Equal Housing Opportunity.

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