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Windsor › ALL OTHERS AREA 66 › 9269 Whispering Pines Trl✓ Source: REIN MLS #10641944 · record updated Aug 10, 2026 · synced every 2 min · your inquiry is never resold
9269 Whispering Pines TRL, WINDSOR VA 23487 - Main photo
9269 Whispering Pines TRL, WINDSOR VA 23487 - Photo 2
9269 Whispering Pines TRL, WINDSOR VA 23487 - Photo 3
9269 Whispering Pines TRL, WINDSOR VA 23487 - Photo 4
9269 Whispering Pines TRL, WINDSOR VA 23487 - Photo 5
3beds
2baths
1,452sqft
23days on market

9269 Whispering Pines Trl, Windsor, VA 23487

Under ContractResidential · built 1993 · ALL OTHERS AREA 66

Facts & features

Type

Residential

Year built

1993

Price / sqft

$262

HOA

None

Taxes

$2,406/yr

County

Isle of Wight County VA

MLS #

10641944

Interior

Bedrooms
3
Full baths
2
Approx. sqft
1,452
Stories
1
Flooring
Carpet, Laminate/LVP, Vinyl
Ensuite bedrooms
1
First-floor bed & full bath
Yes
Total rooms
7
Other rooms
1st Floor BR, 1st Floor Primary BR, Attic, Foyer, PBR with Bath, Pantry, Utility Room
Appliances
Dishwasher, Dryer, Microwave, Elec Range, Refrigerator, Washer
Equipment
Backup Generator, Cable Hookup, Ceiling Fan, Generator Hookup, Hot Tub, Jetted Tub

Construction & exterior

Style
Ranch
Subtype
Detached
Foundation
Crawl
Roof
Composite
Exterior
Vinyl
Pool
No Pool
Fencing
Back Fenced

Utilities & systems

Heating
Forced Hot Air, Heat Pump, Programmable Thermostat
Cooling
Heat Pump
Water heater
Electric
Water
Well
Sewer
Septic

Lot, parking & ownership

Lot size
5.9300
Subdivision
ALL OTHERS AREA 66
Zoning
RR
Ownership
Fee Simple
Garage
Yes
Parking
Garage Det 1 Car, Oversized Gar, Multi Car, Driveway Spc
Possession
CLOSING
Miscellaneous
Fuel In Tank Conveys
Disclosures
Disclosure Statement

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

About this home

Hunter's paradise on 5.93 private acres! Zoned Rural Residential, this peaceful property offers the perfect blend of privacy, comfort, and country living. Surrounded by abundant wildlife, it's an ideal retreat for hunters, nature lovers, or anyone looking to escape the hustle and bustle. Enjoy your morning coffee on the full-length front porch while watching deer, birds, and other wildlife. The approximately 1-acre fenced yard is perfect for pets, gardening, or outdoor activities. A detached garage/workshop with upper-level storage provides plenty of room for projects, equipment, or recreational gear. Chickens and horses are welcome, making this property well-suited for a rural lifestyle. The nearly 1,500-square-foot ranch features an open-concept living and dining area with vaulted ceilings and a centrally located wood stove, creating a warm and inviting gathering space. Ceiling fans throughout add year-round comfort. The spacious kitchen includes granite countertops, a pantry, and ample cabinet and counter space. Down the hall are three bedrooms, including a first-floor primary suite with a private bath featuring a relaxing jetted tub. Additional features include a 27.5 kW automatic whole-house generator, providing dependable backup power for added peace of mind. If you've been searching for acreage, privacy, abundant wildlife, and the comforts of country living, this exceptional property is ready to welcome you home.

Listing courtesy of Tara Reichardt · Abbitt Realty Company LLC · REIN MLS #10641944

Tom & Dariya's overview

Our read on this home

by Tom & Dariya Milan, REALTORS® · Brokered by LPT Realty

At a glance

A 1993-built, three-bedroom, two-bath home on Whispering Pines Trail in Windsor, Virginia — 1,452 square feet of single-family living in Isle of Wight County, roughly 33 minutes from Joint Staff J7 Suffolk and 38 minutes from Joint Base Langley-Eustis.

Keep searching in Windsor

See homes for sale zoned for Windsor High School and homes for sale zoned for Windsor Elementary School.

Read the full overview ↓

Why this home stands out

What sets 9269 Whispering Pines Trail apart is its position in a quieter corner of Windsor — a small-town Isle of Wight County community that still draws buyers who want elbow room, lower density, and manageable commutes to two major military installations. The 1993 construction puts it in a mature neighborhood with established trees and a settled street feel that newer subdivisions simply haven't had time to develop.

ALL OTHERS AREA 66 and the Windsor real estate market

Windsor, Virginia sits in Isle of Wight County — a slower-paced, largely rural locality that borders Suffolk to the east and Southampton County to the south. The town itself is compact and walkable at its core, with a Main Street that carries the kind of low-key, small-town character that's genuinely hard to find this close to Hampton Roads. Whispering Pines Trail is a residential street with mature tree cover, the sort of block that anchors everyday life away from the noise of larger suburban corridors. Windsor's position along Route 460 keeps it connected — Norfolk is roughly an hour away, Suffolk is a straight shot east, and the broader Hampton Roads metro is accessible without the traffic density that comes with living closer to the coast. Isle of Wight County is known for its rural preservation ethic and relatively low property tax environment, which resonates with buyers comparing Windsor homes to options deeper inside the metro.

What's nearby

Daily life in Windsor is straightforward. Groceries, pharmacy runs, and hardware store trips are all handled locally or in nearby Suffolk, which is about 20 minutes east on Route 460. Franklin, roughly 20 minutes southwest, adds more dining and retail options. Outdoor recreation is a real draw here — Windsor has town parks, and the broader Isle of Wight County offers access to the Blackwater River corridor and Ragged Island Wildlife Management Area. The pace is unhurried, and the drive times to larger Hampton Roads amenities — restaurants, medical centers, and entertainment — are manageable for buyers who prioritize space and quiet over walkability scores.

For different buyers

For military families relocating

For military households weighing a permanent change of station, 9269 Whispering Pines Trail puts you within 33 minutes of Joint Staff J7 Suffolk and 38 minutes of Joint Base Langley-Eustis — two installations that cover a wide range of assignments. Isle of Wight County's lower cost basis stretches a VA loan further than comparable square footage closer to the water, and the commute corridors along Route 460 are well-traveled by military commuters.

For first-time buyers

If you're buying your first home and want space without the price pressure of Virginia Beach or Chesapeake, Windsor is worth a serious look. Three bedrooms, two baths, and 1,452 square feet on a residential street in Isle of Wight County gives you room to grow. Families comparing homes for sale zoned for Windsor High School and homes for sale zoned for Windsor Elementary School will find that this address falls within those attendance zones — a practical anchor for households planning ahead.

More buyer questions

How far is 9269 Whispering Pines Trail from Joint Base Langley-Eustis?

The drive from Whispering Pines Trail to Joint Base Langley-Eustis (Fort Eustis) is approximately 38 minutes under normal traffic conditions, primarily along Route 460 east toward Newport News.

How far is 9269 Whispering Pines Trail from Joint Staff J7 Suffolk?

Joint Staff J7 in Suffolk is roughly 33 minutes from this address, making it one of the closer major installations for buyers stationed there.

Is 9269 Whispering Pines Trail in a flood zone?

Flood zone designation for this address is covered in the FloodRisk tile on this page — check that section for the current FEMA map classification.

Does Windsor, Virginia have an HOA for Whispering Pines Trail?

HOA status for this specific street varies by subdivision plat — confirm with Isle of Wight County records or a title search whether a homeowners association applies to this address.

What is the property type and lot character at 9269 Whispering Pines Trail?

This is a single-family residential home built in 1993, offering 1,452 square feet across three bedrooms and two bathrooms on a tree-lined residential street in Windsor, Isle of Wight County, Virginia 23487.

Tom and Dariya Milan at LPT Realty know Windsor and the surrounding Isle of Wight County market well — reach out to talk through what this address means for your next move.

Summary generated by AI from public records and publicly available information.

Homes like this one sell fast — see the next one first

Windsor$320K – $440K3+ beds

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Schools

VaHome School Score

Our own 1–10 rating, scored from Virginia Department of Education data.

VaHome School Score — calculated by VaHome.com from Virginia Department of Education assessment, progress, and attendance data. Attendance zones come from the MLS listing record; confirm the current zone with the school division before making an offer.

Flood & environment

FEMA flood zone X · outside the high-risk area · FIRM 51093C

Flood Risk

Looking up FEMA flood zone…

Hurricane Evacuation Zone

Not in a designated hurricane evacuation zone.

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

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

$2,283/mo

Principal & interest

$1,972

Property tax

$201

Home insurance

$111

PMI

None

HOA/Condo (paid separately)

None

Estimate only. Association (HOA/condo) fees are paid separately and are not included in the payment above. 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

Asking vs. assessment

125% of $305,100

City assessment record · taxes $2,406/yr

Land share of assessed value

29% — $89,400

Improvements $215,700 · assessor record ✓

Own a home nearby? See what it is worth today — What's your Windsor home worth?

Sale & Tax History

List Price

$380,000

Price / Sq Ft

$262

Annual Taxes

$2,406

Monthly Tax

$201

HOA

None

Tax Rate (effective)

0.63%

Sale Timeline (this listing)

EventDatePriceDetail
ListedJul 18, 2026$380,000—
Currently listed—$380,000—

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

25% above assessment

Total Assessed

$305,100

Land

$89,400

Improvement

$215,700

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:

Windsor Assessor (Google)

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

Is 9269 Whispering Pines Trl in a good school zone?+
The assigned zones on the listing record are Windsor Elementary (VaHome School Score 4.6/10), Georgie D. Tyler Middle School (VaHome School Score 7.4/10), Windsor (VaHome School Score 5.8/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 9269 Whispering Pines Trl 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 9269 Whispering Pines Trl have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 9269 Whispering Pines Trl built?+
It was built in 1993, 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

Brokered by LPT Realty · Hampton Roads · answer their own phone

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

Listing courtesy of Tara Reichardt · Abbitt Realty Company LLC · REIN MLS #10641944

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.

Schedule a private tour

Free, no obligation — your inquiry goes to Tom & Dariya, never resold.

9269 Whispering Pines Trl, Windsor — photo

See it in person — the record only says so much.

Call or text (757) 777-7577

9269 Whispering Pines Trl, Windsor, Virginia 23487 · MLS #10641944 · 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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