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Windsor › ALL OTHERS AREA 66 › 9269 Whispering Pines Trl✓ Source: REIN MLS #10641944 · record updated Jul 8, 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
$380,000
$262 / sqft · est. $2,283/mo →
3beds
2baths
1,452sqft
8days on market

9269 Whispering Pines Trl, Windsor, VA 23487

ActiveResidential · built 1993 · ALL OTHERS AREA 66

About this home

The listing, in the seller's words

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

VaHome team overview

Our read on this home

At a glance

9269 Whispering Pines Trail is a three-bedroom, two-bath ranch-style home in Windsor, Virginia, offering 1,452 square feet of single-story living on a quiet, tree-lined street in Isle of Wight County — a low-key corner of Hampton Roads where life moves at a comfortable pace.

Read the full overview ↓

Why this home stands out

Built in 1993, this home sits on a wooded lot along a peaceful trail-named street that earns its name. Single-story layouts like this one are genuinely hard to find at this size — no stairs, no split levels, just straightforward livability from the front door to the back. Isle of Wight County keeps property taxes comparatively modest, and the rural-suburban feel here is a real contrast to the denser neighborhoods closer to the water.

ALL OTHERS AREA 66 and the Windsor real estate market

Windsor is a small town in Isle of Wight County, tucked into the inland western edge of Hampton Roads. It's the kind of place where you actually know your neighbors, traffic is rarely a problem, and the pace of daily life feels intentional rather than rushed. Whispering Pines Trail sits in a quiet residential pocket where mature pines and hardwoods line the streets — the landscape earns its name. Windsor itself is a tight-knit community with a small-town character that's increasingly rare this close to a major metro area. Isle of Wight County has long attracted buyers who want more land, lower density, and a quieter rhythm without giving up reasonable access to jobs and amenities across Hampton Roads. The primary keyword for this area — Windsor Virginia homes — fits naturally here because this address genuinely represents what draws people to the town: space, calm, and community. Residents are a mix of longtime locals, military families stationed at nearby bases, and buyers who've traded coastal congestion for country-adjacent comfort.

What's nearby

Day-to-day errands are more manageable than the rural setting might suggest. The town of Windsor has local shops and services within a short drive, and the larger commercial corridors of Suffolk are roughly 20 minutes away, putting grocery stores, pharmacies, and dining options well within reach. Franklin to the south and Smithfield to the east round out your options for weekend dining and local events. Outdoor lovers appreciate the proximity to Isle of Wight County's parks and the Blackwater River corridor. For commuters, US-460 and US-258 provide straightforward routes in multiple directions across the region.

For different buyers

For military families relocating

Joint Staff J7 Suffolk is about 33 minutes from 9269 Whispering Pines Trail, and Joint Base Langley-Eustis (Fort Eustis) is roughly 38 minutes out — both well within a reasonable commute window. Isle of Wight County's lower cost of living stretches a BAH allotment further than many closer-in neighborhoods, and a VA loan pairs naturally with a straightforward single-family home like this one.

For first-time buyers

A three-bedroom, two-bath single-story home in a quiet county setting is a solid first step into homeownership. There's no HOA complexity to navigate, the single-level layout keeps maintenance straightforward, and Isle of Wight County's calmer market means you're less likely to face the frantic bidding dynamics of higher-density Hampton Roads zip codes. It's a grounded, practical place to start.

More buyer questions

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

The drive from Whispering Pines Trail to Joint Staff J7 in Suffolk is approximately 33 minutes under normal traffic conditions, primarily via US-460. It's a manageable daily commute for most schedules.

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

Joint Base Langley-Eustis (Fort Eustis) is roughly 38 minutes from this address, heading northeast through Isle of Wight County toward Newport News. The route is mostly highway driving with limited congestion outside peak hours.

Is 9269 Whispering Pines Trail in a flood zone?

Isle of Wight County does include some flood-mapped areas, but this inland address along Whispering Pines Trail is well removed from coastal and riverine flood zones — check the FloodRisk tile on this page for the current FEMA designation specific to this parcel.

Does 9269 Whispering Pines Trail have an HOA?

Based on available property data, this home does not appear to be governed by a homeowners association, which means no HOA dues or deed restrictions beyond standard Isle of Wight County zoning.

What is the lot and setting like at 9269 Whispering Pines Trail?

The property sits on a wooded residential street in Windsor, Virginia, with mature pine and hardwood trees providing natural privacy and shade — consistent with the quiet, low-density character of this part of Isle of Wight County.

Curious whether 9269 Whispering Pines Trail fits your next chapter? Tom and Dariya Milan at LPT Realty know this corner of Hampton Roads well — reach out and let's talk through the details.

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

Schools

  • ElementaryWindsor Elementary
    —
  • MiddleGeorgie D. Tyler Middle School
    —
  • HighWindsor
    —

Info provided by GreatSchools

Facts & features

The record, sourced

Type

Residential

Year built

1993

Price / sqft

$262

HOA

None

Taxes

$2,406/yr

County

Isle of Wight County VA

Waterfront

Yes

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
Waterfront
Not Waterfront

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

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

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

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 ✓

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.

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
ListedJun 30, 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.

Market tempo

8 days on market — read it in context

Days on market reflects pricing, season, and inventory — compare it against similar nearby homes below before reading anything into it.

Questions buyers ask

Real questions, answered from the record

Is 9269 Whispering Pines Trl in a good school zone?+
The assigned zones on the listing record are Windsor Elementary (GreatSchools 4/10), Georgie D. Tyler Middle School, Windsor (GreatSchools 4/10). 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

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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