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Windsor › ALL OTHERS AREA 65 › 8368 Whispering Pines Trl✓ Source: REIN MLS #10641278 · record updated Sep 1, 2026 · synced every 2 min · your inquiry is never resold
8368 Whispering Pines TRL, WINDSOR VA 23487 - Main photo
8368 Whispering Pines TRL, WINDSOR VA 23487 - Photo 2
8368 Whispering Pines TRL, WINDSOR VA 23487 - Photo 3
8368 Whispering Pines TRL, WINDSOR VA 23487 - Photo 4
8368 Whispering Pines TRL, WINDSOR VA 23487 - Photo 5
3beds
2baths
2,208sqft
69days on market

8368 Whispering Pines Trl, Windsor, VA 23487

ActiveResidential · built 1975 · ALL OTHERS AREA 65

Facts & features

Type

Residential

Year built

1975

Price / sqft

$181

HOA

None

Taxes

$1,913/yr

County

Isle of Wight County VA

MLS #

10641278

Interior

Bedrooms
3
Full baths
2
Approx. sqft
2,208
Stories
2
Flooring
Carpet, Ceramic, Laminate/LVP, Wood
Ensuite bedrooms
1
First-floor bed & full bath
Yes
Total rooms
8
Other rooms
1st Floor BR, 1st Floor Primary BR, Attic, Breakfast Area, PBR with Bath, Porch, Utility Closet, Workshop
Appliances
220 V Elec, Dryer, Dryer Hookup, Microwave, Elec Range, Refrigerator, Washer, Washer Hookup
Equipment
Attic Fan, Cable Hookup, Ceiling Fan, Generator Hookup, Jetted Tub, Satellite Dish
Accessibility
Main Floor Laundry

Construction & exterior

Style
Mobile Home, Split-Level
Subtype
Detached
Foundation
Crawl
Roof
Asphalt Shingle
Exterior
Vinyl
Pool
No Pool

Utilities & systems

Heating
Propane Gas
Cooling
Central Air
Water heater
Gas
Water
Well
Sewer
Septic

Lot, parking & ownership

Lot size
4.4600
Subdivision
ALL OTHERS AREA 65
Zoning
RAC
Ownership
Fee Simple
Garage
Yes
Parking
Garage Det 3+ Car, Oversized Gar, Multi Car, Off Street
Possession
CLOSING
Disclosures
Disclosure Statement

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

About this home

Welcome to Whispering Pines Trail, a rare opportunity to own a beautifully updated home on 4.46 private acres in Windsor. This 3-bedroom, 2-bath home offers 2,208 square feet of move-in ready living space with a fully updated kitchen, renovated primary bath, new flooring, paint, and trim throughout. The spacious upstairs family room is wired for surround sound and projector, with the screen conveying. Outdoors, you'll find exceptional workshop and storage space including a 30'x86' main shop, a 26'x37' secondary shop and cinder block pump house with room for additional storage. Enjoy the peace and privacy of country living while having room for hobbies, equipment, recreation, or a home-based business. A truly unique property offering space, versatility, and endless possibilities in desirable Windsor. Owner Financing available.

Listing courtesy of Leslie Brennan · Aweigh Real Estate · REIN MLS #10641278

Tom & Dariya's overview

Our read on this home

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

At a glance

Set on a quiet trail in Windsor, Virginia, this 1975-built, 2,208-square-foot home offers three bedrooms, two baths, and the kind of elbow room that's hard to find in Isle of Wight County — all within a straightforward commute to the region's major military installations.

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 8368 Whispering Pines Trail apart is the combination of generous square footage and a 1975 construction era that tends to mean wider floor plans and sturdier bones than many newer builds in the area. At 2,208 square feet across three bedrooms and two full baths, there's genuine breathing room here — space to spread out, host, and make the layout your own without feeling squeezed into a cookie-cutter footprint.

ALL OTHERS AREA 65 and the Windsor real estate market

Windsor is one of those small Virginia towns that earns real loyalty from the people who land here. Situated in Isle of Wight County, it sits at a comfortable remove from the congestion of Hampton Roads while still keeping you connected to everything the region offers. The pace is quieter, the lots tend to run larger, and neighbors actually wave. Whispering Pines Trail fits that character well — a residential street where mature trees line the road and the surroundings feel genuinely settled rather than hastily developed. Windsor itself is a tight-knit community with a small-town downtown, local businesses, and a sense that people put down roots and stay. Isle of Wight County has long attracted buyers who want space without sacrificing access, and Windsor delivers on both counts. If you're weighing options across the region, this address represents a distinctive take on what Windsor, Virginia living can look like.

What's nearby

Day-to-day errands are manageable from Whispering Pines Trail. Windsor's town center is just a short drive away for basics, and the broader Isle of Wight County corridor along Route 460 connects you to grocery stores, pharmacies, and dining without a long haul. Smithfield — known for its historic downtown and waterfront — is roughly 20 minutes east, adding a destination-worthy option for weekend meals or a stroll. Franklin is similarly accessible to the west. Outdoor options include Windsor's local parks and the broader green spaces Isle of Wight County maintains. The region's rural character means you're never far from open land, farm stands, or a genuinely quiet afternoon.

For different buyers

For military families relocating

Joint Staff J7 in Suffolk is about 33 minutes from Whispering Pines Trail, and Joint Base Langley-Eustis (Fort Eustis) runs roughly 40 minutes out — both well within a reasonable daily drive. Isle of Wight County gives military households more square footage per dollar than closer-in Hampton Roads zip codes, and a VA loan can make the math work even better. The 2,208-square-foot layout handles the practical demands of a military household with room to spare.

For families upgrading

Families comparing homes for sale zoned for Windsor High School and homes for sale zoned for Windsor Elementary School will find 8368 Whispering Pines Trail worth a close look. Three bedrooms and two full baths across 2,208 square feet gives growing households genuine flexibility — dedicated space for a home office, a playroom, or a guest room without anyone feeling crowded. Windsor's community feel and Isle of Wight County's quieter pace make the upgrade feel complete.

More buyer questions

How far is 8368 Whispering Pines Trail from Joint Staff J7 Suffolk?

The drive from Whispering Pines Trail to Joint Staff J7 in Suffolk runs approximately 33 minutes under typical conditions. Joint Base Langley-Eustis (Fort Eustis) is roughly 40 minutes in the other direction, making this address a reasonable midpoint for dual-military households.

What is the square footage and layout of 8368 Whispering Pines Trail?

The home offers 2,208 square feet of living space across three bedrooms and two full baths, built in 1975. The floor plan reflects the wider, more open layouts common to that construction era.

Is 8368 Whispering Pines Trail in a flood zone?

Flood zone information for this address is covered in the FloodRisk tile on this page, which pulls current FEMA map data. We recommend reviewing that section and discussing it with your agent before making any decisions.

What county is 8368 Whispering Pines Trail in?

The property is located in Isle of Wight County, Virginia, within the town of Windsor — zip code 23487.

Can a VA loan be used to purchase 8368 Whispering Pines Trail?

Yes — as a single-family residential property in Virginia, this home is generally eligible for VA loan financing, subject to standard VA appraisal and condition requirements. A VA loan can be one of the most powerful tools available to eligible buyers in this market.

Tom and Dariya Milan at LPT Realty know Windsor and Isle of Wight County well — reach out to get a straight answer on whether 8368 Whispering Pines Trail is the right fit for you.

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

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

Windsor$340K – $460K3+ 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

$2,352/mo

Principal & interest

$2,076

Property tax

$159

Home insurance

$117

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

166% of $241,500

City assessment record · taxes $1,913/yr

Land share of assessed value

32% — $76,100

Improvements $165,400 · assessor record ✓

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

Sale & Tax History

List Price

$400,000

Price / Sq Ft

$181

Annual Taxes

$1,913

Monthly Tax

$159

HOA

None

Tax Rate (effective)

0.48%

Sale Timeline (this listing)

EventDatePriceDetail
ListedJun 24, 2026$400,000—
Price reducedSep 1, 2026$400,000−$50,000
Currently listed—$400,000—

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

66% above assessment

Total Assessed

$241,500

Land

$76,100

Improvement

$165,400

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

69 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

Is 8368 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 8368 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 8368 Whispering Pines Trl have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 8368 Whispering Pines Trl built?+
It was built in 1975, 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 Leslie Brennan · Aweigh Real Estate · REIN MLS #10641278

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.

8368 Whispering Pines Trl, Windsor — photo

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

Call or text (757) 777-7577

8368 Whispering Pines Trl, Windsor, Virginia 23487 · MLS #10641278 · 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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