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Windsor › ALL OTHERS AREA 65 › 8368 Whispering Pines Trl✓ Source: REIN MLS #10641278 · record updated Oct 7, 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
105days 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

$170

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

Three-bedroom, two-bath home on a quiet Windsor lot. Built in 1975 with 2,208 square feet of living space. About 33 minutes to Joint Staff J7 Suffolk. A solid foundation for your next chapter.

Keep searching in Windsor

See all Windsor homes for sale, including homes for sale zoned for Windsor High School and homes for sale zoned for Windsor Elementary School. Browse every listing among homes for sale in Windsor — updated from the REIN MLS every few minutes.

Read the full overview ↓

Why this home stands out

This ranch-style home sits on a peaceful residential street in Windsor. The layout offers practical space across three bedrooms and two full baths. Natural light flows through the main living areas. The lot provides room to stretch out and settle in. You'll find the bones of a home ready for your vision and updates. Windsor homes for sale in this price range don't often hit the market.

ALL OTHERS AREA 65 and the Windsor real estate market

Windsor is a quiet corner of Isle of Wight County, where tree-lined streets and modest homes define the character. Neighbors tend to stay put, and the pace is slower than the nearby cities. You're surrounded by open space and farmland that keeps the area feeling rural and calm. The community is close-knit without being cramped. Driving to Suffolk takes about 15 minutes; Hampton and Newport News are within 30 to 40 minutes. US Route 258 is your main corridor for getting around. Anyone comparing homes for sale in Windsor will notice how affordable the area remains. Schools serve the neighborhood through Isle of Wight County's system. This is the kind of place where you know your neighbors and the roads stay quiet.

What's nearby

Windsor's main services cluster along US 258 and in nearby Suffolk. A grocery store and pharmacy are about 10 minutes away by car. Coffee shops and casual dining options dot the route into downtown Suffolk, roughly 15 minutes north. For outdoor recreation, you're close to several county parks and boat launches on the Blackwater River. The nearest gas station is about 5 minutes away. Daily errands are manageable without a long drive.

For different buyers

Base commute and VA loan notes

About 33 minutes to Joint Staff J7 Suffolk and 40 minutes to Joint Base Langley-Eustis. VA loan financing is widely available in this market. The home's age and solid construction make it a straightforward purchase. You can close and move in without major delays or surprises.

Room to grow

Three bedrooms give you room to grow, and two full baths reduce morning conflicts. The lot size lets you add a garden, play space, or future expansion. The open floor plan in the main living area adapts to how your household uses the home. Storage runs throughout the house, and the single-story layout keeps life simple.

More buyer questions

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

About 33 minutes by car via US 258 north. It's a straightforward commute on major roads.

What school zones serve this address?

The property falls within the zones for homes for sale zoned for Windsor Elementary School and homes for sale zoned for Windsor High School, both part of Isle of Wight County Schools.

Is this a one-story or two-story home?

It's a single-story ranch-style home, which means no stairs to climb and easier maintenance overall.

How far is Windsor from Hampton Roads cities?

Suffolk is about 15 minutes away. Hampton and Newport News are 30 to 40 minutes depending on traffic and your destination.

Can VA loan buyers finance a home here?

Yes. VA loan financing is common in Windsor and throughout Isle of Wight County, making this area accessible to eligible buyers.

Ready to explore 8368 Whispering Pines TRL? Reach out to Tom and Dariya Milan at LPT Realty to schedule a tour today.

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

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

Windsor$315K – $435K3+ 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 (FEMA)

Source: FEMA National Flood Hazard Layer · FIRM 51093C

Low / Moderate Risk

FEMA flood zone

X (low to moderate risk)

Base flood elevation

Not applicable in low-risk zones

Zone X is outside the Special Flood Hazard Area; FEMA doesn\u2019t define a BFE here.

Property elevation

66.3 ft above sea level

USGS 3DEP digital elevation model

Outside the high-risk Special Flood Hazard Area. Federal flood insurance is NOT required, though optional preferred-rate NFIP coverage is still worth considering in coastal Hampton Roads.

Data sources: Flood zone and base flood elevation come from FEMA\u2019s National Flood Hazard Layer. Property elevation is sampled from a single point on the parcel using the USGS National Map elevation service \u2014 actual elevations across a single property can vary by several feet higher or lower than the figure shown. Use these numbers as a starting reference and do your own due diligence (a professional survey or elevation certificate) before relying on them for any financial, insurance, or construction decision.

Hurricane Evacuation Zone

Not in a designated hurricane evacuation zone.

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

Windsor homes 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

$2,215/mo

Principal & interest

$1,946

Property tax

$159

Home insurance

$109

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

155% 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

$375,000

Price / Sq Ft

$170

Annual Taxes

$1,913

Monthly Tax

$159

HOA

None

Tax Rate (effective)

0.51%

Sale Timeline (this listing)

EventDatePriceDetail
ListedJun 24, 2026$375,000—
Price reducedOct 7, 2026$375,000−$25,000
Currently listed—$375,000—

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

55% 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

105 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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