1 days on market
$380,000
9269 Whispering Pines Trl
Windsor, Virginia 23487
MLS# 10641944 · ALL OTHERS AREA 66 · Isle of Wight County VA
Updated 10 hours ago · Source: REIN MLS
Est. payment
$2,283/mo
Edit below
Price / sq ft
$262
1,452 sq ft
Days on market
1
New listing
HOA
None
Year built
1993
33 yrs old
Beds
3
Full Baths
2
Half Baths
0
Sq Ft
1,452
Garage
Yes
Schools
- ElementaryWindsor Elementary—
- MiddleGeorgie D. Tyler Middle School—
- HighWindsor—
Info provided by GreatSchools
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…
Listed by Tara Reichardt · Abbitt Realty Company LLC
VaHome Team property overview
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 full property overview ↓Show less ↑
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.
Frequently asked 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.
Location & Neighborhood
Places within ~1 mile, ordered by distance from this property. Powered by Google Places.
Flood Risk
Property Details
Bedrooms
3
Full Baths
2
Half Baths
0
Approx Sq Ft
1,452
Stories
1
Fireplaces
0
Flooring
Carpet, Laminate/LVP, Vinyl
Heating
Cooling
Laundry
Interior Features
N/A
Appliances
Dishwasher, Dryer, Microwave, Elec Range, Refrigerator, Washer
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)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | Jun 29, 2026 | $380,000 | — |
| Currently listed | — | $380,000 | — |
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:
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.
Military Commute
Drive times to nearest basesDrive 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.
Estimate your monthly payment
$2,283/moPrincipal & 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.
Listed by Abbitt Realty Company LLC · MLS# 10641944
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$380,000
9269 Whispering Pines TRL, WINDSOR VA 23487
Windsor, Virginia 23487
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