18 days on market
Aerial flyover rendering — usually ready in a couple minutes.
$320,000
14242 Trump Town Rd
Windsor, Virginia 23487
MLS# 10634365 · WINDSOR · Isle of Wight County VA
Updated Jun 2, 2026 · Source: REIN MLS
Est. payment
$1,850/mo
Edit below
Price / sq ft
$344
931 sq ft
Days on market
18
HOA
None
Year built
1950
76 yrs old
Beds
2
Full Baths
1
Half Baths
0
Sq Ft
931
Garage
No
Schools
- ElementaryWindsor Elementary—
- MiddleGeorgie D. Tyler Middle School—
- HighWindsor—
Info provided by GreatSchools
About this home
Modern Luxury Meets Country Living in Windsor! Experience the perfect blend of high-end style and rural tranquility on this stunning 1.5-acre home. This meticulously renovated 2-bedroom, 1-bath home offers "new everything," providing total peace of mind and upscale comfort. Step into a bright interior featuring a chef's kitchen with premium appliances and a spa-like bath. Thoughtfully designed for efficiency, the lay…
Listed by Stacy O'Neill · Fathom Realty
VaHome Team property overview
14242 Trump Town Road is a compact two-bedroom, one-bath home in Windsor, Virginia — Isle of Wight County — built in 1950 and offering 931 square feet of straightforward, low-maintenance living in a quiet rural corner of Hampton Roads.
Read full property overview ↓Show less ↑
Why this home stands out
What sets this address apart is the combination of genuine small-town quiet and surprising regional access. Windsor sits at a comfortable remove from the noise of the metro, yet Fort Eustis and the Suffolk installations are both within a half-hour drive. For buyers who want breathing room, a manageable footprint, and reasonable commute lines to two major military hubs, this property checks an uncommon set of boxes.
About the Windsor real estate market
Windsor, Virginia is one of Isle of Wight County's quieter towns — a place where the pace slows down without cutting you off from the rest of Hampton Roads. The surrounding landscape is largely rural, with open fields, tree lines, and the kind of road noise that fades to almost nothing after dark. Trump Town Road itself sits on the western edge of the Hampton Roads metro area, which means you get the calm of country living while staying within a practical drive of Suffolk, Newport News, and the broader region. Windsor Virginia real estate tends to attract buyers who are done trading square footage for a city address and are ready for something more grounded. Isle of Wight County is known for its low-density character, its working agricultural land, and a community identity that's distinctly its own — not a suburb, not a rural afterthought, but a town that knows what it is. Daily life here moves at your speed.
What's nearby
Windsor's small commercial core puts everyday essentials within a short drive. You'll find grocery options, a pharmacy, and local dining along Windsor Boulevard without needing to leave town. For a broader selection, Suffolk is roughly 20 minutes east and carries the full range of big-box retail, restaurants, and services. Franklin to the southwest adds another option for errands and dining. Outdoor life is easy to access too — the Blackwater region and its trail and paddling corridors are nearby, and Isle of Wight County parks offer open green space without a long drive.
For different buyers
For military families relocating
Joint Base Langley-Eustis (Fort Eustis) is about 32 minutes from this address, and Joint Staff J7 Suffolk runs roughly 33 minutes in the other direction — making 14242 Trump Town Road a genuinely central option for dual-military households or anyone weighing a VA loan purchase near two installations. The low-maintenance footprint also keeps monthly overhead predictable on a military budget.
For first-time buyers
At 931 square feet with two bedrooms and one bath, this 1950-built home is sized right for a first purchase — enough space to live comfortably, not so much that upkeep becomes a second job. Windsor's quieter market and Isle of Wight County's lower-density character mean you're not competing in the same frenzied pool as buyers closer to the coast. It's a practical, grounded entry point.
Frequently asked questions
How far is 14242 Trump Town Road from Joint Base Langley-Eustis (Fort Eustis)?
The drive from this address to Fort Eustis runs approximately 32 minutes under normal traffic conditions, heading northeast toward Newport News via Route 460 and I-664.
How far is 14242 Trump Town Road from Joint Staff J7 Suffolk?
The Suffolk installation is roughly 33 minutes east, making this address a practical midpoint option for personnel assigned to either installation.
What county is 14242 Trump Town Road in?
This property is located in Isle of Wight County, Virginia — a jurisdiction known for its rural character, low density, and stable, community-oriented identity.
Is 14242 Trump Town Road in a flood zone?
Flood zone status for this address is displayed in the FloodRisk tile on this page — check that section for the current FEMA designation and what it means for insurance requirements.
Can a VA loan be used to purchase a home at this address?
Yes — eligible veterans, active-duty service members, and qualifying surviving spouses can use a VA loan on a residential property like this one; the VA loan tile on this page has more detail on eligibility and process.
Want to know more about 14242 Trump Town Road or explore comparable homes in Windsor and Isle of Wight County? Tom and Dariya Milan at LPT Realty are ready to help.
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
2
Full Baths
1
Half Baths
0
Approx Sq Ft
931
Stories
1
Fireplaces
0
Flooring
Laminate/LVP
Heating
Cooling
Laundry
Interior Features
N/A
Appliances
Dishwasher, Dryer, Elec Range, Refrigerator, Washer
Sale & Tax History
List Price
$320,000
Price / Sq Ft
$344
Annual Taxes
$1,153
Monthly Tax
$96
HOA
None
Tax Rate (effective)
0.36%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | May 16, 2026 | $320,000 | — |
| Currently listed | — | $320,000 | — |
Public-Records Assessment
Source: City Assessor via Hampton Roads Regional Parcels. Fetched May 19, 2026.
Total Assessed
$143,500
Land
$67,500
Improvement
$76,000
Parcel ID: 29-01-021
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
$1,850/moPrincipal & interest
$1,660
Property tax
$96
Home insurance
$93
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 Fathom Realty · MLS# 10634365
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$320,000
14242 Trump Town RD, WINDSOR VA 23487
Windsor, Virginia 23487
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