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Windsor › WINDSOR › 14242 Trump Town Rd✓ Source: REIN MLS #10634365 · record updated Jul 10, 2026 · synced every 2 min · your inquiry is never resold
14242 Trump Town RD, WINDSOR VA 23487 - Main photo
$320,000
$344 / sqft · est. $1,850/mo →
2beds
1baths
931sqft
29days on market

14242 Trump Town Rd, Windsor, VA 23487

SoldResidential · built 1950 · WINDSOR

Facts & features

Type

Residential

Year built

1950

Price / sqft

$344

HOA

None

Taxes

$1,153/yr

County

Isle of Wight County VA

MLS #

10634365

Interior

Bedrooms
2
Full baths
1
Approx. sqft
931
Stories
1
Flooring
Laminate/LVP
First-floor bed & full bath
Yes
Total rooms
5
Other rooms
1st Floor Primary BR, Porch, Utility Room
Appliances
Dishwasher, Dryer, Elec Range, Refrigerator, Washer
Equipment
Ceiling Fan

Construction & exterior

Style
Bungalow
Subtype
Detached
Foundation
Crawl
Roof
Asphalt Shingle
Exterior
Vinyl
Pool
No Pool

Utilities & systems

Heating
Electric
Cooling
Central Air
Water heater
Electric
Water
Well
Sewer
Septic

Lot, parking & ownership

Lot size
1.5000
Subdivision
WINDSOR
Ownership
Fee Simple
Garage
No
Parking
3 Space, Carport, Driveway Spc
Possession
SETTLEMENT
Miscellaneous
Rehabilitated
Disclosures
Disclosure Statement

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

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 layout includes a dedicated laundry room and a functional mudroom. Move in with zero worries thanks to a new roof, HVAC, siding, and energy-efficient windows. Built for the hobbyist or craftsman, the property boasts a massive 3-stall pole barn with a spacious attached workshop. Whether you need room for equipment, animals, or creative projects, this acreage delivers. Don't miss out—schedule your private tour today and see this gem in person!

Listing courtesy of Stacy O'Neill · Fathom Realty · REIN MLS #10634365

VaHome team overview

Our read on this home

by Tom & Dariya Milan, REALTORS® · LPT Realty

At a glance

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.

Keep searching in Windsor

See homes for sale zoned for Windsor High School and homes for sale zoned for Windsor Elementary School. Nearby, look at Deerfield / Windsor homes for sale.

Read the full overview ↓

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.

More buyer 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.

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

In the Deerfield / Windsor neighborhood of Windsor.

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

$1,850/mo

Principal & interest

$1,660

Property tax

$96

Home insurance

$93

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

223% of $143,500

City assessment record · taxes $1,153/yr

Land share of assessed value

47% — $67,500

Improvements $76,000 · assessor record ✓

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)

EventDatePriceDetail
Price reducedMay 30, 2026$320,000−$45,000
ListedJul 6, 2026$320,000—
SoldJul 10, 2026$320,000—

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

123% above assessment

Total Assessed

$143,500

Land

$67,500

Improvement

$76,000

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:

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.

Questions buyers ask

Is 14242 Trump Town Rd 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 14242 Trump Town Rd 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 14242 Trump Town Rd have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 14242 Trump Town Rd built?+
It was built in 1950, 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 Stacy O'Neill · Fathom Realty · REIN MLS #10634365

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.

This home has sold

Curious what it means for your own plans? Ask about similar homes nearby, or what your home might sell for in this market.

🏡 Similar homes for saleWhat's my home worth?
14242 Trump Town Rd, Windsor — photo

This one's sold — the next one doesn't have to be.

🏡 Homes for sale in WindsorCall or text (757) 777-7577

14242 Trump Town Rd, Windsor, Virginia 23487 · MLS #10634365 · 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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