4 days on market
$365,000
14242 Trump Town Rd
Windsor, Virginia 23487
MLS# 10634365 · WINDSOR · Isle of Wight County VA
Updated 5 days ago · Source: REIN MLS
Est. payment
$2,096/mo
Edit below
Price / sq ft
$392
931 sq ft
Days on market
4
New listing
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 two-bedroom, one-bath home on a quiet Windsor, Virginia road — compact at 931 square feet, rooted in 1950s character, and sitting within a 35-minute drive of two major military installations in Isle of Wight County.
Read full property overview ↓Show less ↑
Why this home stands out
What sets this address apart is its combination of genuine rural quiet and surprising regional access. Windsor sits at a crossroads that puts Joint Base Langley-Eustis and Joint Staff J7 Suffolk both within a half-hour commute, yet the pace of life on Trump Town Road feels a world away from base traffic. The 1950s bones give the home a solidity you don't always find in newer construction at this size.
About the Windsor real estate market
Windsor is a small town in Isle of Wight County — the kind of place where you know your neighbors and the pace of daily life is genuinely unhurried. For anyone weighing city versus suburbs, Windsor offers a third path: a rural small-town rhythm with easy highway access to Hampton Roads, Suffolk, and Newport News. The town itself has a tight-knit community feel, with local shops, a historic downtown core, and farmland that gives the area an open, uncluttered character. Isle of Wight County is consistently recognized for its quality of life, and Windsor sits at the heart of it. You're not far from the amenities of Suffolk to the east or Smithfield to the north, yet Trump Town Road itself is quiet enough that you can hear the wind in the trees. This is the kind of address that makes sense for someone who wants space, simplicity, and a genuine sense of place — without sacrificing reasonable access to the broader Hampton Roads region.
What's nearby
Day-to-day errands are manageable from this address. Windsor's small commercial corridor covers the basics, and the town of Smithfield — about 15 minutes north — adds grocery options, local restaurants, and pharmacies. Suffolk, roughly 20 minutes east, expands your choices considerably with major retailers, dining, and services along Route 58 and Godwin Boulevard. Outdoor options include the Isle of Wight County parks system and the broader rural landscape that makes this corner of Virginia genuinely pleasant for anyone who values open space over urban density.
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 is roughly 33 minutes out — both manageable commutes from Windsor. For service members using a VA loan, a modest two-bedroom in Isle of Wight County can be a smart foothold in a region where BAH rates reflect the broader Hampton Roads market. The rural quiet here is a real bonus after a long duty day.
For first-time buyers
At 931 square feet, 14242 Trump Town Road is the kind of home that doesn't overwhelm a first-time buyer — financially or logistically. The 1950s construction means real walls, real floors, and a straightforward floor plan. Isle of Wight County's lower cost of living compared to the urban core of Hampton Roads makes this a realistic entry point for buyers exploring homes for sale 23321 and surrounding zip codes who want ownership without overextending.
Frequently asked questions
How far is 14242 Trump Town Road from Joint Base Langley-Eustis (Fort Eustis)?
The drive from this address to Joint Base Langley-Eustis (Fort Eustis) is approximately 32 minutes under normal traffic conditions, heading northeast via Route 460 and Interstate 664.
How far is 14242 Trump Town Road from Joint Staff J7 Suffolk?
Joint Staff J7 Suffolk is about 33 minutes from this address, making it a comparable commute to Fort Eustis for service members assigned there.
What county is 14242 Trump Town Road in?
This address is in Isle of Wight County, Virginia — a jurisdiction known for its rural character, low density, and proximity to the broader Hampton Roads metro area.
Is 14242 Trump Town Road in a flood zone?
Flood zone status for this address is detailed in the FloodRisk tile on this page — check that section for the most current FEMA designation and what it means practically for this property.
What is the lot and home size at 14242 Trump Town Road?
The home is 931 square feet with two bedrooms and one bath, built in 1950 — a compact, manageable footprint on a residential road in Windsor, Virginia.
Want to know more about 14242 Trump Town Road or Windsor's market? Tom and Dariya Milan at LPT Realty are ready to walk you through everything — reach out and let's talk.
Summary generated by AI from public records and publicly available information.
Location & Neighborhood
Location & Street View
14242 Trump Town RD, Windsor
Map and Street View imagery © Google. Imagery may not be current.
Map data ©Google. Click and drag inside the map to explore the surrounding area.
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
$365,000
Price / Sq Ft
$392
Annual Taxes
$1,153
Monthly Tax
$96
HOA
None
Tax Rate (effective)
0.32%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | May 15, 2026 | $365,000 | — |
| Currently listed | — | $365,000 | — |
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
$2,096/moPrincipal & interest
$1,894
Property tax
$96
Home insurance
$106
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.
$365,000
14242 Trump Town RD, WINDSOR VA 23487
Windsor, Virginia 23487
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