17 days on market
$355,000
26 N Court St
Windsor, Virginia 23487
MLS# 10639208 · WINDSOR · Isle of Wight County VA
Updated 2 days ago · Source: REIN MLS
Est. payment
$2,122/mo
Edit below
Price / sq ft
$204
1,739 sq ft
Days on market
17
HOA
None
Year built
1951
75 yrs old
Beds
4
Full Baths
2
Half Baths
0
Sq Ft
1,739
Garage
No
Schools
- ElementaryWindsor Elementary—
- MiddleGeorgie D. Tyler Middle School—
- HighWindsor—
Info provided by GreatSchools
About this home
This house has it all - land, charm and updates throughout! On just under an acre of land, the whimsy of this house, coupled with the thoughtful updates throughout, make this the perfect place to call home. Freshly painted, new refrigerator, new dishwasher, and curated updates, all you have to do is bring your toothbrush. Picture starting your morning with coffee in the sunroom or reading a book by the cozy fireplace…
Listed by Margo Savage · A Better Way Realty Inc.
VaHome Team property overview
26 N Court Street is a four-bedroom, two-bath home built in 1951 in the small town of Windsor, Virginia. At 1,739 square feet, it offers genuine room to spread out in a quiet, close-knit community in Isle of Wight County.
Read full property overview ↓Show less ↑
Why this home stands out
Homes with four bedrooms in a town as compact and walkable as Windsor are genuinely hard to come by. This 1951-built residence gives you the square footage — 1,739 feet across four bedrooms and two full baths — without the sprawl of a large suburban subdivision. The lot sits right in the heart of town, meaning errands, green space, and neighbors are all within easy reach on foot or a short drive.
About the Windsor real estate market
Windsor, Virginia is a small incorporated town in Isle of Wight County, roughly midway between Suffolk and Smithfield along Route 460. It has the kind of unhurried, small-town character that's increasingly rare in Hampton Roads — tree-lined streets, a genuine town center, and a pace of life that feels deliberate rather than rushed. 26 N Court Street Windsor Virginia 23487 sits right in the core of that town fabric, close to the municipal buildings, local parks, and the handful of shops and eateries that give Windsor its identity. Isle of Wight County is known for strong local governance and a rural-to-suburban balance that attracts buyers who want space without total isolation. For anyone weighing Hampton Roads options, Windsor offers a quieter alternative to Virginia Beach or Chesapeake while still keeping you connected to the broader metro via Route 460.
What's nearby
Day-to-day life in Windsor is straightforward. The town's small commercial corridor puts basic conveniences within a few minutes of N Court Street. Smithfield, about 15 minutes east, expands your options considerably — you'll find grocery stores, pharmacies, restaurants, and the charming historic downtown along Main Street. Suffolk is roughly 20 minutes west and brings a full range of big-box retail, dining, and services. Windsor Community Park is close by for outdoor time, and the Isle of Wight County Museum in Smithfield is worth the short drive for local history. Regional access to I-664 is manageable from this location.
For different buyers
For military families relocating
Joint Staff J7 in Suffolk is about 21 minutes from 26 N Court Street — a reasonable daily commute that keeps you out of the densest Hampton Roads traffic corridors. NSA Northwest Annex is roughly 43 minutes away. For service members using a VA loan, Isle of Wight County offers more square footage per dollar than many closer-in markets, and four bedrooms gives the whole family genuine breathing room.
For first-time buyers
If you're stepping into homeownership for the first time, Windsor offers something rare: a four-bedroom home in a real town center at a price point that's more accessible than comparable square footage in Virginia Beach or Chesapeake. The 1951 construction means solid bones, and the walkable town layout means you won't feel isolated. A VA loan can make the numbers work especially well for buyers with military ties in the region.
Frequently asked questions
How far is 26 N Court Street from Joint Staff J7 Suffolk?
The drive from 26 N Court Street to Joint Staff J7 in Suffolk is approximately 21 minutes via Route 460 West, making it one of the more manageable commutes in the region without the congestion of the I-64 corridor.
What is the flood risk at 26 N Court Street, Windsor, VA?
Flood zone information for this address is displayed in the dedicated FloodRisk tile on this page, which pulls current FEMA map data for the most accurate and up-to-date designation.
Is there an HOA at 26 N Court Street in Windsor?
This property is not part of a homeowners association, so there are no HOA rules or dues attached to the home.
What is the lot and property type at 26 N Court Street?
26 N Court Street is a single-family residential property built in 1951, offering 1,739 square feet across four bedrooms and two full baths within the town limits of Windsor, Virginia.
Where is Windsor, Virginia located relative to the rest of Hampton Roads?
Windsor sits in Isle of Wight County along Route 460, roughly 20 minutes west of Smithfield and about 20–25 minutes from Suffolk, placing it on the western edge of the Hampton Roads metro area with straightforward access to the broader region.
Want to know more about 26 N Court Street or Windsor's market? Tom and Dariya Milan at LPT Realty are happy to walk you through everything — reach out anytime.
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
4
Full Baths
2
Half Baths
0
Approx Sq Ft
1,739
Stories
2
Fireplaces
0
Flooring
Concrete, Vinyl, Wood
Heating
Cooling
Laundry
Interior Features
N/A
Appliances
Dishwasher, Disposal, Dryer Hookup, Gas Range, Refrigerator, Washer Hookup
Sale & Tax History
List Price
$355,000
Price / Sq Ft
$204
Annual Taxes
$2,123
Monthly Tax
$177
HOA
None
Tax Rate (effective)
0.60%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | Jun 12, 2026 | $355,000 | — |
| Currently listed | — | $355,000 | — |
Public-Records Assessment
Source: City Assessor via Hampton Roads Regional Parcels. Fetched Jun 20, 2026.
Total Assessed
$268,700
Land
$55,000
Improvement
$213,700
Parcel ID: 54B-01-030
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
$2,122/moPrincipal & interest
$1,842
Property tax
$177
Home insurance
$104
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 A Better Way Realty Inc. · MLS# 10639208
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$355,000
26 N Court ST, WINDSOR VA 23487
Windsor, Virginia 23487
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