58 days on market
$299,999
44 N Court St
Windsor, Virginia 23487
MLS# 10624538 · ALL OTHERS AREA 65 · Isle of Wight County VA
Updated Mar 21, 2026 · Source: REIN MLS
Est. payment
$1,839/mo
Edit below
Price / sq ft
$144
2,086 sq ft
Days on market
58
HOA
None
Year built
1960
66 yrs old
Beds
4
Full Baths
2
Half Baths
0
Sq Ft
2,086
Garage
No
Schools
- ElementaryWindsor Elementary—
- MiddleGeorgie D. Tyler Middle School—
- HighWindsor—
Info provided by GreatSchools
About this home
This 4-bedroom, 2-bath ranch offers comfortable one-level living with a spacious and functional layout. Interior features a blend of laminate and wood flooring throughout the main living areas. Enjoy a large backyard perfect for relaxing, entertaining, or outdoor activities. Conveniently located near dining, schools, shopping, and major roadways for easy commuting.Short sale subject to lender approval. Short sale bei…
Listed by Ronald Sawyer · RE/MAX Prime
VaHome Team property overview
Meet 44 N Court Street — a four-bedroom, two-bath home on nearly half an acre in the heart of Windsor, Virginia. Built in 1960 and spanning 2,086 square feet, this property offers genuine space, a manageable small-town setting, and easy access to the greater Hampton Roads region.
Read full property overview ↓Show less ↑
Why this home stands out
What sets 44 N Court Street apart is the combination of lot size and livable square footage that's genuinely hard to find in Windsor's compact downtown core. Nearly half an acre gives you room to breathe — space for a garden, a fire pit, or simply a backyard that doesn't feel borrowed from your neighbor. The 1960 build means solid bones and proportions that newer construction rarely replicates, all within walking distance of the town's everyday essentials.
ALL OTHERS AREA 65 and the Windsor real estate market
Windsor is a small incorporated town in Isle of Wight County, sitting roughly midway between Suffolk and Franklin along US-460. It's the kind of place where neighbors know each other's names and the pace of daily life is deliberately unhurried. The town center — where 44 N Court Street sits — is compact enough to walk most errands but connected enough to reach the broader Hampton Roads metro in under 30 minutes. For buyers who've been sifting through competitive suburban markets or even researching va foreclosures, Windsor often surfaces as a genuinely overlooked pocket of value in southeastern Virginia. Isle of Wight County carries a reputation for well-managed local government, low congestion, and a strong sense of community identity. You're close to the agricultural landscape that defines the region, yet the amenities of Suffolk, Chesapeake, and Norfolk are all within a reasonable drive. It's small-town Virginia living with metropolitan access — a balance that's increasingly difficult to find.
What's nearby
Daily errands are surprisingly easy from 44 N Court Street. Dollar General is just 0.3 miles away, and a BP station sits 0.4 miles out for quick convenience needs. When you want to eat out, Redd's Filling Station, Domino's Pizza, and Burger King are all within a third of a mile. Fizz Fusion coffee shop is equally close for a morning pick-me-up. Families will appreciate Coastal Point Gymnastics and Sports Centre right in the neighborhood, and green space is genuinely abundant — Robinson Park, Garris Event Park, and Centennial Park are all within 0.4 miles, giving kids and adults plenty of room to get outside.
For different buyers
For military families relocating
Joint Staff J7 Suffolk is approximately 21 minutes from 44 N Court Street, making Windsor a practical home base for personnel assigned there. NSA Northwest Annex is reachable in about 43 minutes. A VA loan can make this property even more accessible, and your BAH rate for the Suffolk area is worth running against the numbers here — Isle of Wight County often surprises buyers on affordability.
For families upgrading
If your current home is feeling tight, 2,086 square feet across four bedrooms gives everyone room to settle in. The 0.43-acre lot adds the kind of outdoor space that growing families genuinely use — room for play sets, gardens, or weekend gatherings. Windsor's small-town environment means kids can move more freely, and the proximity to multiple parks within walking distance makes that even easier.
Frequently asked questions
How far is 44 N Court Street from Joint Staff J7 Suffolk?
The drive from 44 N Court Street to Joint Staff J7 Suffolk is approximately 21 minutes under normal traffic conditions. That makes Windsor a realistic daily commute for personnel assigned to that installation.
What is the lot size at 44 N Court Street?
The lot measures 0.43 acres, which is notably generous for a property located this close to Windsor's town center. It provides meaningful outdoor space on all sides of the home.
Is 44 N Court Street in a flood zone?
Flood zone designation for this property is detailed in the FloodRisk tile on this page — check that section for the current FEMA map classification and what it means practically for insurance.
What parks are near 44 N Court Street in Windsor?
Robinson Park and Garris Event Park are both within 0.3 miles, and Centennial Park is 0.4 miles away. All three are walkable from the property, giving residents easy access to green space without getting in a car.
Does Windsor, Virginia have an HOA?
44 N Court Street is not listed under a mandatory HOA, though you should confirm current deed restrictions with your agent during the due-diligence period. Isle of Wight County's zoning rules govern the property in the absence of a community association.
Tom and Dariya Milan at LPT Realty know Windsor and Isle of Wight County well. Reach out to get a straight answer on this address and what it could mean for you.
Summary generated by AI from public records and publicly available information.
Location & Neighborhood
Location & Street View
44 N Court ST, 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
4
Full Baths
2
Half Baths
0
Approx Sq Ft
2,086
Stories
1
Fireplaces
0
Flooring
Laminate/LVP, Vinyl, Wood
Heating
Cooling
Laundry
Interior Features
N/A
Appliances
Dishwasher, Dryer Hookup, Microwave, Elec Range, Refrigerator, Washer Hookup
Sale & Tax History
List Price
$299,999
Price / Sq Ft
$144
Annual Taxes
$2,333
Monthly Tax
$194
HOA
None
Tax Rate (effective)
0.78%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | Mar 12, 2026 | $299,999 | — |
| Currently listed | — | $299,999 | — |
Public-Records Assessment
Source: Isle of Wight via Hampton Roads Regional Parcels. Fetched May 11, 2026.
Total Assessed
$295,700
Land
$55,000
Improvement
$240,700
Parcel ID: 54B-01-039 · View on city GIS portal
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
$1,839/moPrincipal & interest
$1,557
Property tax
$194
Home insurance
$87
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 RE/MAX Prime · MLS# 10624538
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$299,999
44 N Court ST, WINDSOR VA 23487
Windsor, Virginia 23487
Request InfoQuick Facts
Schedule a tour
In-person or videoClick a day to pick a time