179 days on market
Aerial flyover rendering — usually ready in a couple minutes.
$265,900
29 N Court St
Windsor, Virginia 23487
MLS# 10611576 · ALL OTHERS AREA 66 · Isle of Wight County VA
Updated May 22, 2026 · Source: REIN MLS
Est. payment
$1,653/mo
Edit below
Price / sq ft
$97
2,729 sq ft
Days on market
179
HOA
None
Year built
1939
87 yrs old
Beds
5
Full Baths
3
Half Baths
1
Sq Ft
2,729
Garage
Yes
Schools
- ElementaryWindsor Elementary—
- MiddleWindsor—
- HighWindsor—
Info provided by GreatSchools
About this home
Come see this 5 bedroom, 3.5 bath home in Windsor with detached garage and in-law suite.
Listed by Kevin Pall · Brooke Madison & Associates
VaHome Team property overview
A five-bedroom, 1939-built home on nearly 0.4 acres in the heart of Windsor, Virginia — offering over 2,700 square feet of character-filled living space, three and a half baths, and a walkable town-center location that puts parks, dining, and everyday errands just steps away.
Read full property overview ↓Show less ↑
Why this home stands out
What sets 29 N Court Street apart is the combination of genuine pre-war architecture and generous square footage that newer construction in this price range rarely delivers. At 2,729 square feet with five bedrooms and a nearly half-acre lot, this 1939 residence gives you room to spread out inside and outside — all within a two-minute walk of Windsor's parks and local dining scene. That's a rare pairing in a small Virginia town.
ALL OTHERS AREA 66 and the Windsor real estate market
Windsor is a small, tight-knit town in Isle of Wight County — the kind of place where you actually know your neighbors and the pace of daily life feels intentional rather than rushed. N Court Street sits right in the walkable core of town, meaning Robinson Park is literally a one-minute stroll and the broader downtown grid is right outside your door. The town has a genuine Main Street character that larger Hampton Roads suburbs have largely traded away for strip malls and traffic. Isle of Wight County governs the area, and Windsor itself serves as the county seat of the surrounding community, giving it a civic energy you don't always find in towns this size. For commuters, the location threads neatly between Suffolk and the broader Hampton Roads metro — close enough to access major employment corridors without the noise and congestion of urban living. If the phrase 'Windsor Virginia homes for sale' has been in your search bar lately, 29 N Court Street is exactly the kind of address that search is meant to surface.
What's nearby
Daily life at 29 N Court Street is genuinely walkable. Robinson Park is 0.1 miles away — a quick walk for morning routines or afternoon wind-downs. Garris Event Park and Centennial Park are both within 0.3 miles, giving you multiple green-space options. For food, Redd's Filling Station and Domino's Pizza are 0.2 miles out, and Shun Xing rounds out the dining variety at the same distance. Fizz Fusion coffee shop is 0.3 miles away — close enough to make it a morning habit. Coastal Point Gymnastics and Sports Centre is also within 0.3 miles. BP and Dollar General handle quick errands at 0.3 miles each.
For different buyers
For military families relocating
Joint Staff J7 in Suffolk is about 21 minutes from 29 N Court Street — a manageable daily commute that keeps you well outside the congestion of closer-in neighborhoods. Five bedrooms means space for a home office, a guest room for visiting family, or a dedicated study area for kids. A VA loan can make a home with this much square footage and lot size more accessible than many buyers expect.
For families upgrading
Five bedrooms and three and a half baths across 2,729 square feet gives a growing family real room to breathe — dedicated spaces for everyone without the compromise of squeezing into a four-bedroom layout. The nearly 0.4-acre lot adds genuine outdoor space, and having Robinson Park, Garris Event Park, and Coastal Point Gymnastics all within a short walk means kids have places to go without a car trip every time.
Frequently asked questions
How far is 29 N Court Street from Joint Staff J7 Suffolk?
The drive to Joint Staff J7 in Suffolk is approximately 21 minutes under normal traffic conditions, making it one of the more practical commutes available from a small-town Isle of Wight County address.
What is the lot size at 29 N Court Street?
The lot measures 0.3972 acres — just under four-tenths of an acre — which is a notably generous footprint for a walkable in-town location in Windsor.
How old is the home at 29 N Court Street?
The home was built in 1939, making it a pre-war residence with over 85 years of architectural history and the kind of structural character that era of construction is known for.
Is 29 N Court Street in a flood zone?
Flood zone designation for this address is detailed in the FloodRisk tile on this page, which pulls current FEMA map data for the specific parcel.
What parks are walkable from 29 N Court Street?
Robinson Park is 0.1 miles away, Garris Event Park is 0.2 miles, and Centennial Park is 0.3 miles — three distinct green spaces all reachable on foot from the front door.
Ready to walk through 29 N Court Street in person? Tom and Dariya Milan at LPT Realty know Windsor well — reach out and let's set up a tour.
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
5
Full Baths
3
Half Baths
1
Approx Sq Ft
2,729
Stories
2
Fireplaces
0
Flooring
Wood
Heating
Cooling
Laundry
Interior Features
N/A
Appliances
Dryer Hookup, Washer Hookup
Sale & Tax History
List Price
$265,900
Price / Sq Ft
$97
Annual Taxes
$2,354
Monthly Tax
$196
HOA
None
Tax Rate (effective)
0.89%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | Nov 24, 2025 | $265,900 | — |
| Currently listed | — | $265,900 | — |
Public-Records Assessment
Source: Isle of Wight via Hampton Roads Regional Parcels. Fetched May 11, 2026.
Total Assessed
$315,100
Land
$55,000
Improvement
$260,100
Parcel ID: 54B-01-068 · 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
$1,653/moPrincipal & interest
$1,380
Property tax
$196
Home insurance
$78
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 Brooke Madison & Associates · MLS# 10611576
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$265,900
29 N Court ST, WINDSOR VA 23487
Windsor, Virginia 23487
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