166 days on market
$285,900
29 N Court St
Windsor, Virginia 23487
MLS# 10611576 · ALL OTHERS AREA 66 · Isle of Wight County VA
Updated May 2, 2026 · Source: REIN MLS
Est. payment
$1,763/mo
Edit below
Price / sq ft
$105
2,729 sq ft
Days on market
166
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
29 N Court Street is a five-bedroom, 1939-built home on nearly 0.4 acres in Windsor, Virginia — offering generous square footage, classic character, and a walkable downtown location that puts parks, dining, and everyday errands within a few minutes on foot.
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Why this home stands out
Few homes in Isle of Wight County combine pre-war architectural bones with this much living space. At 2,729 square feet across five bedrooms and three and a half baths, 29 N Court Street gives growing households real room to breathe. The nearly 0.4-acre lot adds outdoor depth that's genuinely hard to find this close to Windsor's compact, walkable town center — and the 1939 construction gives the property a solidity and character that newer builds rarely replicate.
ALL OTHERS AREA 66 and the Windsor real estate market
Windsor is a small incorporated town in Isle of Wight County, sitting at the quiet center of Virginia's rural Hampton Roads corridor. It's the kind of place where neighbors actually know each other, the pace is unhurried, and the surrounding countryside gives everyday life a grounded, small-town feel. N Court Street sits right in the heart of it — close enough to walk to Robinson Park or grab a bite at Redd's Filling Station, but far enough from the noise of larger cities to feel genuinely peaceful. For buyers who've been scrolling past houses on the beach in Outer Banks dreaming of a different kind of lifestyle, Windsor offers something more rooted: a real community, real land, and a home with real history. The town is part of Isle of Wight County, which has seen steady interest from buyers seeking more space without sacrificing reasonable commute access to the broader Hampton Roads region.
What's nearby
Everything you need day-to-day is within a short walk of N Court Street. Robinson Park is just 0.1 miles away — perfect for morning walks or afternoon downtime. Garris Event Park and Centennial Park are both within 0.3 miles, giving you multiple outdoor options. When hunger hits, Redd's Filling Station, Domino's Pizza, and Shun Xing are all within 0.2 miles. Fizz Fusion coffee shop is a quick 0.3-mile stroll. For quick errands, both a BP and a Dollar General are within 0.3 miles. Coastal Point Gymnastics and Sports Centre rounds out the mix for active households.
For different buyers
For military families relocating
Joint Staff J7 Suffolk is roughly 21 minutes from N Court Street — a manageable daily commute that keeps you connected to base without living on top of it. NSA Northwest Annex is about 43 minutes out. With five bedrooms and nearly 2,800 square feet, there's space for a home office, a guest room, or whatever your household needs. A VA loan can make a property like this especially accessible — worth exploring if you haven't already.
For families upgrading
Five bedrooms and three and a half baths across 2,729 square feet means everyone gets their own space — and then some. The nearly 0.4-acre lot gives kids room to actually play outside, while Robinson Park just 0.1 miles away adds even more green space to daily life. Windsor's small-town setting pairs well with a home this size: you get the breathing room without the suburban sprawl.
Frequently asked questions
How far is 29 N Court Street from Joint Staff J7 Suffolk?
The drive from 29 N Court Street to Joint Staff J7 Suffolk is approximately 21 minutes under normal traffic conditions. That makes it one of the more manageable commutes in the area for personnel assigned there.
What is the lot size at 29 N Court Street?
The lot measures approximately 0.3972 acres — just under four-tenths of an acre — which is a notably generous footprint for a property this close to Windsor's town center.
Is 29 N Court Street in a flood zone?
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.
What year was 29 N Court Street built?
The home was built in 1939, giving it over 85 years of history and the kind of structural character — thick walls, period details, mature landscaping potential — that's difficult to replicate in newer construction.
Are there parks near 29 N Court Street in Windsor?
Yes — Robinson Park is just 0.1 miles away, Garris Event Park is 0.2 miles out, and Centennial Park is within 0.3 miles, making this one of the more park-accessible addresses in Windsor.
Want to know more about 29 N Court Street or Windsor's current 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
Location & Street View
29 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
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
$285,900
Price / Sq Ft
$105
Annual Taxes
$2,354
Monthly Tax
$196
HOA
None
Tax Rate (effective)
0.82%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | Nov 25, 2025 | $285,900 | — |
| Currently listed | — | $285,900 | — |
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
$1,763/moPrincipal & interest
$1,483
Property tax
$196
Home insurance
$83
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.
$285,900
29 N Court ST, WINDSOR VA 23487
Windsor, Virginia 23487
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