29 N Court St, Windsor, VA 23487

Why this home stands out

Few homes in Isle of Wight County combine pre-war architectural bones with 2,729 square feet of living space and a lot approaching 0.4 acres — all within two blocks of parks, restaurants, and everyday conveniences. The 1939 build year means real craftsmanship: thicker walls, distinct proportions, and the kind of presence that newer construction rarely replicates. Five bedrooms give you room to grow, host, or work from home without compromise.

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 neighbors actually know each other and the pace of life feels intentional. North Court Street sits close to the heart of downtown, so you're never far from a local café, a park bench, or a quick errand. The town's tree-lined streets and modest scale create a genuinely walkable environment that's increasingly rare in Hampton Roads. Windsor has been growing steadily, drawing families and professionals who want more land for their dollar without sacrificing access to the broader metro. Isle of Wight County manages the jurisdiction, keeping taxes and services tied to one of Virginia's more financially stable localities. The town is also well-positioned along Route 460, giving you a practical corridor toward Suffolk, Smithfield, and beyond — making Windsor homes a compelling option for buyers comparing properties across the region.

What's nearby

Day-to-day life from 29 N Court Street is genuinely convenient. Garris Event Park, Robinson Park, and Centennial Park are all within 0.2 miles — step outside and you're practically there. Stella's Kitchen, El Rodeo Mexican Restaurant Windsor, and Shun Xing are all within a third of a mile for quick dinners. Fizz Fusion and The Rusted Root Cafe handle your coffee needs at 0.5 and 0.8 miles respectively. Groceries are covered by BP at 0.2 miles, Dollar General at 0.5, and Food Lion at 0.9. Coastal Point Gymnastics and Sports Centre and Anytime Fitness are both under a mile for staying active.

For different buyers

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