Why this home stands out
Homes built in 1796 are rare anywhere in Hampton Roads, and this one sits on South Church Street — one of Smithfield's most storied corridors. At 4,400 square feet across four bedrooms and three and a half baths, the scale is genuinely generous for a historic property. You're getting architectural depth that simply cannot be replicated, in a town that has worked hard to preserve exactly that character.
ALL OTHERS AREA 66 and the Smithfield real estate market
Smithfield, Virginia is one of the most distinctive small cities in the Hampton Roads region — a compact, walkable downtown anchored by 18th- and 19th-century architecture, the Pagan River, and a genuine sense of place that larger suburbs rarely achieve. South Church Street sits at the quiet, residential edge of that downtown core, where wide lots and mature trees line the road and neighbors tend to know each other by name. Isle of Wight County governs the area, which means a different tax jurisdiction than Virginia Beach or Norfolk — something worth noting as you compare locations across the region. The primary keyword for this area is Smithfield VA historic home, and 338 S Church Street represents exactly what that phrase means at its fullest. Residents here walk to local breweries, coffee shops, and the river trail without touching a car. The town hosts seasonal festivals along the waterfront, and the broader Isle of Wight County offers a quieter pace than the denser cities to the east while keeping you within a reasonable drive of the full Hampton Roads metro.
What's nearby
Daily errands and leisure are genuinely walkable from 338 S Church Street. Windsor Park North is just 0.1 miles away, and Windsor Castle Park — a beloved riverside green space — is only 0.4 miles out. Wharf Hill Brewing Company is a two-minute walk at 0.2 miles, and Cure Coffeehouse is 0.3 miles for your morning routine. The Main Gourmet and Hamtown Mercantile both sit within 0.3 miles for specialty grocery needs, with Chili Hill Food Market just a bit further at 0.4 miles. For fitness, EnCore Pilates and Physical Therapy is 0.5 miles away, and the Luter Family YMCA is 0.7 miles — an easy bike ride or short drive.
For different buyers
For military families relocating
Joint Base Langley-Eustis (Fort Eustis) is approximately 24 minutes from 338 S Church Street, and NSA Northwest Annex is about 29 minutes out. For service members using a VA loan, a historic property of this scale in a walkable small city is a genuinely uncommon combination. Isle of Wight County's jurisdiction also means a different cost profile than the denser Hampton Roads cities closer to base.
For buyers drawn to character
If what you're looking for is a home with a story — real architectural bones, a documented history, and a street address that carries weight — 338 S Church Street delivers. Built in 1796 and spanning more than 4,400 square feet, this is the kind of property that defines a block rather than blending into one. Smithfield's preservation ethic means the neighborhood around it matches that standard.
More buyer questions
How far is 338 S Church Street from Joint Base Langley-Eustis?
The drive from 338 S Church Street to Joint Base Langley-Eustis (Fort Eustis) is approximately 24 minutes under normal traffic conditions, heading east via Route 10. NSA Northwest Annex is about 29 minutes away.
What is the architectural style and age of 338 S Church Street?
The home was built in 1796, making it one of the older residential structures in Smithfield and the broader Isle of Wight County area. Properties of this era in Hampton Roads typically reflect Federal or Colonial-era construction traditions.
Is 338 S Church Street in a walkable area of Smithfield?
Yes — South Church Street places you within a short walk of Wharf Hill Brewing Company, Cure Coffeehouse, Windsor Castle Park, and multiple local markets, making it one of the more walkable addresses in Smithfield's historic downtown.
What county is 338 S Church Street located in?
338 S Church Street falls within Isle of Wight County, Virginia, which governs the Town of Smithfield. This is a separate jurisdiction from the larger Hampton Roads cities like Norfolk or Virginia Beach.
Is 338 S Church Street in a flood zone?
Smithfield's proximity to the Pagan River means flood zone status is a relevant question for properties in this area — check the FloodRisk tile on this page for the specific FEMA designation assigned to this address.
Want to walk South Church Street and see what 1796 looks like in person? Tom and Dariya Milan at LPT Realty know this market well — reach out and let's set something up.
