4408 Winchester Dr

About this home

This stunning all-brick Cape Cod blends old-world character with modern updates. From the distinctive front entry and arched doorways to the inviting front porch swing, every detail adds to its charm. Inside, you'll find newly installed hardwood floors, fresh paint, updated kitchen cabinets and countertops, new shelving, and a new furnace. The home also features a brand-new downstairs HVAC system and an updated circu…

Listed by Tiffany Moffit · Iron Valley Real Estate HR

Sale & Tax History

Sale Timeline (this listing)

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.

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.

About buying in Portsmouth

Homes for sale in Portsmouth, VA combine historic charm with the most affordable entry prices in Hampton Roads. Olde Towne Portsmouth (23704) features cobblestone streets and Federalist-era row houses overlooking the Elizabeth River, with active listings typically ranging $250K-$500K. Western Portsmouth's Churchland neighborhood (23703) offers larger suburban homes, top schools, and direct commutes to Norfolk Naval Shipyard. Park View (23707) and Cradock (23702) provide some of the most affordable single-family inventory in the region, often under $200K. Portsmouth's biggest employers are Norfolk Naval Shipyard (one of the largest ship-repair facilities in the country) and Naval Medical Center Portsmouth — Hampton Roads' largest military hospital. Active-duty military and shipyard families make up a significant share of buyers, and VA loan financing is common. Portsmouth Public Schools includes Churchland High, Manor High, and I.C. Norcom High; Churchland is consistently among the city's top-performing high schools. Buyers looking for waterfront views without Virginia Beach prices often find Portsmouth's Olde Towne and Hodges Ferry areas particularly attractive. Browse every active Portsmouth listing below, refreshed hourly from the REIN MLS.

See more Portsmouth homes for sale →

Drive 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.