4425 Winchester Dr

About this home

Charming 3-bedroom, 2-bath ranch home in Portsmouth, VA, offering solid bones and incredible potential! Freshly painted and ready for your personal touch, this home features spacious living areas, a functional layout, and sits on a generous lot just under a quarter acre Great for first-time homebuyers, investors, or buyers looking to build equity, this property needs a little TLC but offers strong upside in a neighb…

Listed by Jason Dunaway · Howard Hanna Real Estate Svcs.

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 every 5 minutes from the REIN MLS.

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