9 days on market
$330,000
4308 Winchester Dr
Portsmouth, Virginia 23707
MLS# 10636138 · GROVE PARK · Portsmouth VA
Updated May 31, 2026 · Source: REIN MLS
Est. payment
$2,069/mo
Edit below
Price / sq ft
$194
1,700 sq ft
Days on market
9
New listing
HOA
None
Year built
1939
87 yrs old
Beds
3
Full Baths
2
Half Baths
0
Sq Ft
1,700
Garage
Yes
About this home
Beautifully maintained home featuring a functional floor plan and an updated kitchen with modern touches, great for everyday living and entertaining. Enjoy spacious living areas, comfortable bedrooms, and a huge backyard offering endless possibilities for outdoor enjoyment. The converted room over the garage provides incredible flexibility and potential for additional living area. Conveniently located near shopping,…
Listed by Victoria Faulkner · Swell Realty Co
VaHome Team property overview
A 1939-built, 3-bedroom, 2-bath home in Portsmouth, Virginia, offering 1,700 square feet of character-filled living space just minutes from Naval Medical Center Portsmouth and Norfolk Naval Shipyard — a rare find in one of Hampton Roads' most storied neighborhoods.
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Why this home stands out
Built in 1939, 4308 Winchester Drive carries the kind of architectural bones that newer construction simply can't replicate — solid craftsmanship, generous room proportions, and the quiet confidence of a home that has stood for more than eight decades. At 1,700 square feet across three bedrooms and two baths, it offers real living space without the sprawl, all within a six-minute drive of Naval Medical Center Portsmouth and seven minutes from Norfolk Naval Shipyard.
GROVE PARK and the Portsmouth real estate market
Winchester Drive sits in a residential pocket of Portsmouth, Virginia, where tree-lined streets and pre-war homes give the area a grounded, established feel that's increasingly rare in Hampton Roads. Portsmouth itself is one of the region's original cities — a place with deep naval heritage, a revitalized waterfront downtown, and neighborhoods that have been home to military families and longtime locals alike for generations. The city sits across the Elizabeth River from Norfolk, connected by the Downtown and Midtown tunnels, which puts you within reach of the broader Hampton Roads metro without sacrificing the lower-key pace that Portsmouth neighborhoods tend to offer. For anyone researching Portsmouth real estate, this stretch of the city represents some of the most accessible, centrally located housing stock in the area — close to two major installations, walkable to everyday conveniences, and surrounded by the kind of mature landscaping and neighborhood character that only comes with time.
What's nearby
Day-to-day errands are genuinely easy from Winchester Drive. A Walmart Supercenter is just 0.8 miles away for full grocery runs, and a Wawa sits within a mile for quick coffee or a grab-and-go stop. When you want to eat out, Vibez Bar and Grill and Culinary Chemist Cuisine are both under 0.7 miles away — solid local options without a long drive. Corner Cafe is a short 0.8-mile trip for a more relaxed morning. Fitness is well covered too, with Zenya Yoga Studio, Sports Performance House, and Crunch Fitness all within a mile. For outdoor time, Links at City Park and Portsmouth City Park are both under a mile — great for weekend walks or afternoon fresh air.
For different buyers
For military families relocating
With Naval Medical Center Portsmouth just six minutes away and Norfolk Naval Shipyard seven minutes out, 4308 Winchester Drive is one of the more strategically located addresses in the city for active-duty families. A VA loan can make ownership here straightforward, and the short commutes mean more time at home and less time in traffic — a real quality-of-life difference across a multi-year tour.
For buyers drawn to character
If you're drawn to homes that have actual history — original-era construction, proportions that feel intentional rather than builder-standard, and a neighborhood with decades of established character — Winchester Drive is worth a serious look. Homes built in 1939 in this part of Portsmouth carry a craftsmanship and solidity that stands apart from anything built in the last thirty years.
Frequently asked questions
How far is 4308 Winchester Drive from Naval Medical Center Portsmouth?
Naval Medical Center Portsmouth is approximately six minutes by car from 4308 Winchester Drive, making it one of the closest residential options to the base in the city.
How far is 4308 Winchester Drive from Norfolk Naval Shipyard?
Norfolk Naval Shipyard is about seven minutes away by car — a short, straightforward commute that keeps daily base access simple.
What is the square footage and layout of 4308 Winchester Drive?
The home offers 1,700 square feet of living space configured across three bedrooms and two full bathrooms, built in 1939 with the room proportions typical of pre-war residential construction.
Is 4308 Winchester Drive 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.
Where are the nearest grocery stores and parks to 4308 Winchester Drive?
A Walmart Supercenter is 0.8 miles away for full grocery shopping, and both Links at City Park and Portsmouth City Park are under a mile from the front door — convenient for both errands and outdoor time.
Want to know more about 4308 Winchester Drive or explore comparable homes in Portsmouth? Tom and Dariya Milan at LPT Realty are ready to help — reach out to get started.
Summary generated by AI from public records and publicly available information.
Location & Neighborhood
Places within ~1 mile, ordered by distance from this property. Powered by Google Places.
Flood Risk
Property Details
Bedrooms
3
Full Baths
2
Half Baths
0
Approx Sq Ft
1,700
Stories
2
Fireplaces
0
Flooring
Other, Wood
Heating
Cooling
Laundry
Interior Features
N/A
Appliances
Dishwasher, Disposal, Dryer Hookup, Microwave, Gas Range, Refrigerator, Washer Hookup
Sale & Tax History
List Price
$330,000
Price / Sq Ft
$194
Annual Taxes
$3,121
Monthly Tax
$260
HOA
None
Tax Rate (effective)
0.95%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | May 22, 2026 | $330,000 | — |
| Currently listed | — | $330,000 | — |
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.
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.
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
$2,069/moPrincipal & interest
$1,712
Property tax
$260
Home insurance
$96
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 Swell Realty Co · MLS# 10636138
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$330,000
4308 Winchester DR, PORTSMOUTH VA 23707
Portsmouth, Virginia 23707
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