8 days on market
$325,000
4201 Winchester Dr
Portsmouth, Virginia 23707
MLS# 10637790 · GROVE PARK · Portsmouth VA
Updated Jun 12, 2026 · Source: REIN MLS
Est. payment
$2,060/mo
Edit below
Price / sq ft
$168
1,936 sq ft
Days on market
8
New listing
HOA
None
Year built
1932
94 yrs old
Beds
4
Full Baths
2
Half Baths
0
Sq Ft
1,936
Garage
No
About this home
Welcome to this beautifully updated 4-bedroom, 2-bath home located in a quiet Portsmouth neighborhood, just minutes from military bases, beaches, hospitals, shopping, dining, and other local amenities. This move-in-ready property offers the perfect blend of character, comfort, and peace of mind with numerous recent improvements throughout. Major updates include a new roof (2022), crawl space waterproofing, basement/c…
Listed by Sneha Rana · Seaside Realty
VaHome Team property overview
Meet 4201 Winchester Drive — a four-bedroom, 1930s-era home in Portsmouth sitting less than ten minutes from two major military installations. With nearly 2,000 square feet of living space and a classic architectural character, this address delivers both history and everyday practicality.
Read full property overview ↓Show less ↑
Why this home stands out
Built in 1932, this home carries the kind of solid craftsmanship that newer construction rarely replicates — thick walls, defined rooms, and a floor plan that actually separates living from sleeping. At 1,936 square feet across four bedrooms and two baths, there's real breathing room here. The proximity to Naval Medical Center Portsmouth and Norfolk Naval Shipyard is hard to beat for anyone working on either installation, and the surrounding Portsmouth streetscape adds genuine neighborhood texture.
GROVE PARK and the Portsmouth real estate market
Winchester Drive sits in a mature Portsmouth residential corridor where the streets are lined with established trees and homes that have real stories behind them. This part of Portsmouth — sometimes called the Midtown corridor — blends working-class roots with a growing creative and community energy. The city itself is one of the most historically layered in Hampton Roads, home to the oldest naval shipyard in the country and a downtown waterfront that's been steadily reinvesting in itself. Portsmouth VA real estate in this zip code tends to attract buyers who want character over cookie-cutter, and proximity to major employers without paying a premium for a trendier address. You're in Portsmouth proper, under Portsmouth city jurisdiction, which means city services and a tight-knit municipal identity. Neighbors here tend to stay — the block has the feel of a place where people actually know each other's names. For anyone who values authenticity over polish, this neighborhood delivers.
What's nearby
Daily errands are genuinely easy from Winchester Drive. A Walmart Supercenter is just 0.8 miles away for full grocery runs, and Wawa and Corner Cafe are both within a mile when you need a quick coffee. Vibez Bar and Grill and Culinary Chemist Cuisine are each about half a mile out — solid options for a weeknight dinner without driving across town. Fitness is well covered too: Zenya Yoga Studio, Sports Performance House, and Crunch Fitness are all within 0.7 miles. When you want some outdoor time, Links at City Park is a mile away and offers a welcome green escape.
For different buyers
For military families relocating
Naval Medical Center Portsmouth is a six-minute drive from this address, and Norfolk Naval Shipyard is seven minutes out — that's about as close as it gets without living on base. For active-duty families managing long shifts and unpredictable schedules, that commute margin matters. A VA loan can make this four-bedroom home even more accessible, and the four-bedroom layout gives growing families the space they actually need.
For buyers drawn to character
If you've toured subdivision after subdivision and felt nothing, 4201 Winchester Drive might be the reset you're looking for. Built in 1932, this home has the bones, the proportions, and the street presence that come from a different era of construction. Four bedrooms and nearly 2,000 square feet give you room to live, while the 90-plus years of history give you something no new build can offer: a home that already has a soul.
Frequently asked questions
How far is 4201 Winchester Drive from Naval Medical Center Portsmouth?
Naval Medical Center Portsmouth is approximately six minutes away by car — one of the closest off-base residential options available in the city. That short commute is a meaningful daily advantage for staff and active-duty personnel assigned there.
How far is 4201 Winchester Drive from Norfolk Naval Shipyard?
Norfolk Naval Shipyard is about seven minutes from this address, making it equally convenient for anyone working or reporting to that installation. The two-base proximity from a single address is genuinely uncommon.
What is the square footage and layout of 4201 Winchester Drive?
The home offers 1,936 square feet of living space with four bedrooms and two full baths. Built in 1932, the floor plan reflects the defined, room-by-room layout typical of that era rather than an open-concept design.
Is 4201 Winchester Drive in a flood zone?
Flood zone information for this address is displayed in the FloodRisk tile on this page, which pulls current FEMA map data. We recommend reviewing that section and discussing it with your agent before making any decisions.
Are there grocery stores and restaurants close to 4201 Winchester Drive?
Yes — a Walmart Supercenter is 0.8 miles away for full grocery shopping, and restaurants like Vibez Bar and Grill and Culinary Chemist Cuisine are within half a mile. Wawa and Corner Cafe are also nearby for quick stops.
Tom and Dariya Milan at LPT Realty know Portsmouth inside and out. Reach out to get the full picture on 4201 Winchester Drive and what it could mean for your next move.
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
4
Full Baths
2
Half Baths
0
Approx Sq Ft
1,936
Stories
2
Fireplaces
0
Flooring
Carpet, Ceramic, Laminate/LVP
Heating
Cooling
Laundry
Interior Features
N/A
Appliances
Dishwasher, Disposal, Dryer Hookup, Elec Range, Refrigerator, Washer Hookup
Sale & Tax History
List Price
$325,000
Price / Sq Ft
$168
Annual Taxes
$3,352
Monthly Tax
$279
HOA
None
Tax Rate (effective)
1.03%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | Jun 4, 2026 | $325,000 | — |
| Currently listed | — | $325,000 | — |
Public-Records Assessment
Source: City Assessor via Hampton Roads Regional Parcels. Fetched Jun 12, 2026.
Total Assessed
$270,330
Land
$78,000
Improvement
$192,330
Parcel ID: 03260250
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
$2,060/moPrincipal & interest
$1,686
Property tax
$279
Home insurance
$95
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 Seaside Realty · MLS# 10637790
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$325,000
4201 Winchester DR, PORTSMOUTH VA 23707
Portsmouth, Virginia 23707
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