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Portsmouth › GROVE PARK › 4201 Winchester Dr✓ Source: REIN MLS #10637790 · record updated Jul 8, 2026 · synced every 5 min · your inquiry is never resold
4201 Winchester DR, PORTSMOUTH VA 23707 - Main photo
4201 Winchester DR, PORTSMOUTH VA 23707 - Photo 2
4201 Winchester DR, PORTSMOUTH VA 23707 - Photo 3
4201 Winchester DR, PORTSMOUTH VA 23707 - Photo 4
4201 Winchester DR, PORTSMOUTH VA 23707 - Photo 5
$315,000
$163 / sqft · est. $2,006/mo →
4beds
2baths
1,936sqft
35days on market

4201 Winchester Dr, Portsmouth, VA 23707

ActiveResidential · built 1932 · GROVE PARK

About this home

The listing, in the seller's words

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/crawl space sealing by Universal Pest, and a basement bio-disinfectant treatment (receipts available). Additional exterior improvements include chimney point molding repairs and new chimney caps. Inside, you'll find fresh paint, brand-new carpet, new quarter round trim, a refinished fireplace, and a beautifully refinished upstairs bathroom. The kitchen has been updated with a new refrigerator and dishwasher, and a new washer is also included. With spacious bedrooms, updated finishes, and extensive maintenance already completed, this home is ready for its next owner to move i

Listing courtesy of Sneha Rana · Seaside Realty · REIN MLS #10637790

VaHome team overview

Our read on this home

At a glance

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 the full overview ↓

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.

More buyer 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.

Schools

Info provided by GreatSchools

Facts & features

The record, sourced

Type

Residential

Year built

1932

Price / sqft

$163

HOA

None

Taxes

$3,352/yr

County

Portsmouth VA

Waterfront

Yes

MLS #

10637790

Sources: REIN MLS record · city assessor · null fields are suppressed, never faked

Flood & environment

The flood answer first — quantified, not buried

FEMA flood zone X · outside the high-risk area · FIRM 515529

Flood Risk

Looking up FEMA flood zone…

Hurricane Evacuation Zone

Evacuation Zone B

Source: Virginia Dept. of Emergency Management — Know Your Zone

Location intelligence

Minutes to real places, not a score

Location & Neighborhood

Places within ~1 mile, ordered by distance from this property. Powered by Google Places.

Military Commute

Drive times to nearest bases

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.

The numbers

Run the real carrying cost

Estimates only — taxes come from the public record; confirm rates with your lender. VA-eligible buyers: $0-down financing may apply.

Estimate your monthly payment

$2,006/mo

Principal & interest

$1,634

Property tax

$279

Home insurance

$92

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.

Value & history

Judge value on real ground

Asking vs. assessment

117% of $270,330

City assessment record · taxes $3,352/yr

Land share of assessed value

29% — $78,000

Improvements $192,330 · assessor record ✓

Why we show no algorithmic estimate.

National AVMs misprice homes whose value drivers they can't see. Instead: the sourced assessment above, the carrying cost, real price history, and honest comparables below.

Price context — similar nearby homes

$255,000 – $380,000

The 6 most similar homes nearby (same city, within ~20% of this size, ~2.5 mi; 6 sold). Context for judging the asking price — not an appraisal or an estimate of this home's value.

204 Wynn ST · 2 mi · 2,000 sqft$380,000 sold 2026-05
1231 Darren DR · 2.1 mi · 1,979 sqft$300,000 sold 2026-05
904 Darren DR · 2 mi · 1,809 sqft$325,000 sold 2026-04

Sale & Tax History

List Price

$315,000

Price / Sq Ft

$163

Annual Taxes

$3,352

Monthly Tax

$279

HOA

None

Tax Rate (effective)

1.06%

Sale Timeline (this listing)

EventDatePriceDetail
ListedJun 3, 2026$315,000—
Price reducedJul 8, 2026$315,000−$5,000
Currently listed—$315,000—

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

17% above assessment

Total Assessed

$270,330

Land

$78,000

Improvement

$192,330

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:

Portsmouth Real Estate Assessor

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.

Market tempo

35 days on market — read it in context

Days on market reflects pricing, season, and inventory — compare it against similar nearby homes below before reading anything into it.

Questions buyers ask

Real questions, answered from the record

Is 4201 Winchester Dr in a good school zone?+
The assigned zones on the listing record are Westhaven Elementary (GreatSchools 1/10), William E. Waters Middle, Manor High (GreatSchools 2/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 4201 Winchester Dr in a flood zone?+
FEMA maps this parcel in Zone X, outside the high-risk Special Flood Hazard Area. See the flood section on this page for details and sources.
Is there a gym near 4201 Winchester Dr?+
Yes — Zenya Yoga Studio & Yoga Academy- Portsmouth Location is about 0.5 miles away, per the cached nearby-places record for this address.
Are there parks near 4201 Winchester Dr?+
Links at City Park is about 1 miles away.
Where is the nearest grocery store to 4201 Winchester Dr?+
Walmart Supercenter is about 0.8 miles away. The closest dining on record is 7-Eleven (0.4 mi).
Does 4201 Winchester Dr have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 4201 Winchester Dr built?+
It was built in 1932, per the listing record.

Answers generated from the listing record, verified school zones, FEMA data, and cached nearby-places data — never invented.

The people

You'll talk to a person, not a lead queue

TD

Tom & Dariya Milan

LPT Realty · Hampton Roads · answer their own phone

✓ Your inquiry goes to Tom & Dariya — never sold to strangers

Listing courtesy of Sneha Rana · Seaside Realty · REIN MLS #10637790

Call or text (757) 777-7577

Ask Dariya — instant answers

Schools, flood, drive times, what it really costs to own — answered from this page's data, by chat or voice.

Schedule a private tour

Free, no obligation — your inquiry goes to Tom & Dariya, never resold.

See it in person — the record only says so much.

Call or text (757) 777-7577

4201 Winchester Dr, Portsmouth, Virginia 23707 · MLS #10637790 · Source: REIN MLS + public record. Information deemed reliable but not guaranteed — verify independently. School zones subject to change; confirm with the local school division. All locations are described by neutral geographic fact. Equal Housing Opportunity.

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