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Portsmouth › GROVE PARK › 4201 Winchester Dr✓ Source: REIN MLS #10652460 · record updated Sep 4, 2026 · synced every 2 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
4beds
2baths
1,936sqft
0days on market

4201 Winchester Dr, Portsmouth, VA 23707

New ListingResidential · built 1932 · GROVE PARK

Facts & features

Type

Residential

Year built

1932

Price / sqft

$163

HOA

None

Taxes

$3,352/yr

County

Portsmouth VA

MLS #

10652460

Interior

Bedrooms
4
Full baths
2
Approx. sqft
1,936
Stories
2
Flooring
Carpet, Ceramic, Laminate/LVP
First-floor bed & full bath
Yes
Total rooms
8
Other rooms
1st Floor BR, Attic, Foyer, Porch, Sun Room
Appliances
Dishwasher, Disposal, Dryer Hookup, Elec Range, Refrigerator, Washer Hookup
Equipment
Cable Hookup, Ceiling Fan

Construction & exterior

Style
Traditional
Subtype
Detached
Foundation
Basement, Crawl
Roof
Asphalt Shingle
Exterior
Shingle
Pool
No Pool
Fencing
Back Fenced,Privacy,Wood Fence

Utilities & systems

Heating
Electric, Heat Pump, Zoned
Cooling
Central Air, Zoned
Water heater
Electric
Water
City/County
Sewer
City/County

Lot, parking & ownership

Subdivision
GROVE PARK
Zoning
UR
Ownership
Fee Simple
Garage
No
Parking
Street
Possession
SETTLEMENT
Disclosures
Disclosure Statement

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

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/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 #10652460

Tom & Dariya's overview

Our read on this home

by Tom & Dariya Milan, REALTORS® · Brokered by LPT Realty

At a glance

Built in 1932, this 4-bedroom, 2-bath Portsmouth home delivers 1,936 square feet of character-rich living just six minutes from Naval Medical Center Portsmouth and seven minutes from Norfolk Naval Shipyard — a rare combination of history, space, and military-base convenience in the 23707 zip code.

Keep searching in Portsmouth

See all Portsmouth homes for sale, including homes for sale in 23707, homes for sale zoned for Manor High School, and homes for sale zoned for Westhaven Elementary School. Browse every listing among homes for sale in Portsmouth — updated from the REIN MLS every few minutes. Nearby, look at Brighton homes for sale, Portsmouth waterfront homes for sale, Portsmouth condos and townhomes for sale, and new construction homes in Portsmouth.

Read the full overview ↓

Why this home stands out

Homes from the early 1930s carry a craftsmanship you simply don't find in newer construction — thicker walls, hardwood-era bones, and proportions that feel genuinely livable rather than squeezed. At 1,936 square feet across four bedrooms, 4201 Winchester Drive gives you room to spread out without sacrificing the charm that defines Portsmouth's older residential corridors. Two full baths, a generous footprint, and proximity to two major military installations make this address unusually practical for its vintage.

GROVE PARK and the Portsmouth real estate market

Winchester Drive sits in a mature, tree-lined section of Portsmouth where the housing stock dates back nearly a century and the streets have a settled, established feel. Portsmouth itself is one of Hampton Roads' most storied cities — an independent city in Virginia with its own deep naval heritage, a revitalized Olde Towne district along the Elizabeth River waterfront, and a tight-knit community identity that newer suburbs rarely replicate. The 23707 zip code places you on the western side of the city, close to the shipyard corridor and the medical center, yet far enough from the industrial waterfront to enjoy quiet residential blocks. For anyone comparing Portsmouth homes for sale, this part of the city tends to attract buyers who value authenticity over cookie-cutter sameness — neighbors who know each other, sidewalks that actually get used, and a sense that the neighborhood has a real history worth being part of.

What's nearby

Daily errands are genuinely low-effort from Winchester Drive. Farm Fresh International covers your full grocery run just 0.6 miles away, and Walmart grocery pickup is within 0.7 miles for those busier weeks. When you'd rather let someone else cook, Peter Seafood is only 0.2 miles out — hard to beat for a quick local seafood fix — and Culinary Chemist Cuisine and Vibez Bar and Grill are both within 0.3 miles for a sit-down evening. Tropical Smoothie Cafe and Starbucks are under a mile for your morning routine. Fitness options cluster nearby too: Crunch Fitness, Zenya Yoga Studio, and Sports Performance House are all 0.6 miles out. Maplewood Park and Woodland Park round out the outdoor options within easy walking distance.

For different buyers

For military families relocating

Naval Medical Center Portsmouth is a six-minute drive from the front door, and Norfolk Naval Shipyard is seven minutes in the opposite direction — two of Hampton Roads' most active installations, both reachable before your coffee gets cold. A VA loan pairs naturally with a home this close to base, and four bedrooms give you the flexibility to handle PCS moves, visiting family, or a dedicated home-office setup without anyone feeling crowded.

For buyers drawn to character

If you've been scrolling past subdivision homes that all look the same, 4201 Winchester Drive is a different conversation. Built in 1932, this is a home with actual bones — the kind of craftsmanship, scale, and neighborhood texture that families comparing homes for sale in Portsmouth consistently find harder to locate than they expected. Four bedrooms and nearly 2,000 square feet leave plenty of room to modernize selectively while keeping what makes a 1930s home worth owning in the first place.

More buyer questions

How far is 4201 Winchester Drive from Naval Medical Center Portsmouth?

Naval Medical Center Portsmouth is approximately six minutes by car from 4201 Winchester Drive, making it one of the closest residential options to the base in the city. The short commute is a consistent draw for medical staff and military personnel assigned there.

How far is 4201 Winchester Drive from Norfolk Naval Shipyard?

Norfolk Naval Shipyard is about seven minutes from the address, placing it well within the range most military families target when searching homes for sale in 23707. Both bases are reachable without highway driving, which keeps the daily commute straightforward.

What schools serve 4201 Winchester Drive?

Buyers comparing homes for sale zoned for Manor High School and homes for sale zoned for Westhaven Elementary School will find that this address falls within those attendance zones — the Schools tile on this page has current boundary and program details.

Is 4201 Winchester Drive in a flood zone?

Flood zone designation for this address is covered in the FloodRisk tile on this page, which pulls current FEMA map data. Your agent can walk you through what that means for insurance during the offer process.

Does the 23707 zip code have an HOA for this property?

4201 Winchester Drive does not carry an HOA, which is typical for the older residential streets in this part of Portsmouth. That means no monthly association dues and no architectural review board to navigate for exterior changes.

Tom and Dariya Milan at LPT Realty know this corner of Portsmouth well — reach out to get a straight-talking walkthrough of what 4201 Winchester Drive looks like as your next home.

Summary generated by AI from public records and publicly available information.

Homes like this one sell fast — see the next one first

Portsmouth$265K – $365K4+ beds

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Schools

VaHome School Score

Our own 1–10 rating, scored from Virginia Department of Education data.

VaHome School Score — calculated by VaHome.com from Virginia Department of Education assessment, progress, and attendance data. Attendance zones come from the MLS listing record; confirm the current zone with the school division before making an offer.

Flood & environment

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

Explore this neighborhood

Brighton

Brighton is a residential neighborhood in Portsmouth, Virginia, characterized by tree-lined streets and a mix of housing styles that reflect its established community roots.

$283K

Median sale · 12 mo

$181

Sold $/sq ft

22d

Days on market

18

For sale now

$46K

HH income

55.2%

Owner-occupied

REIN MLS closed sales, trailing 12 mo · U.S. Census ACS 2024 5-year

Explore Brighton →
Map of Brighton with neighborhood boundaryNeighborhood

Portsmouth real estate →

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/Condo (paid separately)

None

Estimate only. Association (HOA/condo) fees are paid separately and are not included in the payment above. 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

Price context — similar nearby homes

$280,000 – $364,500

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.

3900 Clifford ST · 0.4 mi · 2,000 sqft$295,000 sold 2026-07
10 California AVE · 0.4 mi · 2,306 sqft$364,500 sold 2026-07
273 Tigerlilly DR · 1.3 mi · 1,964 sqft$280,000 sold 2026-05

Own a home nearby? See what it is worth today — What's your Portsmouth home worth?

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
ListedSep 4, 2026$315,000—
Currently listed—$315,000—

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:

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

0 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

Is 4201 Winchester Dr in a good school zone?+
The assigned zones on the listing record are Westhaven Elementary (VaHome School Score 1.8/10), William E. Waters Middle, Manor High (VaHome School Score 3.6/10). 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.
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

Brokered by 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 #10652460

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.

4201 Winchester Dr, Portsmouth — photo

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

Call or text (757) 777-7577

4201 Winchester Dr, Portsmouth, Virginia 23707 · MLS #10652460 · 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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