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Portsmouth › GROVE PARK › 4201 Winchester Dr✓ Source: REIN MLS #10652460 · record updated Sep 16, 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
12days on market

4201 Winchester Dr, Portsmouth, VA 23707

Under ContractResidential · 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 · city assessor · 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

Meet 4201 Winchester Drive—a 1,936-square-foot, four-bedroom home built in 1932 with classic character and solid bones. You're minutes from Naval Medical Center Portsmouth and Norfolk Naval Shipyard. This is the kind of block that anchors homes for sale in 23707.

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

Built in the early 1930s, this home carries vintage charm through its original details and layout. Four bedrooms and two bathrooms give you room to spread out. The lot is deep and quiet, set back from the street. Daily life is easy here—restaurants, gyms, and grocery options are all within a short drive. You'll find the neighborhood walkable and established, with mature trees and a real sense of place.

GROVE PARK and the Portsmouth real estate market

Winchester Drive sits in a historic Portsmouth neighborhood where tree-lined streets and established homes define the character. The block itself is calm and residential, with good spacing between properties. Portsmouth is a waterfront city with deep roots in naval history and shipbuilding. Getting around is straightforward—major roads connect you to downtown, the waterfront, and the broader Hampton Roads area. If you are comparing homes for sale in Portsmouth, note that this location puts you close to both Naval Medical Center Portsmouth and Norfolk Naval Shipyard, making commutes short and predictable. The city offers a mix of local shops, restaurants, and parks. You're never far from what you need.

What's nearby

Peter Seafood and Culinary Chemist Cuisine sit just a few blocks away, so dinner options are close. Vibez Bar and Grill is equally near. For groceries, Farm Fresh International and Walmart Online Grocery Pickup are within a mile. Coffee runs to 7-Eleven, Tropical Smoothie Cafe, or Starbucks take just minutes. Fitness options include Zenya Yoga Studio, Crunch Fitness, and Sports Performance House—all under a mile. Maplewood Park, Woodland Park, and Seaboard Square offer green space and recreation nearby.

For different buyers

Base commute and VA loan notes

Naval Medical Center Portsmouth is about 6 minutes away; Norfolk Naval Shipyard sits 7 minutes out. VA loan financing is common in this area, and the home's established condition means you can move in without major surprises. The neighborhood's proximity to both commands makes daily commutes straightforward and predictable.

Room to grow

Four bedrooms and two bathrooms give you real room to grow. The 1,936-square-foot layout spreads across the lot, and the deep yard offers space for outdoor projects. Storage and a classic floor plan mean you can adapt the home to your needs without fighting the structure.

More buyer questions

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

About 6 minutes by car. The commute is short and straightforward from this neighborhood.

What year was this home built?

1932. The home carries original character and solid bones from the early 1930s era.

Are there grocery stores near this address?

Yes. Farm Fresh International is 0.6 miles away, and Walmart Online Grocery Pickup is 0.7 miles out.

What schools are nearby if you're comparing homes for sale zoned for Manor High School and homes for sale zoned for Westhaven Elementary School?

This address is zoned for both schools. Check the Schools tile on this page for details on programs and ratings.

Is there parking and garage space at this property?

The home includes garage space typical of 1930s construction. Details are in the listing photos and property specs.

Ready to explore 4201 Winchester Drive? Contact Tom & Dariya Milan to schedule a tour and learn more about this Portsmouth 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

By subscribing you agree to receive listing emails from Tom & Dariya Milan, Realtors, at most one a day. Unsubscribe anytime · Privacy PolicyBrokered by LPT Realty

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 neighborhood in Portsmouth, Virginia. It has tree-lined streets and a mix of home styles. They reflect the area's deep local roots.

$286K

Median sale · 12 mo

$180

Sold $/sq ft

23d

Days on market

20

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

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 ✓

Price context — similar nearby homes

$195,650 – $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

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—

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.

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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