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Portsmouth › GROVE PARK › 4408 Winchester Dr✓ Source: REIN MLS #10629963 · record updated May 30, 2026 · synced every 5 min · your inquiry is never resold
4408 Winchester DR, PORTSMOUTH VA 23707 - Main photo
$348,900
$142 / sqft · est. $2,243/mo →
5beds
2baths
2,449sqft
3days on market

4408 Winchester Dr, Portsmouth, VA 23707

SoldResidential · built 1946 · GROVE PARK

About this home

The listing, in the seller's words

This stunning all-brick Cape Cod blends old-world character with modern updates. From the distinctive front entry and arched doorways to the inviting front porch swing, every detail adds to its charm. Inside, you'll find newly installed hardwood floors, fresh paint, updated kitchen cabinets and countertops, new shelving, and a new furnace. The home also features a brand-new downstairs HVAC system and an updated circuit board for the upstairs unit. A spacious two-story detached garage offers electricity and a dedicated workshop, for hobbies or storage. The covered back patio provides a cozy setting for relaxing evenings or entertaining. This beautifully refreshed home is ready to welcome its next owners. No flood insurance required.

Listing courtesy of Tiffany Moffit · Iron Valley Real Estate HR · REIN MLS #10629963

Schools

Info provided by GreatSchools

Facts & features

The record, sourced

Type

Residential

Year built

1946

Price / sqft

$142

HOA

None

Taxes

$3,975/yr

County

Portsmouth VA

Waterfront

Yes

MLS #

10629963

Sources: REIN MLS record · 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

$2,243/mo

Principal & interest

$1,810

Property tax

$331

Home insurance

$102

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

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

$305,000 – $575,000

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.

414 West RD · 1 mi · 2,400 sqft$440,000 sold 2026-06
209 Truxton AVE · 1.3 mi · 2,462 sqft$337,000 sold 2026-04
501 Riverside DR · 0.8 mi · 2,080 sqft$575,000 sold 2026-05

Sale & Tax History

List Price

$348,900

Price / Sq Ft

$142

Annual Taxes

$3,975

Monthly Tax

$331

HOA

None

Tax Rate (effective)

1.14%

Sale Timeline (this listing)

EventDatePriceDetail
ListedMay 27, 2026$348,900—
SoldMay 29, 2026$348,900—

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

Real questions, answered from the record

Is 4408 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 4408 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 4408 Winchester Dr?+
Yes — Zenya Yoga Studio & Yoga Academy- Portsmouth Location is about 0.6 miles away, per the cached nearby-places record for this address.
Are there parks near 4408 Winchester Dr?+
Links at City Park is about 0.8 miles away.
Where is the nearest grocery store to 4408 Winchester Dr?+
Dollar General is about 0.9 miles away. The closest dining on record is 7-Eleven (0.5 mi).
Does 4408 Winchester Dr have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 4408 Winchester Dr built?+
It was built in 1946, 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 Tiffany Moffit · Iron Valley Real Estate HR · REIN MLS #10629963

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.

This home has sold

Curious what it means for your own plans? Ask about similar homes nearby, or what your home might sell for in this market.

🏡 Similar homes for saleWhat's my home worth?

This one's sold — the next one doesn't have to be.

🏡 Homes for sale in PortsmouthCall or text (757) 777-7577

4408 Winchester Dr, Portsmouth, Virginia 23707 · MLS #10629963 · 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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