Home/Virginia/Portsmouth/WESTHAVEN/4438 Winchester DR, PORTSMOUTH VA 23707
4438 Winchester DR, PORTSMOUTH VA 23707 - Main photo
Coming Soon
Active
Under Contract
Sold
Off Market

6 days on market

$390,000

4438 Winchester Dr

Portsmouth, Virginia 23707

MLS# 10631204 · WESTHAVEN · Portsmouth VA

Updated 4 days ago · Source: REIN MLS

Est. payment

$2,446/mo

Edit below

Price / sq ft

$187

2,088 sq ft

Days on market

6

New listing

HOA

None

Year built

1947

79 yrs old

Beds

4

Full Baths

2

Half Baths

0

Sq Ft

2,088

Garage

Yes

Residential2 StorySingle FamilyWaterfront — Not Waterfront

Schools

Info provided by GreatSchools

About this home

Charming and spacious Cape Cod offering 2,088 sq ft of comfortable living! This beautifully maintained 3-bedroom, 2-bath home features gleaming hardwood floors and a warm, inviting layout perfect for everyday living and entertaining. The bright kitchen is equipped with a disposal, microwave, and refrigerator. Also include is a washer and dryer for added convenience. Enjoy abundant storage throughout, ensuring everyth…

Listed by Kris Weaver · Atlantic Sothebys Int'l Realty

Location & Neighborhood

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Flood Risk

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Property Details

Bedrooms

4

Full Baths

2

Half Baths

0

Approx Sq Ft

2,088

Stories

2

Fireplaces

0

Flooring

Carpet, Ceramic, Vinyl

Heating

Cooling

Laundry

Interior Features

N/A

Appliances

Disposal, Dryer, Dryer Hookup, Microwave, Range, Refrigerator, Washer, Washer Hookup

Sale & Tax History

List Price

$390,000

Price / Sq Ft

$187

Annual Taxes

$3,703

Monthly Tax

$309

HOA

None

Tax Rate (effective)

0.95%

Sale Timeline (this listing)

EventDatePriceDetail
ListedMay 30, 2026$390,000
Currently listed$390,000

Public-Records Assessment

Source: Portsmouth via Hampton Roads Regional Parcels. Fetched May 11, 2026.

31% above assessment

Total Assessed

$298,660

Land

$105,000

Improvement

$193,660

Parcel ID: 03210020 · View on city GIS portal

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.

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.

See more Portsmouth homes for sale →

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.

Estimate your monthly payment

$2,446/mo

Principal & interest

$2,024

Property tax

$309

Home insurance

$114

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 Atlantic Sothebys Int'l Realty · MLS# 10631204

Data provided by REIN MLS. Information deemed reliable but not guaranteed.

SOLD

$390,000

4438 Winchester DR, PORTSMOUTH VA 23707

Portsmouth, Virginia 23707

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Quick Facts

TypeResidential
Year Built1947
Lot Size0.4900
Taxes$3,703/yr
HOANone
Heating
Cooling

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