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✓ Source: REIN MLS #10659758 · record updated Oct 30, 2026 · synced every 2 min · your inquiry is never resold
4230 Winchester DR, PORTSMOUTH VA 23707 - Main photo
4230 Winchester DR, PORTSMOUTH VA 23707 - Photo 2
4230 Winchester DR, PORTSMOUTH VA 23707 - Photo 3
4230 Winchester DR, PORTSMOUTH VA 23707 - Photo 4
4230 Winchester DR, PORTSMOUTH VA 23707 - Photo 5
4beds
2baths
2,579sqft
3days on market

4230 Winchester Dr, Portsmouth, VA 23707

New ListingResidential · built 1900 · GROVE PARK

About this home

Make memories in this bright and spacious home in Grove Park, Portsmouth! The 4+ BR, 2 BA home boasts 2,600 sq.ft. of living space. Complete peace of mind with major systems updated within the last 6 years including a NEW ROOF, NEW WINDOWS, and an efficient 2- ZONE HVAC SYSTEM with heat pump and new ductwork. A country sitting porch leads to the interior which features fresh paint, hardwood floors in living and dining rooms, new carpet in bedrooms & den with durable LVP in the bathrooms. Enjoy cooking in the wide-open kitchen/dining area equipped with updated appliances. A quaint back porch of windows for growing plants and accesses the backyard. Relax in the expansive den, where French doors lead out to a private, screened-in porch—for outdoor relaxation and outdoor living. A quick commute to military bases, shipyards, shopping, and dining. Move right in to this 12 room, 3 porch home and enjoy living from day one with a one-year home warranty. LAYOUT FIRST FLOOR Front porch Living room Dining room Kitchen/back porch Large pantry Laundry room Den Full bathroom Screened porch with outdoor access LAYOUT SECOND FLOOR 4 bedrooms Bonus room Spacious full bathroom Access to full-sized floored attic

Listing courtesy of Christine Hudson · Investment Realty Corporation · REIN MLS #10659758

Facts & features

Type

Residential

Year built

1900

Price / sqft

$147

HOA

None

Taxes

$3,366/yr

County

Portsmouth VA

MLS #

10659758

Interior

Bedrooms
4
Full baths
2
Approx. sqft
2,579
Stories
2
Flooring
Carpet, Ceramic, Laminate/LVP, Wood
Ensuite bedrooms
1
First-floor bed & full bath
Yes
Total rooms
12
Other rooms
1st Floor Primary BR, Attic, PBR with Bath, Office/Study, Pantry, Porch, Spare Room, Utility Room
Appliances
Dishwasher, Disposal, Dryer, Microwave, Elec Range, Refrigerator, Washer
Equipment
Ceiling Fan

Construction & exterior

Style
Transitional
Subtype
Detached
Foundation
Crawl
Roof
Asphalt Shingle
Exterior
Shingle
Pool
No Pool
Fencing
Partial,Privacy

Utilities & systems

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

Lot, parking & ownership

Lot size
0.1800
Subdivision
GROVE PARK
Zoning
UR
Ownership
Fee Simple
Garage
No
Parking
2 Space, Off Street, Driveway Spc
Possession
CLOSING
Miscellaneous
Warranty Plan

Sources: REIN MLS record

Tom & Dariya's overview

Our read on this home

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

At a glance

4230 Winchester Drive is a four-bedroom, two-bath home in Portsmouth, Virginia, built in 1900 and offering 2,579 square feet of living space. Naval Medical Center Portsmouth is about six minutes away. This address sits in the heart of the 23707 zip code, close to parks, dining, and fitness options.

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 Simonsdale Elementary School. 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 built at the turn of the twentieth century carry a character that newer construction simply cannot replicate. At 2,579 square feet, 4230 Winchester Drive gives you genuine room to spread out. Four bedrooms and two full baths make the floor plan flexible. The 1900 build year means thick walls, tall ceilings, and the kind of craftsmanship that defines older Portsmouth neighborhoods. Two major military installations sit within seven minutes, and daily errands are easy to handle without a long drive.

GROVE PARK and the Portsmouth real estate market

Winchester Drive sits in a well-established part of Portsmouth, where early-twentieth-century homes line shaded streets. The housing stock here tends to be larger than what you find in newer subdivisions, and the lots reflect an era when builders left room to breathe. Sidewalks connect the blocks, and neighbors tend to know one another. Portsmouth City Park is about a mile away, anchoring the area with green space and the Links at City Park golf course. Portsmouth itself is one of the seven cities of Hampton Roads. It borders Norfolk to the east and the Elizabeth River runs along its edge. Downtown Portsmouth has a walkable waterfront district with restaurants and a ferry connection to Norfolk. Getting around is straightforward — Interstate 264 and U.S. Route 17 both provide quick access to the broader region. Anyone comparing Portsmouth homes for sale will notice that the 23707 zip code offers some of the most substantial historic square footage in the city.

What's nearby

Griff's Restaurant and Sports Lounge is just 0.3 miles away, making a casual dinner an easy walk. Chef Skip 757 and Ellen's Homestyle and BBQ Express are both within 0.4 miles for more local flavor. Wawa and Tropical Smoothie Cafe are 0.6 miles out when you need a quick morning stop. Farm Fresh International handles the weekly grocery run at 0.7 miles. Crunch Fitness Portsmouth is 0.4 miles away for daily workouts, and Zenya Yoga Studio rounds out the fitness options at 0.9 miles. Portsmouth City Park and the Links at City Park are both about a mile from the front door.

For different buyers

Base commute and VA loan notes

Naval Medical Center Portsmouth is about six minutes from 4230 Winchester Drive. Norfolk Naval Shipyard is roughly seven minutes in the other direction. VA loan financing is widely used in this part of Portsmouth, and the 23707 zip code has a strong track record with VA appraisals. The four-bedroom layout and proximity to two installations make this address worth a close look on any base-commute checklist.

For buyers drawn to character

A home built in 1900 brings details you cannot order from a builder catalog. High ceilings, solid construction, and a floor plan shaped by a different era of craftsmanship define 4230 Winchester Drive. At 2,579 square feet, there is real space to work with. Buyers who want homes for sale in 23707 with genuine historic bones will find this address stands apart from anything built in the last fifty years.

More buyer questions

How far is 4230 Winchester Drive from Naval Medical Center Portsmouth?

The drive is about six minutes under normal traffic conditions. The address sits in one of the closest residential pockets to that installation in the city.

How far is 4230 Winchester Drive from Norfolk Naval Shipyard?

Norfolk Naval Shipyard is roughly seven minutes away by car. Both major installations are reachable without getting on a highway.

What school zones apply to 4230 Winchester Drive?

Buyers comparing homes for sale zoned for Manor High School and homes for sale zoned for Simonsdale Elementary School will want to confirm current zoning directly with Portsmouth City Public Schools, as boundaries can change.

Is 4230 Winchester Drive in a flood zone?

Flood zone status for this address is covered in the FloodRisk tile on this page. Your agent can pull the current FEMA map panel for the 23707 zip code.

Does 4230 Winchester Drive have an HOA?

There is no HOA associated with this address. Owners are not subject to association dues or deed restrictions from a homeowners association.

Ready to walk through 4230 Winchester Drive? Contact Tom and Dariya Milan at vahome.com to schedule your visit and get straight answers about this Portsmouth address.

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

How Far Is?

Driving distance by road and typical drive time via Google Maps, to the nearest location of each.

Also nearby

Distances are straight-line (as the crow flies) from this property, not driving miles. Places within ~1 mile, nearest first. Powered by Google Places.

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

Portsmouth$320K – $440K4+ 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 (FEMA)

Source: FEMA National Flood Hazard Layer · FIRM 515529

Low / Moderate Risk

FEMA flood zone

X (low to moderate risk)

Base flood elevation

Not applicable in low-risk zones

Zone X is outside the Special Flood Hazard Area; FEMA doesn\u2019t define a BFE here.

Property elevation

13.3 ft above sea level

USGS 3DEP digital elevation model

Outside the high-risk Special Flood Hazard Area. Federal flood insurance is NOT required, though optional preferred-rate NFIP coverage is still worth considering in coastal Hampton Roads.

Data sources: Flood zone and base flood elevation come from FEMA\u2019s National Flood Hazard Layer. Property elevation is sampled from a single point on the parcel using the USGS National Map elevation service \u2014 actual elevations across a single property can vary by several feet higher or lower than the figure shown. Use these numbers as a starting reference and do your own due diligence (a professional survey or elevation certificate) before relying on them for any financial, insurance, or construction decision.

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.

$273K

Median sale · 12 mo

$171

Sold $/sq ft

27d

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 homes for sale →

Military Commute

Drive times to nearest bases

NMCP

Navy

15min·4.4mi

NNSY

Navy

13min·4.7mi

USCG Portsmouth

Coast Guard

15min·5.9mi

USCG Finance Ctr

Coast Guard

24min·16.4mi

NSA HR

Navy

32min·13.1mi

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

Payment Calculator

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

$2,363/mo

Principal & interest

$1,971

Property tax

$281

Home insurance

$111

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

Comparables

Price context — similar nearby homes

$365,000 – $439,900

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.

2954 Greenwood DR · 1.5 mi · 2,508 sqft$375,000 sold 2026-08
303 Goldenstar LN · 1.4 mi · 2,421 sqft$390,000 sold 2026-01
3405 Woodstock ST · 1.2 mi · 2,247 sqft$398,900 sold 2026-06

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

Sale & Tax History

List Price

$379,900

Price / Sq Ft

$147

Annual Taxes

$3,366

Monthly Tax

$281

HOA

None

Tax Rate (effective)

0.89%

Sale Timeline (this listing)

EventDatePriceDetail
ListedOct 27, 2026$379,900—
Currently listed—$379,900—

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.

Market tempo

3 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 4230 Winchester Dr in a good school zone?+
The assigned zones on the listing record are Simonsdale Elementary (VaHome School Score 2.3/10), William E. Waters Middle, Manor High (VaHome School Score 3.2/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 4230 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 4230 Winchester Dr have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 4230 Winchester Dr built?+
It was built in 1900, 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

Listing courtesy of Christine Hudson · Investment Realty Corporation · REIN MLS #10659758

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.

4230 Winchester Dr, Portsmouth — photo

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

Call or text (757) 777-7577

4230 Winchester Dr, Portsmouth, Virginia 23707 · MLS #10659758 · 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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