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Portsmouth › SOUTHAMPTON › 4419 S Highgate Cir✓ Source: REIN MLS #10636133 · record updated Aug 13, 2026 · synced every 2 min · your inquiry is never resold
4419 S Highgate CIR, PORTSMOUTH VA 23703 - Main photo
4419 S Highgate CIR, PORTSMOUTH VA 23703 - Photo 2
4419 S Highgate CIR, PORTSMOUTH VA 23703 - Photo 3
4419 S Highgate CIR, PORTSMOUTH VA 23703 - Photo 4
4419 S Highgate CIR, PORTSMOUTH VA 23703 - Photo 5
$360,000
$229 / sqft · est. $2,282/mo →
3beds
2.1baths
1,569sqft
83days on market

4419 S Highgate Cir, Portsmouth, VA 23703

Under ContractResidential · built 1977 · SOUTHAMPTON

Facts & features

Type

Residential

Year built

1977

Price / sqft

$229

HOA

None

Taxes

$3,712/yr

County

Portsmouth VA

MLS #

10636133

Interior

Bedrooms
3
Full baths
2
Half baths
1
Approx. sqft
1,569
Stories
2
Flooring
Ceramic, Laminate/LVP
Total rooms
7
Other rooms
Attic, PBR with Bath
Appliances
Dishwasher, Disposal, Dryer, Microwave, Elec Range, Refrigerator, Washer

Construction & exterior

Style
Transitional
Subtype
Detached
Foundation
Crawl
Roof
Asphalt Shingle
Exterior
Vinyl
Pool
No Pool
Fencing
Wood Fence

Utilities & systems

Heating
Electric
Cooling
Central Air
Water heater
Electric
Water
City/County
Sewer
City/County

Lot, parking & ownership

Lot size
0.2800
Subdivision
SOUTHAMPTON
Zoning
GR
Ownership
Fee Simple
Garage
Yes
Parking
Garage Att 1 Car, Multi Car, Driveway Spc, Street
Possession
SETTLEMENT
Disclosures
Disclosure Statement, Pet on Premises

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

About this home

Tucked away on a quiet cul-de-sac in the sought-after Churchland area of Portsmouth, this inviting two-story colonial offers a blend of classic charm and comfortable everyday living. The huge, beautifully landscaped backyard creates a peaceful outdoor retreat, complete with a spacious deck for relaxing or entertaining. Inside, the home features 3 bedrooms and 2.5 baths, along with dedicated living and dining spaces that provide flexibility for gatherings, work, or quiet evenings at home. The eat-in kitchen offers a welcoming space for casual meals, while the gas fireplace adds warmth and character to the main living area. The new roof and water heater offer peace of mind as well. Situated near shopping, dining, parks, and major commuter routes, this home offers convenience while maintaining the feel of a charming neighborhood setting.

Listing courtesy of Kendall Bradshaw · Creed Realty · REIN MLS #10636133

VaHome team overview

Our read on this home

by Tom & Dariya Milan, REALTORS® · LPT Realty

At a glance

4419 S Highgate Circle is a three-bedroom, two-and-a-half-bath home in Portsmouth, Virginia, built in 1977 and offering 1,569 square feet of living space just minutes from NSA Northwest Annex and surrounded by genuine neighborhood greenery.

Read the full overview ↓

Why this home stands out

What sets this address apart is its rare three-minute proximity to NSA Northwest Annex — a commute so short it changes your daily rhythm entirely. Pair that with Hoffler Creek Wildlife Preserve literally around the corner, and you get a home where wildlife trails and a major installation are both within easy reach. That combination is genuinely hard to find in this price tier of Portsmouth.

SOUTHAMPTON and the Portsmouth real estate market

Portsmouth Virginia is one of Hampton Roads' most underrated cities — a place with real history, waterfront character, and neighborhoods that feel lived-in rather than manufactured. The Churchland area, where S Highgate Circle sits, is a well-established residential pocket on the western side of the city, known for mature trees, quiet streets, and a strong sense of community. Homes here were built with space in mind — lots tend to be generous, and the streetscape has the settled, unhurried feel that newer developments rarely replicate. Daily life is easy here: you're close to shopping corridors along Route 17, and the broader city connects you quickly to the rest of Hampton Roads via I-664 and the Downtown Tunnel. Portsmouth rewards people who look past the surface — it offers genuine character, accessible neighborhoods, and a location that puts multiple military installations within a short drive.

What's nearby

Step outside and Hoffler Creek Wildlife Preserve is just 0.4 miles away — a 300-plus-acre natural sanctuary with walking trails, a kayak launch, and regular wildlife sightings that make it feel more like a state park than a neighborhood amenity. Churchland Park is another 0.8 miles out and offers open green space for weekend afternoons. Both parks give this address a walkable outdoor lifestyle that's rare for a suburban street. Beyond the parks, everyday errands along the Route 17 corridor are a short drive, keeping convenience close without the noise of a busy commercial strip right outside your door.

For different buyers

For military families relocating

NSA Northwest Annex is three minutes from your front door — that's not a rounding error, it's a genuine lifestyle upgrade. NSA Hampton Roads is reachable in about ten minutes. For military households managing deployments, duty schedules, and everything in between, a commute this short frees up real time. A VA loan can make this address even more accessible; it's worth running the numbers with someone who knows the Hampton Roads market.

For first-time buyers

At 1,569 square feet with three bedrooms and two and a half baths, this home gives first-time buyers a real foothold — enough space to grow into without the overhead of a much larger property. The 1977 build means the bones are solid and the layout is practical. Add in the proximity to Hoffler Creek Wildlife Preserve and the short drive to everyday conveniences, and this is a strong starting point in an established Portsmouth neighborhood.

More buyer questions

How far is 4419 S Highgate Circle from NSA Northwest Annex?

NSA Northwest Annex is approximately a three-minute drive from this address, making it one of the closest residential options to that installation in the area.

How far is 4419 S Highgate Circle from NSA Hampton Roads?

NSA Hampton Roads is roughly ten minutes away by car, giving households with ties to either installation a genuinely convenient location.

What parks are near 4419 S Highgate Circle?

Hoffler Creek Wildlife Preserve is just 0.4 miles away and offers trails, a kayak launch, and abundant wildlife; Churchland Park is 0.8 miles out and provides open recreational space.

Is 4419 S Highgate Circle in a flood zone?

Flood zone information for this address is displayed in the FloodRisk tile on this page — check there for the most current FEMA designation.

Does 4419 S Highgate Circle have a garage?

Garage details for this property are best confirmed through the current listing data or a walkthrough with your agent, as configuration can vary from the original build.

Curious whether 4419 S Highgate Circle fits your situation? Tom and Dariya Milan know this corner of Portsmouth well — reach out and let's talk through it.

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

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 D

Source: Virginia Dept. of Emergency Management — Know Your Zone

Explore this neighborhood

Churchland

Churchland is an established residential neighborhood in Portsmouth, Virginia, known for its tree-lined streets and collection of well-maintained homes spanning multiple decades.

$330K

Median sale · 12 mo

$207

Sold $/sq ft

21d

Days on market

5

For sale now

$66K

HH income

46%

Owner-occupied

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

Explore Churchland →
Map of Churchland with neighborhood boundaryNeighborhood

Portsmouth homes for sale →

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

$2,282/mo

Principal & interest

$1,868

Property tax

$309

Home insurance

$105

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

120% of $299,360

City assessment record · taxes $3,712/yr

Land share of assessed value

32% — $95,400

Improvements $203,960 · assessor record ✓

Price context — similar nearby homes

$250,000 – $379,900

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.

3508 Carter RD · 2.1 mi · 1,604 sqft$379,900 sold 2026-04
5605 Greenefield DR S · 2.2 mi · 1,550 sqft$360,000 sold 2026-05
3505 Pine RD · 2.1 mi · 1,517 sqft$352,000 sold 2026-08

Sale & Tax History

List Price

$360,000

Price / Sq Ft

$229

Annual Taxes

$3,712

Monthly Tax

$309

HOA

None

Tax Rate (effective)

1.03%

Sale Timeline (this listing)

EventDatePriceDetail
ListedMay 22, 2026$360,000—
Price increasedAug 7, 2026$360,000+$10,000
Currently listed—$360,000—

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

20% above assessment

Total Assessed

$299,360

Land

$95,400

Improvement

$203,960

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 4419 S Highgate Cir in a good school zone?+
The assigned zones on the listing record are Churchland Academy Elementary (VaHome School Score 4.3/10), Churchland Middle (VaHome School Score 2.7/10), Churchland (VaHome School Score 5.9/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 4419 S Highgate Cir 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.
Are there parks near 4419 S Highgate Cir?+
Hoffler Creek Wildlife Preserve is about 0.4 miles away.
Does 4419 S Highgate Cir have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 4419 S Highgate Cir built?+
It was built in 1977, 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 Kendall Bradshaw · Creed Realty · REIN MLS #10636133

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.

4419 S Highgate Cir, Portsmouth — photo

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

Call or text (757) 777-7577

4419 S Highgate Cir, Portsmouth, Virginia 23703 · MLS #10636133 · 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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