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Chesapeake › GLENLEIGH › 744 Helmsdale Way✓ Source: REIN MLS #10641959 · record updated Jul 16, 2026 · synced every 2 min · your inquiry is never resold
744 Helmsdale WAY, CHESAPEAKE VA 23320 - Main photo
744 Helmsdale WAY, CHESAPEAKE VA 23320 - Photo 2
744 Helmsdale WAY, CHESAPEAKE VA 23320 - Photo 3
744 Helmsdale WAY, CHESAPEAKE VA 23320 - Photo 4
744 Helmsdale WAY, CHESAPEAKE VA 23320 - Photo 5
$449,000
$226 / sqft · est. $2,789/mo →
4beds
2.1baths
1,984sqft
17days on market

744 Helmsdale Way, Chesapeake, VA 23320

ActiveResidential · built 1984 · GLENLEIGH

About this home

The listing, in the seller's words

Discover timeless charm in this beautiful, traditional home located in the heart of Chesapeake. Featuring 4 bedrooms, 2.5 bathrooms, and a spacious two-story layout, this home includes a bedroom with its own en suite bath, making it great for guests or added privacy. Gather around the cozy fireplace on cool evenings, or enjoy casual meals in the bright breakfast area. Step outside to a fully fenced backyard, great for entertaining, pets, or relaxing outdoors. Recent upgrades, including new siding and roof (2021) and a remodeled primary bathroom (2025), enhance both the home's beauty and value. An attached garage and attic complete this exceptional property. Don't miss your opportunity to make this Chesapeake gem your own!

Listing courtesy of Angela Kennedy · 1st Class Real Estate Integrity · REIN MLS #10641959

VaHome team overview

Our read on this home

At a glance

744 Helmsdale Way is a four-bedroom, two-and-a-half-bath single-family home in Chesapeake, Virginia, offering 1,984 square feet of living space built in 1984. It sits just minutes from the USCG Finance Center and a short drive from Norfolk Naval Shipyard.

Read the full overview ↓

Why this home stands out

What sets 744 Helmsdale Way apart is its combination of established neighborhood character and genuine practicality. Four true bedrooms give growing households real breathing room, while the half-bath on the main level keeps daily routines from turning into a traffic jam. The 1984 build era means solid construction with mature landscaping that newer subdivisions simply can't replicate — and two major military installations are practically around the corner.

GLENLEIGH and the Chesapeake real estate market

Chesapeake is one of the most livable cities in Hampton Roads, and the area around Helmsdale Way reflects exactly why. This part of the 23320 zip code sits in the heart of the city — close to the Great Bridge corridor and the broader Greenbrier district — where tree-lined streets and established lots give the whole area a settled, unhurried feel. Neighbors here tend to stay a while, which shows in the well-kept yards and the general sense of community. Chesapeake consistently ranks among Virginia's safest and most family-friendly cities, and daily errands are genuinely easy to handle without crossing city lines. You're far enough from the congestion of downtown Norfolk to feel removed, yet connected enough that a commute to any major Hampton Roads employer stays manageable. It's the kind of address that feels like a real home base rather than just a place to park.

What's nearby

Daily life runs smoothly from Helmsdale Way. Greenbrier Mall and the surrounding retail corridor put grocery stores, pharmacies, and a wide range of dining options within a few minutes by car. Kroger and Harris Teeter are both close, and the Greenbrier area has no shortage of coffee shops for a quick morning stop. For outdoor time, Northwest River Park and Chesapeake City Park offer trails, open space, and family-friendly amenities not far from the door. Interstate 64 access is straightforward, connecting you to the rest of Hampton Roads without a complicated route.

For different buyers

For military families relocating

The USCG Finance Center Chesapeake is literally four minutes away, making 744 Helmsdale Way one of the most commute-efficient addresses in the city for Coast Guard personnel. Norfolk Naval Shipyard is reachable in about eleven minutes. A VA loan can make this kind of location even more accessible — four bedrooms and two and a half baths give a military family real space to settle in between assignments.

For families upgrading

If you've outgrown a smaller home and need four actual bedrooms — not three bedrooms and an office someone has to share — Helmsdale Way delivers. The layout gives parents and kids their own space, the half-bath keeps mornings moving, and the established neighborhood means you're buying into a community rather than a construction zone. There's genuine room to grow here.

More buyer questions

How far is 744 Helmsdale Way from Norfolk Naval Shipyard?

Norfolk Naval Shipyard is approximately eleven minutes from 744 Helmsdale Way under typical traffic conditions. The route is straightforward and avoids most of the congestion common to other Shipyard commutes from the Hampton Roads area.

How far is 744 Helmsdale Way from the USCG Finance Center Chesapeake?

The USCG Finance Center Chesapeake is about four minutes away, making this one of the closest residential addresses to that installation in the city.

What is the flood zone status for 744 Helmsdale Way?

Flood zone information for this property is displayed in the dedicated FloodRisk tile on this page, which pulls current FEMA map data for the parcel.

Is there an HOA at 744 Helmsdale Way?

HOA status for this property should be confirmed during the due-diligence period, as community association rules and requirements can change over time.

What are the nearest grocery stores to 744 Helmsdale Way?

The Greenbrier corridor, just a few minutes away, includes both Kroger and Harris Teeter locations along with a broad range of pharmacies, restaurants, and everyday retail.

Ready to see 744 Helmsdale Way in person? Reach out to Tom and Dariya Milan at LPT Realty to schedule a walkthrough and get your questions answered.

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

Schools

Info provided by GreatSchools

Facts & features

The record, sourced

Type

Residential

Year built

1984

Price / sqft

$226

HOA

None

Taxes

$3,934/yr

County

Chesapeake VA

Waterfront

Yes

MLS #

10641959

Interior

Bedrooms
4
Full baths
2
Half baths
1
Approx. sqft
1,984
Stories
2
Flooring
Carpet, Ceramic, Laminate/LVP
Ensuite bedrooms
1
Total rooms
7
Other rooms
Attic, Breakfast Area, Fin. Rm Over Gar, PBR with Bath
Appliances
Dishwasher, Microwave, Elec Range, Refrigerator
Equipment
Cable Hookup, Ceiling Fan

Construction & exterior

Style
Traditional
Subtype
Detached
Foundation
Slab
Roof
Asphalt Shingle
Exterior
Vinyl
Pool
No Pool
Fencing
Back Fenced,Full,Wood Fence
Waterfront
Not Waterfront

Utilities & systems

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

Lot, parking & ownership

Lot size
0.2930
Subdivision
GLENLEIGH
Ownership
Fee Simple
Garage
Yes
Parking
Garage Att 1 Car, 4 Space
Possession
CLOSING
Disclosures
Disclosure Statement

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

Flood & environment

FEMA flood zone X · outside the high-risk area · FIRM 510034

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

Riverwalk

Riverwalk is a master-planned community in Chesapeake, Virginia, set among mature hardwoods along the Eastern Branch of the Elizabeth River in the 23320 ZIP code, in the Greenbrier area.

$335K

Median sale · 12 mo

$206

Sold $/sq ft

13d

Days on market

24

For sale now

$87K

HH income

70%

Owner-occupied

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

Explore Riverwalk →
Map of Riverwalk with neighborhood boundaryNeighborhood

homes for sale in Chesapeake →

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

$2,789/mo

Principal & interest

$2,330

Property tax

$328

Home insurance

$131

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

Asking vs. assessment

115% of $389,500

City assessment record · taxes $3,934/yr

Land share of assessed value

39% — $150,000

Improvements $239,500 · assessor record ✓

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

$429,900 – $550,000

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.

1440 New Mill DR · 2.3 mi · 2,060 sqft$475,000 sold 2026-07
728 Luther ST · 2.2 mi · 1,810 sqft$429,900 sold 2026-04
349 Briarfield DR · 2.8 mi · 1,965 sqft$500,500 sold 2026-03

Sale & Tax History

List Price

$449,000

Price / Sq Ft

$226

Annual Taxes

$3,934

Monthly Tax

$328

HOA

None

Tax Rate (effective)

0.88%

Sale Timeline (this listing)

EventDatePriceDetail
ListedJun 29, 2026$449,000—
Price reducedJul 16, 2026$449,000−$6,000
Currently listed—$449,000—

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

15% above assessment

Total Assessed

$389,500

Land

$150,000

Improvement

$239,500

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:

Chesapeake 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

17 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

Real questions, answered from the record

Is 744 Helmsdale Way in a good school zone?+
The assigned zones on the listing record are B.M. Williams Primary, Crestwood Middle (GreatSchools 5/10), Oscar Smith (GreatSchools 7/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 744 Helmsdale Way 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 744 Helmsdale Way?+
Yes — CVCA cheer gym is about 0.5 miles away, per the cached nearby-places record for this address.
Are there parks near 744 Helmsdale Way?+
Oak Grove Park is about 0.4 miles away.
Where is the nearest grocery store to 744 Helmsdale Way?+
Food Lion is about 0.6 miles away. The closest dining on record is Royal China (0.4 mi).
Does 744 Helmsdale Way have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 744 Helmsdale Way built?+
It was built in 1984, 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 Angela Kennedy · 1st Class Real Estate Integrity · REIN MLS #10641959

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.

744 Helmsdale Way, Chesapeake — photo

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

Call or text (757) 777-7577

744 Helmsdale Way, Chesapeake, Virginia 23320 · MLS #10641959 · 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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