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Chesapeake › GLENLEIGH › 744 Helmsdale Way✓ Source: REIN MLS #10654335 · record updated Sep 18, 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
4beds
2.1baths
1,984sqft
0days on market

744 Helmsdale Way, Chesapeake, VA 23320

New ListingResidential · built 1984 · GLENLEIGH

Facts & features

Type

Residential

Year built

1984

Price / sqft

$214

HOA

None

Taxes

$3,934/yr

County

Chesapeake VA

MLS #

10654335

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, Foyer, PBR with Bath, Office/Study, Porch, Utility Closet
Appliances
Dishwasher, Microwave, Elec Range, Refrigerator
Equipment
Cable Hookup, Ceiling Fan, Jetted Tub

Construction & exterior

Style
Traditional
Subtype
Detached
Foundation
Slab
Roof
Asphalt Shingle
Exterior
Vinyl
Pool
No Pool
Fencing
Back Fenced,Full,Wood Fence

Utilities & systems

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

Lot, parking & ownership

Lot size
0.2900
Subdivision
GLENLEIGH
Ownership
Fee Simple
Garage
Yes
Parking
Garage Att 1 Car, 4 Space
Possession
CLOSING
Disclosures
Disclosure Statement

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

About this home

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 #10654335

Tom & Dariya's overview

Our read on this home

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

At a glance

744 Helmsdale Way is a four-bedroom, 2.5-bath single-family home in Chesapeake, Virginia, built in 1984 and offering 1,984 square feet of living space. It sits minutes from USCG Finance Center Chesapeake and connects quickly to Norfolk Naval Shipyard — a practical address in a well-rooted neighborhood.

Keep searching in Chesapeake

See all Chesapeake homes for sale, including homes for sale in 23320 and homes for sale zoned for Oscar Smith High School. Browse every listing among homes for sale in Chesapeake — updated from the REIN MLS every few minutes. Nearby, look at Riverwalk homes for sale, Chesapeake waterfront homes for sale, Chesapeake condos and townhomes for sale, and new construction homes in Chesapeake.

Read the full overview ↓

Why this home stands out

What sets 744 Helmsdale Way apart is the combination of square footage, bedroom count, and location that's genuinely hard to replicate at this zip code. Four bedrooms in a 1984-built home means real room dimensions — not the chopped-up layouts common in newer builds. Add a half-bath for guests, a two-decade-plus neighborhood that has already found its character, and sub-five-minute access to a federal installation, and you have a property that checks serious boxes for a wide range of buyers comparing Chesapeake homes for sale.

GLENLEIGH and the Chesapeake real estate market

Helmsdale Way sits within the 23320 zip code, one of Chesapeake's most established residential corridors. The streets here have a settled, mature feel — tree lines that have had decades to fill in, sidewalks that actually get used, and neighbors who tend to stay. Chesapeake itself is Virginia's second-largest city by land area, which means you get genuine suburban breathing room without sacrificing urban access. City services are solid, traffic patterns are predictable, and the overall pace leans residential without feeling remote. The 23320 corridor in particular draws buyers who want proximity to the region's military and federal employment hubs while keeping a clear separation between work and home. Families comparing homes for sale in Chesapeake consistently find that this part of the city delivers on both counts — neighborhood stability and commute practicality — in a way that newer fringe developments simply haven't had time to earn yet.

What's nearby

Day-to-day errands are easy from Helmsdale Way. Food Lion is 0.7 miles out for a full grocery run, and Herbal Farmacy at 0.9 miles covers specialty and wellness needs. Royal China and Subway are both within 0.6 miles when dinner plans change last minute. Coffee is covered by Viking Cafe at 0.8 miles — a local spot worth the short drive — and 7-Eleven locations at 0.6 and 0.7 miles for quick morning stops. Oak Grove Park is just 0.4 miles away, making it a realistic walk for an afternoon outside. CVCA Cheer Gym at 0.4 miles and Nuleeu Nutrition and Wellness at 0.9 miles round out the fitness options close to home.

For different buyers

For military families relocating

USCG Finance Center Chesapeake is four minutes away — that's not a commute, that's a short drive. Norfolk Naval Shipyard adds a second major installation within 11 minutes, which matters when orders change or a second household earner works at a different command. A VA loan pairs naturally with a four-bedroom footprint, and the 23320 zip code keeps BAH working efficiently. Families who've been through a few PCS cycles will recognize how rare that combination is.

For families upgrading

Four bedrooms and 1,984 square feet give a growing family genuine flexibility — a dedicated guest room, a home office, or that playroom you've been waiting to have. The half-bath keeps the main living areas functional when the house is full. Oak Grove Park is a short walk, CVCA Cheer Gym is under half a mile, and families comparing homes for sale zoned for Oscar Smith High School will find 744 Helmsdale Way in that zone. The neighborhood's maturity means your kids are growing up on streets with history, not a construction site.

More buyer questions

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

The drive is approximately four minutes under normal traffic conditions, making it one of the closest residential options to that installation in the area.

How far is 744 Helmsdale Way from Norfolk Naval Shipyard?

Norfolk Naval Shipyard is roughly 11 minutes by car, a commute that works well for early-morning muster schedules and shift rotations common at the Shipyard.

Is 744 Helmsdale Way in a flood zone?

Flood zone designation for this address is covered in the FloodRisk tile on this page — check that section for the current FEMA map classification and what it means for insurance.

What zip code is 744 Helmsdale Way in?

The property is in zip code 23320, one of Chesapeake's most established residential zip codes, with straightforward access to both city services and regional employment centers. Buyers browsing homes for sale in 23320 will find this corridor consistently well-represented.

Does 744 Helmsdale Way have an HOA?

HOA status for this address should be confirmed through current disclosure documents — your agent can pull that detail during the due-diligence process.

Tom and Dariya Milan know this part of Chesapeake well. Reach out to get your questions answered and schedule a walkthrough of 744 Helmsdale Way at your convenience.

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

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

Chesapeake$360K – $490K4+ beds

By subscribing you agree to receive listing emails from Tom & Dariya Milan, Realtors, at most one a day. Unsubscribe anytime · Privacy PolicyBrokered by LPT Realty

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 510034

Flood Risk

Looking up FEMA flood 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.

$315K

Median sale · 12 mo

$206

Sold $/sq ft

18d

Days on market

17

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

Chesapeake 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

$2,657/mo

Principal & interest

$2,205

Property tax

$328

Home insurance

$124

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

Price context — similar nearby homes

$305,000 – $474,000

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.

612 Estates WAY · 0.4 mi · 2,210 sqft$400,000 sold 2026-05
828 Hardwood DR · 0.8 mi · 1,812 sqft$465,500 sold 2026-03
424 Rose Garden Ln · 0.9 mi · 2,160 sqft$474,000 sold 2026-07

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

Sale & Tax History

List Price

$425,000

Price / Sq Ft

$214

Annual Taxes

$3,934

Monthly Tax

$328

HOA

None

Tax Rate (effective)

0.93%

Sale Timeline (this listing)

EventDatePriceDetail
ListedSep 18, 2026$425,000—
Currently listed—$425,000—

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

0 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 744 Helmsdale Way in a good school zone?+
The assigned zones on the listing record are B.M. Williams Primary, Crestwood Middle (VaHome School Score 3.9/10), Oscar Smith (VaHome School Score 3.7/10). 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

Brokered by 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 #10654335

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 #10654335 · 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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