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Chesapeake › GLENLEIGH › 744 Helmsdale Way✓ Source: REIN MLS #10654335 · record updated Sep 26, 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
8days on market

744 Helmsdale Way, Chesapeake, VA 23320

ActiveResidential · 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, 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 · city assessor · 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

Four-bedroom, two-bath home built in 1984 on a residential lot in Chesapeake. About 1,984 square feet of living space. Just minutes from USCG Finance Center Chesapeake and Norfolk Naval Shipyard.

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

This 1984-built home sits on a solid foundation with four bedrooms and over two full baths. The layout gives you space to spread out, and the lot supports the kind of everyday living that makes a house feel like home. Whether you're comparing Chesapeake homes for sale or looking for your next move, this address offers straightforward appeal and room to make it yours.

GLENLEIGH and the Chesapeake real estate market

Chesapeake's residential neighborhoods blend suburban comfort with practical access to the water and military installations. Tree-lined streets and single-family homes define the area around 744 Helmsdale Way. The city itself spans over 400 square miles, mixing quiet neighborhoods with commercial corridors and waterfront character. Getting around is easy on major roads like Battlefield Boulevard and Military Highway. Downtown Norfolk and Virginia Beach are both within a 20-minute drive. If you're exploring homes for sale in 23320, you'll find this zip code sits in the heart of Chesapeake's established residential belt. Schools, parks, and shopping anchor the community rhythm here.

What's nearby

USCG Finance Center Chesapeake is about four minutes away by car. Norfolk Naval Shipyard sits roughly 11 minutes south. Local grocery stores, pharmacies, and casual dining cluster within five minutes of the home. Greenbrier Mall and retail corridors are a short drive. Several parks and recreational areas dot the neighborhood, offering green space for outdoor time. The Elizabeth River and waterfront access points are within 15 minutes.

For different buyers

Base commute and VA loan notes

Four bedrooms and two baths give you room to settle in. USCG Finance Center Chesapeake is roughly four minutes away, and Norfolk Naval Shipyard is about 11 minutes out. VA loan financing is common in this area, and the home's 1984 construction means solid bones and move-in readiness.

Room to grow

Four bedrooms mean space for children, a home office, or a guest room. The 1,984-square-foot layout spreads across the lot, and two full baths plus a half-bath reduce morning conflicts. A residential lot gives you room to breathe and outdoor space for play or projects.

More buyer questions

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

About four minutes by car. It's one of the closest military installations to this address.

What is the commute to Norfolk Naval Shipyard from this home?

Roughly 11 minutes, depending on traffic and your exact route through Chesapeake.

Are there homes for sale in Chesapeake with four bedrooms near this location?

Yes. This address offers four bedrooms and sits in an established residential neighborhood where similar layouts are common in the area.

Can I use a VA loan to buy homes for sale zoned for Oscar Smith High School?

VA loan financing is widely available in Chesapeake and this zip code. Talk to a lender about your eligibility and the specific property.

What year was 744 Helmsdale Way built?

The home was built in 1984, giving it nearly four decades of established neighborhood character and proven construction.

Ready to explore this Chesapeake home? Contact Tom & Dariya Milan at LPT Realty to schedule a visit and learn more about 744 Helmsdale Way.

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 (FEMA)

Source: FEMA National Flood Hazard Layer · FIRM 510034

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

19.4 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.

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. It sits among mature hardwoods along the Eastern Branch of the Elizabeth River.

$295K

Median sale · 12 mo

$207

Sold $/sq ft

16d

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

Asking vs. assessment

109% of $389,500

City assessment record · taxes $3,934/yr

Land share of assessed value

39% — $150,000

Improvements $239,500 · assessor record ✓

Price context — similar nearby homes

$395,000 – $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.

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
217 Cedar RD · 2.7 mi · 2,066 sqft$450,000 sold 2026-04

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 19, 2026$425,000—
Currently listed—$425,000—

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

9% 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

8 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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