0 days on market
$455,000
744 Helmsdale Way
Chesapeake, Virginia 23320
MLS# 10641959 · GLENLEIGH · Chesapeake VA
Updated yesterday · Source: REIN MLS
Est. payment
$2,821/mo
Edit below
Price / sq ft
$229
1,984 sq ft
Days on market
0
New listing
HOA
None
Year built
1984
42 yrs old
Beds
4
Full Baths
2
Half Baths
1
Sq Ft
1,984
Garage
Yes
Schools
- ElementaryB.M. Williams Primary—
- MiddleCrestwood Middle School5/10
- 3/10
Info provided by GreatSchools
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 fo…
Listed by Angela Kennedy · 1st Class Real Estate Integrity
VaHome Team property overview
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 full property overview ↓Show less ↑
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.
Frequently asked 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.
Location & Neighborhood
Places within ~1 mile, ordered by distance from this property. Powered by Google Places.
Flood Risk
Property Details
Bedrooms
4
Full Baths
2
Half Baths
1
Approx Sq Ft
1,984
Stories
2
Fireplaces
0
Flooring
Carpet, Ceramic, Laminate/LVP
Heating
Cooling
Laundry
Interior Features
N/A
Appliances
Dishwasher, Microwave, Elec Range, Refrigerator
Sale & Tax History
List Price
$455,000
Price / Sq Ft
$229
Annual Taxes
$3,934
Monthly Tax
$328
HOA
None
Tax Rate (effective)
0.86%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | Jun 29, 2026 | $455,000 | — |
| Currently listed | — | $455,000 | — |
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:
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.
About buying in Chesapeake
Homes for sale in Chesapeake, VA appeal to buyers who want suburban space, top-rated schools, and easy access to Virginia Beach and Norfolk. The city's geography splits roughly into five corridors: Greenbrier (23320) with newer construction and shopping near the mall; Great Bridge (23320, 23322) with the historic Battlefield district and excellent schools; Hickory (23322) with large-lot family homes and Hickory High; Western Branch (23321) near the Portsmouth border with mature trees and starter homes; and Deep Creek / South Norfolk (23323, 23324) with affordable inventory and waterfront access. Buyer demand is anchored by Chesapeake Public Schools — among the highest-rated in Hampton Roads — including Hickory High, Grassfield High, Great Bridge High, and Western Branch High. Median home prices range from $300K starter homes in Deep Creek to $600K+ Great Bridge family homes and $1M+ luxury estates in Hickory's gated communities. Chesapeake's commute is excellent for buyers working in Virginia Beach, Norfolk Naval Shipyard, or Newport News Shipbuilding via the I-664 and I-64 corridors. Below you'll find every active Chesapeake MLS listing pulled every 5 minutes from the REIN feed.
Military Commute
Drive times to nearest basesDrive 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.
Estimate your monthly payment
$2,821/moPrincipal & interest
$2,361
Property tax
$328
Home insurance
$133
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.
Listed by 1st Class Real Estate Integrity · MLS# 10641959
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$455,000
744 Helmsdale WAY, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
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