# 744 Helmsdale Way, Chesapeake, VA 23320

> **TL;DR:** 4bd/3ba single family, $425,000 ($214/sqft), built 1984, 1,984 sqft.
> Fireplace, A/C. Est. $2,273/mo. Listed 44 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $425,000 |
| Price/sqft | $214 |
| Bedrooms | 4 |
| Bathrooms | 2 full, 1 half |
| Square Feet | 1,984 |
| Year Built | 1984 |
| Lot Size | 12,632 sqft (0.29 acres) |
| Property Type | Single Family (Other) |
| Status | Active |
| Days on Market | 44 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $2,149 |
| Estimated Insurance | $124 |
| **Total** | **$2,273** |

## Nearby Schools

- **Elementary:** B.M. Williams Primary
- **Middle:** Crestwood Middle

## Key Amenities

- Fireplace
- A/C

## Property Highlights

- Built in 1984
- 0.29 acre lot
- Fireplace

## Description

### Agent Description
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!

## Location

- **Address:** 744 Helmsdale Way, Chesapeake, VA 23320
- **County:** Chesapeake VA
- **Neighborhood:** GLENLEIGH
- **Coordinates:** 36.750955, -76.26305
- **Google Maps:** https://www.google.com/maps?q=36.750955,-76.26305

## Virtual Tour & Media

- **Video Tour:** https://tours.americanrealestatemedia.com/744_helmsdale_way-4895?branding=false

## Listing Agent

- **Name:** Angela Kennedy
- **Brokerage:** 1st Class Real Estate Integrity
- **Broker Phone:** (757) 431-7521
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/744-Helmsdale-Way_Chesapeake_VA_23320_M68949-26774?f=listhub&s=REINVA&m=10654335&c=propsimple)

## Photos

![744 Helmsdale Way - Photo 1](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f451475889r.jpg)

![744 Helmsdale Way - Photo 2](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f3642462257r.jpg)

![744 Helmsdale Way - Photo 3](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f1279588522r.jpg)

![744 Helmsdale Way - Photo 4](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f2838850179r.jpg)

![744 Helmsdale Way - Photo 5](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f212083275r.jpg)

![744 Helmsdale Way - Photo 6](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f2694253063r.jpg)

![744 Helmsdale Way - Photo 7](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f3282116059r.jpg)

![744 Helmsdale Way - Photo 8](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f4192252790r.jpg)

![744 Helmsdale Way - Photo 9](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f3927232253r.jpg)

![744 Helmsdale Way - Photo 10](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f3585578334r.jpg)

![744 Helmsdale Way - Photo 11](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f453538750r.jpg)

![744 Helmsdale Way - Photo 12](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f2992430017r.jpg)

![744 Helmsdale Way - Photo 13](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f1609567847r.jpg)

![744 Helmsdale Way - Photo 14](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f3236759452r.jpg)

![744 Helmsdale Way - Photo 15](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f2147647026r.jpg)

![744 Helmsdale Way - Photo 16](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f3321534749r.jpg)

![744 Helmsdale Way - Photo 17](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f104126110r.jpg)

![744 Helmsdale Way - Photo 18](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f2345138630r.jpg)

![744 Helmsdale Way - Photo 19](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f3261531444r.jpg)

![744 Helmsdale Way - Photo 20](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f1036452079r.jpg)

![744 Helmsdale Way - Photo 21](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f4159684002r.jpg)

![744 Helmsdale Way - Photo 22](http://lh.rdcpix.com/5db5b1235fb32bd2fc61b138ce78225al-f3665283782r.jpg)

---

**MLS#:** 10654335 | **Updated:** 2026-10-29
**Source:** listhub

*Copyright © 2026 Real Estate Information Network, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.ai/listing/744-helmsdale-way-chesapeake-va-23320-38393ea44e394f16887bff29ebf3bc86)

---

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