Please reload the page to update with the latest MLS information available.

Please reload the page to update with the latest MLS information available.

Please reload the page to update with the latest MLS information available.

Reload
 
Listing provided courtesy of 1st Class Real Estate Integrity- MLS# 10641959MLS Provider

744 Helmsdale WayChesapeake, VA 23320

Single Family · 4 Beds · 2 Full Baths · 1 Half Bath · 1,984 Sq. ft. | 0.29 Acres
$455,000 New Listing

744 Helmsdale Way Overview

Time on Site:
1 day
Visits:
1

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!

Love this property?
Create a profile so you can receive updates on this property as soon as they happen!
View Map

744 Helmsdale Way Facts & Features

  • Type Single Family
  • Sq. ft. 1,984
  • Price/Sq.ft. $229
  • Lot 0.29 Acres

Details

General

Association/HOA

  • Assoc Mgmt Co: n/a
  • Association Fee: $0.00
  • Association Name: n/a
  • Association: No
  • Fees Condo Monthly: 0

School Information

  • Elementary School: B.M. Williams Primary
  • Middle Or Junior School: Crestwood Middle
  • High School: Oscar Smith

Building Information

  • New Construction: No
  • Year Built: 1984

Location/Region

  • County Or Parish: Chesapeake VA
  • MLS Area Major: 32 - South Chesapeake
  • Subdivision Name: GLENLEIGH

Tax Information

  • Tax Annual Amount: $3,934.00

General Information

  • Contingency Exists: Non Contingent
  • Disclosures: Disclosure Statement
  • Ownership: Simple
  • Property Sub Type: Detached
  • Property Type: Residential

Interior

Building Information

  • Equipment: Cable Hookup,Ceiling Fan

Parking Information

  • Garage Square Feet: 264
  • Garage: Yes

Beds/Baths

  • Bathrooms Full: 2
  • Bathrooms Half: 1
  • Bathrooms Total: 2.10
  • Bedrooms Total: 4
  • First Flr Bed Full Bath YN: No
  • Num Beds With Ensuite: 1

Building Interior

  • Water Heater Type: Electric

General Information

  • Appliances: Dishwasher, Microwave, Elec Range, Refrigerator
  • Cooling: Central Air
  • Fireplaces Total: 1
  • Flooring: Carpet, Ceramic, Laminate/LVP
  • Foundation Details: Slab
  • Heating: Heat Pump
  • Interior Features: Fireplace Wood, Scuttle Access
  • Living Area: 1984
  • Rooms: Attic, Breakfast Area, Fin. Rm Over Gar, PBR with Bath
  • Rooms Total: 7
  • Stories Total: 2.0000

Exterior

Parking Information

  • Parking Features: Garage Att 1 Car, 4 Space

Lot Information

  • Lot Size Acres: 0.2930
  • Water Source: City/County

Waterfront/View

  • Waterfront Features: Not Waterfront
  • Waterfront: No

Building Exterior/Construction

  • Architectural Style: Traditional
  • Exterior Siding: Vinyl
  • Fence YN: Yes
  • Roof: Asphalt Shingle

General Information

  • Exterior Features: Deck
  • Fencing: Back Fenced, Full, Wood Fence
  • Pool Features: No Pool
  • Sewer: City/County

Schools

School data courtesy of LiveBy, Inc. School ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating.

744 Helmsdale Way Monthly Cost

$
$ %
%
$
$
* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

744 Helmsdale Way Market Data

Based on the last 30 days in this zip code

$491,000
Average List Price
$201
Average Price per Square Foot
0
Properties Sold
23
Average Days on Market
3
Properties for Sale
Calculations provided by Reliance Network

744 Helmsdale Way History

Date Event Value Agent
6/29/2026Source: REIN MLS Added to Database
June 29, 2026