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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!

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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

Find, Buy & Move into Your Home with Us.

Instead of having a mortgage team here, an insurance agent there, a REALTOR® down the street, an inspector and a moving company across town, you have one team with one goal and one focus: you. Ask for “All-Inclusive” Buying.

Enjoy the sense of confidence knowing your Long & Foster full team can handle it all. Your agent is supported by a team of specialists in Mortgage, Insurance, Title, Inspection, Moving and Property Management who are there to guide you every step of the way. They’ll make sure things run smoothly, closing happens on time, and you arrive at your dream home according to plan.

Accolades:
98 %
Customer
Satisfaction
4.8

311 Reviews
Top Services:
  • Buying
  • Selling
  • Rental Properties
  • Investment Properties
  • Luxury Properties
Key Advantages:
  • Be your guide with expert knowledge of your area
  • Help find your home and offer objective information and opinions
  • Stand in your corner during negotiations
  • Assist with paperwork and details to get you to closing
  • Connect you to vendors if work is needed

Our mortgage affiliate, Prosperity Home Mortgage, will get you approved for a mortgage before shopping for a home. This will make your offer stand out and give you an edge in a highly competitive market. If you are already pre-approved, no problem, we can take a “second look” and try to get you even better terms.

Accolades:
97 %
Customer
Satisfaction
5.0

3,803 Reviews
Top Services:
  • Fixed & adjustable rate mortgages
  • FHA and VA mortgage programs
  • Rapid Close™
  • USDA Loans
Key Advantages:
  • Full suite of mortgage programs to meet your specific needs
  • Friendly professionals guide through every step of the loan process
  • We help you find and lock in on the market’s best interest rate
  • We work closely with your title company to ensure accurate closing

We help you make good decisions when you’re buying a home and learn how to be a better homeowner after you move-in. We streamline your inspection journey, provide thorough and accurate results, and get you to closing peacefully. Schedule a confirmed inspection online 24x7.

Accolades:
97 %
Customer
Satisfaction
5.0

240 Reviews
Top Services:
  • Home Inspection
  • Radon Gas
  • Termite Inspection
  • Test Indoor Air Quality
  • Pay at Closing*
Key Advantages:
  • Scheduling online 24x7 confirm a convenient date & time for you & your agents
  • High-tech journey makes it easy to sign agreement, make payment, view reports
  • One stop shop for home, radon & termite
  • Knowledgeable, friendly inspectors teach you about your home and property
  • Custom homeowner’s manual teaches you how to maintain your home

* A Long & Foster exclusive benefit. If you work with RGS Title or Sage Title Group and Insight Inspections, your can enjoy a $55 discount and the flexibility to pay for the inspection at settlement. This new approach combines the best of both the title and inspection worlds, creating a seamless and integrated journey.

We carefully examine your new home’s title, get your legal documents in order, and safeguard your investment. With a team of specialists who expect the unexpected, you can anticipate an on-time, worry-free closing.

Accolades:
97 %
Customer
Satisfaction
4.9

Reviews
Top Services:
  • Title Search & Status
  • Title Insurance
  • Document Prep
  • Closing Coordination
  • Filing & Recording
Key Advantages:
  • Ensure that there are no unresolved claims or liens on your home’s title
  • Help secure insurance against unexpected title challenges
  • Prepare closing paperwork to ensure documents are in compliance with laws
  • Coordinate with all parties to schedule final closing
  • File & record your paperwork with the courthouse

We help you secure the proper coverage at a competitive price to protect your largest investment — your home. Our insurance agents work closely with you to understand your risk exposures, educate you on your options, protect you from the unexpected, and develop insurance strategies to offer ongoing service to address your ever-changing insurance needs.

Accolades:
98 %
Customer
Satisfaction
4.9

77 Reviews
Top Services:
  • Home Insurance
  • Auto Insurance
  • Umbrella Insurance
  • Motorcycle, Boat, RV and more
Key Advantages:
  • Specialize in real estate and bundle other policies for savings
  • Work with 10+ leading carriers to secure the best coverage at the best cost
  • Save you time by shopping for you
  • We’re independent - we find and present you with the best offers and let you decide
  • Guide you with ongoing service and support

We ensure a smooth, stress-free move so you can start enjoying your new home as soon as you move in. Whether you’re headed down the street or across the country, our moving specialists will make sure you don’t have to lift a finger.

Accolades:
98 %
Customer
Satisfaction
4.6

953 Reviews
Top Services:
  • Packing & Unpacking
  • Decluttering
  • Storage
  • Local or Long Distance
  • International Moving
Key Advantages:
  • 30-minute guided virtual survey with next business day Guaranteed quote
  • Best Price Guarantee*†
  • 2-months free storage*‡
  • $20,000 full value protection*
  • Personal move concierge - from first call until last box is delivered

* Long & Foster Customers Only. † Examples of qualified movers: any major van line (United, Mayflower, Atlas, North American, etc) for local: JK, Hilldrup, Town and Country, Able, Interstate, All my Sons, Olympia, Gentle Giant. ‡ 2 Months Free Storage Program: If you’re moving from DE, MD, DC or VA and to DE, MD, DC or VA, we offer 2 months of free storage for all of the contents of your home. There is no charge for the storage of the items for 2 months. There is a cost for pickup of the items to go to storage and for delivery of items from storage to the new home.

We are the next generation of property management. With our streamlined processes, best-in-class service, and transparent financial updates, we help investors achieve financial success through real estate.

Accolades:
98 %
Customer
Satisfaction
4.8

120 Reviews
Top Services:
  • Property Surveys
  • Marketing
  • Tenant Screening
  • Maintenance
  • Lease Enforcement
Key Advantages:
  • We’ll guide and help identify the right properties to invest in
  • Use of smart devices, predictive data and analytics to help maintain properties
  • Get more free time when we handle billing and payments
  • We continuously monitor state and federal landlord/tenant laws
  • Become more knowledgeable with quarterly portfolio reviews & guidance

  • Enjoy the sense of confidence knowing your Long & Foster full team can handle it all. Your agent is supported by a team of specialists in Mortgage, Insurance, Title, Inspection, Moving and Property Management who are there to guide you every step of the way. They’ll make sure things run smoothly, closing happens on time, and you arrive at your dream home according to plan.

    Accolades:
    98 %
    Customer
    Satisfaction
    4.8

    311 Reviews
    Top Services:
    • Buying
    • Selling
    • Rental Properties
    • Investment Properties
    • Luxury Properties
    Key Advantages:
    • Be your guide with expert knowledge of your area
    • Help find your home and offer objective information and opinions
    • Stand in your corner during negotiations
    • Assist with paperwork and details to get you to closing
    • Connect you to vendors if work is needed

  • Our mortgage affiliate, Prosperity Home Mortgage, will get you approved for a mortgage before shopping for a home. This will make your offer stand out and give you an edge in a highly competitive market. If you are already pre-approved, no problem, we can take a “second look” and try to get you even better terms.

    Accolades:
    97 %
    Customer
    Satisfaction
    5.0

    3,803 Reviews
    Top Services:
    • Fixed & adjustable rate mortgages
    • FHA and VA mortgage programs
    • Rapid Close™
    • USDA Loans
    Key Advantages:
    • Full suite of mortgage programs to meet your specific needs
    • Friendly professionals guide through every step of the loan process
    • We help you find and lock in on the market’s best interest rate
    • We work closely with your title company to ensure accurate closing

  • We carefully examine your new home’s title, get your legal documents in order, and safeguard your investment. With a team of specialists who expect the unexpected, you can anticipate an on-time, worry-free closing.

    Accolades:
    97 %
    Customer
    Satisfaction
    4.9

    Reviews
    Top Services:
    • Title Search & Status
    • Title Insurance
    • Document Prep
    • Closing Coordination
    • Filing & Recording
    Key Advantages:
    • Ensure that there are no unresolved claims or liens on your home’s title
    • Help secure insurance against unexpected title challenges
    • Prepare closing paperwork to ensure documents are in compliance with laws
    • Coordinate with all parties to schedule final closing
    • File & record your paperwork with the courthouse

  • We help you secure the proper coverage at a competitive price to protect your largest investment — your home. Our insurance agents work closely with you to understand your risk exposures, educate you on your options, protect you from the unexpected, and develop insurance strategies to offer ongoing service to address your ever-changing insurance needs.

    Accolades:
    98 %
    Customer
    Satisfaction
    4.9

    77 Reviews
    Top Services:
    • Home Insurance
    • Auto Insurance
    • Umbrella Insurance
    • Motorcycle, Boat, RV and more
    Key Advantages:
    • Specialize in real estate and bundle other policies for savings
    • Work with 10+ leading carriers to secure the best coverage at the best cost
    • Save you time by shopping for you
    • We’re independent - we find and present you with the best offers and let you decide
    • Guide you with ongoing service and support

  • We help you make good decisions when you’re buying a home and learn how to be a better homeowner after you move-in. We streamline your inspection journey, provide thorough and accurate results, and get you to closing peacefully. Schedule a confirmed inspection online 24x7.

    Accolades:
    97 %
    Customer
    Satisfaction
    5.0

    240 Reviews
    Top Services:
    • Home Inspection
    • Radon Gas
    • Termite Inspection
    • Test Indoor Air Quality
    • Pay at Closing*
    Key Advantages:
    • Scheduling online 24x7 confirm a convenient date & time for you & your agents
    • High-tech journey makes it easy to sign agreement, make payment, view reports
    • One stop shop for home, radon & termite
    • Knowledgeable, friendly inspectors teach you about your home and property
    • Custom homeowner’s manual teaches you how to maintain your home

    * A Long & Foster exclusive benefit. If you work with RGS Title or Sage Title Group and Insight Inspections, your can enjoy a $55 discount and the flexibility to pay for the inspection at settlement. This new approach combines the best of both the title and inspection worlds, creating a seamless and integrated journey.

  • We ensure a smooth, stress-free move so you can start enjoying your new home as soon as you move in. Whether you’re headed down the street or across the country, our moving specialists will make sure you don’t have to lift a finger.

    Accolades:
    98 %
    Customer
    Satisfaction
    4.6

    953 Reviews
    Top Services:
    • Packing & Unpacking
    • Decluttering
    • Storage
    • Local or Long Distance
    • International Moving
    Key Advantages:
    • 30-minute guided virtual survey with next business day Guaranteed quote
    • Best Price Guarantee*†
    • 2-months free storage*‡
    • $20,000 full value protection*
    • Personal move concierge - from first call until last box is delivered

    * Long & Foster Customers Only. † Examples of qualified movers: any major van line (United, Mayflower, Atlas, North American, etc) for local: JK, Hilldrup, Town and Country, Able, Interstate, All my Sons, Olympia, Gentle Giant. ‡ 2 Months Free Storage Program: If you’re moving from DE, MD, DC or VA and to DE, MD, DC or VA, we offer 2 months of free storage for all of the contents of your home. There is no charge for the storage of the items for 2 months. There is a cost for pickup of the items to go to storage and for delivery of items from storage to the new home.

  • We are the next generation of property management. With our streamlined processes, best-in-class service, and transparent financial updates, we help investors achieve financial success through real estate.

    Accolades:
    98 %
    Customer
    Satisfaction
    4.8

    120 Reviews
    Top Services:
    • Property Surveys
    • Marketing
    • Tenant Screening
    • Maintenance
    • Lease Enforcement
    Key Advantages:
    • We’ll guide and help identify the right properties to invest in
    • Use of smart devices, predictive data and analytics to help maintain properties
    • Get more free time when we handle billing and payments
    • We continuously monitor state and federal landlord/tenant laws
    • Become more knowledgeable with quarterly portfolio reviews & guidance

744 Helmsdale Way Neighborhood

Community

23320 (CHESAPEAKE) Demographics

37
Median Age
1,757
Population Density (per sq. mile)
48%
College Educated
$75,816
Estimated Median Income
14,557
Estimated Total Home Owners
8,898
Estimated Total Renters
62% / 38%
Estimated Owner / Renter Divide
3
Estimated Average Household Size
Community data courtesy of LiveBy, Inc.

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