744 Helmsdale WAY Chesapeake, VA ^$ 425,000

744 Helmsdale WAY

^$ 425,000

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744 Helmsdale WAY

Chesapeake, VA, 23320

^$ 425,000

Bedrooms4 Baths2.1 Sq 1,984

Monthly Estimate*

^$ 2,935

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Single Family Home for sale in Chesapeake, VA

for $425,000 with 4 bedrooms and 2 full baths, 1 half bath. This 1,984 square foot home was built in 1984 on a lot size of 0.29.

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!

Single Family Active

Price

^$ 425,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 3,934

Style

Traditional

Lot Size

0.29

Year Built

1984

Town/City

Chesapeake

County/Region

Chesapeake City

MLS | Web ID

10654335

Features

Interior

Interior Features Fireplace Wood Scuttle Access Walk-In Attic Walk-In Closet

Other Rooms Attic Breakfast Area Fin. Rm Over Gar Foyer PBR with Bath Porch Utility Closet

Fireplaces 1

Equipment Cable Hookup Ceiling Fan Jetted Tub

General

Heating Heat Pump

Water Type City/County

Cooling Central Air

Ownership Type Simple

Waterfront Description Not Waterfront

Roof Asphalt Shingle

Appliances Dishwasher Microwave Elec Range Refrigerator

Unit Description 2 Living Lvl Det Single Fam

Parking Garage Att 1 Car 4 Space

Style Traditional

Property Type Residential

Area 32 - South Chesapeake

Subdivision Name GLENLEIGH

HOA Y/N 0

Sub Type Detached

New Construction Y/N 0

Elementary School B.M. Williams Primary

High School Oscar Smith

Middle School Crestwood Middle

Fees HOA/POA Monthly 0

Fees Condo Monthly 0

Non Non Contingent

Exterior

Waterfront 0

Exterior Features Deck

Siding Vinyl

Fence? 1

Foundation Slab

Pool No Pool

Garage Y/N 1

* Excluded Features

List By

Angela Kennedy

Listing Agent

1St Class Real Estate Integrity

Broker

Affordability Calculator

$3,263

Per Month

Monthly Principal & Interest: $2,935
Monthly Property Taxes: $328
Monthly Home Insurance: --

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Yearly Property Taxes

Yearly Home Insurance

Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends
Schools

Single family listings in Chesapeake, VA

Average List Price ^$563,998

Percent of Sale Price 33%

About Chesapeake, VA

244,523 Population

23% Since 2002

^$70,156 Median Income

38.59 Median Age

33% Households with Children

View more area information

Trends Information provided by ATTOM Data Solutions.

239731 Elementary School

239827 Middle School

Oscar Smith High School High School

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744 Helmsdale WAY, Chesapeake, VA, 23320 is a Single Family Home for sale at $425,000 with 1,984 sqft and a lot size of 0.29. 744 Helmsdale WAY has 4 bedrooms, 2.1 baths, and was built in 1984. The property's zip code is 23320 which is in Chesapeake, VA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

The listings data displayed on this medium comes in part from the Real Estate Information Network, Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.

©2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.

Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.

This application does not include information on all of the properties available for sale at this time.

REIN updates its listings on a daily basis. Data last updated 10/18/2026.

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744 Helmsdale WAY

Single Family Home for sale in Chesapeake, VA

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