For sale

$425,000

744 Helmsdale Way, Chesapeake, VA 23320

4beds

1,984sqft

$2,877/mo

Get pre-qualified

Single Family Residence

Built in 1984

0.29 Acres Lot

$425,900 Zestimate^®

$214/sqft

$-- HOA

What's special

Cozy fireplaceFully fenced backyardAttached garageBright breakfast areaSpacious two-story layout

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!

21 days
1,133
147

Likely to sell faster than

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 4
Bathrooms: 3
Full bathrooms: 2
1/2 bathrooms: 1

Rooms

Room types: Attic, Breakfast Area, Fin. Rm Over Gar, PBR with Bath, Utility Closet

Heating

Heat Pump

Cooling

Central Air

Appliances

Included: Dishwasher, Microwave, Electric Range, Refrigerator, Electric Water Heater

Features

Walk-In Closet(s), Ceiling Fan(s), Entrance Foyer
Flooring: Carpet, Ceramic Tile, Laminate/LVP
Attic: Scuttle,Walk-In
Number of fireplaces: 1
Fireplace features: Wood Burning
Common walls with other units/homes: No Common Walls

Interior area

Total interior livable area: 1,984 sqft

Video & virtual tour

View virtual tour

Property

Parking

Total spaces: 1
Parking features: Garage Att 1 Car, 4 Space
Attached garage spaces: 1

Features

Levels: Two
Stories: 2
Patio & porch: Deck, Porch
Pool features: None
Has spa: Yes
Spa features: Bath
Fencing: Back Yard,Full,Wood,Fenced
Waterfront features: Not Waterfront

Lot

Size: 0.29 Acres

Details

Parcel number: 0368001000230

Construction

Type & style

Home type: SingleFamily
Architectural style: Traditional
Property subtype: Single Family Residence

Materials

Vinyl Siding
Foundation: Slab
Roof: Asphalt Shingle

Condition

New construction: No
Year built: 1984

Utilities & green energy

Sewer: City/County
Water: City/County
Utilities for property: Cable Hookup

Community & HOA

Community

Subdivision: Glenleigh

HOA

Has HOA: No

Location

Region: Chesapeake

Financial & listing details

Price per square foot: $214/sqft
Tax assessed value: $389,500
Annual tax amount: $3,934
Date on market: 9/18/2026

Estimated market value

$425,900

$405,000 - $447,000

$2,739/mo

Price history

Price history is unavailable.

Public tax history

Year	Property taxes	Tax assessment
2025	$3,934 +2.1%	$389,500 +2.1%
2024	$3,853 +3.9%	$381,500 +3.9%
2023	$3,709 +4.4%	$367,200 +8.5%
2022	$3,552 +15.9%	$338,300 +15.9%
2021	$3,065	$291,900 +7.1%
2020	--	$272,600 +4.5%
2019	$2,738 +3.3%	$260,800 +3.3%
2018	$2,650 +3.1%	$252,400 +3.1%
2017	$2,571 +3.1%	$244,900 +3.1%
2016	$2,494	$237,500
2015	$2,494	$237,500
2014	$2,494 +0%	$237,500
2013	$2,494	$237,500
2012	$2,494 -5.6%	$237,500 -5.6%
2011	$2,641 -2.7%	$251,500 -2.7%
2010	$2,715 -5%	$258,600 -5%
2009	$2,858 -1.3%	$272,200 -1.3%
2008	$2,896 -0.4%	$275,800 +0.6%
2007	$2,907 +3%	$274,200 +7.9%
2006	$2,822 +36.2%	$254,200 +57.1%
2004	$2,071 +15.7%	$161,800 +15.7%
2003	$1,789 +6%	$139,800 +6%
2002	$1,688 +3.4%	$131,900 +3.4%
2001	$1,633	$127,600