0 days on market
$499,700
1254 Winfall Dr
Chesapeake, Virginia 23323
MLS# 10641441 · ALBEMARLE ACRES · Chesapeake VA
Updated 3 days ago · Source: REIN MLS
Est. payment
$3,167/mo
Edit below
Price / sq ft
$167
3,000 sq ft
Days on market
0
New listing
HOA
None
Year built
1986
40 yrs old
Beds
4
Full Baths
2
Half Baths
1
Sq Ft
3,000
Garage
Yes
Schools
- ElementaryButts Road Primary—
- MiddleHickory Middle School7/10
- 9/10
Info provided by GreatSchools
About this home
Easy Fixer Upper. GREAT NEIGHBORHOOD and Great House/Bones. Priced well below market value! **Selling As-Is. No Contingencies. Cash Preferred. **Perfect for Handyman, Investor or Landlord.
Listed by Tierra Walker-Holloway · Walker One Property Group LLC
VaHome Team property overview
A four-bedroom, 1986-built home in Chesapeake offering 3,000 square feet of living space, two and a half baths, and a location that puts you within eight minutes of USCG Finance Center and a short drive from the broader Hampton Roads corridor.
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Why this home stands out
Three thousand square feet built in 1986 means you get the generous room proportions that era was known for — wide living areas, a proper dining room, and bedrooms that actually fit furniture. The half-bath on the main level is a quiet convenience that smaller homes skip entirely. Chesapeake's western zip gives you space, lower density, and real lot size without sacrificing access to the region's employment hubs.
ALBEMARLE ACRES and the Chesapeake real estate market
Winfall Drive sits in the western reaches of Chesapeake, Virginia — a city that consistently ranks among the largest by land area on the East Coast and carries a reputation for quieter, more spread-out living compared to its neighbors across the city lines. The 23323 zip code is a workhorse part of Chesapeake: established, tree-lined, and populated by families who value elbow room and a slower residential pace. Streets here tend to be wide, lots tend to be generous, and the overall feel leans suburban without the cookie-cutter sameness of newer master-planned communities. Chesapeake as a whole offers a rare combination — genuine city infrastructure and services wrapped around neighborhoods that still feel like neighborhoods. You're connected to the broader Hampton Roads metro without being swallowed by it. Western Chesapeake also benefits from proximity to the Great Dismal Swamp National Wildlife Refuge, which keeps a natural buffer to the south and west and gives the area a greener, more open character than you'd find closer to the coast.
What's nearby
Daily life is well-supported from Winfall Drive. Grocery runs, pharmacy stops, and big-box errands are all within a short drive along the Battlefield Boulevard and Western Branch corridors. The Great Dismal Swamp National Wildlife Refuge is practically a backyard amenity — miles of hiking and paddling trails just a few minutes south. Western Branch area parks offer ball fields, walking paths, and open green space for weekend use. Commuters heading toward Norfolk Naval Shipyard in Portsmouth can typically make the trip in around twenty minutes depending on the route, keeping that major employment center well within range.
For different buyers
For military families relocating
USCG Finance Center Chesapeake is roughly eight minutes away — a genuinely short commute by Hampton Roads standards. Norfolk Naval Shipyard in Portsmouth is about twenty minutes out, making this address workable for dual-military households or those expecting future orders to either installation. A VA loan can make financing a home this size more accessible than many buyers expect, and the square footage gives you room to grow through multiple duty station cycles.
For families upgrading
Four bedrooms and 3,000 square feet give a growing family real breathing room — dedicated space for a home office, a guest room, or a playroom without anyone feeling squeezed. The half-bath on the main level means morning routines don't bottleneck upstairs. Western Chesapeake's established neighborhoods tend to attract long-term residents, which translates to stable, community-oriented streets where kids can actually play outside.
Frequently asked questions
How far is 1254 Winfall DR from USCG Finance Center Chesapeake?
The drive is approximately eight minutes under normal traffic conditions, making it one of the closer residential options to that installation in the area.
How far is 1254 Winfall DR from Norfolk Naval Shipyard?
Norfolk Naval Shipyard in Portsmouth is roughly twenty minutes from Winfall Drive, a manageable daily commute for most schedules.
What is the lot and neighborhood character like on Winfall DR?
Western Chesapeake's 23323 zip tends toward established, tree-lined residential streets with generous lot sizes and a lower-density feel compared to more urban parts of Hampton Roads.
Is 1254 Winfall DR in a flood zone?
Flood zone status for this address is detailed in the FloodRisk tile on this page — check that section for the current FEMA designation and what it means practically for insurance.
Does 1254 Winfall DR have an HOA?
HOA status for this address should be confirmed through current disclosure documents; if an HOA applies, the governing documents will outline any community rules and shared amenity details.
Tom and Dariya Milan at LPT Realty know western Chesapeake well — reach out to get your questions answered and arrange a closer look at 1254 Winfall Drive.
Summary generated by AI from public records and publicly available information.
Location & Neighborhood
Places within ~1 mile, ordered by distance from this property. Powered by Google Places.
Flood Risk
Property Details
Bedrooms
4
Full Baths
2
Half Baths
1
Approx Sq Ft
3,000
Stories
2
Fireplaces
0
Flooring
Carpet, Vinyl, Wood
Heating
Cooling
Laundry
Interior Features
N/A
Appliances
None
Sale & Tax History
List Price
$499,700
Price / Sq Ft
$167
Annual Taxes
$5,138
Monthly Tax
$428
HOA
None
Tax Rate (effective)
1.03%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | Jun 25, 2026 | $499,700 | — |
| Currently listed | — | $499,700 | — |
Looking for multi-year tax assessments or prior sales? REIN MLS only ships data for the current listing. For full property history, check the city assessor record:
Tax data above from REIN public-records sync. Sale timeline tracked from this listing's first appearance in our feed forward; prior owner sales are not included.
Comparable Properties
Comps are selected by city, bed count, square footage and price proximity. Composite similarity score weights bed match, sqft variance, price variance, and straight-line distance.
About buying in Chesapeake
Homes for sale in Chesapeake, VA appeal to buyers who want suburban space, top-rated schools, and easy access to Virginia Beach and Norfolk. The city's geography splits roughly into five corridors: Greenbrier (23320) with newer construction and shopping near the mall; Great Bridge (23320, 23322) with the historic Battlefield district and excellent schools; Hickory (23322) with large-lot family homes and Hickory High; Western Branch (23321) near the Portsmouth border with mature trees and starter homes; and Deep Creek / South Norfolk (23323, 23324) with affordable inventory and waterfront access. Buyer demand is anchored by Chesapeake Public Schools — among the highest-rated in Hampton Roads — including Hickory High, Grassfield High, Great Bridge High, and Western Branch High. Median home prices range from $300K starter homes in Deep Creek to $600K+ Great Bridge family homes and $1M+ luxury estates in Hickory's gated communities. Chesapeake's commute is excellent for buyers working in Virginia Beach, Norfolk Naval Shipyard, or Newport News Shipbuilding via the I-664 and I-64 corridors. Below you'll find every active Chesapeake MLS listing pulled every 5 minutes from the REIN feed.
Military Commute
Drive times to nearest basesDrive times via Google Maps with current traffic patterns. Times are typical and may vary by time of day. Use the "Analyze" button up top to see live drive time to your saved base.
Estimate your monthly payment
$3,167/moPrincipal & interest
$2,593
Property tax
$428
Home insurance
$146
PMI
None
HOA
None
Estimate only. Insurance assumed at 0.35% of home value annually. Actual taxes, insurance, and rate will vary by lender, credit, and property. Contact a lender for a personalized quote.
Listed by Walker One Property Group LLC · MLS# 10641441
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$499,700
1254 Winfall DR, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
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