82 days on market
$459,999
208 Old Dr
Chesapeake, Virginia 23322
MLS# 10628054 · WILSON HEIGHTS · Chesapeake VA
Updated 5 days ago · Source: REIN MLS
Est. payment
$2,793/mo
Edit below
Price / sq ft
$287
1,600 sq ft
Days on market
82
HOA
None
Year built
1961
65 yrs old
Beds
3
Full Baths
3
Half Baths
0
Sq Ft
1,600
Garage
Yes
About this home
Beautifully updated ranch home located in the heart of Great Bridge! This 3-bedroom, 3-full-bath home has been completely refreshed with a brand-new roof, new windows, fresh paint, and new LVP flooring and carpet throughout. The updated kitchen features new appliances and modern finishes, making it move-in ready from day one. Situated on a spacious .40-acre lot, the home offers a huge, fully fenced backyard—perfect f…
Listed by Jennifer Smithson · Light Box Realty
VaHome Team property overview
208 Old Drive is a three-bedroom, three-bath ranch-style home on a generous 0.4-acre lot in Chesapeake's Wilson Heights neighborhood. Built in 1961, it offers 1,600 square feet of single-level living with the kind of established lot space that newer subdivisions rarely deliver.
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Why this home stands out
What sets 208 Old Drive apart is that lot. Nearly half an acre in an established neighborhood means real yard space — room for a garden, a fire pit, a playset, or simply room to breathe. The three full bathrooms across 1,600 square feet is a configuration that's genuinely uncommon in homes of this era and size, and it makes daily routines dramatically smoother for anyone sharing the house.
WILSON HEIGHTS and the Chesapeake real estate market
Wilson Heights sits in the southern reaches of Chesapeake, a city that consistently ranks among the safest and most livable in Virginia. The neighborhood has the settled, unhurried character that comes from decades of owner-occupied homes on generous lots — mature trees, quiet streets, and neighbors who tend to stay a while. It's not a flashy new development; it's the kind of place where the landscaping has had time to grow in and the streets feel genuinely lived-in. Chesapeake itself gives you access to excellent parks, a strong local dining scene, and easy connections to the rest of Hampton Roads without the congestion of the more urban cores. The Great Dismal Swamp National Wildlife Refuge is practically in the backyard of the broader city, and the Chesapeake Expressway puts the Outer Banks within a reasonable drive. For everyday life, South Chesapeake blends suburban calm with solid infrastructure — a combination that's harder to find than it sounds.
What's nearby
Daily errands are straightforward from 208 Old Drive. Grocery options including Harris Teeter and Food Lion are within a short drive, and the Battlefield Boulevard corridor puts pharmacies, coffee shops, and casual dining well within reach. Chesapeake City Park offers trails, athletic fields, and open green space just a few minutes away. For dining, the South Chesapeake area has a solid mix of local spots and familiar chains along the Greenbrier and Great Bridge corridors. Interstate 64 and Route 168 are both accessible without a complicated commute, connecting you to Virginia Beach, Norfolk, and points north.
For different buyers
For military families relocating
The USCG Finance Center Chesapeake is roughly six minutes away — a commute that's genuinely rare to find paired with a home this size on this much land. Norfolk Naval Shipyard is about 17 minutes out. If you're using a VA loan, the combination of an established neighborhood, three full baths, and a large lot makes 208 Old Drive a practical fit for a military household at nearly any stage.
For families upgrading
Three full bathrooms in a 1,600-square-foot home means no one is waiting in line on a school morning. The 0.4-acre lot gives kids actual outdoor space — not a postage-stamp backyard, but room to run. Wilson Heights has the quiet, stable feel that families tend to gravitate toward, and the single-level layout makes the home accessible for everyone from toddlers to grandparents visiting for the holidays.
Frequently asked questions
How far is 208 Old Drive from Norfolk Naval Shipyard?
Norfolk Naval Shipyard is approximately 17 minutes from 208 Old Drive under normal traffic conditions, making it a workable daily commute from South Chesapeake.
How far is 208 Old Drive from the USCG Finance Center Chesapeake?
The USCG Finance Center Chesapeake is about six minutes away — one of the shortest base commutes you'll find attached to a home with this much lot space in the area.
What is the lot size at 208 Old Drive?
The lot measures 0.4 acres, which is notably generous for an established neighborhood in South Chesapeake and provides significant usable outdoor space.
Is 208 Old Drive in a flood zone?
Flood zone information for this address is detailed in the FloodRisk tile on this page, which pulls current FEMA map data for the specific parcel.
What architectural style is 208 Old Drive?
The home is a ranch-style single-family residence built in 1961, a construction era known for solid masonry foundations, straightforward floor plans, and single-level layouts that age well with minimal structural complexity.
Tom and Dariya Milan at LPT Realty know Wilson Heights and South Chesapeake well. Reach out to get a straight answer on whether 208 Old Drive fits where you're headed.
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
3
Full Baths
3
Half Baths
0
Approx Sq Ft
1,600
Stories
1
Fireplaces
0
Flooring
Carpet, Laminate/LVP
Heating
Cooling
Laundry
Interior Features
N/A
Appliances
Dishwasher, Dryer Hookup, Microwave, Elec Range, Refrigerator, Washer Hookup
Sale & Tax History
List Price
$459,999
Price / Sq Ft
$287
Annual Taxes
$3,261
Monthly Tax
$272
HOA
None
Tax Rate (effective)
0.71%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | Apr 2, 2026 | $459,999 | — |
| Currently listed | — | $459,999 | — |
Public-Records Assessment
Source: City Assessor via Hampton Roads Regional Parcels. Fetched Jun 23, 2026.
Total Assessed
$322,900
Land
$190,000
Improvement
$132,900
Parcel ID: 0481008000150
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
$2,793/moPrincipal & interest
$2,387
Property tax
$272
Home insurance
$134
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 Light Box Realty · MLS# 10628054
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$459,999
208 Old DR, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
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