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ChesapeakeWILSON HEIGHTS208 Old Dr✓ Source: REIN MLS #10628054 · record updated Jul 1, 2026 · synced every 2 min · your inquiry is never resold
208 Old DR, CHESAPEAKE VA 23322 - Main photo
$459,999
$287 / sqft · est. $2,793/mo →
3beds
3baths
1,600sqft
90days on market

208 Old Dr, Chesapeake, VA 23322

SoldResidential · built 1961 · WILSON HEIGHTS

About this home

The listing, in the seller's words

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 for entertaining, pets, or enjoying outdoor living. Conveniently located near shopping, dining, and top-rated schools, this home combines quality updates with an unbeatable location. A must-see!

Listing courtesy of Jennifer Smithson · Light Box Realty · REIN MLS #10628054

VaHome team overview

Our read on this home

At a glance

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.

Read the full overview ↓

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.

More buyer 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.

Schools

Info provided by GreatSchools

Facts & features

The record, sourced

Type

Residential

Year built

1961

Price / sqft

$287

HOA

None

Taxes

$3,261/yr

County

Chesapeake VA

Waterfront

Yes

MLS #

10628054

Interior

Bedrooms
3
Full baths
3
Approx. sqft
1,600
Stories
1
Flooring
Carpet, Laminate/LVP
Ensuite bedrooms
2
First-floor bed & full bath
Yes
Total rooms
6
Other rooms
1st Floor BR, 1st Floor Primary BR, Attic, PBR with Bath, Utility Room
Appliances
Dishwasher, Dryer Hookup, Microwave, Elec Range, Refrigerator, Washer Hookup
Accessibility
Main Floor Laundry

Construction & exterior

Style
Ranch
Subtype
Detached
Foundation
Crawl
Roof
Asphalt Shingle
Exterior
Brick
Pool
No Pool
Fencing
Back Fenced
Waterfront
Not Waterfront

Utilities & systems

Heating
Heat Pump
Cooling
Central Air
Water heater
Electric
Water
City/County
Sewer
City/County

Lot, parking & ownership

Lot size
0.4000
Subdivision
WILSON HEIGHTS
Ownership
Fee Simple
Garage
Yes
Parking
Converted Gar, Multi Car, Driveway Spc
Possession
CLOSE
Miscellaneous
Rehabilitated
Disclosures
Disclosure Statement

Sources: REIN MLS record · city assessor · null fields are suppressed, never faked

Flood & environment

FEMA flood zone X · outside the high-risk area · FIRM 510034

Flood Risk

Looking up FEMA flood zone…

Hurricane Evacuation Zone

Evacuation Zone B

Source: Virginia Dept. of Emergency Management — Know Your Zone

Explore this neighborhood

Harbor Watch

Harbor Watch is a waterfront condominium community in the Great Bridge area of southern Chesapeake (ZIP 23320), set along the Atlantic Intracoastal Waterway near the southern branch of the Elizabeth River.

5

For sale now

$101K

HH income

52.4%

Owner-occupied

U.S. Census ACS 2024 5-year

Explore Harbor Watch
Map of Harbor Watch with neighborhood boundaryNeighborhood

Chesapeake real estate

Location intelligence

Minutes to real places, not a score

Location & Neighborhood

Places within ~1 mile, ordered by distance from this property. Powered by Google Places.

Military Commute

Drive times to nearest bases

Drive 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.

The numbers

Run the real carrying cost

Estimates only — taxes come from the public record; confirm rates with your lender. VA-eligible buyers: $0-down financing may apply.

Estimate your monthly payment

$2,793/mo

Principal & 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.

Value & history

Why the land carries the value

Asking vs. assessment

142% of $322,900

City assessment record · taxes $3,261/yr

Land share of assessed value

59% — $190,000

Improvements $132,900 · assessor record ✓

Why we show no algorithmic estimate.

National AVMs misprice homes whose value drivers they can't see. Instead: the sourced assessment above, the carrying cost, real price history, and honest comparables below.

Price context — similar nearby homes

$295,000$480,000

The 6 most similar homes nearby (same city, within ~20% of this size, ~2.5 mi; 6 sold). Context for judging the asking price — not an appraisal or an estimate of this home's value.

253 N Hill LN · 1.3 mi · 1,600 sqft$299,900 sold 2026-07
125 Millwood AVE · 1.2 mi · 1,742 sqft$452,555 sold 2026-06
500 Greenway DR · 1.3 mi · 1,444 sqft$359,900 sold 2026-05

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)

EventDatePriceDetail
ListedApr 2, 2026$459,999
SoldJul 1, 2026$459,999

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

42% above assessment

Total Assessed

$322,900

Land

$190,000

Improvement

$132,900

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:

Chesapeake Real Estate Assessor

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.

Questions buyers ask

Real questions, answered from the record

Is 208 Old Dr in a good school zone?+
The assigned zones on the listing record are Great Bridge Primary, Great Bridge Middle (GreatSchools 7/10), Great Bridge (GreatSchools 7/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 208 Old Dr in a flood zone?+
FEMA maps this parcel in Zone X, outside the high-risk Special Flood Hazard Area. See the flood section on this page for details and sources.
Is there a gym near 208 Old Dr?+
Yes — RISE Personal Training is about 0.2 miles away, per the cached nearby-places record for this address.
Are there parks near 208 Old Dr?+
Judge Eileen Olds Courtyard Park is about 0.4 miles away.
Where is the nearest grocery store to 208 Old Dr?+
Kroger Bakery is about 0.4 miles away. The closest dining on record is Mister Jim's (0.3 mi).
Does 208 Old Dr have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 208 Old Dr built?+
It was built in 1961, per the listing record.

Answers generated from the listing record, verified school zones, FEMA data, and cached nearby-places data — never invented.

The people

You'll talk to a person, not a lead queue

TD

Tom & Dariya Milan

LPT Realty · Hampton Roads · answer their own phone

✓ Your inquiry goes to Tom & Dariya — never sold to strangers

Listing courtesy of Jennifer Smithson · Light Box Realty · REIN MLS #10628054

Call or text (757) 777-7577

Ask Dariya — instant answers

Schools, flood, drive times, what it really costs to own — answered from this page's data, by chat or voice.

This home has sold

Curious what it means for your own plans? Ask about similar homes nearby, or what your home might sell for in this market.

208 Old Dr, Chesapeake — photo

This one's sold — the next one doesn't have to be.

208 Old Dr, Chesapeake, Virginia 23322 · MLS #10628054 · Source: REIN MLS + public record. Information deemed reliable but not guaranteed — verify independently. School zones subject to change; confirm with the local school division. All locations are described by neutral geographic fact. Equal Housing Opportunity.