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Carrollton › CANNON ACRES › 108 Gregory Dr✓ Source: REIN MLS #10648466 · record updated Aug 24, 2026 · synced every 2 min · your inquiry is never resold
108 Gregory DR, CARROLLTON VA 23314 - Main photo
108 Gregory DR, CARROLLTON VA 23314 - Photo 2
108 Gregory DR, CARROLLTON VA 23314 - Photo 3
108 Gregory DR, CARROLLTON VA 23314 - Photo 4
108 Gregory DR, CARROLLTON VA 23314 - Photo 5
$389,000
$246 / sqft · est. $2,377/mo →
4beds
2baths
1,580sqft
4days on market

108 Gregory Dr, Carrollton, VA 23314

Under ContractResidential · built 1985 · CANNON ACRES

Facts & features

Type

Residential

Year built

1985

Price / sqft

$246

HOA

None

Taxes

$2,942/yr

County

Isle of Wight County VA

MLS #

10648466

Interior

Bedrooms
4
Full baths
2
Approx. sqft
1,580
Stories
1
Flooring
Carpet, Laminate/LVP
First-floor bed & full bath
Yes
Total rooms
7
Other rooms
1st Floor BR, 1st Floor Primary BR, Attic, Breakfast Area, Converted Gar, Porch, Utility Closet
Appliances
Dishwasher, Disposal, Dryer, Microwave, Elec Range, Refrigerator, Washer

Construction & exterior

Style
Cape Cod
Subtype
Detached
Foundation
Crawl
Roof
Asphalt Shingle
Exterior
Vinyl
Pool
No Pool
Fencing
Back Fenced

Utilities & systems

Heating
Forced Hot Air
Cooling
Central Air
Water heater
Electric
Water
City/County
Sewer
Septic

Lot, parking & ownership

Lot size
0.3500
Subdivision
CANNON ACRES
Zoning
SR
Ownership
Fee Simple
Garage
No
Parking
Off Street, Driveway Spc
Possession
CLOSING
Disclosures
Disclosure Statement

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

About this home

CLASSIC CAPE COD with Fresh Paint & New Flooring Throughout, Eat-In Kitchen with Stylish Shaker Cabinets, Quartz Countertops, & Stainless Steel Appliances, Living Room with Fireplace, Spacious Family Room. Nice Floorplan with 2 Bedrooms/1 Bath on 1st Floor, 2 Bedrooms/1 Bath on 2nd Floor. Large Backyard, Deck, & Storage Shed. Established Neighborhood with Convenient Access to Suffolk, Smithfield, & James River Bridge.

Listing courtesy of Faith Turner · CENTURY 21 Nachman Realty · REIN MLS #10648466

VaHome team overview

Our read on this home

by Tom & Dariya Milan, REALTORS® · LPT Realty

At a glance

108 Gregory Drive is a four-bedroom, two-bath ranch-style home in Carrollton, Virginia, built in 1985 and spanning 1,580 square feet. Sitting in Isle of Wight County with quick access to two Navy installations, it's a practical, well-located address in a quiet residential pocket of the Hampton Roads region.

Keep searching in Carrollton

See homes for sale zoned for Smithfield High School and homes for sale zoned for Carrollton Elementary School.

Read the full overview ↓

Why this home stands out

What sets 108 Gregory Drive apart is its combination of single-story living, a four-bedroom floor plan, and a location that keeps two major military installations within a short commute. Carrollton is one of the calmer corners of Hampton Roads — no congestion, no high-density development pressing in from every side — and this address sits right in the middle of that breathing room, with everyday conveniences less than a mile away.

CANNON ACRES and the Carrollton real estate market

Carrollton occupies a quiet stretch of Isle of Wight County on the western shore of the James River, just across the Monitor-Merrimac Memorial Bridge-Tunnel from the heart of Hampton Roads. The feel here is decidedly suburban-rural: wide lots, mature trees, and a pace that doesn't match the bustle you'll find closer to Norfolk or Virginia Beach. Gregory Drive is a residential street in that same spirit — the kind of block where neighbors know each other and weekend mornings are genuinely quiet. Isle of Wight County governs the area, which means lower density and a different character than the independent cities that dominate most of Hampton Roads. Families comparing Carrollton homes for sale often cite that county feel as a deciding factor. You're still within reach of everything — Newport News, Suffolk, and the broader Hampton Roads metro are all accessible — but you come home to something that feels genuinely removed from the noise.

What's nearby

Daily life is easy to manage from Gregory Drive. Fatboy's Grill & Steamshack is just 0.2 miles away, making weeknight dinners a short walk or drive. Bubba-N-Frank's Carrollton and Cone Slingers are both within 0.3 miles — solid options when you want something casual and local. For groceries, you have three choices within a mile: Dollar General at 0.8 miles, Publix Super Market at Bartlett Station at 0.9 miles, and Jeb's Market at 1.0 mile. Royal Farms, also at 0.9 miles, handles the morning coffee run. The everyday errands largely take care of themselves without leaving the immediate area.

For different buyers

For military families relocating

NSA Northwest Annex is 17 minutes from the front door, and NSA Hampton Roads is about 21 minutes out — both well within a reasonable commute window. A VA loan is a natural fit for this price range and property type, and Isle of Wight County's lower cost of living stretches BAH further than comparable properties closer to the base gates. Single-story living also makes this a practical choice for households managing deployments or frequent moves.

For families upgrading

Four bedrooms and single-story living give growing families real flexibility — a dedicated home office, a guest room, and still space for the kids. Families comparing homes for sale zoned for Carrollton Elementary School and homes for sale zoned for Smithfield High School will find that 108 Gregory Drive falls within both attendance zones, making this a straightforward choice for households planning to stay through the school years. The surrounding neighborhood is calm, and the nearby restaurant and grocery options mean less time in the car.

More buyer questions

How far is 108 Gregory Drive from NSA Northwest Annex?

NSA Northwest Annex is approximately 17 minutes from 108 Gregory Drive under typical traffic conditions. NSA Hampton Roads is about 21 minutes in the same direction, making this address workable for personnel assigned to either installation.

Is 108 Gregory Drive in a flood zone?

Flood zone status for 108 Gregory Drive is covered in the FloodRisk tile on this page, which pulls current FEMA map data for the specific parcel. Review that section for the most accurate and up-to-date designation.

What county is 108 Gregory Drive in?

108 Gregory Drive is in Isle of Wight County, Virginia — not one of the independent cities that make up most of Hampton Roads. That distinction affects tax jurisdiction, zoning, and the overall density of the surrounding area.

Does 108 Gregory Drive have a garage?

Garage details for this specific property are listed in the full feature breakdown on this page. The 1985 build year and single-story ranch style are consistent with attached or carport configurations common to the era and neighborhood.

What is the lot like at 108 Gregory Drive?

108 Gregory Drive sits on a residential lot in a low-density Carrollton neighborhood characterized by mature landscaping and generous spacing between homes. Specific lot dimensions are listed in the property details section of this page.

Tom and Dariya Milan at LPT Realty know Carrollton and Isle of Wight County well. Reach out to talk through 108 Gregory Drive or explore what else is available in the area.

Summary generated by AI from public records and publicly available information.

Homes like this one sell fast — see the next one first

Carrollton$330K – $450K4+ beds

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Schools

VaHome School Score

Our own 1–10 rating, scored from Virginia Department of Education data.

VaHome School Score — calculated by VaHome.com from Virginia Department of Education assessment, progress, and attendance data. Attendance zones come from the MLS listing record; confirm the current zone with the school division before making an offer.

Flood & environment

FEMA flood zone X · outside the high-risk area · FIRM 51093C

Flood Risk

Looking up FEMA flood zone…

Hurricane Evacuation Zone

Evacuation Zone C

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

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

$2,377/mo

Principal & interest

$2,018

Property tax

$245

Home insurance

$113

PMI

None

HOA/Condo (paid separately)

None

Estimate only. Association (HOA/condo) fees are paid separately and are not included in the payment above. 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

Judge value on real ground

Price context — similar nearby homes

$265,000 – $419,990

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.

401 Cannon DR · 0.1 mi · 1,550 sqft$401,000 sold 2026-06
15007 Ashby WAY E · 0.3 mi · 1,658 sqft$395,000 sold 2026-01
909 Kathy Ann WAY · 1.1 mi · 1,507 sqft$265,000 sold 2026-08

Sale & Tax History

List Price

$389,000

Price / Sq Ft

$246

Annual Taxes

$2,942

Monthly Tax

$245

HOA

None

Tax Rate (effective)

0.76%

Sale Timeline (this listing)

EventDatePriceDetail
ListedAug 20, 2026$389,000—
Currently listed—$389,000—

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:

Carrollton Assessor (Google)

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

Is 108 Gregory Dr in a good school zone?+
The assigned zones on the listing record are Carrollton Elementary (VaHome School Score 6.3/10), Smithfield Middle (VaHome School Score 6.1/10), Smithfield (VaHome School Score 5.1/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 108 Gregory 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.
Does 108 Gregory Dr have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 108 Gregory Dr built?+
It was built in 1985, 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 Faith Turner · CENTURY 21 Nachman Realty · REIN MLS #10648466

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.

Schedule a private tour

Free, no obligation — your inquiry goes to Tom & Dariya, never resold.

108 Gregory Dr, Carrollton — photo

See it in person — the record only says so much.

Call or text (757) 777-7577

108 Gregory Dr, Carrollton, Virginia 23314 · MLS #10648466 · 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.

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