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Chesapeake › HICKORY › 1441 Whittamore Rd✓ Source: REIN MLS #10650780 · record updated Sep 12, 2026 · synced every 2 min · your inquiry is never resold
1441 Whittamore RD, CHESAPEAKE VA 23322 - Main photo
1441 Whittamore RD, CHESAPEAKE VA 23322 - Photo 2
1441 Whittamore RD, CHESAPEAKE VA 23322 - Photo 3
1441 Whittamore RD, CHESAPEAKE VA 23322 - Photo 4
1441 Whittamore RD, CHESAPEAKE VA 23322 - Photo 5
5beds
2baths
1,800sqft
8days on market

1441 Whittamore Rd, Chesapeake, VA 23322

ActiveResidential · built 1957 · HICKORY

Facts & features

Type

Residential

Year built

1957

Price / sqft

$261

HOA

None

Taxes

$2,795/yr

County

Chesapeake VA

MLS #

10650780

Interior

Bedrooms
5
Full baths
2
Approx. sqft
1,800
Stories
2
Flooring
Carpet, Laminate/LVP
Ensuite bedrooms
1
First-floor bed & full bath
Yes
Total rooms
7
Other rooms
1st Floor BR, 1st Floor Primary BR, PBR with Bath, Porch, Sun Room, Utility Room
Appliances
Dishwasher, Disposal, Dryer Hookup, Microwave, Elec Range, Washer Hookup

Construction & exterior

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

Utilities & systems

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

Lot, parking & ownership

Lot size
0.9500
Subdivision
HICKORY
Zoning
R15
Ownership
Fee Simple
Garage
No
Parking
Multi Car
Possession
AT CLOSING
Disclosures
Disclosure Statement

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

About this home

Welcome to a rare opportunity in Chesapeake's sought-after Hickory school district! Set on a full acre, this beautifully transformed 5-bedroom, 2-bath home offers the space and setting to enjoy a touch of country living while staying near the conveniences of the city. The renovation goes far beyond cosmetics, with a new roof, siding, windows, HVAC, flooring, carpet, plumbing, septic tank, appliances and more. Inside, fresh modern finishes create a bright, move-in-ready home with room for everyone. Outside, the expansive acre lot opens the door to gardens, outdoor entertaining, hobbies, animals or simply having more room to enjoy the outdoors. With golf courses nearby and easy access to everything Chesapeake has to offer, this property delivers a unique blend of space, location and modern living. Nearly everything has been refreshed or replaced- just bring your furniture and start enjoying the Hickory lifestyle!

Listing courtesy of Alexis Currie · Long & Foster Real Estate Inc. · REIN MLS #10650780

Tom & Dariya's overview

Our read on this home

by Tom & Dariya Milan, REALTORS® · Brokered by LPT Realty

At a glance

A five-bedroom, two-bath home built in 1957 on Whittamore Road in Chesapeake's 23322 zip code — 1,800 square feet of mid-century bones in a quiet residential pocket, eleven minutes from USCG Finance Center Chesapeake and a short drive to NAS Oceana.

Keep searching in Chesapeake

See all Chesapeake homes for sale, including homes for sale in 23322, homes for sale zoned for Hickory High School, and homes for sale zoned for Southwestern Elementary School. Browse every listing among homes for sale in Chesapeake — updated from the REIN MLS every few minutes. Nearby, look at Hickory homes for sale, Chesapeake waterfront homes for sale, Chesapeake condos and townhomes for sale, and new construction homes in Chesapeake.

Read the full overview ↓

Why this home stands out

Five bedrooms in an 1,800-square-foot footprint is a genuinely rare find among Chesapeake homes for sale at this price tier — most homes this size top out at three or four. Whether you need dedicated home-office space, room for extended family, or simply the flexibility of an extra bedroom that can grow with your household, 1441 Whittamore Road delivers headroom that comparably aged homes in the area rarely match.

HICKORY and the Chesapeake real estate market

Whittamore Road sits in the southern Chesapeake corridor — a part of the city where the pace slows down without sacrificing convenience. Chesapeake is Virginia's second-largest city by land area, and the 23322 zip code captures some of its most established residential character: tree-lined streets, generous lot spacing, and neighbors who tend to stay for decades. The area around this address feels genuinely residential rather than transitional — no big-box sprawl out the front door, just a steady, settled neighborhood that has been putting down roots since the mid-twentieth century. City services here are handled by Chesapeake's well-regarded municipal infrastructure, and the broader Hickory area of the city has long attracted families who want suburban breathing room without a rural commute. If you are browsing homes for sale in Chesapeake and prioritizing stability over flash, this corner of the city earns a close look.

What's nearby

Day-to-day errands are manageable from Whittamore Road. Handsprings, Etc — a local gym less than a mile away — means your fitness routine doesn't require a long drive. The broader Chesapeake retail corridor along Battlefield Boulevard is within easy reach for groceries, pharmacies, and dining. NAS Oceana sits about twenty-three minutes northeast, opening up additional commissary and exchange access for eligible households. The combination of a quiet street address and practical proximity to everyday amenities is one of the steadier selling points of the homes for sale in 23322.

For different buyers

For military families relocating

Eleven minutes to USCG Finance Center Chesapeake makes 1441 Whittamore Road a natural fit for Coast Guard households. NAS Oceana is reachable in about twenty-three minutes as well, and a VA loan can make the five-bedroom layout even more accessible — giving you the space for a home office or a guest room without stretching the floor plan. Chesapeake's stable property values also tend to hold well across PCS cycles.

For families upgrading

Families comparing homes for sale zoned for Hickory High School and homes for sale zoned for Southwestern Elementary School will find 1441 Whittamore Road worth a serious look. Five bedrooms give every member of the household their own space, and the 1957 construction era means solid bones — thick walls, established lots, and a neighborhood character that newer subdivisions simply haven't had time to develop yet.

More buyer questions

How far is 1441 Whittamore Road from USCG Finance Center Chesapeake?

The drive is approximately eleven minutes under normal traffic conditions, making it one of the closer residential options to that installation in the southern Chesapeake area.

How far is 1441 Whittamore Road from NAS Oceana?

NAS Oceana is roughly twenty-three minutes northeast of the property, a reasonable commute for personnel stationed there who want to live in Chesapeake.

Is 1441 Whittamore Road in a flood zone?

Flood zone status for this address is detailed in the FloodRisk tile on this page — review that section for the current FEMA designation before making any decisions.

What is the lot and home size at 1441 Whittamore Road?

The home offers 1,800 square feet of living space across five bedrooms and two bathrooms, built in 1957 on a residential lot in Chesapeake's 23322 zip code.

Does 1441 Whittamore Road have an HOA?

Based on available information, this property does not carry a mandatory HOA, which is common for mid-century homes in established Chesapeake neighborhoods like this one.

Tom and Dariya Milan at LPT Realty know this part of Chesapeake well — reach out to get a straightforward read on what 1441 Whittamore Road could mean for your next chapter.

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

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

Chesapeake$395K – $545K5+ 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 510034

Flood Risk

Looking up FEMA flood zone…

Hurricane Evacuation Zone

Evacuation Zone D

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

Military Aircraft Zone Information

Aircraft Noise

>75 dB DNL

Accident Potential Zone

Not in a mapped Accident Potential Zone

Source: U.S. Navy AICUZ — Air Installations Compatible Use Zones (via city GIS)

Explore this neighborhood

Hickory

Hickory is a rural-meets-suburban community in the southern reaches of Chesapeake, Virginia, set along the Battlefield Boulevard South corridor as it runs toward the North Carolina line.

$625K

Median sale · 12 mo

$245

Sold $/sq ft

18d

Days on market

39

For sale now

$132K

HH income

82.9%

Owner-occupied

REIN MLS closed sales, trailing 12 mo · U.S. Census ACS 2024 5-year

Explore Hickory →
Map of Hickory with neighborhood boundaryNeighborhood

see more Chesapeake homes →

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

$2,808/mo

Principal & interest

$2,438

Property tax

$233

Home insurance

$137

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

$200,000 – $465,000

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.

1441 Whittamore RD · 0 mi · 1,645 sqft$200,000 sold 2026-02
1457 Whittamore RD · 0.1 mi · 1,935 sqft$285,000 sold 2026-03
1616 Whittamore RD · 0.4 mi · 1,792 sqft$460,000 sold 2026-06

Own a home nearby? See what it is worth today — What's your Chesapeake home worth?

Sale & Tax History

List Price

$469,900

Price / Sq Ft

$261

Annual Taxes

$2,795

Monthly Tax

$233

HOA

None

Tax Rate (effective)

0.59%

Sale Timeline (this listing)

EventDatePriceDetail
ListedSep 5, 2026$469,900—
Currently listed—$469,900—

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.

Market tempo

8 days on market — read it in context

Days on market reflects pricing, season, and inventory — compare it against similar nearby homes below before reading anything into it.

Questions buyers ask

Is 1441 Whittamore Rd in a good school zone?+
The assigned zones on the listing record are Southwestern Elementary (VaHome School Score 4.8/10), Hickory Middle (VaHome School Score 9.2/10), Hickory (VaHome School Score 8.8/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 1441 Whittamore Rd 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 1441 Whittamore Rd have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 1441 Whittamore Rd built?+
It was built in 1957, 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

Brokered by LPT Realty · Hampton Roads · answer their own phone

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

Listing courtesy of Alexis Currie · Long & Foster Real Estate Inc. · REIN MLS #10650780

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.

1441 Whittamore Rd, Chesapeake — photo

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

Call or text (757) 777-7577

1441 Whittamore Rd, Chesapeake, Virginia 23322 · MLS #10650780 · 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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