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Chesapeake › HICKORY › 1441 Whittamore Rd✓ Source: REIN MLS #10650780 · record updated Sep 26, 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
22days 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

Meet 1441 Whittamore Road in Chesapeake—a five-bedroom, two-bath home built in 1957 with 1,800 square feet of living space. The layout offers room to spread out, and you're just 11 minutes from USCG Finance Center Chesapeake. Homes for sale in 23322 often appeal to buyers seeking established neighborhoods with character and convenience.

Read the full overview ↓

Why this home stands out

This 1957-built home sits on a solid foundation with classic mid-century bones and a floor plan designed for real living. Five bedrooms mean flexible space for a home office, guest room, or hobby space. The two-bath setup keeps things practical, and the 1,800 square feet unfolds across a single story. Whittamore Road itself is a quiet, tree-lined street that feels removed from the bustle. The bones are honest and ready for your vision.

HICKORY and the Chesapeake real estate market

Whittamore Road runs through an established Chesapeake neighborhood where mid-century homes anchor quiet blocks. The streets here carry a sense of permanence—neighbors tend their yards, and the pace is unhurried. You're in the kind of setting that defines suburban Chesapeake living: close enough to everything that matters, far enough from the noise. The city itself spreads across 430 square miles, making it Virginia's largest by land area. Getting around is straightforward: major roads like George Washington Memorial Highway and Route 17 connect you to shopping, dining, and employment centers. Downtown Norfolk is about 20 minutes north. If you're comparing homes for sale in Chesapeake, this address sits in a zone with the kind of stability that comes from houses that have stood for decades. The neighborhood offers a grounded community feel.

What's nearby

Nearby conveniences include grocery stores, pharmacies, and casual dining within a five-minute drive. Greenbrier Mall and its surrounding retail cluster sit about ten minutes away. Parks and recreation areas dot the area—you'll find green space for walking and outdoor activity close by. The Chesapeake Public Library system has branches within easy reach. Route 17 runs nearby, giving you quick access to the broader city. The pace here is deliberate—nothing feels rushed or cramped.

For different buyers

Base commute and VA loan notes

About 11 minutes to USCG Finance Center Chesapeake and 19 minutes to NSA Northwest Annex puts this address in a practical commute zone for active duty and civilian personnel. VA loan financing is common in this neighborhood, and the five-bedroom layout means move-in flexibility. The 1957 construction and single-story footprint often appeal to buyers seeking established, lower-maintenance properties.

Room to grow

Five bedrooms give you genuine room to grow—separate spaces for kids, a home office, and a guest room all fit comfortably. The two-bath setup serves a household well, and 1,800 square feet spreads across a practical single-story floor plan. A fenced yard offers outdoor space, and the quiet street is the kind of block where children play safely.

More buyer questions

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

About 11 minutes by car, making it a straightforward commute for active duty and civilian personnel assigned there.

What zones serve this address?

This address falls within the zones for homes for sale zoned for Hickory High School and homes for sale zoned for Southwestern Elementary School, serving the neighborhood's school-age population.

Is there a second military base nearby?

Yes—NSA Northwest Annex is about 19 minutes away, offering another employment option for personnel in the area.

What year was this home built, and what's the layout like?

Built in 1957, the home offers five bedrooms, two baths, and 1,800 square feet across a single-story floor plan designed for practical living.

Are there shopping and dining options nearby?

Yes—Greenbrier Mall and local retail are about ten minutes away, and everyday conveniences like grocery stores and restaurants are within five minutes.

Ready to explore this Chesapeake home? Reach out to learn more about 1441 Whittamore Road and what it 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

By subscribing you agree to receive listing emails from Tom & Dariya Milan, Realtors, at most one a day. Unsubscribe anytime · Privacy PolicyBrokered by LPT Realty

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 (FEMA)

Source: FEMA National Flood Hazard Layer · FIRM 510034

Low / Moderate Risk

FEMA flood zone

X (low to moderate risk)

Base flood elevation

Not applicable in low-risk zones

Zone X is outside the Special Flood Hazard Area; FEMA doesn\u2019t define a BFE here.

Property elevation

9.9 ft above sea level

USGS 3DEP digital elevation model

Outside the high-risk Special Flood Hazard Area. Federal flood insurance is NOT required, though optional preferred-rate NFIP coverage is still worth considering in coastal Hampton Roads.

Data sources: Flood zone and base flood elevation come from FEMA\u2019s National Flood Hazard Layer. Property elevation is sampled from a single point on the parcel using the USGS National Map elevation service \u2014 actual elevations across a single property can vary by several feet higher or lower than the figure shown. Use these numbers as a starting reference and do your own due diligence (a professional survey or elevation certificate) before relying on them for any financial, insurance, or construction decision.

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 place where country meets suburb. It sits in the far south of Chesapeake, Virginia. The area runs along the Battlefield Boulevard South corridor toward the North Carolina line.

$637K

Median sale · 12 mo

$246

Sold $/sq ft

19d

Days on market

30

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 – $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.

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

22 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 6.3/10), Hickory Middle (VaHome School Score 9/10), Hickory (VaHome School Score 8.7/10). 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

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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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