For sale

$469,900

Est. $2,942/mo —

•

1,800

sq ft

1441 Whittamore Rd, Chesapeake, VA 23322

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!

Single-familyProperty Type

1957Year Built

0.95 acresLot Size

$261Price/Sq.Ft.

Listed by Alexis Currie • Long1 & Foster Real Estate Inc.

Listing updated: Sep 13, 2026 at 03:58am

Redfin checked: a minute ago

•Source:REINMLS #10650780

Payment calculator

$2,942 per month

Principal and interest$2,564

Property taxes

$233

HOA dues

Home insurance

$145

Utilities

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Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN TODAY, 11AM TO 1PM
$775,000
4 beds2.5 baths2,434 sq ft
1120 Beaver Dam Rd, Chesapeake, VA 23322
OPEN TODAY, 11AM TO 1PM3D WALKTHROUGH
$324,900
3 beds2 baths1,361 sq ft
1513 Wingfield Ave, Chesapeake, VA 23325
OPEN TODAY, 11AM TO 3PM
$319,000
2 beds1 bath1,374 sq ft
1789 Joplin Ln, Virginia Beach, VA 23464
REDFIN OPEN TODAY, 12PM TO 2PM3D WALKTHROUGH
$475,000
4 beds4 baths2,150 sq ft
1209 Holly Ave, Chesapeake, VA 23324
OPEN TODAY, 12PM TO 3PM3D WALKTHROUGH
$565,000
3 beds2.5 baths1,832 sq ft
704 Woodcott Dr, Chesapeake, VA 23322
REDFIN OPEN TODAY, 1PM TO 3PM3D WALKTHROUGH
$249,000
3 beds1.5 baths1,081 sq ft
1309 Green Cedar Ln, Virginia Beach, VA 23453
OPEN TODAY, 1PM TO 3PM
$498,500
4 beds2.5 baths2,248 sq ft
4216 Grove Ct, Virginia Beach, VA 23462
OPEN TODAY, 2PM TO 5PM
$409,900
5 beds3.5 baths3,000 sq ft
2210 Chestnut St, Portsmouth, VA 23704
OPEN SUN, 11AM TO 2PM
$375,000
3 beds1.5 baths1,300 sq ft
1700 Darrow St, Virginia Beach, VA 23456
OPEN SUN, 1PM TO 3PM
$345,900
4 beds2 baths1,500 sq ft
28 Hinton Ave, Chesapeake, VA 23323

Around this home

Schools

K - 12
Preschool & daycare

Southeastern Elementary School

Public PreK-5 • Assigned • 3.8mi

8/10

Hickory Middle School

Public 6-8 • Assigned • 3.7mi

9/10

Hickory High School

Public 9-12 • Assigned • 4.0mi

9/10

Provided by GreatSchools

About Butts

Road

Butts Road, located between I-64 and the Great Dismal Swamp National Wildlife Refuge, is a suburban and semi-rural Chesapeake neighborhood with wide arterial corridors and pockets of wooded lowland. The neighborhood’s character concentrates around the Butts Station Road and Battlefield Boulevard corridor, where big-box retail, local eateries, and steady commuter traffic set the daily rhythm. Housing trends toward newer subdivisions and townhome communities set back from the main roads, with cul-de-sacs and retention ponds shaping the streetscape. Greenway edges and drainage canals hint at the area’s coastal-plain geography. For a cultural anchor, the nearby Chesapeake Arboretum and Chesapeake Planetarium add a quieter, civic-minded counterpoint to the commercial strips.

Provided by Walk Score and Local Logic

Offer insights

1441 Whittamore Rd · $469,900

Strong offer

$480K and above

75% chance or better to win

Why $480K+ is a strong offer

DAYS ON MARKET

The average home goes pending in 30 days.

SALE-TO-LIST

Most homes are selling 0% below list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Sun room
Porch
Utility room

Bedrooms
Master bedroom with ensuite (first floor)
Additional bedroom

Bathrooms
2 full bathrooms

Kitchen
Electric range
Microwave
Dishwasher
Disposal

Laundry & utility
Washer hookup
Dryer hookup
Utility room

Flooring
Carpet
Laminate

Heating & cooling
Forced hot air heating
Central air conditioning

Sale and tax history for 1441 Whittamore Rd

Sale History
Tax History

Date

Event

Price

REINMLS #10650780

Sep 4, 2026

Listed

$469,900

$261/sq ft

REINMLS #10615955

Feb 26, 2026

Sold

$200,000

$111/sq ft

Jan 13, 2026

Listed

$249,000

$138/sq ft

Wonderful opportunity to secure property in Hickory section of Chesapeake. Home needs work. City website property lines not accurate, city working to update. More than likely cash or rehab financing only. Floor dips downstairs, ceiling missing drywall, possible microbial growth at upstairs ceiling and on some walls, doors, wood rot at some of the windows. Setup showing via Showing time. Subject to court approval (usually adds 2 weeks to typical process) and special warranty deed. Park in the gravel driveway as long as it does not block access to the house behind the subject property or they can park in the grass behind the house. Owners will mark septic lines over next couple days. Please exercise caution entering home, the living room floor sags.

Year

Property tax

Land + Additions

Assessment*

2025

$2,794 (+3.7%)

$150,000 + $126,600

$276,600

2024

$2,695 (+6.1%)

$140,000 + $126,800

$266,800

2023

$2,540 (+8.9%)

$130,000 + $121,500

$251,500

2022

$2,333 (+22.9%)

$115,000 + $116,000

$231,000

2021

$1,898 (+9.9%)

$85,000 + $95,800

$180,800

2020

$1,727 (+8.3%)

$70,000 + $94,500

$164,500

2019

$1,595

$70,000 + $81,900

$151,900

2018

$1,595 (+1.1%)

$70,000 + $81,900

$151,900

2017

$1,578 (+15.1%)

$70,000 + $80,300

$150,300

2015

$1,371

$60,000 + $80,300

$140,300

2014

$1,371 (+0.7%)

$45,000 + $85,600

$130,600

2013

$1,361

$45,000 + $84,600

$129,600

2012

$1,361

$45,000 + $84,600

$129,600

Public record

Public record
Permits

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

0.94 Acres

Year renovated

—

Finished Sq. Ft.

1,553

Unfinished Sq. Ft.

—

Total Sq. Ft.

1,553

Year built

1957

Style

Single Family Residential

County

Chesapeake

APN

0621004000071

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 9, 2026.

Apr 10, 2026 • Active

Residential electrical

Upgrade the electrical service from 100 amps to 200 amps.

Electrical

Apr 9, 2026 • Active

Residential plumbing

Install or replace plumbing or electrical fixtures.

Plumbing

Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.

Climate risks

3/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.15% chance of being in a wildfire in next 30 years

8/10 Heat Factor

7 days above 106° expected this year, 16 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

1/10 Air Factor

0 unhealthy days expected this year, 0 days in 30 years

Provided by First Street

Historical weather

Chesapeake, VA • 23322

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

90/ 100

Exceptional sunlight

Sunscore

This home receives average direct sun exposure in Chesapeake. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.5 hrs

6.5 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 1441 Whittamore Rd

$469,137

$763 under list price of $470K

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $450K to $539K.

SOLD JUN 30, 2026
$460,000 Last sold price
4 beds2.5 baths1,792 sq ft
1616 Whittamore Rd, Chesapeake, VA 23322
$4/sq ft
smaller lot
59 years newer
SOLD JUN 23, 2026
$482,500 Last sold price
3 beds2 baths1,470 sq ft
513 Corapeake Dr, Chesapeake, VA 23322
$67/sq ft
smaller lot
14 years newer
SOLD MAY 14, 2026
$529,900 Last sold price
4 beds2 baths1,838 sq ft
1014 Weeping Willow Dr, Chesapeake, VA 23322
$27/sq ft
smaller lot
28 years newer
SOLD AUG 27, 2026
$449,900 Last sold price
5 beds2 baths1,929 sq ft
1024 Weeping Willow Dr, Chesapeake, VA 23322
$28/sq ft
smaller lot
28 years newer
SOLD JUN 29, 2026
$539,000 Last sold price
3 beds2 baths2,056 sq ft
1705 Mount Pleasant Rd, Chesapeake, VA 23322
$1/sq ft
larger lot
32 years newer
SOLD AUG 24, 2026
$465,000 Last sold price
4 beds2 baths1,480 sq ft
814 Gloss St, Chesapeake, VA 23322
$53/sq ft
smaller lot
32 years newer

Rental earnings

Est. $1,950 per month, based on comparable rentals

Tour for free, no strings attached

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Early Access listings

EARLY ACCESSCENTURY 21® COMING SOON

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4 beds2.5 baths2,312 sq ft

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New listings for sale in 23322

OPEN TODAY, 11AM TO 1PM

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1120 Beaver Dam Rd, Chesapeake, VA 23322

NEW 23 HRS AGO

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NEW 25 HRS AGO

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$758,900

6 beds3 baths3,414 sq ft

237 Castleberry Dr, Chesapeake, VA 23322

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OPEN TODAY, 12PM TO 3PM3D WALKTHROUGH

$565,000

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704 Woodcott Dr, Chesapeake, VA 23322

$580,000

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Details provided by REINMLS and may not match the public record. Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Payment calculator

See this home in person

Nearby open houses (10)

Around this home

Schools

Offer insights

Property details

Sale and tax history for 1441 Whittamore Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 1441 Whittamore Rd

Early Access listings

Nearby similar homes

New listings for sale in 23322

More real estate resources