For sale

$455,000

Est. $2,826/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

$253Price/Sq.Ft.

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

Listing updated: Oct 30, 2026 at 02:35pm

Redfin checked: 2 minutes ago

•Source:REINMLS #10659859

Payment calculator

$2,826 per month

Principal and interest$2,452

Property taxes

$233

HOA dues

Home insurance

$140

Utilities

Add

5 minutes to get started. No credit impact.

Affordability tools

See this home in person

This home is unavailable to tour on this day.

Next available date: Wednesday, November 4

Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN TODAY, 4PM TO 7PM3D WALKTHROUGH
$525,000
4 beds3.5 baths2,571 sq ft
891 Bells Mill Rd, Chesapeake, VA 23322
0.9 acre lot • 2 garage spots • Built 1945
OPEN FRI, 11AM TO 5PM
$597,530
4 beds2.5 baths2,518 sq ft
733 Crestfield Dr, Chesapeake, VA 23320
0.25 acre lot • 2 garage spots • Built 2026
OPEN FRI, 2:30PM TO 5:30PM
$735,000
5 beds3 baths3,337 sq ft
804 Catrina Ln, Chesapeake, VA 23322
0.23 acre lot • 2 garage spots • Built 2001
LIVE VIDEO OPEN SAT3D WALKTHROUGH
$310,000
3 beds1.5 baths1,216 sq ft
1020 Still Harbor Cir, Chesapeake, VA 23320
$52 HOA • 2 parking spots • Built 1985
OPEN SAT, 11AM TO 1PM
$269,000
3 beds1 bath1,120 sq ft
402 Cabot St, Portsmouth, VA 23702
6,969 sq ft lot • Built 1954 • Listed 5 days
OPEN SAT, 11AM TO 1PM3D WALKTHROUGH
$700,000
5 beds4 baths3,438 sq ft
4812 Knollwood Ct, Virginia Beach, VA 23464
0.34 acre lot • 2 garage spots • Pool
OPEN SAT, 11AM TO 1PM3D WALKTHROUGH
$510,000
4 beds2 baths1,744 sq ft
700 Gladesdale Dr, Chesapeake, VA 23322
1.02 acre lot • Garage • Built 1986
OPEN SAT, 12PM TO 2PM
$335,000
3 beds2.5 baths1,734 sq ft
1700 Oliver Ave, Chesapeake, VA 23324
2,613 sq ft lot • 2 parking spots • Built 2003
OPEN SAT, 12PM TO 2PM
$460,000
5 beds2.5 baths2,850 sq ft
5240 Prestwick St, Virginia Beach, VA 23464
2 garage spots • Built 1983 • Listed 8 days
OPEN SAT, 1PM TO 4PM
$349,999
3 beds2 baths1,399 sq ft
2204 Ardmore Ave, Chesapeake, VA 23324
Garage • Built 1959

Interested in buying?

Make a winning offer with the help of a local agent

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 · $455,000

Strong offer

$468K and above

75% chance or better to win

Why $468K+ is a strong offer

DAYS ON MARKET

The average home goes pending in 35 days.

SALE-TO-LIST

Most homes are selling 1% below list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Sunroom

Bedrooms
First-floor master bedroom

Bathrooms
2 full bathrooms

Kitchen
Dishwasher
Disposal
Microwave
Electric range

Laundry & utility
Washer hookup
Dryer hookup

Flooring
Carpet
Laminate

Heating & cooling
Forced hot air
Central air

Sale and tax history for 1441 Whittamore Rd

Sale History
Tax History

Date

Event

Price

REINMLS #10659859

Oct 30, 2026

Listed

$455,000

$253/sq ft

REINMLS #10650780

Oct 28, 2026

Listing Removed

—

Oct 13, 2026

Price Changed

$464,900

$258/sq ft

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*

2026

$3,010 (+7.7%)

$170,000 + $128,000

$298,000

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

0.74 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 Oct 12, 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

$454,783

$217 under list price of $455K

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $415K to $576K.

SOLD SEP 9, 2026
$430,000 Last sold price
4 beds2 baths1,596 sq ft
1421 Avon Rd, Chesapeake, VA 23322
$16/sq ft
17 years newer
SOLD JUL 6, 2026
$460,000 Last sold price
4 beds2 baths1,568 sq ft
812 Gloss St, Chesapeake, VA 23322
$40/sq ft
32 years newer
SOLD SEP 29, 2026
$480,000 Last sold price
4 beds2 baths1,856 sq ft
1213 Fentress Rd, Chesapeake, VA 23322
$6/sq ft
8 years older
SOLD JUL 1, 2026
$576,000 Last sold price
4 beds2.5 baths2,560 sq ft
705 Hilltop Ct, Chesapeake, VA 23322
$28/sq ft
37 years newer
SOLD APR 1, 2026
$475,000 Last sold price
4 beds2.5 baths2,120 sq ft
509 Hatteras Cres, Chesapeake, VA 23322
$29/sq ft
30 years newer
SOLD OCT 1, 2026
$415,000 Last sold price
4 beds2 baths1,378 sq ft
720 Albemarle Ct, Chesapeake, VA 23322
$48/sq ft
31 years newer

Rental earnings

Est. $1,948 per month, based on comparable rentals

Tour for free, no strings attached

Takes about 5 minutes & won’t affect your credit

Ask a question

(757) 704-5037

Nearby similar homes

3D & VIDEO TOUR

$980,000

6 beds4 baths4,800 sq ft

821 Redleafe Cir, Chesapeake, VA 23320

Custom home • First-floor bedroom • In-ground pool

$679,900

4 beds3 baths3,000 sq ft

1239 Pacels Way, Chesapeake, VA 23322

2 garage spots • Built 2000 • Listed 26 days

$599,500

4 beds2.5 baths2,698 sq ft

613 Corapeake Dr, Chesapeake, VA 23322

Colonial home • 0.23 acre lot • 2 garage spots

$665,000

5 beds2.5 baths3,490 sq ft

1617 Banff Ct, Chesapeake, VA 23320

Paved patio • Gazebo • Furnished pool house

NEW CONSTRUCTION

$703,705

4 beds3.5 baths2,803 sq ft

2037 Charwood Dr, Chesapeake, VA 23320

0.25 acre lot • 2 garage spots • Built 2026

NEW CONSTRUCTION

$626,955

4 beds2.5 baths2,652 sq ft

2048 Charwood Dr, Chesapeake, VA 23320

Open-concept layout • Large kitchen • Flex space

New listings for sale in 23322

COMING SOON

$715,000

4 beds3.5 baths3,455 sq ft

1312 Woodview Lair, Chesapeake, VA 23322

All brick home • Open floor plan • Hardwood flooring

NEW 9 HRS AGO

$550,000

4 beds2.5 baths3,200 sq ft

609 Saber Dr, Chesapeake, VA 23322

Sunroom • Deck • Backyard

$725,000

5 beds4 baths3,110 sq ft

1908 Ferguson Loop, Chesapeake, VA 23322

Cul-de-sac • Cozy front porch • Hardwood floors

NEW 33 HRS AGO

$760,000

5 beds3 baths4,160 sq ft

208 Leicester Ct, Chesapeake, VA 23322

Open floor plan • Custom library • Built-in shelving

NEW 34 HRS AGO

$530,000

4 beds3 baths2,485 sq ft

309 Barcelona Dr, Chesapeake, VA 23320

Front porch • Big attic • Expansive kitchen

NEW 1 DAY AGO3D WALKTHROUGH

$729,900

4 beds2.5 baths2,547 sq ft

409 Cairns Rd, Chesapeake, VA 23322

2 garage spots • Pool • Built 2020

NEW 1 DAY AGO

$545,000

4 beds2.5 baths2,396 sq ft

1108 Hillside Trce, Chesapeake, VA 23322

Bamboo wood flooring • Cathedral ceiling • 0.33 acre lot

OPEN TODAY, 4PM TO 7PM3D WALKTHROUGH

$525,000

4 beds3.5 baths2,571 sq ft

891 Bells Mill Rd, Chesapeake, VA 23322

Private driveway • In-law suite • Dual showerheads

NEW 1 DAY AGO

$700,000

6 beds3 baths3,204 sq ft

909 Sydenham Blvd, Chesapeake, VA 23322

Corner lot • Private pool • Recent updates

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

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

Redfin Brokerage Licenses

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

23320 homes for sale
23321 homes for sale
23322 homes for sale
23456 homes for sale
23435 homes for sale

Houses for rent in Chesapeake	Agents near me	Richmond, VA homes for sale	Chesapeake Housing Market
Houses for sale near me	Arlington, VA homes for sale	McLean, VA homes for sale
Land for sale near me	Alexandria, VA homes for sale	Chesapeake, VA homes for sale
Open Houses near me	Virginia Beach, VA homes for sale	Chesapeake Property Records
Condos for sale near me	Fairfax, VA homes for sale	VA New Listings

Virginia Beach homes for sale
Norfolk homes for sale
Suffolk homes for sale

About this home

Payment calculator

Affordability tools

See this home in person

Nearby open houses (10)

Interested in buying?

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

Nearby similar homes

New listings for sale in 23322

More real estate resources