For sale

$950,000

Est. $5,572/mo —

•

3,252

sq ft

1908 Benefit Rd, Chesapeake, VA 23322

About this home

Welcome to your private 3.25-acre country oasis, where luxury finishes, heavy-duty infrastructure, and absolute peace of mind converge. This beautifully updated single-story home offers an open-concept layout and highly functional spaces, making it a rare market find. INTERIOR HIGHLIGHTS Step inside to a bright, airy open floor plan where the living and dining areas flow seamlessly into the chef-inspired kitchen. The kitchen is outfitted with premium Cambria countertops for unmatched durability and sleek modern style. The primary suite serves as a spa-like retreat, boasting natural quartzite surfaces, a deep jetted soaking tub, and a massive 4x4 walk-in shower. Upstairs, a versatile finished room over the garage (FROG) and a charming attic dormer offer excellent bonus spaces for a home office, media room, gym, or guest quarters. OUTDOOR LIVING & ENTERTAINING Embrace the scenic acreage from your choice of outdoor living areas. Relax on the welcoming covered front porch, or host unforgettable gatherings on the expansive rear covered patio. The outdoor living experience is anchored by a fully equipped outdoor kitchen, great for weekend barbecues and dining al fresco while overlooking your sprawling, private acreage. THE ULTIMATE DETACHED WORKSHOP A true standout feature is the massive 2,200 sq. ft. detached workshop. This incredible building is fully powered and completely climate-controlled with heating and cooling, making it an ideal setup for a home business, car enthusiast, hobbyist, or extensive machinery storage. PREMIUM SYSTEMS & INFRASTRUCTURE No expense was spared on the home's mechanics and structural integrity: * Power Security: Whole-home generator supported by a recently added 500-gallon propane tank. * Efficiency: All-new energy-efficient windows and updated insulation throughout. * Roof & Plumbing: Roof is approx. 4 years young. All plumbing has been fully updated with zero cast iron. * Utilities: Tankless water heater for endless hot water; septic system recently serviced. Welcome Home.

Single-familyProperty Type

1971Year Built

3.25 acresLot Size

$292Price/Sq.Ft.

2 car garageParking

Listed by Jason Houser • North End Realty Group

Listing updated: Aug 17, 2026 at 08:15pm

Redfin checked: 2 minutes ago

•Source:REINMLS #10648261

Payment calculator

$5,572 per month

Principal and interest$4,741

Property taxes

$561

HOA dues

Home insurance

$269

Utilities

Add

5 minutes to get started. No credit impact.

Discover your buying power

Find out if this home is within budget

Down payment assistance

View down payment assistance programs for this home

See this home in person

Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN THU, 4PM TO 6PM
$899,900
4 beds3.5 baths2,720 sq ft
1421 Saint Brides Road West, Chesapeake, VA 23322
OPEN THU, 6PM TO 8PM
$799,000
4 beds3 baths3,223 sq ft
2020 Sanderson Rd, Chesapeake, VA 23322
OPEN SAT, 11AM TO 2PM
$325,000
2 beds2.5 baths1,582 sq ft
1213 Killington Sq, Chesapeake, VA 23320
OPEN SAT, 11AM TO 1PM3D WALKTHROUGH
$649,900
4 beds2.5 baths2,948 sq ft
1004 Fairway Dr, Chesapeake, VA 23320
OPEN SAT, 11AM TO 2PM
$705,000
5 beds3 baths3,094 sq ft
913 Hathaway Ct, Chesapeake, VA 23322
OPEN SAT, 11AM TO 2PM
$429,999
3 beds2.5 baths2,225 sq ft
808 Monroe Ct, Chesapeake, VA 23320
OPEN SAT, 11AM TO 2PM3D WALKTHROUGH
$709,000
4 beds3 baths3,200 sq ft
816 Forest Lakes Cir, Chesapeake, VA 23322
OPEN SAT, 11AM TO 2PM
$549,900
4 beds3.5 baths2,337 sq ft
1044 Olmstead St, Chesapeake, VA 23323
OPEN SAT, 1PM TO 4PM3D WALKTHROUGH
$545,900
3 beds3.5 baths2,200 sq ft
916 Jennings Ln, Chesapeake, VA 23322
OPEN SAT, 1PM TO 4PM3D WALKTHROUGH
$545,900
3 beds3.5 baths2,200 sq ft
908 Jennings Ln, Chesapeake, VA 23322

Around this home

Schools

K - 12
Preschool & daycare

Grassfield Elementary School

Public PreK-5 • Assigned • 6.4mi

10/10

Hickory Middle School

Public 6-8 • Assigned • 4.5mi

9/10

Grassfield High School

Public 9-12 • Assigned • 5.9mi

9/10

Provided by GreatSchools

About Pleasant

Grove

Pleasant Grove, located between Great Bridge and the North Carolina line, is a rural and residential Chesapeake neighborhood with working farmland and pine-wooded backroads. The neighborhood’s character concentrates around the Battlefield Blvd S and Pleasant Grove Rd crossroads, where feed stores, roadside produce stands, and small service shops set a practical, country cadence. Homes tend toward ranchers and newer builds on larger lots, with long driveways and wide skies. Two-lane roads and drainage canals trace the landscape, and evenings read quieter than the commercial corridors to the north. Outdoor time centers on nearby waterways and open fields rather than sidewalks.

Provided by Walk Score and Local Logic

Offer insights

1908 Benefit Rd · $950,000

Strong offer

$962K and above

75% chance or better to win

Why $962K+ is a strong offer

DAYS ON MARKET

The average home goes pending in 28 days.

SALE-TO-LIST

Most homes are selling 0% above list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Backup generator
Cable hookup
Ceiling fan(s)
Jetted tub
Water softener
Walk-in attic
One fireplace

Bedrooms
Master bedroom with ensuite
First-floor master bedroom
Additional bedroom(s)

Bathrooms
3 full bathrooms

Kitchen
Electric range
Microwave
Dishwasher
Refrigerator

Laundry & utility
Washer hookup
Dryer hookup
Utility room

Flooring
Ceramic flooring
Laminate flooring

Heating & cooling
Heat pump heating
Electric heating
Central air conditioning

Sale and tax history for 1908 Benefit Rd

Sale History
Tax History

Date

Event

Price

REINMLS #10648261

Aug 7, 2026

Listed

$950,000

$292/sq ft

Public Records

Apr 20, 2017

Sold

$351,000

$108/sq ft

REINMLS #1654962

Feb 27, 2017

Price Changed

$360,000

$111/sq ft

Nov 21, 2016

Listed

$365,000

$112/sq ft

REINMLS #1

Jul 31, 2014

Price Changed

$374,900

$115/sq ft

Public Records

Jun 7, 2006

Sold

$390,000

$120/sq ft

Public Records

Oct 25, 2005

Sold

$267,000

$82/sq ft

Public Records

Jul 26, 1999

Sold

$157,000

$48/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$6,736 (+10.0%)

$237,100 + $429,800

$666,900

2024

$6,122 (+7.9%)

$217,100 + $389,000

$606,100

2023

$5,675 (+10.2%)

$187,100 + $374,800

$561,900

2022

$5,151 (+27.4%)

$167,100 + $342,900

$510,000

2021

$4,043 (+0.9%)

$151,900 + $233,100

$385,000

2020

$4,006 (+4.2%)

$151,900 + $229,600

$381,500

2019

$3,844 (+12.3%)

$136,500 + $229,600

$366,100

2018

$3,422 (+3.8%)

$136,500 + $229,600

$366,100

2017

$3,295 (+1.1%)

$136,300 + $177,500

$313,800

2015

$3,260

$136,300 + $174,200

$310,500

2014

$3,260

$136,300 + $174,200

$310,500

2013

$3,260

$136,300 + $174,200

$310,500

2012

$3,260

$136,300 + $174,200

$310,500

Public record

Public record
Zoning
Permits

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

3.25 Acres

Year renovated

—

Finished Sq. Ft.

2,829

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,829

Year built

1971

Style

Single Family Residential

County

Chesapeake

APN

0830000000062

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jun 4, 2026.

A-1

Agricultural District

This district is created primarily for the protection of the agricultural industry and rural section of the city from the invasion of urban and suburban uses and to preserve agricultural lands, forest lands and open space in the interest of the health, safety and welfare of the community. This district is not intended for major residential development; therefore, residential development and subdivisions for residential purposes in the A-1 agricultural district are prohibited except for minor subdivisions, as that term is defined in section 3-403 of this ordinance, preservation divisions, as that term is defined in section 10-201 of this ordinance, and conditional cluster developments approved in accordance with section 6-2200 et seq. of this ordinance.

Permitted uses

Include but are not limited to:

Equestrian facility
Livestock production
Community / recreation center
Day care facility
Housing-Single unit
Fire house
Library
Police station
Communications tower
Agriculture-Cropland

Climate risks

5/10 Flood Factor

Estimated 35-47% chance of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.46% chance of being in a wildfire in next 30 years

9/10 Heat Factor

7 days above 108° 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

95/ 100

Exceptional sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.7 hrs

6.6 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 1908 Benefit Rd

$947,729

$2,271 under list price of $950K

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $685K to $1.1M.

BOUGHT WITH REDFIN AUG 14, 2026
$885,000 Last sold price
4 beds3.5 baths3,200 sq ft
2025 Hallmark Way, Chesapeake, VA 23323
$15/sq ft
22 years newer
SOLD JUL 23, 2026
$685,000 Last sold price
4 beds2.5 baths3,203 sq ft
353 Sign Pine Rd, Chesapeake, VA 23322
$78/sq ft
9 years newer
SOLD JUL 15, 2026
$794,540 Last sold price
4 beds3.5 baths2,766 sq ft
1421 Taft Rd, Chesapeake, VA 23322
$5/sq ft
larger lot
54 years newer
SOLD AUG 14, 2026
$720,000 Last sold price
5 beds2.5 baths3,157 sq ft
1932 Ferguson Loop, Chesapeake, VA 23322
$64/sq ft
smaller lot
47 years newer
SOLD JUN 16, 2026
$875,000 Last sold price
4 beds2.5 baths2,885 sq ft
3341 Country Mill Run, Chesapeake, VA 23322
$11/sq ft
smaller lot
15 years newer
SOLD MAR 10, 2026
$1,075,000 Last sold price
4 beds3.5 baths3,901 sq ft
1621 Water View Cir, Chesapeake, VA 23322
$16/sq ft
smaller lot
35 years newer

Rental earnings

Est. $2,861 per month, based on comparable rentals

Tour for free, no strings attached

Make a winning offer with the help of a local agent

Ask a question

Nearby similar homes

$410,000

4 beds2 baths1,607 sq ft

2728 Blacksmith Trl, Chesapeake, VA 23322

3D WALKTHROUGH

$649,900

6 beds2.5 baths3,369 sq ft

568 Waters Rd, Chesapeake, VA 23322

$699,900

5 beds3 baths2,800 sq ft

1021 Mimi Ct, Chesapeake, VA 23322

LISTED BY REDFIN3D WALKTHROUGH

$630,000

4 beds2.5 baths2,681 sq ft

2101 Beeblossom Ln, Chesapeake, VA 23323

NEW CONSTRUCTION3D WALKTHROUGH

$609,000

5 beds3 baths2,600 sq ft

789 Caddie St, Chesapeake, VA 23322

3D WALKTHROUGH

$620,000

4 beds2.5 baths3,014 sq ft

609 Edgewood Arch, Chesapeake, VA 23322

New listings for sale in 23322

NEW 1 HR AGO

$425,000

3 beds2 baths2,051 sq ft

844 Jo Anne Cir, Chesapeake, VA 23322

NEW 1 HR AGO

$614,000

4 beds2.5 baths2,445 sq ft

1912 Merano Ln, Chesapeake, VA 23322

COMING SOON

$589,900

4 beds2.5 baths2,806 sq ft

305 Sherwood Forest Rd, Chesapeake, VA 23322

FOR SALE BY OWNER

$599,900

4 beds2.5 baths2,150 sq ft

924 Whisper Hollow Dr, Chesapeake, VA 23322

COMING SOON

$1,500,000

6 beds3.5 baths7,155 sq ft

1120 Kathleen Ln, Chesapeake, VA 23322

3D WALKTHROUGH

$555,000

3 beds2.5 baths2,351 sq ft

316 Middleton Way, Chesapeake, VA 23322

3D WALKTHROUGH

$879,000

4 beds3 baths3,000 sq ft

517 New Zealand Reach, Chesapeake, VA 23322

$724,900

4 beds2.5 baths3,640 sq ft

801 Aston Pl, Chesapeake, VA 23322

$1,699,000

4 beds3.5 baths3,224 sq ft

3959 Bunch Walnuts Rd, Chesapeake, VA 23322

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.

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

Southern Chesapeake homes for sale
Pleasant Grove homes for sale

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

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 1908 Benefit Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 1908 Benefit Rd

Nearby similar homes

New listings for sale in 23322

More real estate resources