OFF MARKET

Off Market Jun 2021 for $304K

$442,479

Est. refi paymentEst. refi $2,203/mo

•

2,623

sq ft

1050 Chester Rd, Winston Salem, NC 27104

About this home

Single-familyProperty Type

1964Year Built

0.48 acresLot Size

$169Est. Price/Sq.Ft.

1 car garageParking

Listed by Stephen Lawing • Leonard Ryden Burr Real Estate

Bought with Sheila Mays • Mays Gibson Inc

Redfin checked: 2 minutes ago

•Source:Triad MLS #1020644

Redfin Estimate

$442,479

$138K since sold in June 2021$5,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 1% lower than the average sale price ($447K) of 6 comparable homes.

SOLD SEP 3, 2026
$638,560
A
4 beds2 baths2,720 sq ft
701 Longbow Rd, Winston Salem, NC 27104
SOLD AUG 17, 2026
$270,000
B
3 beds2 baths2,510 sq ft
3533 Woodmere Pl, Winston Salem, NC 27106
SOLD SEP 4, 2026
$530,000
C
4 beds3 baths2,832 sq ft
1030 Yorkshire Rd, Winston Salem, NC 27106
SOLD JUN 16, 2026
$519,000
D
4 beds2 baths3,031 sq ft
640 Quarterstaff Rd, Winston Salem, NC 27104
SOLD DEC 16, 2025
$450,000
E
4 beds2.5 baths2,613 sq ft
621 Quarterstaff Rd, Winston Salem, NC 27104
SOLD MAY 18, 2026
$275,000
F
3 beds2 baths2,672 sq ft
680 Chester Rd, Winston Salem, NC 27104

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Earn from this home

Sell

$196,996

Est. take-home

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Refinance

Est. cash available

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Rent

$2,433/mo

Redfin rental estimate

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Market trends in 27104, NC

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

98.7%

+0.4% MoM

Median sale price

$353K

$3K MoM

Avg. days on market

34d

1 days MoM

Recently sold homes

149

7 MoM

New listings for sale

COMING SOON
$415,000
3 beds2 baths2,037 sq ft
441 Horace Mann Ave, Winston Salem, NC 27104
NEW 18 HRS AGO
$389,900
3 beds2.5 baths3,000 sq ft
3016 Kinnamon Rd, Winston Salem, NC 27104
NEW 20 HRS AGO
$359,900
3 beds2.5 baths2,456 sq ft
670 Alpine Rd, Winston Salem, NC 27104
COMING SOON
$650,000
5 beds2 baths2,686 sq ft
1612 Lynwood Ave, Winston Salem, NC 27104
3D WALKTHROUGH
$270,000
3 beds3 baths2,165 sq ft
204 Ridgelea Ct, Winston Salem, NC 27104
OPEN SUN, 2PM TO 4PM
$369,900
4 beds2 baths1,940 sq ft
4733 Eastwin Dr, Winston Salem, NC 27104
$345,000
3 beds2 baths1,480 sq ft
5201 Old Plantation Cir, Winston Salem, NC 27104
FOR SALE BY OWNER
$475,000
3 beds3 baths4,068 sq ft
1236 Huntingdon Rd, Winston Salem, NC 27104
OPEN SAT, 1PM TO 3PM
$499,000
2 beds2 baths1,889 sq ft
849 Chester Rd, Winston Salem, NC 27104
$447,900
3 beds2.5 baths2,393 sq ft
401 Wind Haven Ln, Winston Salem, NC 27104
See all

Provided by Redfin

Sale history for 1050 Chester Rd

Year

Property tax

Land + Additions

Assessment*

2025

$4,256 (−6.7%)

$72,500 + $313,600

$386,100

2024

$4,561 (+32.0%)

$60,000 + $265,100

$325,100

2022

$3,454 (+3.5%)

2021

$3,338 (+1.2%)

$60,000 + $198,700

$258,700

2020

$3,299 (−0.7%)

$52,500 + $186,400

$238,900

2019

$3,323 (+5.3%)

$52,500 + $186,400

$238,900

2018

$3,156

$52,500 + $186,400

$238,900

2017

$3,156 (+0.7%)

$52,500 + $186,400

$238,900

2016

$3,133 (+1.6%)

$52,500 + $186,400

$238,900

2015

$3,085 (+3.1%)

$55,000 + $183,113

$238,113

2014

$2,992

$55,000 + $183,113

$238,113

Tax history for 1050 Chester Rd

Year

Property tax

Land + Additions

Assessment*

2025

$4,256 (−6.7%)

$72,500 + $313,600

$386,100

2024

$4,561 (+32.0%)

$60,000 + $265,100

$325,100

2022

$3,454 (+3.5%)

2021

$3,338 (+1.2%)

$60,000 + $198,700

$258,700

2020

$3,299 (−0.7%)

$52,500 + $186,400

$238,900

2019

$3,323 (+5.3%)

$52,500 + $186,400

$238,900

2018

$3,156

$52,500 + $186,400

$238,900

2017

$3,156 (+0.7%)

$52,500 + $186,400

$238,900

2016

$3,133 (+1.6%)

$52,500 + $186,400

$238,900

2015

$3,085 (+3.1%)

$55,000 + $183,113

$238,113

2014

$2,992

$55,000 + $183,113

$238,113

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Zoning

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

0.48 Acres

Year renovated

1995

Sq. Ft.

2,073

Year built

1964

Style

Single Family Residential

County

Forsyth County

APN

6816011880

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 17, 2026.

RS9

Residential Single Family District

The RS-9 District is primarily intended to accommodate relatively high density single family detached dwellings in urban areas.; This district is intended for application in GMAs 2 and 3 and may be suitable in Metro Activity Centers where public facilities, including public water and sewer, public roads, parks, and other governmental support services, are available.

Permitted uses

Include but are not limited to:

Livestock production
Religious facility
Housing-Group
Housing-Single unit
Fire house
Police station
Recreation
Agriculture-Cropland

Property details

Parking

Parking / Garage Information
# of Garage Spaces: 1
Garage Description: Lower Level Garage
Parking Features: Driveway, Garage

Interior

Bathroom Information
# of Bathrooms (Full): 2
# of Bathrooms (1/2): 1

Basement Information
Basement YN: No
Basement: Partial

Room Information
# of Rooms: 14

Interior Features
Attic Description: Access Only
Flooring: Carpet, Vinyl

Exterior

Exterior Features
Other Equipment: Intercom
Fencing: None

Pool Information
Pool Features: None

Lot Information
Lot Features: City Lot, Near Public Transit, Level, Subdivided
Lot Size Acres: 0.48
Miscellaneous: Public Transportation Nearby

Land Information
Land Description: Flat, Subdivision
Water Source: Public

Property Information
Property Type: Residential
Property Sub Type: Stick/Site Built
Structure Type: House
Built Information: Existing
Year Built: 1964
# of Fireplaces: 1
Fireplace Features: Basement
Appliances: Electric Water Heater

Building Information
Building Area Total: 2,623
Levels: Multi/Split
Construction Materials: Brick, Wood Siding

Financial

Tax Information
Tax Annual Amount: $3,298.97

Utilities

Utility Information
Sewer: Public Sewer
Water Heater: Electric

Heating & Cooling
Cooling: Central Air, Zoned
Heating: Hot Water, Fireplace(s), Oil
Heating Fuel: Oil

Location

HOA Information
Association: Winston-Salem
Association YN: No

Location Details
Directions: From Robinhood Rd headed west from WS. Turn left on Peacehaven then right on Chester. Home is on the left.

Community Information
Subdivision Name: Sherwood Forest

Public facts

Beds: 5
Baths: 2.5
Sq. Ft.: 2,073
Stories: 1.0
Lot Size: 0.48 acres
Style: Single Family Residential
Year Built: 1964
Year Renovated: 1995
County: Forsyth County
APN: 6816011880

Home facts updated by county records on Aug 17, 2026

Around this home

Schools

Jefferson Elementary

Public PreK-5 • Assigned • 1.9mi

9/10

Jefferson Middle

Public 6-8 • Assigned • 0.4mi

7/10

Mount Tabor High

Public 9-12 • Assigned • 1.1mi

4/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

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

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 102° expected this year, 17 days in 30 years

4/10 Wind Factor

8% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Winston Salem, NC • 27104

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9 hours in June and 5.1 hours in December, which is comparable to the U.S. average for solar exposure.

9 hrs

5.1 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$421,000 – $509,000

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Nearby similar homes

$1,500,000

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3 beds1.5 baths1,640 sq ft

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155 Monroe St, Winston Salem, NC 27104

3D WALKTHROUGH

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3443 Scarsborough Dr, Winston Salem, NC 27104

3D WALKTHROUGH

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OPEN SAT, 1PM TO 3PM3D WALKTHROUGH

$499,000

2 beds2 baths1,889 sq ft

849 Chester Rd, Winston Salem, NC 27104

New listings for sale in 27104

COMING SOON

$415,000

3 beds2 baths2,037 sq ft

441 Horace Mann Ave, Winston Salem, NC 27104

NEW 18 HRS AGO

$389,900

3 beds2.5 baths3,000 sq ft

3016 Kinnamon Rd, Winston Salem, NC 27104

NEW 20 HRS AGO

$359,900

3 beds2.5 baths2,456 sq ft

670 Alpine Rd, Winston Salem, NC 27104

COMING SOON

$650,000

5 beds2 baths2,686 sq ft

1612 Lynwood Ave, Winston Salem, NC 27104

3D WALKTHROUGH

$270,000

3 beds3 baths2,165 sq ft

204 Ridgelea Ct, Winston Salem, NC 27104

OPEN SUN, 2PM TO 4PM

$369,900

4 beds2 baths1,940 sq ft

4733 Eastwin Dr, Winston Salem, NC 27104

$345,000

3 beds2 baths1,480 sq ft

5201 Old Plantation Cir, Winston Salem, NC 27104

FOR SALE BY OWNER

$475,000

3 beds3 baths4,068 sq ft

1236 Huntingdon Rd, Winston Salem, NC 27104

OPEN SAT, 1PM TO 3PM

$499,000

2 beds2 baths1,889 sq ft

849 Chester Rd, Winston Salem, NC 27104

Home values near 1050 Chester Rd

Data from public records.

Address	Redfin Estimate
1101 Chester Road, Winston Salem, NC 5 Beds \| 3.5 Baths \| 4020 Sq. Ft.	$755,465
1020 Chester Road, Winston Salem, NC 5 Beds \| 4 Baths \| 4026 Sq. Ft.	$687,287

Address	Redfin Estimate
1121 Chester Road, Winston Salem, NC 3 Beds \| 2.5 Baths \| 1980 Sq. Ft.	$338,590
1000 Chester Road, Winston Salem, NC 3 Beds \| 2.5 Baths \| 3094 Sq. Ft.	$517,338

Address	Redfin Estimate
1111 Chester Road, Winston Salem, NC 4 Beds \| 2.5 Baths \| 2794 Sq. Ft.	$455,808
1040 Chester Road, Winston Salem, NC 4 Beds \| 3 Baths \| 3120 Sq. Ft.	$527,362

Property information provided by Triad MLS when last listed in 2021. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 27104, NC

Sale history for 1050 Chester Rd

Tax history for 1050 Chester Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 27104

Home values near 1050 Chester Rd

More real estate resources