OFF MARKET

Off Market Jun 2021 for $485K

$645,163

Est. refi paymentEst. refi $3,597/mo

•

2,760

sq ft

1291 Chester Rd, Winston Salem, NC 27104

About this home

Extraordinary 1-level home with no steps. Custom built. Impeccably maintained. Many unique features. Oversized living room with gas log fireplace and nice built-ins. Master bedroom has study and sitting areas. Beautiful sunroom off living room opens to different decks, one with hot tub. Formal dining room with tray ceiling. Dining/kitchen totally renovated 2014 with granite, ceramic tile, stainless steel appliances. Screened porch and grilling deck off kitchen. Lots of chair rail, crown and picture moulding. Permanent steps in attached garage leads to 515 sq feet of stand-up storage space. Very level, .55 acre lot. Walk to Glenridge pool.

Single-familyProperty Type

1987Year Built

0.55 acresLot Size

$234Est. Price/Sq.Ft.

2 car garageParking

Listed by George Munford • Berkshire Hathaway HomeServices Carolinas Realty

Bought with Ronda Cooper • Allen Tate Winston Salem-Hanes Mall Blvd

Redfin checked: 2 minutes ago

•Source:Triad MLS #1020696

Redfin Estimate

$645,163

$160K since sold in June 2021$2,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 28% higher than the average sale price ($504K) of 6 comparable homes.

SOLD AUG 26, 2026
$777,000
A
3 beds2 baths2,612 sq ft
1275 Thornhill Ln, Winston Salem, NC 27106
SOLD AUG 17, 2026
$270,000
B
3 beds2 baths2,510 sq ft
3533 Woodmere Pl, Winston Salem, NC 27106
SOLD JUN 17, 2026
$448,000
C
3 beds2 baths2,476 sq ft
820 Woodcrest Dr, Winston Salem, NC 27104
SOLD AUG 26, 2026
$495,000
D
3 beds3 baths3,048 sq ft
4109 Allistair Rd, Winston Salem, NC 27104
SOLD JUN 18, 2026
$549,000
E
3 beds3 baths2,633 sq ft
3807 Dewsbury Rd, Winston Salem, NC 27104
SOLD JUN 30, 2026
$485,000
F
3 beds2 baths2,377 sq ft
1156 Huntingdon Rd, Winston Salem, NC 27104

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Earn from this home

Sell

$258,046

Est. take-home

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Refinance

Est. cash available

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Rent

$2,801/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

$350K

$2K MoM

Avg. days on market

34d

0 days MoM

Recently sold homes

144

4 MoM

New listings for sale

$219,000
2 beds2 baths1,130 sq ft
113 Pebble Ridge Ln, Winston Salem, NC 27104
NEW 12 HRS AGO
$575,000
3 beds2.5 baths2,042 sq ft
136 Lawndale Dr, Winston Salem, NC 27104
OPEN SUN, 2PM TO 4PM
$395,000
3 beds2.5 baths2,145 sq ft
1610 W First St, Winston Salem, NC 27104
3D WALKTHROUGH
$250,000
3 beds2.5 baths1,393 sq ft
420 Herndon Dr, Winston Salem, NC 27104
$215,000
2 beds1 bath814 sq ft
710 N Avalon Rd, Winston-Salem, NC 27104
$699,000
3 beds2.5 baths3,356 sq ft
311 Muirfield Dr, Winston Salem, NC 27106
OPEN SUN, 2PM TO 4PM
$689,000
3 beds2.5 baths2,500 sq ft
185 Westhaven Cir, Winston Salem, NC 27104
OPEN TODAY, 4PM TO 6PM
$274,900
3 beds2 baths1,524 sq ft
103 Briar Ridge Cir, Winston Salem, NC 27104
OPEN SAT, 2PM TO 4PM
$147,500
1 bed1 bath920 sq ft
128 Cedar Lake Trl, Winston Salem, NC 27104
$649,900
4 beds3 baths3,563 sq ft
719 Quarterstaff Rd, Winston Salem, NC 27104
See all

Provided by Redfin

Sale history for 1291 Chester Rd

Year

Property tax

Land + Additions

Assessment*

2025

$6,634 (+3.7%)

$95,000 + $506,900

$601,900

2024

$6,398 (+6.8%)

$82,000 + $374,100

$456,100

2022

$5,992 (+16.1%)

$82,000 + $374,100

$456,100

2021

$5,163 (+0.5%)

$82,000 + $374,100

$456,100

2020

$5,136 (−0.7%)

$70,000 + $301,900

$371,900

2019

$5,173 (+5.3%)

$70,000 + $301,900

$371,900

2018

$4,912

$70,000 + $301,900

$371,900

2017

$4,912 (+5.6%)

$70,000 + $301,900

$371,900

2016

$4,650 (+2.4%)

$70,000 + $301,900

$371,900

2015

$4,543 (+3.1%)

$65,000 + $288,391

$353,391

2014

$4,406

$65,000 + $285,617

$350,617

Tax history for 1291 Chester Rd

Year

Property tax

Land + Additions

Assessment*

2025

$6,634 (+3.7%)

$95,000 + $506,900

$601,900

2024

$6,398 (+6.8%)

$82,000 + $374,100

$456,100

2022

$5,992 (+16.1%)

$82,000 + $374,100

$456,100

2021

$5,163 (+0.5%)

$82,000 + $374,100

$456,100

2020

$5,136 (−0.7%)

$70,000 + $301,900

$371,900

2019

$5,173 (+5.3%)

$70,000 + $301,900

$371,900

2018

$4,912

$70,000 + $301,900

$371,900

2017

$4,912 (+5.6%)

$70,000 + $301,900

$371,900

2016

$4,650 (+2.4%)

$70,000 + $301,900

$371,900

2015

$4,543 (+3.1%)

$65,000 + $288,391

$353,391

2014

$4,406

$65,000 + $285,617

$350,617

*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

Stories

Lot width

—

Lot depth

—

Lot size

0.55 Acres

Year renovated

1994

Sq. Ft.

2,895

Year built

1987

Style

Single Family Residential

County

Forsyth County

APN

6806810808

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: 2
Garage Description: Attached Garage
Parking Features: Driveway, Garage, Paved, On Street, Garage Door Opener, Attached

Interior

Bathroom Information
# of Bathrooms (Full): 2
# of Bathrooms (1/2): 0

Basement Information
Basement YN: No
Basement: Crawl Space

Room Information
# of Rooms: 8

Interior Features
Has Primary On Main
Attic Description: Floored Attic, Permanent Stairs, Walk in Attic
Energy Features: Insulated Windows
Flooring: Carpet, Laminate, Tile
Interior Features: Built-in Features, Ceiling Fan(s), Dead Bolt(s), Soaking Tub, Pantry, Separate Shower, Wet Bar

Exterior

Exterior Features
Exterior Features: Lighting, Dog Run, Garden

Pool Information
Pool Features: Community

Lot Information
Lot Number: 113
Lot Features: City Lot, Cul-De-Sac, Level, Partially Wooded
Lot Size Acres: 0.55
Lot Size Dimensions: 50 x 233.63 x 212.29 x 172.74

Land Information
Land Description: Cul-De-Sac, Level, Partially Wooded
Water Source: Public

Property Information
Property Type: Residential
Property Sub Type: Stick/Site Built
Structure Type: House
Built Information: Existing
Year Built: 1987
# of Fireplaces: 1
Fireplace Features: Gas Log, Living Room
Appliances: Microwave, Oven, Built-in Range, Dishwasher, Disposal, Exhaust Fan, Gas Water Heater
Laundry Features: Dryer Connection, Main Level, Washer Hookup

Building Information
Building Area Total: 2,760
Foundation Details: Slab
Levels: One
Construction Materials: Brick, Vinyl Siding

Financial

Tax Information
Tax Annual Amount: $5,135.57

Utilities

Utility Information
Sewer: Public Sewer
Water Heater: Gas

Heating & Cooling
Cooling: Central Air, Zoned
Heating: Forced Air, Zoned, Natural Gas
Heating Fuel: Natural Gas

Location

HOA Information
Association: Winston-Salem
Association YN: Yes
Association Fee: $550
Association Fee Frequency: Annually

Location Details
Directions: West on Robinhood Road. Left on Peacehaven. Right on Chester. All the way to the end.

Community Information
Subdivision Name: Glenridge

Public facts

Beds: 3
Baths: 2.0
Sq. Ft.: 2,895
Stories: 1.0
Lot Size: 0.55 acres
Style: Single Family Residential
Year Built: 1987
Year Renovated: 1994
County: Forsyth County
APN: 6806810808

Home facts updated by county records on Aug 17, 2026

Around this home

Schools

Jefferson Elementary

Public PreK-5 • Assigned • 1.5mi

9/10

Jefferson Middle

Public 6-8 • Assigned • 0.5mi

7/10

Mount Tabor High

Public 9-12 • Assigned • 1.3mi

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

$613,000 – $742,000

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Nearby similar homes

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3D WALKTHROUGH

$378,900

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New listings for sale in 27104

$219,000

2 beds2 baths1,130 sq ft

113 Pebble Ridge Ln, Winston Salem, NC 27104

NEW 12 HRS AGO

$575,000

3 beds2.5 baths2,042 sq ft

136 Lawndale Dr, Winston Salem, NC 27104

OPEN SUN, 2PM TO 4PM

$395,000

3 beds2.5 baths2,145 sq ft

1610 W First St, Winston Salem, NC 27104

3D WALKTHROUGH

$250,000

3 beds2.5 baths1,393 sq ft

420 Herndon Dr, Winston Salem, NC 27104

$215,000

2 beds1 bath814 sq ft

710 N Avalon Rd, Winston-Salem, NC 27104

$699,000

3 beds2.5 baths3,356 sq ft

311 Muirfield Dr, Winston Salem, NC 27106

OPEN SUN, 2PM TO 4PM

$689,000

3 beds2.5 baths2,500 sq ft

185 Westhaven Cir, Winston Salem, NC 27104

OPEN TODAY, 4PM TO 6PM

$274,900

3 beds2 baths1,524 sq ft

103 Briar Ridge Cir, Winston Salem, NC 27104

OPEN SAT, 2PM TO 4PM

$147,500

1 bed1 bath920 sq ft

128 Cedar Lake Trl, Winston Salem, NC 27104

Home values near 1291 Chester Rd

Data from public records.

Address	Redfin Estimate
1250 Chester Road, Winston Salem, NC 4 Beds \| 3.5 Baths \| 3625 Sq. Ft.	$649,537
1280 Chester Road, Winston Salem, NC 4 Beds \| 2.5 Baths \| 2886 Sq. Ft.	$590,593

Address	Redfin Estimate
1270 Chester Road, Winston Salem, NC 4 Beds \| 4 Baths \| 3938 Sq. Ft.	$642,511
1271 Chester Road, Winston Salem, NC 4 Beds \| 3.5 Baths \| 3130 Sq. Ft.	$596,541

Address	Redfin Estimate
1260 Chester Road, Winston Salem, NC 4 Beds \| 4 Baths \| 3807 Sq. Ft.	$670,393
1281 Chester Road, Winston Salem, NC 5 Beds \| 5 Baths \| 4748 Sq. Ft.	$817,807

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 1291 Chester Rd

Tax history for 1291 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 1291 Chester Rd

More real estate resources