OFF MARKET

Off Market Oct 2016 for $449K

$770,582

Est. refi paymentEst. refi $3,491/mo

•

4,020

sq ft

1101 Chester Rd, Winston Salem, NC 27104

About this home

Beautifully renovated classic Sherwood Forest home on lovely street. Custom kitchen with white cabinetry, honed granite, Thermador appliances and huge work island opens to breakfast and family room with fireplace and built-in bookshelves. Hardwood floors throughout. Lots of large windows make for bright and sunny elegant formal rooms. Fenced backyard with mature plantings, brick patio and deck. Two car carport. All above ground square footage. This one is just perfect!

Single-familyProperty Type

1964Year Built

0.46 acresLot Size

$192Est. Price/Sq.Ft.

2 car garageParking

Listed by Molly Haus • Leonard Ryden Burr Real Estate

Bought with Julie Carter • Leonard Ryden Burr Real Estate

Redfin checked: 2 minutes ago

•Source:Triad MLS #788862

Redfin Estimate

$770,582

$322K since sold in October 2016$8,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 26.3% higher than the average sale price ($610K) of 6 comparable homes.

SOLD MAY 1, 2026
$560,950
A
4 beds3.5 baths3,030 sq ft
3750 Kirklees Rd, Winston Salem, NC 27104
SOLD AUG 6, 2026
$630,000
B
3 beds3 baths3,739 sq ft
440 Sherwood Forest Rd, Winston Salem, NC 27104
SOLD JAN 13, 2026
$582,000
C
4 beds4 baths4,236 sq ft
1147 Strathmore Cir, Winston Salem, NC 27104
SOLD MAR 25, 2026
$537,000
D
4 beds3 baths3,193 sq ft
731 Quarterstaff Rd, Winston Salem, NC 27104
SOLD MAY 22, 2026
$742,000
E
4 beds3 baths3,084 sq ft
3380 Kirklees Rd, Winston Salem, NC 27104
SOLD JUL 3, 2026
$610,000
F
5 beds4 baths3,570 sq ft
4751 Blair Ct, Winston Salem, NC 27104

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Earn from this home

Sell

$441,266

Est. take-home

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Refinance

Est. cash available

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Rent

$3,306/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

98.4%

0.2% 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

$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
COMING SOON
$219,000
2 beds2 baths1,130 sq ft
113 Pebble Ridge Ln, Winston Salem, NC 27104
OPEN SUN, 2PM TO 4PM
$689,000
3 beds2.5 baths2,500 sq ft
185 Westhaven Cir, Winston Salem, NC 27104
OPEN THU, 4PM TO 6PM
$274,900
3 beds2 baths1,524 sq ft
103 Briar Ridge Cir, Winston Salem, NC 27104
$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
$250,000
3 beds2 baths1,557 sq ft
4816 Tiffany Ave, Winston Salem, NC 27104
$465,000
4 beds2.5 baths2,850 sq ft
5645 Stone Crossing Dr, Winston Salem, NC 27104
$775,000
3 beds2.5 baths2,627 sq ft
3420 Meridian Way, Winston Salem, NC 27104
See all

Provided by Redfin

Sale history for 1101 Chester Rd

Date

Event

Price

Triad MLS #788862

Oct 24, 2016

Sold

$449,000

$112/sq ft

Aug 16, 2016

Pending

—

Aug 2, 2016

Price Changed

$449,900

$112/sq ft

May 16, 2016

Price Changed

$459,900

$114/sq ft

Mar 30, 2016

Listed

$465,000

$116/sq ft

Triad MLS #701211

May 14, 2014

Sold

$440,000

$109/sq ft

Mar 24, 2014

Listed

$460,000

$114/sq ft

+11

Incredible opportunity in Sherwood Forest. Beautifully renovated throughout with impeccable attention to detail. Gorgeous remodeled kitchen w/ custom inset cabinets, Thermador appliances, honed granite, center island. Huge rooms w/ gracious flow - large open kitchen, breakfast, den area w/ French doors to private backyard, brick patio & newly built deck. ML Master BR suite also opens to deck. Hardwoods throughout ML. Recent paint, A/C, water heater. All above grade SF. Truly stunning, a classic!

Public Records

May 24, 2010

Sold

$352,500

$88/sq ft

Public Records

Jul 31, 1997

Sold

$322,000

$80/sq ft

Public Records

Jun 19, 1989

Sold

$269,500

$67/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$7,434 (+20.1%)

$72,500 + $602,000

$674,500

2024

$6,191 (+6.8%)

$60,000 + $381,300

$441,300

2022

$5,798 (+1.8%)

$60,000 + $381,300

$441,300

2021

$5,694 (+2.7%)

$60,000 + $381,300

$441,300

2020

$5,542 (−0.7%)

$52,500 + $348,800

$401,300

2019

$5,582 (+5.3%)

$52,500 + $348,800

$401,300

2018

$5,301

$52,500 + $348,800

$401,300

2017

$5,301 (+8.6%)

$52,500 + $348,800

$401,300

2016

$4,881 (+1.6%)

$52,500 + $348,800

$401,300

2015

$4,806

$55,000 + $315,858

$370,858

Tax history for 1101 Chester Rd

Year

Property tax

Land + Additions

Assessment*

2025

$7,434 (+20.1%)

$72,500 + $602,000

$674,500

2024

$6,191 (+6.8%)

$60,000 + $381,300

$441,300

2022

$5,798 (+1.8%)

$60,000 + $381,300

$441,300

2021

$5,694 (+2.7%)

$60,000 + $381,300

$441,300

2020

$5,542 (−0.7%)

$52,500 + $348,800

$401,300

2019

$5,582 (+5.3%)

$52,500 + $348,800

$401,300

2018

$5,301

$52,500 + $348,800

$401,300

2017

$5,301 (+8.6%)

$52,500 + $348,800

$401,300

2016

$4,881 (+1.6%)

$52,500 + $348,800

$401,300

2015

$4,806

$55,000 + $315,858

$370,858

*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

3.5

Stories

1.5

Lot width

—

Lot depth

—

Lot size

0.46 Acres

Year renovated

1997

Sq. Ft.

4,020

Year built

1964

Style

Single Family Residential

County

Forsyth County

APN

6816020043

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 Carport
Parking Features: Driveway, Attached Carport

Interior

Bathroom Information
# of Bathrooms (Full): 3
# of Bathrooms (1/2): 1

Basement Information
Basement YN: No
Basement: Crawl Space

Room Information
# of Rooms: 10

Interior Features
Has Primary On Main
Flooring: Carpet, Tile, Wood
Interior Features: Built-in Features, Dead Bolt(s), Kitchen Island, Pantry

Exterior

Exterior Features
Fencing: Fenced

Lot Information
Lot Size Acres: 0.46
Lot Size Dimensions: 135 x 129 x 28 x 115 x 150
Miscellaneous: Cable

Land Information
Water Source: Public

Property Information
Property Type: Residential
Property Sub Type: Stick/Site Built
Structure Type: House
Built Information: Existing
Year Built: 1964
Other Structures: Storage
# of Fireplaces: 1
Fireplace Features: Den
Appliances: Built-in Range, Dishwasher, Disposal, Double Oven, Exhaust Fan, Gas Water Heater
Laundry Features: Dryer Connection, Main Level, Washer Hookup
Security Features: Security Lights, Smoke Detector(s)

Building Information
Building Area Total: 4,020
Levels: One and One Half
Construction Materials: Brick

Financial

Tax Information
Tax Annual Amount: $4,881.05

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: No

School / Neighborhood
Elementary School: Call School Board
Middle Or Junior School: Call School Board
High School: Call School Board

Location Details
Directions: Stratford Road to Robinhood, left on Peacehaven, Right on Chester.

Community Information
Subdivision Name: Sherwood Forest

Public facts

Beds: 5
Baths: 3.5
Sq. Ft.: 4,020
Stories: 1.5
Lot Size: 0.46 acres
Style: Single Family Residential
Year Built: 1964
Year Renovated: 1997
County: Forsyth County
APN: 6816020043

Home facts updated by county records on Aug 17, 2026

Around this home

Schools

Jefferson Elementary

Public PreK-5 • Assigned • 1.8mi

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

$733,000 – $887,000

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Nearby similar homes

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3D WALKTHROUGH

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3D WALKTHROUGH

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New listings for sale in 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

COMING SOON

$219,000

2 beds2 baths1,130 sq ft

113 Pebble Ridge Ln, Winston Salem, NC 27104

OPEN SUN, 2PM TO 4PM

$689,000

3 beds2.5 baths2,500 sq ft

185 Westhaven Cir, Winston Salem, NC 27104

OPEN THU, 4PM TO 6PM

$274,900

3 beds2 baths1,524 sq ft

103 Briar Ridge Cir, Winston Salem, NC 27104

$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

$250,000

3 beds2 baths1,557 sq ft

4816 Tiffany Ave, Winston Salem, NC 27104

$465,000

4 beds2.5 baths2,850 sq ft

5645 Stone Crossing Dr, Winston Salem, NC 27104

Home values near 1101 Chester Rd

Data from public records.

Address	Redfin Estimate
1121 Chester Road, Winston Salem, NC 3 Beds \| 2.5 Baths \| 1980 Sq. Ft.	$344,610
1030 Chester Road, Winston Salem, NC 4 Beds \| 3.5 Baths \| 3805 Sq. Ft.	$611,773

Address	Redfin Estimate
1111 Chester Road, Winston Salem, NC 4 Beds \| 2.5 Baths \| 2794 Sq. Ft.	$468,330
1100 Chester Road, Winston Salem, NC 4 Beds \| 2.5 Baths \| 3214 Sq. Ft.	$477,696

Address	Redfin Estimate
1040 Chester Road, Winston Salem, NC 4 Beds \| 3 Baths \| 3120 Sq. Ft.	$538,495
1050 Chester Road, Winston Salem, NC 5 Beds \| 2.5 Baths \| 2623 Sq. Ft.	$439,274

Property information provided by Triad MLS when last listed in 2016. 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 1101 Chester Rd

Tax history for 1101 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 1101 Chester Rd

More real estate resources