CONTINGENT

Contingent

$499,000

Est. $3,204/mo —

•

1,889

sq ft

849 Chester Rd, Winston Salem, NC 27104

About this home

Charming brick ranch in the highly sought-after Sherwood Forest! Situated on approximately a half an acre, this home offers character, flexible living space & a beautiful outdoor setting. The distinctive painted brick exterior gives the home a fresh, inviting personality. Enjoy the new patio, newly landscaped backyard & new fence. Inside, the main level features a welcoming living room w/built-ins, dining area & a bright sunroom. Two bedrooms on the main level w/additional unheated flexible spaces in the basement that remain comfortable year-round including a den, office & extra storage area that provide plenty of possibilities for expansion. A circle driveway & two-car carport provide abundant parking & easy access to the home. A whole-house generator adds peace of mind. Located close to shopping, dining, parks & everything Winston-Salem has to offer. A home w/character, flexibility & a beautiful setting that is ready for its next owner! Check out the 3D online tour.

Single-familyProperty Type

1956Year Built

0.56 acresLot Size

$264Price/Sq.Ft.

2 car garageParking

Listed by Carol Milligan • Howard Hanna Allen Tate High Point

Listing updated: Oct 20, 2026 at 01:09am

Redfin checked: a minute ago

•Source:Triad MLS #1235103

Payment calculator

$3,204 per month

Principal and interest$2,723

Property taxes

$356

HOA dues

Home insurance

$125

Utilities

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Affordability tools

Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN SAT, 10AM TO 12PM
$339,000
3 beds2 baths2,314 sq ft
2640 Amesbury Rd, Winston Salem, NC 27103
0.45 acre lot • 2 garage spots • Built 1970
OPEN SAT, 1PM TO 5PM
$318,000
4 beds2 baths1,764 sq ft
4703 Mount Hope Dr, Winston Salem, NC 27107
6,969 sq ft lot • 2 garage spots • Built 2026
OPEN SAT, 2PM TO 4PM
$309,500
3 beds2 baths1,484 sq ft
1009 Chockecherry Ln, Lewisville, NC 27023
0.26 acre lot • Garage • Built 1987
OPEN SUN, 1PM TO 3PM3D WALKTHROUGH
$749,000
4 beds3.5 baths3,764 sq ft
225 Heatherwood Dr, Winston Salem, NC 27107
0.46 acre lot • 3 garage spots • Pool
OPEN SUN, 2PM TO 4PM
$398,500
3 beds2 baths2,010 sq ft
261 Kingsmill Dr, Advance, NC 27006
0.3 acre lot • 2 garage spots • Built 1995
OPEN SUN, 2PM TO 4PM
$255,000
3 beds2.5 baths1,351 sq ft
1491 Wakefield Farm Ln, Kernersville, NC 27284
5,227 sq ft lot • Garage • Built 2010
OPEN SUN, 2PM TO 4PM
$509,000
4 beds3.5 baths3,136 sq ft
3415 Willow Wind Dr, Pfafftown, NC 27040
0.3 acre lot • 2 garage spots • Built 1993
OPEN SUN, 2PM TO 4PM
$255,000
2 beds2.5 baths1,237 sq ft
1694 Granby Heights Dr, Winston Salem, NC 27103
$175 HOA • Built 2024
OPEN SUN, 2PM TO 4PM
$325,000
3 beds2.5 baths2,323 sq ft
427 Summergate Dr, Winston Salem, NC 27103
5,662 sq ft lot • 2 garage spots • Pool
OPEN SUN, 2PM TO 4PM3D WALKTHROUGH
$272,000
3 beds2 baths1,379 sq ft
4751 Eagle Path, Winston Salem, NC 27127
9,147 sq ft lot • 2 garage spots • Built 2004

Around this home

Schools

K - 12
Preschool & daycare

Sherwood Forest Elementary

Public PreK-5 • Assigned • 0.4mi

9/10

Jefferson Middle

Public 6-8 • Assigned • 0.5mi

7/10

Mount Tabor High

Public 9-12 • Assigned • 1.2mi

4/10

Provided by GreatSchools

About Old Sherwood

Forest

Old Sherwood Forest, located between Reynolda Road and Silas Creek Parkway, is a residential and historic Winston-Salem neighborhood with winding streets and mid-century architecture. The character concentrates around the Reynolda Road corridor near the Reynolda Village shops, where brick storefronts, galleries, and cafe patios set a polished, walkable rhythm. Architectural lines lean toward ranches and split-levels under mature trees, with a quiet, established streetscape. Reynolda House Museum of American Art and the Southeastern Center for Contemporary Art anchor the cultural calendar nearby. Reynolda Gardens adds a landscaped, seasonal backdrop for afternoon loops. Wake Forest University edges the area with collegiate energy and green space.

Provided by Walk Score and Local Logic

Market insights

849 Chester Rd · $499,000

DAYS ON MARKET

The average home goes pending in 49 days.

SALE-TO-LIST

Most homes are selling 2% below list price.

LIST PRICE

Median sale price in this area is $314,350. (37% lower than this home)

PRICE DROP

27% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Built-in features
Ceiling fans
Deadbolts
Separate shower
Solid surface counters
Floored attic with pull-down stairs
Gas-log fireplace in the living room

Bedrooms
Primary bedroom on the main level

Bathrooms
2 full bathrooms

Kitchen
Pantry
Oven
Dishwasher
Garbage disposal
Gas cooktop
Range hood

Laundry & utility
Washer hookup and dryer connection in the basement
Gas water heater

Flooring
Tile
Wood

Heating & cooling
Forced-air heating with natural gas
Central air conditioning

Sale and tax history for 849 Chester Rd

Sale History
Tax History

Date

Event

Price

Triad MLS #1235103

Oct 8, 2026

Contingent

—

Sep 10, 2026

Listed

$499,000

$264/sq ft

Public Records

Mar 23, 2026

Sold

$485,000

$257/sq ft

Triad MLS #1209600

Mar 23, 2026

Sold

$484,900

$257/sq ft

Mar 17, 2026

Pending

—

Feb 23, 2026

Contingent

—

Feb 19, 2026

Listed

$449,900

$238/sq ft

+29

Welcome to 849 Chester Road, nestled in the highly sought-after Sherwood Forest neighborhood! Designed for comfortable main-level living, this home showcases an inviting open-concept floor plan with seamless flow between the living, dining, and kitchen areas—ideal for both everyday living and effortless entertaining. The spacious primary suite provides a peaceful retreat, while the additional bedrooms offer versatility—perfect for guests, a home office, or flexible living space to suit your needs. While not currently heated or cooled the unfinished basement maintains a comfortable year-round temperature and comes complete with a den, office area, and abundant storage. Step outside to enjoy the large, fenced backyard with an expansive deck—perfect for gatherings, grilling, or relaxing evenings at home. A convenient carport and circular driveway provide ample parking and easy access. For added peace of mind the home is equipped with a Generac generator! Book your showing today!

Triad MLS #1090966

Jan 23, 2023

Sold

$375,000

$199/sq ft

Jan 7, 2023

Pending

—

Dec 3, 2022

Contingent

—

Dec 1, 2022

Listed

$365,000

$193/sq ft

+17

You asked and Santa has delivered early! Don't miss your chance to call this perfectly renovated move-in ready home your very own! The kitchen to living room flows seamlessly - allowing for an entertainers paradise. Grill out on your large deck while watching the game outside or cozy up by the gas logs in your beautiful living room. Built-ins throughout keep the charm and character, while the updates provide the modern flare you've been looking for. This meticulously maintained home has so much to offer including a brand new HVAC, whole house generator, all new windows (2019), fresh paint, etc.. Located in the heart of highly desired Sherwood Forest. Convenient to shopping, restaurants, hospitals and major highways. Please see agent only remarks.

Triad MLS #893349

Aug 10, 2018

Sold

$228,000

$121/sq ft

Jul 31, 2018

Pending

—

Jul 8, 2018

Contingent

—

Jul 2, 2018

Listed

$225,000

$119/sq ft

Public Records

Jul 6, 2016

Sold

$222,000

$118/sq ft

Triad MLS #784843

Jul 6, 2016

Sold

$221,950

$117/sq ft

May 12, 2016

Pending

—

Apr 29, 2016

Price Changed

$229,900

$122/sq ft

Mar 28, 2016

Price Changed

$235,000

$124/sq ft

Feb 24, 2016

Listed

$239,900

$127/sq ft

Public Records

Jun 14, 2012

Sold

$212,000

$112/sq ft

Triad MLS #640001

Jun 14, 2012

Sold

$211,500

$112/sq ft

Apr 13, 2012

Listed

$224,900

$119/sq ft

Public Records

Apr 5, 2011

Sold

$219,000

$116/sq ft

Public Records

Oct 21, 1996

Sold

$112,000

$59/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$4,118 (+7.2%)

$66,000 + $307,600

$373,600

2024

$3,839 (+4.8%)

$62,900 + $210,800

$273,700

2022

$3,664 (+1.8%)

$62,900 + $216,000

$278,900

2021

$3,598 (+23.7%)

$62,900 + $216,000

$278,900

2020

$2,908 (−0.7%)

$62,900 + $147,700

$210,600

2019

$2,929 (+5.3%)

$62,900 + $147,700

$210,600

2018

$2,782 (−7.7%)

$62,900 + $147,700

$210,600

2017

$3,014 (+22.0%)

2016

$2,470 (+1.6%)

2015

$2,432 (+3.1%)

$59,950 + $127,755

$187,705

2014

$2,359

$59,950 + $127,755

$187,705

Public record

Public record
Zoning

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

0.56 Acres

Year renovated

2005

Finished Sq. Ft.

1,596

Unfinished Sq. Ft.

—

Total Sq. Ft.

1,596

Year built

1956

Style

Single Family Residential

County

Forsyth County

APN

6816019200

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 23, 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

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

6 days above 102° expected this year, 16 days in 30 years

4/10 Wind Factor

9% 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

96/ 100

Exceptional sunlight

Sunscore

This home receives average direct sun exposure in Winston Salem. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.6 hrs

6.4 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 849 Chester Rd

$488,650

$10K under list price of $499K

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $310K to $530K.

SOLD OCT 2, 2026
$455,000 Last sold price
3 beds2 baths1,789 sq ft
3371 York Rd, Winston Salem, NC 27106
$10/sq ft
smaller lot
49 years newer
SOLD JUN 30, 2026
$485,000 Last sold price
3 beds2 baths2,377 sq ft
1156 Huntingdon Rd, Winston Salem, NC 27104
$60/sq ft
smaller lot
1 year older
SOLD SEP 29, 2026
$500,000 Last sold price
5 beds3 baths2,608 sq ft
3249 Paddington Ln, Winston Salem, NC 27106
$72/sq ft
smaller lot
2 years newer
SOLD SEP 4, 2026
$530,000 Last sold price
4 beds3 baths2,832 sq ft
1030 Yorkshire Rd, Winston Salem, NC 27106
$77/sq ft
8 years newer
SOLD MAY 1, 2026
$525,000 Last sold price
3 beds3 baths2,882 sq ft
3740 Derbyshire Rd, Winston Salem, NC 27104
$82/sq ft
8 years newer
SOLD JUN 17, 2026
$310,000 Last sold price
3 beds2 baths1,889 sq ft
1245 Peace Haven Rd, Winston Salem, NC 27104
$100/sq ft
smaller lot
1 year older

Rental earnings

Est. $2,072 per month, based on comparable rentals

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(336) 891-9464

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

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Payment calculator

Affordability tools

Open houses

Nearby open houses (10)

Around this home

Schools

Market insights

Property details

Sale and tax history for 849 Chester Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 849 Chester Rd

This home may not be allowing tours right now

Nearby similar homes

New listings for sale in 27104

More real estate resources