OFF MARKET

Off Market Apr 2013 for $275K

$556,189

Est. refi paymentEst. refi $1,473/mo

•

3,580

sq ft

661 Chester Rd, Winston Salem, NC 27104

About this home

One of the most striking exteriors in Sherwood Forest; custom built; excellent floor plan with large formal dining room and comfortable breakfast room; house designed to add 4th bedroom on 2nd flr; professionally landscaped; master bedroom on main floor; cozy den opens to large slate sunroom and patio; corian counters, tile backsplash in kitchen; lower level playroom with kitchen could be in-law suite; 20 x 16 workshop (with fireplace) could be additional playroom space; large detached storage building.

Single-familyProperty Type

1966Year Built

0.67 acresLot Size

$155Est. Price/Sq.Ft.

2 car garageParking

Listed by George Munford • Berkshire Hathaway HomeServices Carolinas Realty

Bought with Dee Parker • Berkshire Hathaway HomeServices Carolinas Realty

Redfin checked: a few seconds ago

•Source:Triad MLS #648305

Redfin Estimate

$556,189

$281K since sold in April 2013$1,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 10% lower than the average sale price ($618K) of 6 comparable homes.

SOLD AUG 6, 2026
$630,000
A
3 beds3 baths3,739 sq ft
440 Sherwood Forest Rd, Winston Salem, NC 27104
SOLD MAY 1, 2026
$740,000
B
3 beds3.5 baths3,553 sq ft
3440 Pennington Ln, Winston Salem, NC 27106
SOLD JUN 29, 2026
$520,000
C
3 beds3 baths3,204 sq ft
1117 Huntingdon Rd, Winston Salem, NC 27104
SOLD MAY 1, 2026
$525,000
D
3 beds3 baths2,882 sq ft
3740 Derbyshire 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 JUN 18, 2026
$549,000
F
3 beds3 baths2,633 sq ft
3807 Dewsbury Rd, Winston Salem, NC 27104

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$370,179

Est. take-home

List your home with Redfin and save $5,562

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$2,683/mo

Redfin rental estimate

List your home for rent

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 661 Chester Rd

Year

Property tax

Land + Additions

Assessment*

2025

$5,112 (+15.5%)

$100,000 + $363,800

$463,800

2024

$4,427 (+6.8%)

$85,000 + $230,600

$315,600

2022

$4,146 (+1.8%)

$85,000 + $230,600

$315,600

2021

$4,072 (+1.5%)

$85,000 + $230,600

$315,600

2020

$4,013 (−0.7%)

$85,000 + $205,600

$290,600

2019

$4,042 (+5.3%)

$85,000 + $205,600

$290,600

2018

$3,839

$85,000 + $205,600

$290,600

2017

$3,839 (+13.9%)

$85,000 + $205,600

$290,600

2016

$3,370 (+1.5%)

$85,000 + $205,600

$290,600

2015

$3,319 (+9.2%)

$85,000 + $171,093

$256,093

2014

$3,040

$85,000 + $156,920

$241,920

Tax history for 661 Chester Rd

Year

Property tax

Land + Additions

Assessment*

2025

$5,112 (+15.5%)

$100,000 + $363,800

$463,800

2024

$4,427 (+6.8%)

$85,000 + $230,600

$315,600

2022

$4,146 (+1.8%)

$85,000 + $230,600

$315,600

2021

$4,072 (+1.5%)

$85,000 + $230,600

$315,600

2020

$4,013 (−0.7%)

$85,000 + $205,600

$290,600

2019

$4,042 (+5.3%)

$85,000 + $205,600

$290,600

2018

$3,839

$85,000 + $205,600

$290,600

2017

$3,839 (+13.9%)

$85,000 + $205,600

$290,600

2016

$3,370 (+1.5%)

$85,000 + $205,600

$290,600

2015

$3,319 (+9.2%)

$85,000 + $171,093

$256,093

2014

$3,040

$85,000 + $156,920

$241,920

*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

0.67 Acres

Year renovated

1987

Sq. Ft.

2,757

Year built

1966

Style

Single Family Residential

County

Forsyth County

APN

6815089995

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: Circular Driveway, Driveway, Garage Door Opener, Attached

Interior

Virtual Tour

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

Basement Information
Basement YN: Yes
Has Basement
Basement: Finished, Unfinished, Partial
Basement Area: 1163

Room Information
# of Rooms: 10

Interior Features
Has Primary On Main
Attic Description: Partially Floored, Pulldown Stairs
Energy Features: Insulated Windows
Flooring: Carpet, Vinyl, Wood
Interior Features: Built-in Features, Ceiling Fan(s), Dead Bolt(s), Pantry, Solid Surface Counter, Wet Bar

Exterior

Exterior Features
Exterior Features: Garden, Sprinkler System
Other Equipment: Irrigation Equipment, Electronic Air Filter

Lot Information
Lot Features: City Lot, Level, Partially Cleared, Partially Wooded
Lot Size Acres: 0.67
Lot Size Dimensions: 120 x 225.91 x 124.19 x 249.41

Land Information
Land Description: Level, Partially Cleared, Partially Wooded
Water Source: Public

Property Information
Property Type: Residential
Property Sub Type: Single Family Residence
Built Information: Existing
Year Built: 1966
Other Structures: Storage
# of Fireplaces: 2
Fireplace Features: Blower Fan, Basement, Den
Appliances: Microwave, Built-in Range, Dishwasher, Disposal, Electric Water Heater, Humidifier
Laundry Features: Dryer Connection, Main Level, Washer Hookup

Building Information
Building Area Total: 4,149
Levels: One and One Half
Construction Materials: Brick, Masonite

Financial

Tax Information
Tax Annual Amount: $3,164.14

Utilities

Utility Information
Sewer: Public Sewer
Water Heater: Electric

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: From Silas Creek Parkway; turn onto Kirklees; Right Chester; house on Right.

Community Information
Subdivision Name: Sherwood Forest

Public facts

Beds: 4
Baths: 3.0
Sq. Ft.: 2,757
Stories: 2.0
Lot Size: 0.67 acres
Style: Single Family Residential
Year Built: 1966
Year Renovated: 1987
County: Forsyth County
APN: 6815089995

Home facts updated by county records on Aug 17, 2026

Around this home

Schools

Sherwood Forest Elementary

Public PreK-5 • Assigned • 0.4mi

9/10

Jefferson Middle

Public 6-8 • Assigned • 1.0mi

7/10

Mount Tabor High

Public 9-12 • Assigned • 1.6mi

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

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

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

$529,000 – $640,000

Reach more buyers when you sell with Redfin. Save up to $5,562 in fees. 3 minutes to get started.

Need the cash from your home fast? Sell to .

Nearby similar homes

LISTED BY REDFIN3D WALKTHROUGH

$350,000

3 beds2 baths1,536 sq ft

4811 Spilsby Ln, Winston Salem, NC 27104

$259,000

3 beds1.5 baths1,319 sq ft

3737 Vandalia Dr, Winston Salem, NC 27104

$1,495,000

5 beds6 baths5,894 sq ft

324 NW Banbury Rd, Winston Salem, NC 27104

$224,900

3 beds2 baths1,192 sq ft

131 Lindbergh St, Winston-Salem, NC 27104

$250,000

2 beds2 baths1,424 sq ft

4009 Alonzo Dr, Winston Salem, NC 27104

$295,000

2 beds2 baths2,041 sq ft

105 Jefferson Forest Ct, Winston Salem, NC 27106

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 661 Chester Rd

Data from public records.

Address	Redfin Estimate
650 Chester Road, Winston Salem, NC 4 Beds \| 3 Baths \| 2976 Sq. Ft.	$558,804
640 Chester Road, Winston Salem, NC 4 Beds \| 2 Baths \| 3379 Sq. Ft.	$488,921

Address	Redfin Estimate
660 Chester Road, Winston Salem, NC 3 Beds \| 2.5 Baths \| 2672 Sq. Ft.	$462,299
681 Chester Road, Winston Salem, NC 4 Beds \| 3 Baths \| 3243 Sq. Ft.	$661,201

Address	Redfin Estimate
630 Chester Road, Winston Salem, NC 4 Beds \| 3 Baths \| 2693 Sq. Ft.	$570,914
691 Chester Road, Winston Salem, NC 4 Beds \| 2 Baths \| 2767 Sq. Ft.	$493,954

Property information provided by Triad MLS when last listed in 2012. This data may not match . 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.

27103 homes for sale
27104 homes for sale
27106 homes for sale
27023 homes for sale
27012 homes for sale

Houses for rent in Winston-Salem	Agents near me	Asheville, NC homes for sale	Winston-Salem Housing Market
Houses for sale near me	Charlotte, NC homes for sale	Apex, NC homes for sale
Land for sale near me	Raleigh, NC homes for sale	Greensboro, NC homes for sale
Open Houses near me	Cary, NC homes for sale	Winston-Salem Property Records
Condos for sale near me	Durham, NC homes for sale	NC New Listings

High Point homes for sale
Kernersville homes for sale
Greensboro homes for sale

Old Sherwood Forest homes for sale
West Suburban Winston-Salem homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 27104, NC

Sale history for 661 Chester Rd

Tax history for 661 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 661 Chester Rd

More real estate resources