CONTINGENT

Contingent

$629,000

Est. $3,850/mo —

•

2,552

sq ft

706 Chester Rd, Winston Salem, NC 27104

About this home

Fully updated ranch on a private, wooded 0.92-acre lot in sought-after Old Sherwood Forest. Every detail has been renovated with high-quality materials—all work permitted. Open-concept living and dining flows into a beautifully appointed kitchen. French doors and plantation shutters bring in natural light throughout. A cozy den and a bright, windowed bonus room add flexible living space. Primary suite is on the main level for easy one-story living. 3 bedrooms, 4 full baths, plus a finished basement with second laundry and inside parking for two cars. Enjoy a large elevated deck overlooking the wooded lot, with stairs down to a secluded stone patio beneath the trees. The private lower-level suite—with its own entrance, full kitchenette, gas fireplace, and off-street parking—has operated as a highly profitable Airbnb, offering turnkey rental income or multigenerational living.

Single-familyProperty Type

1958Year Built

0.92 acresLot Size

$246Price/Sq.Ft.

2 car garageParking

Listed by David Shatzman • Keller Williams Realty Elite

Listing updated: Aug 23, 2026 at 09:13am

Redfin checked: 3 minutes ago

•Source:Triad MLS #1231155

Payment calculator

$3,850 per month

Principal and interest$3,306

Property taxes

$397

HOA dues

Home insurance

$147

Utilities

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Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN SAT, 11AM TO 1PM
$362,000
3 beds2.5 baths2,495 sq ft
2513 Newington Ct, Clemmons, NC 27012
OPEN SAT, 12PM TO 2PM
$97,300
2 beds1 bath780 sq ft
570 Mission Rd, Winston Salem, NC 27103
OPEN SAT, 12PM TO 2PM
$385,000
4 beds2.5 baths2,856 sq ft
4330 Witherow Rd, Winston Salem, NC 27106
OPEN SAT, 1PM TO 3PM3D WALKTHROUGH
$142,500
2 beds1 bath941 sq ft
2410 Marble St, Winston Salem, NC 27107
OPEN SAT, 2PM TO 4PM3D WALKTHROUGH
$407,800
3 beds2.5 baths2,342 sq ft
206 Timber Hill Ct, Rural Hall, NC 27045
OPEN SUN, 2PM TO 4PM
$235,000
3 beds2 baths1,248 sq ft
4313 Walnut Hollow Dr, Winston Salem, NC 27127
OPEN SUN, 2PM TO 4PM
$749,900
4 beds3.5 baths3,000 sq ft
4803 Hampton Oak Ct, Clemmons, NC 27012
OPEN SUN, 2PM TO 4PM
$338,500
4 beds3 baths2,178 sq ft
2576 Viola Ct, Winston Salem, NC 27127
OPEN SUN, 2PM TO 4PM
$439,500
4 beds3 baths2,469 sq ft
5930 Alani Ct, Winston Salem, NC 27103
OPEN SEP 10, 4PM TO 6PM
$274,900
3 beds2 baths1,524 sq ft
103 Briar Ridge Cir, Winston Salem, NC 27104

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 • 0.8mi

7/10

Mount Tabor High

Public 9-12 • Assigned • 1.5mi

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

706 Chester Rd · $629,000

DAYS ON MARKET

The average home goes pending in 43 days.

SALE-TO-LIST

Most homes are selling 2% below list price.

LIST PRICE

Median sale price in this area is $339,063. (46% lower than this home)

PRICE DROP

24% 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
Primary bedroom on the main level
In-law floorplan
Pantry
Solid surface counters
Permanent stairs to attic

Bathrooms
4 full bathrooms

Kitchen
Microwave
Oven
Cooktop (including gas cooktop)
Range hood
Dishwasher
Disposal
Exhaust fan

Laundry & utility
Washer/dryer connections on main level and in basement
Second washer and second dryer connections
Electric water heater

Flooring
Wood flooring

Heating & cooling
Central air
Dual fuel heating system
Heat pump
Forced air
Fireplaces for supplemental heat (2 fireplaces)
Electric and natural gas heating fuel

Sale and tax history for 706 Chester Rd

Sale History
Tax History

Date

Event

Price

Triad MLS #1231155

Aug 23, 2026

Contingent

—

Aug 21, 2026

Listed

$629,000

$246/sq ft

Aug 16, 2026

Coming Soon

$629,000

$246/sq ft

HCMLS #209458

Jul 27, 2018

Sold

$235,000

$92/sq ft

Jul 26, 2018

Listed

$239,900

$94/sq ft

Triad MLS #883258

Jul 26, 2018

Sold

$235,000

$92/sq ft

Jul 14, 2018

Pending

—

Jun 19, 2018

Contingent

—

Jun 10, 2018

Relisted

—

May 25, 2018

Contingent

—

May 11, 2018

Price Changed

$239,900

$94/sq ft

Apr 30, 2018

Price Changed

$249,900

$98/sq ft

Apr 20, 2018

Listed

$259,900

$102/sq ft

+19

Back on the Market! Hardwoods Refinished in Bedrooms! Opportunity awaits with this well maintained ranch in beautiful Sherwood Forest. Move right in or bring your imagination and unlock this homes potential. Features include: Hardwoods; Plantation Shutters; Full master bath; Fireplace; Wrap-around Driveway; Newer Roof; Gutter guards; walk-up attic storage; and much more! Did we mention the large private lot within walking distance of parks and Sherwood Elementary? Don't wait! Schedule your showing today!

Year

Property tax

Land + Additions

Assessment*

2025

$4,595 (+18.7%)

$100,000 + $316,900

$416,900

2024

$3,872 (+10.2%)

$85,000 + $191,000

$276,000

2022

$3,513 (+1.8%)

$85,000 + $182,400

$267,400

2021

$3,450 (+5.0%)

$85,000 + $182,400

$267,400

2020

$3,285 (+7.7%)

$85,000 + $152,900

$237,900

2019

$3,050 (+5.3%)

$85,000 + $134,300

$219,300

2018

$2,897

$85,000 + $134,300

$219,300

2017

$2,897 (+9.8%)

$85,000 + $134,300

$219,300

2016

$2,637 (+1.5%)

$85,000 + $134,300

$219,300

2015

$2,597 (+3.1%)

$85,000 + $115,422

$200,422

2014

$2,518

$85,000 + $115,422

$200,422

Public record

Public record
Zoning

Beds

Baths

3.5

Stories

Lot width

—

Lot depth

—

Lot size

0.92 Acres

Year renovated

1993

Finished Sq. Ft.

2,470

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,470

Year built

1958

Style

Single Family Residential

County

Forsyth County

APN

6815095841

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

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, 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 ranks in the top 26% for direct sun exposure in the zip code. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.3 hrs

6.4 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 706 Chester Rd

We cannot show automated home-value estimates for this home.

Nearby homes have recently sold between $445,000 and $655,000.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $445K to $655K.

SOLD JUN 18, 2026
$549,000 Last sold price
3 beds3 baths2,633 sq ft
3807 Dewsbury Rd, Winston Salem, NC 27104
$37/sq ft
smaller lot
SOLD MAY 8, 2026
$575,000 Last sold price
3 beds2.5 baths2,361 sq ft
3308 York Rd, Winston Salem, NC 27106
$2/sq ft
smaller lot
1 year newer
SOLD AUG 10, 2026
$612,000 Last sold price
4 beds2.5 baths3,134 sq ft
370 Staffordshire Rd, Winston Salem, NC 27104
$51/sq ft
smaller lot
11 years newer
SOLD APR 9, 2026
$655,000 Last sold price
3 beds2 baths2,240 sq ft
3244 Nottingham Rd, Winston Salem, NC 27104
$46/sq ft
7 years older
SOLD MAR 20, 2026
$500,000 Last sold price
4 beds3 baths2,734 sq ft
3614 Broadsword Rd, Winston Salem, NC 27104
$63/sq ft
smaller lot
1 year newer
SOLD AUG 27, 2026
$445,000 Last sold price
3 beds2.5 baths1,752 sq ft
708 Finsbury Rd, Winston Salem, NC 27104
$8/sq ft
smaller lot

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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

Open houses

Nearby open houses (10)

Around this home

Schools

Market insights

Property details

Sale and tax history for 706 Chester Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 706 Chester Rd

This home may not be allowing tours right now

Nearby similar homes

New listings for sale in 27106

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