SOLD NOV 19, 2025

Off market nov 2025 for $525K

$512,763

Est. refi paymentEst. refi $2,626/mo

•

3,200

sq ft

744 Chestnut Ridge Ct, Winston Salem, NC 27103

About this home

Welcome to this exceptional property featuring a fantastic floor plan designed for both comfort and style. The main level showcases beautiful hardwood floors throughout, leading to a spacious living room with a vaulted ceiling and a cozy gas fireplace. Enjoy the sun-drenched 20x25 great room, complete with handsome built-ins, perfect for gatherings or relaxation. The main level also boasts a primary suite. Upstairs, you’ll find three additional bedrooms along with an office featuring wood floors and built-ins. Step outside to a beautifully landscaped yard, highlighted by a charming front porch, a fenced backyard, and inviting wrap-around side and back porches. Located conveniently near I-40, Hwy 421, and the Village of Clemmons, this home offers both tranquility and accessibility. Don’t miss the opportunity to make this your new home!

Single-familyProperty Type

2001Year Built

0.28 acresLot Size

$160Est. Price/Sq.Ft.

2 car garageParking

Listed by Cindy Rosenberg • Berkshire Hathaway HomeServices Carolinas Realty

Bought with Jeff Norris • J Norris Real Estate

Redfin checked: 3 minutes ago

•Source:Triad MLS #1198607

Redfin Estimate

$512,763

$12K since sold in November 2025$2,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 32.8% higher than the average sale price ($386K) of 6 comparable homes.

SOLD OCT 9, 2026
$365,000
A
4 beds2.5 baths2,205 sq ft
6711 Fairwood Ct, Clemmons, NC 27012
SOLD JUL 8, 2026
$380,000
B
4 beds2.5 baths2,290 sq ft
117 Huron Ct, Winston Salem, NC 27103
SOLD SEP 22, 2026
$425,000
C
3 beds2.5 baths2,453 sq ft
2525 Brook Stone Dr, Clemmons, NC 27012
SOLD APR 30, 2026
$420,000
D
4 beds2.5 baths2,988 sq ft
970 Boyer Dr, Clemmons, NC 27012
SOLD MAY 22, 2026
$372,000
E
3 beds2.5 baths2,210 sq ft
6721 Fairwood Ct, Clemmons, NC 27012
SOLD JUL 9, 2026
$355,000
F
4 beds3 baths2,549 sq ft
1748 Harper Spring Dr, Clemmons, NC 27012

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Earn from this home

Sell

$68,246

Est. take-home

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Refinance

Est. cash available

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Rent

$2,652/mo

Redfin rental estimate

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Market trends in 27103, NC

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

98.1%

+0.1% MoM

Median sale price

$284K

$1K MoM

Avg. days on market

43d

0 days MoM

Recently sold homes

152

14 MoM

New listings for sale

NEW 13 HRS AGO
$220,000
3 beds2.5 baths1,432 sq ft
2938 Saint Marks Rd Unit B, Winston Salem, NC 27103
NEW 20 HRS AGO
$300,000
3 beds1.5 baths1,731 sq ft
4641 Bridle Path, Winston Salem, NC 27103
NEW 23 HRS AGO
$549,000
4 beds3.5 baths3,980 sq ft
1736 Huntington Woods Ct, Winston Salem, NC 27103
$409,000
3 beds2.5 baths1,812 sq ft
121 Carolina Rose Ct, Winston-Salem, NC 27103
COMING SOON
$425,000
4 beds2 baths2,372 sq ft
1800 Sandersted Rd, Winston Salem, NC 27103
$649,000
4 beds3.5 baths2,466 sq ft
451 S Hawthorne Rd #105, Winston-Salem, NC 27103
$649,000
4 beds3.5 baths2,466 sq ft
451 S Hawthorne Rd, Winston Salem, NC 27103
$349,900
3 beds1.5 baths1,148 sq ft
707 Bellview St, Winston Salem, NC 27103
$235,000
2 beds2 baths1,092 sq ft
3317 Hyde Place Cir, Winston Salem, NC 27103
$255,000
2 beds2.5 baths1,237 sq ft
1694 Granby Heights Dr, Winston Salem, NC 27103
See all

Provided by Redfin

Sale history for 744 Chestnut Ridge Ct

Date

Event

Price

Triad MLS #1198607

Nov 19, 2025

Sold

$525,000

$164/sq ft

Oct 29, 2025

Pending

—

Oct 14, 2025

Contingent

—

Oct 9, 2025

Listed

$530,000

$166/sq ft

Triad MLS #1019708

May 28, 2021

Sold

$400,000

$125/sq ft

May 6, 2021

Pending

—

Apr 12, 2021

Contingent

—

Apr 9, 2021

Listed

$385,000

$120/sq ft

+45

Special, one of a kind "Charleston-style" home in superb location! From the welcoming front porch to the serene setting of the wrap around side and back porch, this is one that you don't want to miss. Plenty of living space inside as well, thanks to the 20 x 25 den addition! 4 bedrooms plus an office, great storage, and tons of hardwood floors. Fenced yard! WS address, Clemmons taxes. Easy access to I40, Hwy 421, and Clemmons shopping and parks!

Public Records

Jun 7, 2018

Sold

$318,100

$99/sq ft

Triad MLS #880038

Jun 4, 2018

Sold

$318,000

$99/sq ft

May 16, 2018

Pending

—

Apr 30, 2018

Contingent

—

Apr 26, 2018

Relisted

—

Apr 24, 2018

Contingent

—

Mar 23, 2018

Listed

$324,900

$102/sq ft

+18

You will look forward to coming home everyday to this lovely home. Relax on the back covered porch & enjoy the serene setting or swing on the front porch. Main level has an open airy feel. Vaulted ceilings in Living Room with gas fireplace. Spacious and sun drenched Great Room with lots of built-ins. Main level master bedroom, laundry and garage. Hardwood floors throughout main. 3 additional bedrooms on upper level, fabulous office with hardwood floors & built-ins. Large walk in closets in all rooms.

Public Records

May 10, 2010

Sold

$274,000

$86/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$3,495 (+10.4%)

$65,000 + $408,800

$473,800

2024

$3,165 (+2.1%)

$57,000 + $275,300

$332,300

2022

$3,098

$57,000 + $275,300

$332,300

2021

$3,098 (+24.1%)

$57,000 + $275,300

$332,300

2020

$2,496 (−1.0%)

$52,500 + $210,600

$263,100

2019

$2,522 (+6.0%)

$52,500 + $210,600

$263,100

2018

$2,378 (+0.4%)

$52,500 + $204,500

$257,000

2017

$2,369 (−3.4%)

$52,500 + $204,500

$257,000

2016

$2,453

$52,500 + $204,500

$257,000

2015

$2,453 (+2.7%)

$42,000 + $222,223

$264,223

2014

$2,389

$42,000 + $222,223

$264,223

Tax history for 744 Chestnut Ridge Ct

Year

Property tax

Land + Additions

Assessment*

2025

$3,495 (+10.4%)

$65,000 + $408,800

$473,800

2024

$3,165 (+2.1%)

$57,000 + $275,300

$332,300

2022

$3,098

$57,000 + $275,300

$332,300

2021

$3,098 (+24.1%)

$57,000 + $275,300

$332,300

2020

$2,496 (−1.0%)

$52,500 + $210,600

$263,100

2019

$2,522 (+6.0%)

$52,500 + $210,600

$263,100

2018

$2,378 (+0.4%)

$52,500 + $204,500

$257,000

2017

$2,369 (−3.4%)

$52,500 + $204,500

$257,000

2016

$2,453

$52,500 + $204,500

$257,000

2015

$2,453 (+2.7%)

$42,000 + $222,223

$264,223

2014

$2,389

$42,000 + $222,223

$264,223

*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

2.5

Stories

1.5

Lot width

—

Lot depth

—

Lot size

0.28 Acres

Year renovated

2003

Sq. Ft.

3,145

Year built

2001

Style

Single Family Residential

County

Forsyth County

APN

5894311131

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.

Property details

Parking

Parking / Garage Information
# of Garage Spaces: 2
Garage Description: Attached Garage
Parking Features: Garage, Driveway, Attached

Interior

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

Basement Information
Basement YN: No
Basement: Crawl Space

Room Information
# of Rooms: 12

Interior Features
Has Primary On Main
Flooring: Carpet, Tile, Wood
Interior Features: Built-in Features, Ceiling Fan(s), Dead Bolt(s), Soaking Tub, Pantry, Separate Shower, Solid Surface Counter, Vaulted Ceiling(s)

Exterior

Exterior Features
Fencing: Fenced

Pool Information
Pool Features: None

Guest House Information
No

Lot Information
Lot Size Acres: 0.28

Land Information
Water Source: Public

Property Information
Property Type: Residential
Property Sub Type: Stick/Site Built
Structure Type: House
Built Information: Existing
Year Built: 2001
# of Fireplaces: 1
Fireplace Features: Gas Log, Living Room
Appliances: Microwave, Dishwasher, Disposal, Free-Standing Range, Gas Water Heater
Laundry Features: Dryer Connection, Main Level, Washer Hookup

Building Information
Building Area Total: 3,200
Levels: One and One Half
Construction Materials: Brick, Cement Siding, Wood Siding

Financial

Tax Information
Tax Annual Amount: $3,360

Utilities

Utility Information
Sewer: Public Sewer
Water Heater: Gas

Heating & Cooling
Cooling: Central Air
Heating: Forced Air, Heat Pump, Electric, Natural Gas
Heating Fuel: Electric, Natural Gas

Location

HOA Information
Association: Winston-Salem
Association YN: Yes
Association Fee: $200
Association Fee Frequency: Annually

Location Details
Directions: 1-40 South; Exit Lewisville-Clemmons Road; Right off the Exit; Right on Peace Haven Road;Left on Chestnut Ridge Road; Right on Chestnut Ridge Court

Community Information
Subdivision Name: Chestnut Ridge

Public facts

Beds: 4
Baths: 2.5
Sq. Ft.: 3,145
Stories: 1.5
Lot Size: 0.28 acres
Style: Single Family Residential
Year Built: 2001
Year Renovated: 2003
County: Forsyth County
APN: 5894311131

Home facts updated by county records on Oct 23, 2026

Around this home

Schools

K - 12
Preschool & daycare

Frank Morgan Elementary School

Public PreK-5 • Assigned • 1.8mi

7/10

Clemmons Middle

Public 6-8 • Assigned • 2.9mi

5/10

West Forsyth High

Public 9-12 • Assigned • 0.9mi

8/10

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 103° expected this year, 18 days in 30 years

3/10 Wind Factor

6% 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 • 27103

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 9.1 hours in June and 5.1 hours in December, which is comparable to the U.S. average for solar exposure.

9.1 hrs

5.1 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$488,000 – $590,000

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New listings for sale in 27103

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NEW 20 HRS AGO

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NEW 23 HRS AGO3D WALKTHROUGH

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COMING SOON

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4 beds2 baths2,372 sq ft

1800 Sandersted Rd, Winston Salem, NC 27103

All brick • Basement garage • Large backyard

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451 S Hawthorne Rd, Winston Salem, NC 27103

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Remodeled bungalow • Open kitchen • Barstool seating

$235,000

2 beds2 baths1,092 sq ft

3317 Hyde Place Cir, Winston Salem, NC 27103

Stone exterior • End unit • Open floorplan

Home values near 744 Chestnut Ridge Ct

Data from public records.

Address	Redfin Estimate
2751 Chestnut Ridge Drive, Winston Salem, NC 4 Beds \| 2.5 Baths \| 2572 Sq. Ft.	$417,987
773 Chestnut Ridge Court, Winston Salem, NC 3 Beds \| 2 Baths \| 1776 Sq. Ft.	$330,285

Address	Redfin Estimate
2740 Chestnut Ridge Drive, Winston Salem, NC 3 Beds \| 2 Baths \| 2270 Sq. Ft.	$435,676
723 Chestnut Ridge Court, Winston Salem, NC 3 Beds \| 2 Baths \| 1937 Sq. Ft.	$355,262

Address	Redfin Estimate
2731 Chestnut Ridge Drive, Winston Salem, NC 4 Beds \| 3.5 Baths \| 2869 Sq. Ft.	$499,270
753 Chestnut Ridge Court, Winston Salem, NC 3 Beds \| 2 Baths \| 1759 Sq. Ft.	$349,352

Property information provided by Triad MLS when last listed in 2025. 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 27103, NC

Sale history for 744 Chestnut Ridge Ct

Tax history for 744 Chestnut Ridge Ct

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 27103

Home values near 744 Chestnut Ridge Ct

More real estate resources