Google street view image for 300 Cutty Sark Rd, Winston Salem, NC 27103

Off market dec 2004 for $208K

$409,417

Est. refi paymentEst. refi $1,394/mo

•

2 ba

•

2,848

sq ft

300 Cutty Sark Rd, Winston Salem, NC 27103

About this home

300 Cutty Sark Rd is a 2,848 square foot house on a 0.41 acre lot with 3 bedrooms and 2 bathrooms. - it last sold on December 28, 2004 for $208,000. Based on Redfin's Winston Salem data, we estimate the home's value is $409,417.

Single-familyProperty Type

1987Year Built

0.41 acresLot Size

$144Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$409,417

$201K since sold in December 2004$2,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 23.1% higher than the average sale price ($333K) of 6 comparable homes.

SOLD JUL 29, 2026
$326,000
A
3 beds2 baths2,244 sq ft
2350 Oakton Dr, Clemmons, NC 27012
SOLD MAY 21, 2026
$325,000
B
3 beds2 baths1,999 sq ft
332 Cutty Sark Rd, Winston Salem, NC 27103
SOLD AUG 13, 2026
$325,000
C
3 beds3 baths2,660 sq ft
175 Red Fox Trl, Winston Salem, NC 27103
SOLD JUN 12, 2026
$300,000
D
3 beds2 baths1,820 sq ft
910 Forestglen Dr, Winston Salem, NC 27103
SOLD APR 28, 2026
$350,000
E
3 beds2 baths2,339 sq ft
660 S Peace Haven Rd, Winston Salem, NC 27103
SOLD SEP 15, 2026
$369,900
F
3 beds2 baths1,693 sq ft
6630 Valleyoak Dr, Clemmons, NC 27012

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Earn from this home

Sell

$317,832

Est. take-home

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Refinance

Est. cash available

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Rent

$2,313/mo

Redfin rental estimate

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Market trends in 27103, NC

Last updated September 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

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2362 Elizabeth Ave, Winston Salem, NC 27103
NEW 30 HRS AGO
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OPEN TODAY, 2PM TO 4PM
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2 beds2.5 baths1,272 sq ft
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See all

Provided by Redfin

Sale history for 300 Cutty Sark Rd

Year

Property tax

Land + Additions

Assessment*

2025

$3,958 (+6.6%)

$63,500 + $295,600

$359,100

2024

$3,713 (+6.8%)

$49,000 + $215,700

$264,700

2022

$3,478 (+11.4%)

2021

$3,121 (+12.6%)

$49,000 + $192,900

$241,900

2020

$2,773 (−0.7%)

$44,000 + $156,800

$200,800

2019

$2,793 (+5.3%)

$44,000 + $156,800

$200,800

2018

$2,652

$44,000 + $156,800

$200,800

2017

$2,652 (−2.7%)

$44,000 + $156,800

$200,800

2016

$2,725 (+1.5%)

$44,000 + $156,800

$200,800

2015

$2,684 (+3.2%)

$36,500 + $170,599

$207,099

2014

$2,602

$36,500 + $170,599

$207,099

Tax history for 300 Cutty Sark Rd

Year

Property tax

Land + Additions

Assessment*

2025

$3,958 (+6.6%)

$63,500 + $295,600

$359,100

2024

$3,713 (+6.8%)

$49,000 + $215,700

$264,700

2022

$3,478 (+11.4%)

2021

$3,121 (+12.6%)

$49,000 + $192,900

$241,900

2020

$2,773 (−0.7%)

$44,000 + $156,800

$200,800

2019

$2,793 (+5.3%)

$44,000 + $156,800

$200,800

2018

$2,652

$44,000 + $156,800

$200,800

2017

$2,652 (−2.7%)

$44,000 + $156,800

$200,800

2016

$2,725 (+1.5%)

$44,000 + $156,800

$200,800

2015

$2,684 (+3.2%)

$36,500 + $170,599

$207,099

2014

$2,602

$36,500 + $170,599

$207,099

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Zoning

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

Interior

Bathroom Information
# of Full Baths: 2
# of Bathroom Fixtures: 6

Heating & Cooling
Heating Type: Heat Pump

Fireplace Information
# of Fireplaces: 1
Has Fireplace

Room Information
# of Rooms: 7

Exterior

Exterior Information
Physical Condition: Average
Foundation Type: Slab
Building Style Type: Ranch
Construction Type: Masonry
Building Construction Quality: Average
Exterior Wall: Brick
Roof Framing Type: Masonry
Roof Shape Type: Gable
Building Type: Single Family

Pool Information
Has Pool

Property Information
Subdivision Name: MCGREGOR DOWNS SEC 02
Living Sq. Ft: 2,848
Ground Floor Sq. Ft: 2,250
Building Sq. Ft: 2,848
# of Stories: 1
Legal Description: LO:005 BL:3899J

Parking & Garage Information
Parking Type: Finished Masonry Garage
Garage/Parking Sq. Ft: 598
Garage / Carport Type: Finished Masonry

Lot Information
# of Buildings: 1
Land Sq. Ft: 17,860
Legal Lot Number: 5
Legal Block Number: 3899J
Municipality Name: WINSTON SALEM TOWNSHIP
Acres: 0.41
Depth Footage: 100
Front Footage: 176
Zoning Code: RS9
County Use Description: SFD DWELLING

Utility Information
Sewer Type: Public
Water Service Type: Public

Financial

Assessor Information
Assessment Year: 2026
Tax District County: WINSTON-SALEM

Public facts

Beds: 3
Baths: 2.0
Sq. Ft.: 2,848
Stories: 1.0
Lot Size: 0.41 acres
Style: Single Family Residential
Year Built: 1987
Year Renovated: 2005
County: Forsyth County
APN: 5893788375

Home facts updated by county records on Oct 23, 2026

Around this home

Schools

Ward Elementary

Public PreK-5 • Assigned • 1.9mi

4/10

Clemmons Middle

Public 6-8 • Assigned • 1.8mi

5/10

West Forsyth High

Public 9-12 • Assigned • 1.9mi

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

$389,000 – $471,000

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Nearby similar homes

NEW 26 HRS AGO

$485,000

4 beds3.5 baths3,012 sq ft

1981 Ernsford Dr, Winston Salem, NC 27103

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OPEN SUN, 2PM TO 4PM

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531 Osborne Rd, Winston Salem, NC 27103

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1435 S Peace Haven Rd, Clemmons, NC 27012

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280 Coghill Dr, Winston Salem, NC 27103

New listings for sale in 27103

NEW 26 HRS AGO

$485,000

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1981 Ernsford Dr, Winston Salem, NC 27103

NEW 26 HRS AGO

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NEW 30 HRS AGO

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2 beds2 baths1,532 sq ft

1120 Kenwood St, Winston Salem, NC 27103

$239,900

3 beds2 baths1,468 sq ft

203 Shenandoah Dr, Winston Salem, NC 27103

OPEN TODAY, 2PM TO 4PM

$247,000

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1902 Ardmore Commons Dr, Winston Salem, NC 27103

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2 beds2.5 baths1,306 sq ft

3369 Myers Ct, Winston Salem, NC 27103

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Home values near 300 Cutty Sark Rd

Data from public records.

Address	Redfin Estimate
308 Cutty Sark Rd, Winston Salem, NC 3 Beds \| 2 Baths \| 2245 Sq. Ft.	$357,963
312 Cutty Sark Rd, Winston Salem, NC 3 Beds \| 2 Baths \| 2350 Sq. Ft.	$385,253

Address	Redfin Estimate
305 Cutty Sark Rd, Winston Salem, NC 3 Beds \| 2.5 Baths \| 2333 Sq. Ft.	$401,778
316 Cutty Sark Rd, Winston Salem, NC 3 Beds \| 2.5 Baths \| 2400 Sq. Ft.	$387,391

Address	Redfin Estimate
304 Cutty Sark Rd, Winston Salem, NC 3 Beds \| 2 Baths \| 2304 Sq. Ft.	$360,577
320 Cutty Sark Rd, Winston Salem, NC 5 Beds \| 4 Baths \| 3675 Sq. Ft.	$438,915

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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 300 Cutty Sark Rd

Tax history for 300 Cutty Sark Rd

Zoning

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 300 Cutty Sark Rd

More real estate resources