OFF MARKET

Off market aug 2020 for $270K

$442,609

Est. refi paymentEst. refi $2,150/mo

•

3,675

sq ft

320 Cutty Sark Rd, Winston Salem, NC 27103

About this home

Spacious 5BD/4BA house located on corner lot in McGregor Downs. 2 bedroom suites on main level, spacious kitchen with 2 dishwashers, pantry and crown molding. Laundry room with sink & cabinets. Den features wood burning FP & crown molding. DR has chair railing & crown molding. Abundant storage throughout home. Large downstairs handicap accessible bedroom/bath ideal for private entrance office or multi-generational family living. Garage access is also wheelchair compatible.

Single-familyProperty Type

1988Year Built

0.36 acresLot Size

$120Est. Price/Sq.Ft.

2 car garageParking

Listed by Greta Frye Wiley • Keller Williams Realty Elite

Listed by Robert Wiley • Keller Williams Realty Elite

Bought with Jai Triplett • eXp Realty, LLC

Redfin checked: a minute ago

•Source:Triad MLS #955526

Redfin Estimate

$442,609

$173K since sold in August 2020$1,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 1.2% lower than the average sale price ($448K) of 6 comparable homes.

SOLD JUL 2, 2026
$421,250
A
4 beds3.5 baths2,656 sq ft
217 Mctavish Ln, Winston Salem, NC 27103
SOLD SEP 1, 2026
$410,000
B
5 beds4.5 baths4,332 sq ft
3040 Cameron Village Ct, Winston Salem, NC 27103
SOLD AUG 14, 2026
$355,000
C
4 beds4 baths3,761 sq ft
524 Cherbourg Ave, Winston Salem, NC 27103
SOLD JUN 17, 2026
$505,000
D
4 beds3.5 baths3,493 sq ft
1708 Briar Lake Rd, Winston Salem, NC 27103
SOLD JUL 20, 2026
$500,000
E
4 beds3 baths3,018 sq ft
1832 Hunters Forest Dr, Winston Salem, NC 27103
SOLD JUL 17, 2026
$497,000
F
4 beds3 baths3,745 sq ft
200 Worthland Ct, Winston Salem, NC 27103

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Earn from this home

Sell

$226,119

Est. take-home

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Refinance

Est. cash available

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Rent

$2,635/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

OPEN SUN, 2PM TO 4PM
$265,000
3 beds1.5 baths1,078 sq ft
4336 Cordova Dr, Winston Salem, NC 27103
NEW 25 HRS AGO
$220,000
3 beds2.5 baths1,432 sq ft
2938 Saint Marks Rd Unit B, Winston Salem, NC 27103
$300,000
3 beds1.5 baths1,731 sq ft
4641 Bridle Path, Winston Salem, NC 27103
3D WALKTHROUGH
$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
See all

Provided by Redfin

Sale history for 320 Cutty Sark Rd

Year

Property tax

Land + Additions

Assessment*

2025

$5,706 (+40.8%)

$63,500 + $454,200

$517,700

2024

$4,053 (+6.8%)

$49,000 + $239,900

$288,900

2022

$3,796 (+1.8%)

$49,000 + $239,900

$288,900

2021

$3,727 (+4.4%)

$49,000 + $239,900

$288,900

2020

$3,571 (−0.7%)

$44,000 + $214,600

$258,600

2019

$3,597 (+5.3%)

$44,000 + $214,600

$258,600

2018

$3,416

$44,000 + $214,600

$258,600

2017

$3,416 (+8.3%)

$44,000 + $214,600

$258,600

2016

$3,154 (+1.5%)

$44,000 + $214,600

$258,600

2015

$3,106 (+3.1%)

$36,500 + $203,197

$239,697

2014

$3,012

$36,500 + $203,197

$239,697

Tax history for 320 Cutty Sark Rd

Year

Property tax

Land + Additions

Assessment*

2025

$5,706 (+40.8%)

$63,500 + $454,200

$517,700

2024

$4,053 (+6.8%)

$49,000 + $239,900

$288,900

2022

$3,796 (+1.8%)

$49,000 + $239,900

$288,900

2021

$3,727 (+4.4%)

$49,000 + $239,900

$288,900

2020

$3,571 (−0.7%)

$44,000 + $214,600

$258,600

2019

$3,597 (+5.3%)

$44,000 + $214,600

$258,600

2018

$3,416

$44,000 + $214,600

$258,600

2017

$3,416 (+8.3%)

$44,000 + $214,600

$258,600

2016

$3,154 (+1.5%)

$44,000 + $214,600

$258,600

2015

$3,106 (+3.1%)

$36,500 + $203,197

$239,697

2014

$3,012

$36,500 + $203,197

$239,697

*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

1.5

Lot width

—

Lot depth

—

Lot size

0.36 Acres

Year renovated

2005

Sq. Ft.

3,676

Year built

1988

Style

Single Family Residential

County

Forsyth County

APN

5893783374

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

Property details

Parking

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

Interior

Virtual Tour

Bathroom Information
# of Bathrooms (Full): 4
# of Bathrooms (1/2): 0

Basement Information
Basement YN: No

Room Information
# of Rooms: 11

Room 1
Type: Living Room
Level: Main
Dimensions: 11ft 5in x 18ft 3in

Room 2
Type: Dining Room
Level: Main
Dimensions: 11ft 4in x 18ft 3in

Room 3
Type: Den
Level: Main
Dimensions: 11ft 0in x 15ft 2in

Room 4
Level: Second
Dimensions: 11ft 10in x 18ft 2in

Room 5
Level: Second
Dimensions: 10ft 7in x 12ft 10in

Room 6
Level: Second
Dimensions: 17ft 5in x 18ft 5in

Room 7
Level: Main
Dimensions: 13ft 2in x 22ft 8in

Room 8
Level: Main
Dimensions: 11ft 6in x 17ft 11in

Room 9
Type: Entry
Level: Main
Dimensions: 5ft 8in x 16ft 0in

Room 10
Type: Laundry
Level: Main
Dimensions: 5ft 7in x 11ft 4in

Room 11
Type: Kitchen
Level: Main
Dimensions: 13ft 8in x 19ft 9in

Interior Features
Attic Description: Pulldown Stairs
Flooring: Carpet, Tile, Vinyl, Wood
Interior Features: Built-in Features, Ceiling Fan(s), Dead Bolt(s), Soaking Tub, Pantry, Separate Shower

Exterior

Exterior Features
Fencing: Fenced

Pool Information
Pool Features: None

Lot Information
Lot Number: 9A
Lot Size Acres: 0.36

Land Information
Water Source: Public

Property Information
Property Type: Residential
Property Sub Type: Stick/Site Built
Structure Type: House
Built Information: Existing
Year Built: 1988
# of Fireplaces: 1
Fireplace Features: Den
Appliances: Microwave, Dishwasher, Disposal, Free-Standing Range, Electric Water Heater
Laundry Features: Dryer Connection, Main Level, Washer Hookup

Building Information
Building Area Total: 3,675
Foundation Details: Slab
Levels: One and One Half
Construction Materials: Brick

Financial

Tax Information
Tax Annual Amount: $3,596.87

Utilities

Utility Information
Sewer: Public Sewer
Water Heater: Electric

Heating & Cooling
Cooling: Central Air
Heating: Forced Air, Electric
Heating Fuel: Electric

Location

HOA Information
Association: Winston-Salem
Association YN: No

School / Neighborhood
Elementary School: Ward
Middle Or Junior School: Clemmons
High School: West Forsyth

Location Details
Directions: 421N, exit 240 Peace Haven Rd, L on S. Peace Haven Rd, L fork onto McGregor Rd, R on McGregor Downs Ln, L on Campbell Glen Ln, R Cutty Sark Rd

Community Information
Subdivision Name: Macgregor Downs

Public facts

Beds: 5
Baths: 4.0
Sq. Ft.: 3,676
Stories: 1.5
Lot Size: 0.36 acres
Style: Single Family Residential
Year Built: 1988
Year Renovated: 2005
County: Forsyth County
APN: 5893783374

Home facts updated by county records on Oct 23, 2026

Around this home

Schools

K - 12
Preschool & daycare

Ward Elementary

Public PreK-5 • Assigned • 2.0mi

4/10

Clemmons Middle

Public 6-8 • Assigned • 1.9mi

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

$421,000 – $509,000

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Nearby similar homes

OPEN SUN, 2PM TO 4PM

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4336 Cordova Dr, Winston Salem, NC 27103

New flooring • Remodeled kitchen • Updated bathrooms

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7,405 sq ft lot • Built 2003 • Listed 17 days

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Granite countertops • Built-in shelving • Peaceful retreat

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Mature landscaping • Hardwood floors • Gas log fireplace

New listings for sale in 27103

OPEN SUN, 2PM TO 4PM

$265,000

3 beds1.5 baths1,078 sq ft

4336 Cordova Dr, Winston Salem, NC 27103

New flooring • Remodeled kitchen • Updated bathrooms

NEW 25 HRS AGO

$220,000

3 beds2.5 baths1,432 sq ft

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0.44 acre lot • Garage • Built 1963

3D WALKTHROUGH

$549,000

4 beds3.5 baths3,980 sq ft

1736 Huntington Woods Ct, Winston Salem, NC 27103

Updated kitchen • Breakfast nook • Screened porch

$409,000

3 beds2.5 baths1,812 sq ft

121 Carolina Rose Ct, Winston-Salem, NC 27103

New community • Main-floor bedrooms • Large walk-in closet

COMING SOON

$425,000

4 beds2 baths2,372 sq ft

1800 Sandersted Rd, Winston Salem, NC 27103

All brick • Basement garage • Large backyard

$649,000

4 beds3.5 baths2,466 sq ft

451 S Hawthorne Rd #105, Winston-Salem, NC 27103

Fenced front yard • Butler's pantry • Wine fridge

$649,000

4 beds3.5 baths2,466 sq ft

451 S Hawthorne Rd, Winston Salem, NC 27103

Fenced front yard • Butler's pantry • Wine fridge

$349,900

3 beds1.5 baths1,148 sq ft

707 Bellview St, Winston Salem, NC 27103

Remodeled bungalow • Open kitchen • Barstool seating

Home values near 320 Cutty Sark Rd

Data from public records.

Address	Redfin Estimate
332 Cutty Sark Rd, Winston Salem, NC 3 Beds \| 2 Baths \| 1999 Sq. Ft.	$362,127
328 Cutty Sark Rd, Winston Salem, NC 4 Beds \| 3 Baths \| 3293 Sq. Ft.	$524,269

Address	Redfin Estimate
308 Cutty Sark Rd, Winston Salem, NC 3 Beds \| 2 Baths \| 2245 Sq. Ft.	$358,563
333 Cutty Sark Rd, Winston Salem, NC 3 Beds \| 2 Baths \| 1973 Sq. Ft.	$342,108

Address	Redfin Estimate
305 Cutty Sark Rd, Winston Salem, NC 3 Beds \| 2.5 Baths \| 2333 Sq. Ft.	$403,444
329 Cutty Sark Rd, Winston Salem, NC 4 Beds \| 2.5 Baths \| 2598 Sq. Ft.	$439,013

Property information provided by Triad MLS when last listed in 2019. 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 320 Cutty Sark Rd

Tax history for 320 Cutty Sark Rd

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 320 Cutty Sark Rd

More real estate resources