OFF MARKET

Off Market Aug 2020 for $270K

$444,006

Est. refi paymentEst. refi $2,173/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

$121Est. 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: 2 minutes ago

•Source:Triad MLS #955526

Redfin Estimate

$444,006

$174K since sold in August 2020$19K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 0.9% 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

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

Earn from this home

Sell

$226,435

Est. take-home

List your home with Redfin and save $4,440

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$2,556/mo

Redfin rental estimate

List your home for rent

Market trends in 27103, NC

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

98.0%

+0.0% MoM

Median sale price

$285K

$14K MoM

Avg. days on market

43d

3 days MoM

Recently sold homes

170

8 MoM

New listings for sale

NEW 6 HRS AGO
$389,000
3 beds2 baths1,444 sq ft
2348 Rosewood Ave, Winston Salem, NC 27103
$289,000
3 beds2 baths2,224 sq ft
2961 Northbridge Rd, Winston Salem, NC 27103
NEW 31 HRS AGO
$260,000
3 beds2.5 baths1,639 sq ft
2902 Saint Marks Rd Unit H, Winston Salem, NC 27103
NEW 31 HRS AGO
$450,000
4 beds3.5 baths3,165 sq ft
2460 Dog Leg Dr, Winston Salem, NC 27103
NEW 32 HRS AGO
$249,900
2 beds2 baths1,241 sq ft
2800 Shadowbrook Ln, Winston Salem, NC 27103
NEW 33 HRS AGO
$265,900
2 beds2 baths1,262 sq ft
2942 Hyde Place Cir, Winston Salem, NC 27103
NEW 33 HRS AGO
$240,000
3 beds2 baths1,226 sq ft
103 Shenandoah Dr, Winston Salem, NC 27103
$300,000
3 beds2 baths988 sq ft
443 Irving St, Winston Salem, NC 27103
COMING SOON
$135,000
2 beds1.5 baths1,056 sq ft
2330 Bay Meadows Ct, Winston Salem, NC 27103
$345,000
3 beds2 baths1,930 sq ft
4880 Hawkwood Trl, 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 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: 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

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 Aug 17, 2026

Around this home

Schools

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

$422,000 – $511,000

Reach more buyers when you sell with Redfin. Save up to $4,440 in fees. 3 minutes to get started.

Need the cash from your home fast? Sell to .

Nearby similar homes

NEW 4 HRS AGO

$449,900

4 beds2.5 baths2,402 sq ft

4558 Jasper Ridge Dr, Clemmons, NC 27012

$425,000

4 beds2.5 baths2,202 sq ft

7626 Rolling Oak Ct, Clemmons, NC 27012

$353,500

3 beds2 baths2,120 sq ft

6648 Springfield Village Ln, Clemmons, NC 27012

OPEN SUN, 2PM TO 4PM

$519,000

4 beds2.5 baths3,275 sq ft

6917 August Dr, Clemmons, NC 27012

NEW 27 HRS AGO3D WALKTHROUGH

$699,900

4 beds4.5 baths3,761 sq ft

1797 Ramhurst Dr, Clemmons, NC 27012

$472,500

3 beds3.5 baths2,592 sq ft

4310 Clarksburg Rd, Clemmons, NC 27012

New listings for sale in 27103

NEW 6 HRS AGO3D WALKTHROUGH

$389,000

3 beds2 baths1,444 sq ft

2348 Rosewood Ave, Winston Salem, NC 27103

$289,000

3 beds2 baths2,224 sq ft

2961 Northbridge Rd, Winston Salem, NC 27103

NEW 31 HRS AGOVIDEO TOUR

$260,000

3 beds2.5 baths1,639 sq ft

2902 Saint Marks Rd Unit H, Winston Salem, NC 27103

NEW 31 HRS AGO

$450,000

4 beds3.5 baths3,165 sq ft

2460 Dog Leg Dr, Winston Salem, NC 27103

NEW 32 HRS AGO

$249,900

2 beds2 baths1,241 sq ft

2800 Shadowbrook Ln, Winston Salem, NC 27103

NEW 33 HRS AGO

$265,900

2 beds2 baths1,262 sq ft

2942 Hyde Place Cir, Winston Salem, NC 27103

NEW 33 HRS AGO

$240,000

3 beds2 baths1,226 sq ft

103 Shenandoah Dr, Winston Salem, NC 27103

$300,000

3 beds2 baths988 sq ft

443 Irving St, Winston Salem, NC 27103

COMING SOON

$135,000

2 beds1.5 baths1,056 sq ft

2330 Bay Meadows Ct, Winston Salem, NC 27103

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.	$365,265
328 Cutty Sark Rd, Winston Salem, NC 4 Beds \| 3 Baths \| 3293 Sq. Ft.	$519,010

Address	Redfin Estimate
308 Cutty Sark Rd, Winston Salem, NC 3 Beds \| 2 Baths \| 2245 Sq. Ft.	$357,596
333 Cutty Sark Rd, Winston Salem, NC 3 Beds \| 2 Baths \| 1973 Sq. Ft.	$338,438

Address	Redfin Estimate
305 Cutty Sark Rd, Winston Salem, NC 3 Beds \| 2.5 Baths \| 2333 Sq. Ft.	$402,325
329 Cutty Sark Rd, Winston Salem, NC 4 Beds \| 2.5 Baths \| 2598 Sq. Ft.	$435,336

Property information provided by Triad MLS when last listed in 2019. 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

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