OFF MARKET

Off market jul 2021 for $312K

$387,391

Est. refi paymentEst. refi $403/mo

•

2,400

sq ft

316 Cutty Sark Rd, Winston Salem, NC 27103

About this home

New floors and paint throughout! Well maintained home in a great location with easy access to shopping and quick route to just about all the main roads! Main level living at it finest with great layout, large eat in kitchen, unique wet bar in den and 2 additional rooms that can be used as dining room, formal sitting room, office, etc! You will love the character of this home! Great layout with laundry/mudroom space right off 2 car garage/owner entry and directly into kitchen! Circle drive, quiet backyard with low maintenance yard with beautiful mature landscaping. This is the one you've been waiting for. Schedule today--it will go FAST!

Single-familyProperty Type

1988Year Built

0.33 acresLot Size

$161Est. Price/Sq.Ft.

2 car garageParking

Listed by Daniela Jewell • Mays Gibson Inc

Bought with Shirley Ramsey • Keller Williams Realty

Redfin checked: a few seconds ago

•Source:Triad MLS #1028996

Redfin Estimate

$387,391

$75K since sold in July 2021$6,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 14.1% higher than the average sale price ($340K) of 6 comparable homes.

SOLD OCT 6, 2026
$478,000
A
3 beds2.5 baths2,141 sq ft
4335 Winterberry Ridge Ct, Winston Salem, NC 27103
SOLD SEP 3, 2026
$230,000
B
3 beds2.5 baths1,849 sq ft
4331 Kinnamon Rd, Winston Salem, NC 27103
SOLD AUG 13, 2026
$290,000
C
3 beds2.5 baths1,856 sq ft
1580 Old Jonestown Rd, Winston Salem, NC 27103
SOLD JAN 28, 2026
$340,000
D
3 beds2.5 baths2,324 sq ft
816 Newington Dr, Clemmons, NC 27012
SOLD JUN 30, 2026
$390,000
E
3 beds2.5 baths1,837 sq ft
4465 Woodsman Way, Winston Salem, NC 27103
SOLD JUL 14, 2026
$309,000
F
3 beds2.5 baths2,226 sq ft
730 Somerset Dr, Winston Salem, NC 27103

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Earn from this home

Sell

$139,070

Est. take-home

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Refinance

Est. cash available

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Rent

$2,184/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

$485,000
4 beds3.5 baths3,012 sq ft
1981 Ernsford Dr, Winston Salem, NC 27103
$549,000
4 beds3 baths3,283 sq ft
2362 Elizabeth Ave, Winston Salem, NC 27103
HOT HOME
$345,000
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
$247,000
2 beds2.5 baths1,272 sq ft
1902 Ardmore Commons Dr, Winston Salem, NC 27103
$232,500
2 beds1 bath1,068 sq ft
1409 Irving St, Winston Salem, NC 27103
$290,000
3 beds2 baths1,582 sq ft
526 Osborne Rd, Winston Salem, NC 27103
$350,000
3 beds2 baths1,812 sq ft
1516 Jonestown Rd, Winston Salem, NC 27103
HOT HOME
$150,000
2 beds1 bath1,197 sq ft
711 Magnolia St, Winston Salem, NC 27103
$349,900
3 beds2.5 baths2,078 sq ft
280 Coghill Dr, Winston Salem, NC 27103
See all

Provided by Redfin

Sale history for 316 Cutty Sark Rd

Year

Property tax

Land + Additions

Assessment*

2025

$3,878 (+5.6%)

$63,500 + $277,400

$340,900

2024

$3,673 (+6.8%)

$49,000 + $212,800

$261,800

2022

$3,440 (+3.9%)

$49,000 + $207,500

$256,500

2021

$3,309 (+14.2%)

$49,000 + $207,500

$256,500

2020

$2,897 (−0.7%)

$44,000 + $165,800

$209,800

2019

$2,918 (+5.3%)

$44,000 + $165,800

$209,800

2018

$2,771

$44,000 + $165,800

$209,800

2017

$2,771 (−2.8%)

$44,000 + $165,800

$209,800

2016

$2,850 (+1.5%)

$44,000 + $165,800

$209,800

2015

$2,807 (+3.1%)

$36,500 + $180,095

$216,595

2014

$2,722

$36,500 + $180,095

$216,595

Tax history for 316 Cutty Sark Rd

Year

Property tax

Land + Additions

Assessment*

2025

$3,878 (+5.6%)

$63,500 + $277,400

$340,900

2024

$3,673 (+6.8%)

$49,000 + $212,800

$261,800

2022

$3,440 (+3.9%)

$49,000 + $207,500

$256,500

2021

$3,309 (+14.2%)

$49,000 + $207,500

$256,500

2020

$2,897 (−0.7%)

$44,000 + $165,800

$209,800

2019

$2,918 (+5.3%)

$44,000 + $165,800

$209,800

2018

$2,771

$44,000 + $165,800

$209,800

2017

$2,771 (−2.8%)

$44,000 + $165,800

$209,800

2016

$2,850 (+1.5%)

$44,000 + $165,800

$209,800

2015

$2,807 (+3.1%)

$36,500 + $180,095

$216,595

2014

$2,722

$36,500 + $180,095

$216,595

*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

Lot width

—

Lot depth

—

Lot size

0.33 Acres

Year renovated

2002

Sq. Ft.

2,397

Year built

1988

Style

Single Family Residential

County

Forsyth County

APN

5893784375

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: Driveway, Garage, Circular Driveway, Garage Door Opener, Attached

Interior

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

Basement Information
Basement YN: No

Room Information
# of Rooms: 8

Room 1
Type: Den
Level: Main
Dimensions: 17ft 1in x 19ft 10in

Room 2
Type: Breakfast
Level: Main
Dimensions: 7ft 11in x 13ft 5in

Room 3
Type: Laundry
Level: Main
Dimensions: 5ft 10in x 7ft 11in

Room 4
Type: Kitchen
Level: Main
Dimensions: 10ft 9in x 13ft 5in

Room 5
Type: Dining Room
Level: Main
Dimensions: 12ft 0in x 15ft 8in

Room 6
Level: Main
Dimensions: 18ft 10in x 12ft 8in

Room 7
Level: Main
Dimensions: 13ft 3in x 13ft 9in

Room 8
Level: Main
Dimensions: 12ft 0in x 11ft 7in

Interior Features
Has Primary On Main
Attic Description: Pulldown Stairs
Flooring: Carpet, Laminate, Vinyl
Interior Features: Great Room, Built-in Features, Kitchen Island, Pantry, Separate Shower, Wet Bar

Exterior

Exterior Features
Exterior Features: Garden

Pool Information
Pool Features: None

Lot Information
Lot Size Acres: 0.33
Lot Size Dimensions: subject to survey
Miscellaneous: Great Room

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
Other Structures: Storage
# of Fireplaces: 1
Fireplace Features: Gas Log, Den
Appliances: Microwave, Dishwasher, Free-Standing Range, Electric Water Heater, Gas Water Heater
Laundry Features: Dryer Connection, Main Level

Building Information
Building Area Total: 2,400
Foundation Details: Slab
Levels: One
Construction Materials: Brick

Financial

Tax Information
Tax Annual Amount: $2,897

Utilities

Utility Information
Sewer: Public Sewer
Water Heater: Electric, Gas

Heating & Cooling
Cooling: Heat Pump
Heating: Heat Pump, Natural Gas
Heating Fuel: Natural Gas

Location

HOA Information
Association: Winston-Salem
Association YN: No

Location Details
Directions: Peacehaven Road, Left on McGregor Road, left into McGregor Downs Ln, Left onto Campbell Glen Ln, Right onto Cutty Sark Rd, home will be on the Left

Community Information
Subdivision Name: Macgregor Downs

Public facts

Beds: 3
Baths: 2.5
Sq. Ft.: 2,397
Stories: 1.0
Lot Size: 0.33 acres
Style: Single Family Residential
Year Built: 1988
Year Renovated: 2002
County: Forsyth County
APN: 5893784375

Home facts updated by county records on Oct 23, 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

$369,000 – $446,000

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Nearby similar homes

$447,500

4 beds3.5 baths3,409 sq ft

413 Hollinswood Ave, Winston Salem, NC 27103

$430,000

3 beds3 baths2,160 sq ft

6858 Greenbrook Dr, Clemmons, NC 27012

$279,900

3 beds2 baths2,037 sq ft

5912 Puritan Ln, Winston Salem, NC 27103

$364,900

4 beds2 baths1,655 sq ft

3714 Littlebrook Dr, Clemmons, NC 27012

$524,900

4 beds2.5 baths2,723 sq ft

1391 Somerset Cove Dr, Winston Salem, NC 27103

$349,999

3 beds2.5 baths2,495 sq ft

2513 Newington Ct, Clemmons, NC 27012

New listings for sale in 27103

$485,000

4 beds3.5 baths3,012 sq ft

1981 Ernsford Dr, Winston Salem, NC 27103

$549,000

4 beds3 baths3,283 sq ft

2362 Elizabeth Ave, Winston Salem, NC 27103

HOT HOME

$345,000

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

$247,000

2 beds2.5 baths1,272 sq ft

1902 Ardmore Commons Dr, Winston Salem, NC 27103

$232,500

2 beds1 bath1,068 sq ft

1409 Irving St, Winston Salem, NC 27103

$290,000

3 beds2 baths1,582 sq ft

526 Osborne Rd, Winston Salem, NC 27103

$350,000

3 beds2 baths1,812 sq ft

1516 Jonestown Rd, Winston Salem, NC 27103

HOT HOME

$150,000

2 beds1 bath1,197 sq ft

711 Magnolia St, Winston Salem, NC 27103

Home values near 316 Cutty Sark Rd

Data from public records.

Address	Redfin Estimate
332 Cutty Sark Road, Winston Salem, NC 3 Beds \| 2 Baths \| 1999 Sq. Ft.	$362,105
328 Cutty Sark Road, Winston Salem, NC 4 Beds \| 3 Baths \| 3293 Sq. Ft.	$521,247

Address	Redfin Estimate
308 Cutty Sark Road, Winston Salem, NC 3 Beds \| 2 Baths \| 2245 Sq. Ft.	$357,963
329 Cutty Sark Road, Winston Salem, NC 4 Beds \| 2.5 Baths \| 2598 Sq. Ft.	$436,643

Address	Redfin Estimate
305 Cutty Sark Road, Winston Salem, NC 3 Beds \| 2.5 Baths \| 2333 Sq. Ft.	$401,778
304 Cutty Sark Road, Winston Salem, NC 3 Beds \| 2 Baths \| 2304 Sq. Ft.	$360,577

Property information provided by Triad MLS when last listed in 2021. 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 316 Cutty Sark Rd

Tax history for 316 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 316 Cutty Sark Rd

More real estate resources