OFF MARKET

Off market jul 2023 for $349K

$403,444

Est. refi paymentEst. refi $2,533/mo

•

2,333

sq ft

305 Cutty Sark Rd, Winston Salem, NC 27103

About this home

Hard to find One level all-brick Ranch in a great location! Lovely open great room with arched doorways, gas fireplace and crown molding throughout. Formal dining room with chair railing and wainscoting. The kitchen is open to breakfast area with bay window and lots of counter space. Home also features a large primary bedroom on main level with private bathroom, walk-in closet, double sinks, separate shower, jetted tub. Hardwoods in secondary bedrooms. Sunroom or den leads to backyard and deck with private setting. Great storage, two car garage. Nice private yard with deck!

Single-familyProperty Type

1993Year Built

0.4 acresLot Size

$173Est. Price/Sq.Ft.

2 car garageParking

Listed by Jennifer Hollowell • Real Broker LLC

Listed by Jennifer Bruton • Real Broker LLC

Bought with Lane Young • Express Home Realty

Redfin checked: 2 minutes ago

•Source:Triad MLS #1102803

Redfin Estimate

$403,444

$54K since sold in July 2023$2,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 20.6% higher than the average sale price ($334K) 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 AUG 13, 2026
$290,000
B
3 beds2.5 baths1,856 sq ft
1580 Old Jonestown Rd, Winston Salem, NC 27103
SOLD JUL 29, 2026
$326,000
C
3 beds2 baths2,244 sq ft
2350 Oakton Dr, Clemmons, NC 27012
SOLD SEP 3, 2026
$230,000
D
3 beds2.5 baths1,849 sq ft
4331 Kinnamon Rd, Winston Salem, NC 27103
SOLD JUN 4, 2026
$373,500
E
3 beds2.5 baths2,365 sq ft
135 Valleyoak Ct, Clemmons, NC 27012
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

$115,202

Est. take-home

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Refinance

Est. cash available

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Rent

$2,202/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 4 HRS AGO
$199,900
2 beds2 baths1,092 sq ft
3361 Hyde Place Cir, Winston Salem, NC 27103
NEW 13 HRS AGO
$206,500
2 beds2.5 baths1,070 sq ft
2671 Halle Ann Cir, Winston Salem, NC 27103
OPEN SUN, 2PM TO 4PM
$265,000
3 beds1.5 baths1,078 sq ft
4336 Cordova Dr, Winston Salem, NC 27103
$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
See all

Provided by Redfin

Sale history for 305 Cutty Sark Rd

Date

Event

Price

Public Records

Jul 26, 2023

Sold

$350,000

$150/sq ft

Triad MLS #1102803

Jul 26, 2023

Sold

$349,900

$150/sq ft

Jul 25, 2023

Pending

—

Jun 29, 2023

Contingent

—

Jun 26, 2023

Price Changed

$349,900

$150/sq ft

Jun 12, 2023

Price Changed

$365,000

$156/sq ft

Jun 5, 2023

Relisted

—

May 17, 2023

Contingent

—

May 5, 2023

Listed

$375,000

$161/sq ft

Apr 30, 2023

Coming Soon

$375,000

$161/sq ft

RENT. #1

May 25, 2023

Rental Removed

—

Triad MLS #761166

Nov 19, 2015

Sold

$242,000

$104/sq ft

Sep 28, 2015

Pending

—

Aug 19, 2015

Price Changed

$248,361

$106/sq ft

Jun 9, 2015

Listed

$255,000

$109/sq ft

+17

Easy, one level living in all brick, open floor plan. New carpet, refinished hardwoods, interior paint. Kitchen offers new cabinets, counters, tile backsplash, flooring, sink, and hardware! Big laundry room with lots of storage. Enclosed sunporch, heated but not included in sq. ft., overlooks wooded privacy. Fine master suite with sitting area. Mature community of quiet streets convenient to both Winston-Salem and Clemmons.

Public Records

Mar 9, 1998

Sold

$207,500

$89/sq ft

Public Records

Aug 27, 1993

Sold

$182,000

$78/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$4,115 (+6.1%)

$63,500 + $309,800

$373,300

2024

$3,877 (+6.8%)

$49,000 + $227,400

$276,400

2022

$3,631 (+1.8%)

$49,000 + $227,400

$276,400

2021

$3,566 (+12.9%)

$49,000 + $227,400

$276,400

2020

$3,158 (−0.7%)

$44,000 + $184,700

$228,700

2019

$3,181 (+5.3%)

$44,000 + $184,700

$228,700

2018

$3,021

$44,000 + $184,700

$228,700

2017

$3,021 (−2.4%)

$44,000 + $184,700

$228,700

2016

$3,096 (+1.5%)

$44,000 + $184,700

$228,700

2015

$3,049 (+3.1%)

$36,500 + $198,812

$235,312

2014

$2,957

$36,500 + $198,812

$235,312

Tax history for 305 Cutty Sark Rd

Year

Property tax

Land + Additions

Assessment*

2025

$4,115 (+6.1%)

$63,500 + $309,800

$373,300

2024

$3,877 (+6.8%)

$49,000 + $227,400

$276,400

2022

$3,631 (+1.8%)

$49,000 + $227,400

$276,400

2021

$3,566 (+12.9%)

$49,000 + $227,400

$276,400

2020

$3,158 (−0.7%)

$44,000 + $184,700

$228,700

2019

$3,181 (+5.3%)

$44,000 + $184,700

$228,700

2018

$3,021

$44,000 + $184,700

$228,700

2017

$3,021 (−2.4%)

$44,000 + $184,700

$228,700

2016

$3,096 (+1.5%)

$44,000 + $184,700

$228,700

2015

$3,049 (+3.1%)

$36,500 + $198,812

$235,312

2014

$2,957

$36,500 + $198,812

$235,312

*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

17,424

Year renovated

2007

Sq. Ft.

2,333

Year built

1993

Style

Single Family Residential

County

Forsyth County

APN

5893787599

Parking Spaces

Basement

Yes

Accessible

HOA Dues

—

Garage

Yes

Features

—

Last updated by owner on Jun 3, 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, Front Load Garage
Parking Features: Driveway, Garage, Paved, Attached, Garage Faces Front

Interior

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

Basement Information
Basement YN: No
Basement: Crawl Space

Room Information
# of Rooms: 9

Room 1
Type: Great Room
Level: Main
Dimensions: 16ft 3in x 20ft 11in

Room 2
Type: Breakfast
Level: Main
Dimensions: 13ft 2in x 11ft 1in

Room 3
Type: Laundry
Level: Main
Dimensions: 6ft 1in x 13ft 9in

Room 4
Type: Dining Room
Level: Main
Dimensions: 11ft 6in x 14ft 3in

Room 5
Type: Kitchen
Level: Main
Dimensions: 13ft 2in x 12ft 7in

Room 6
Type: Sunroom
Level: Main
Dimensions: 17ft 0in x 19ft 9in

Room 7
Level: Main
Dimensions: 21ft 2in x 17ft 6in

Room 8
Level: Main
Dimensions: 11ft 2in x 14ft 4in

Room 9
Level: Main
Dimensions: 11ft 6in x 11ft 2in

Interior Features
Has Primary On Main
Attic Description: Pulldown Stairs
Flooring: Carpet, Tile, Vinyl, Wood
Interior Features: Great Room, Arched Doorways, Ceiling Fan(s), Dead Bolt(s), Kitchen Island, Separate Shower

Exterior

Exterior Features
Fencing: None

Pool Information
Pool Features: None

Guest House Information
No

Lot Information
Lot Features: Cleared, Level
Lot Size Acres: 0.4
Lot Size Dimensions: 177 x 100 x 176 x 100
Miscellaneous: Cable, Great Room

Land Information
Land Description: Clear, Flat
Water Source: Public

Property Information
Property Type: Residential
Property Sub Type: Stick/Site Built
Structure Type: House
Built Information: Existing
Year Built: 1993
# of Fireplaces: 1
Fireplace Features: Gas Log, Great Room, Living Room
Appliances: Microwave, Oven, Built-in Range, Dishwasher, Disposal, Gas Water Heater
Laundry Features: Dryer Connection, Main Level, Washer Hookup

Building Information
Building Area Total: 2,333
Levels: One
Construction Materials: Brick

Financial

Tax Information
Tax Annual Amount: $3,631.34

Utilities

Utility Information
Sewer: Public Sewer
Water Heater: Gas

Heating & Cooling
Cooling: Central Air
Heating: Forced Air, Natural Gas
Heating Fuel: Natural Gas

Location

HOA Information
Association: Winston-Salem
Association YN: No

School / Neighborhood
Elementary School: Ward
Middle Or Junior School: Clemmons
High School: West Forsyth
Additional School Info Zone: BUYER AGENT TO VERIFY

Location Details
Directions: US-421 N to exit 240 Peace Haven Road. Turn left on S. Peacehaven Road. Turn left on MacGregor Road. Turn right on McGregor Downs Lane. Turn left on Campbell Glen Lane, right on Cutty Sark Road. Second home on right.

Community Information
Subdivision Name: Macgregor Downs

Public facts

Beds: 3
Baths: 2.5
Sq. Ft.: 2,333
Stories: 1.0
Parking Spaces: 2
Basement: Yes
Accessible: No
Lot Size: 0.4 acres
Style: Single Family Residential
Year Built: 1993
Year Renovated: 2007
County: Forsyth County
APN: 5893787599
HOA Dues: —
Garage: Yes
Features: —

Home facts updated by owner on Jun 3, 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

6/10 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

$384,000 – $464,000

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New listings for sale in 27103

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4641 Bridle Path, Winston Salem, NC 27103

0.44 acre lot • Garage • Built 1963

3D WALKTHROUGH

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4 beds3.5 baths3,980 sq ft

1736 Huntington Woods Ct, Winston Salem, NC 27103

Updated kitchen • Breakfast nook • Screened porch

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121 Carolina Rose Ct, Winston-Salem, NC 27103

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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

$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

Home values near 305 Cutty Sark Rd

Data from public records.

Address	Redfin Estimate
308 Cutty Sark Rd, Winston Salem, NC 3 Beds \| 2 Baths \| 2245 Sq. Ft.	$358,563
312 Cutty Sark Rd, Winston Salem, NC 3 Beds \| 2 Baths \| 2350 Sq. Ft.	$386,858

Address	Redfin Estimate
304 Cutty Sark Rd, Winston Salem, NC 3 Beds \| 2 Baths \| 2304 Sq. Ft.	$359,583
316 Cutty Sark Rd, Winston Salem, NC 3 Beds \| 2.5 Baths \| 2400 Sq. Ft.	$388,364

Address	Redfin Estimate
300 Cutty Sark Rd, Winston Salem, NC 3 Beds \| 2 Baths \| 2848 Sq. Ft.	$409,692
320 Cutty Sark Rd, Winston Salem, NC 5 Beds \| 4 Baths \| 3675 Sq. Ft.	$442,609

Property information provided by undefined .

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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 305 Cutty Sark Rd

Tax history for 305 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 305 Cutty Sark Rd

More real estate resources