Duplex at 301 Upton Street, Winston-Salem NC 27103

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 2 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 3 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 4 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 5 of 42

+37 more

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 6 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 7 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 8 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 9 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 10 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 11 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 12 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 13 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 14 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 15 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 16 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 17 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 18 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 19 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 20 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 21 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 22 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 23 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 24 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 25 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 26 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 27 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 28 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 29 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 30 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 31 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 32 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 33 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 34 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 35 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 36 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 37 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 38 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 39 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 40 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 41 of 42

Duplex at 301 Upton Street, Winston-Salem NC 27103, photo 42 of 42

42 photos

$329,000

301 Upton Street, Winston-Salem NC 27103

Winston-Salem, NC 27103

Listed by Lucas Dargis

Bedrooms

N/A

Bathrooms

N/A

Living area

N/A

Year built

1910

About this home

Turnkey duplex/mixed-use property in Hanestown, between Buena Vista & Ardmore! Zoned PB (Pedestrian Business), offering 2,260 total sq ft split into 2 units with separate entrances. Ideal for traditional duplex, house hack, in-law suite, small business office, or mid-term medical rental. FEATURES: Main unit (1,580 sq ft): 3BD/1.5BA. Lower ground-level unit (680 sq ft): 1BD/1BA. Has operated as a duplex for 5 years. Major capital updates: NEW roof, dual HVACs with dedicated lower-level dehumidifier, full basement waterproofing, and full interior turn with fresh paint, new flooring & repairs. Post-renovation home inspection available. LOCATION: 1 block to Hanestown Park, 3 blocks to Walmart, 1 mi to Novant Health Forsyth, 2 mi to Atrium Health Wake Forest Baptist, 1.3 mi to Thruway, 1.5 mi to Hanes Mall, 3 mi to Downtown. Schools: Moore Elem (0.7m), Wiley Middle (2m), Reynolds High (2.1m). DISCLOSURE: This property is being sold by the owner, who is a licensed NC real estate broker.

Property details

MLS: Triad MLS
MLS #: 1240060
Property type: Duplex
Subdivision: N/A
Status: Active
Days on market: N/A
On market date: October 29, 2026
Stories: N/A
Total bathrooms: N/A
Garage spaces: 1
Parking spaces: N/A
Lot size: 0.25 acres

Location

Get directions →

Loading map…

Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary

Moore Magnet Elementary

0.73 mi away · Grades -1-5

Zoned school (attendance boundary, 2015-16 data)

3.3

Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating

State rating: C (2025)

Enrollment: 416
Student:teacher ratio: 13.4:1
District: Winston Salem / Forsyth County Schools

Middle

Wiley Magnet Middle

1.99 mi away · Grades 6-8

Zoned school (attendance boundary, 2015-16 data)

2.3

Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating

State rating: D (2025)

Enrollment: 773
Student:teacher ratio: 16.4:1
District: Winston Salem / Forsyth County Schools

High

Early College of Forsyth Co

1.74 mi away · Grades 9-12

Zoned school (attendance boundary, 2015-16 data)

3.8

Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating

State rating: A (2025)

Enrollment: 260
Student:teacher ratio: 28.9:1
District: Winston Salem / Forsyth County Schools

Walkability

Blended score for Winston-Salem's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). EPA National Walkability Index only -- nearby-amenity data not cached yet for this area.

Walkable

out of 100

EPA National Walkability Index

14.7 / 20 -- Above average walkable

Market position

How this listing compares to current activity in Winston-Salem, from live MLS data.

On the market 0 days -- 85 fewer days than Winston-Salem's current average of 85 days.

For reference, the median list price across 1,671 active listings in Winston-Salem right now is $274,900.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

Home price

Down payment

Interest rate

Loan term

Adjust tax / insurance estimates

Property tax

% / yr

Home insurance

/mo

Est. monthly payment

$2,131/mo

$65,800 down

$263,200 loan

Principal & interest$1,707

Property tax (est.)$274

Home insurance (est.)$150

Similar homes you might like

New

$367,900

3329 Cider Hill Court, Winston-Salem NC 27127

Listed by Michael Sceau

$299,900

5038 Pinewood Drive, Winston-Salem NC 27106

Winston-Salem, 27106

0 sqft

20 days on market

Listed by McKenzie Ziegler

$364,900

3336 Cider Hill Court, Winston-Salem NC 27127

Winston-Salem, 27127

0 sqft

96 days on market

Listed by Michael Sceau

$359,900

3341 Cider Hill Court, Winston-Salem NC 27127

Listed by Michael Sceau

$285,500

613 N Dunleith Avenue, Winston-Salem NC 27101

Data source: Listing information provided by Triad MLS via Trestle/CoreLogic. Last updated 1 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.