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Stick/Site Built at 523 W First Street, Winston-Salem NC 27101
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$409,900

523 W First Street, Winston-Salem NC 27101
Winston-Salem, NC 27101
Listed by Abby Atwell
Bedrooms
3
Bathrooms
3
Living area
2,215 sqft
Year built
1923

About this home

Rare find in Winston-Salem's historic Holly Avenue neighborhood-this beautifully updated 1923 bungalow delivers character, flexibility & income potential. Live in it as a stunning single-family home or make it a live-in investment w/built-in rental income. Main level shines with soaring ceilings, hardwoods, gas FP, separate dining room & sun drenched updated kitchen. Primary suite features a freestanding soaking tub & separate tile shower. Half bath & laundry w/W&D included. Upstairs: a fully self-contained apartment w/private entrance, living room, kitchen, 2 bedrooms, full bath w/clawfoot tub & washer & dryer-ready to rent from day one, host guests, or convert to a 4th bedroom. Ample storage in the large closets, bsmt & shed out back. Wide rocking chair front porch, fenced yard & off street parking-genuine rarities this close to downtown. Live next to W-S's best restaurants, coffee shops, shops, event spaces & parks. Historic charm, modern updates & a location that can't be beat!

Property details

MLS
Triad MLS
MLS #
1223191
Property type
Stick/Site Built
Subdivision
Holly Avenue Historic District
Status
Active
Days on market
123
On market date
June 4, 2026
Stories
N/A
Total bathrooms
3
Garage spaces
N/A
Parking spaces
N/A
Lot size
0.08 acres

Location

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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
Brunson Elementary
0.86 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
374
Student:teacher ratio
12.9:1
District
Winston Salem / Forsyth County Schools
Middle
Wiley Magnet Middle
0.97 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
2.17 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). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

90
Highly walkable
out of 100
EPA National Walkability Index
16.7 / 20 -- Most walkable
Google Places amenity density
100 / 100
Restaurants & cafes20
Grocery stores7
Parks20
Schools20
Transit stops20
Pharmacies2

Market position

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

On the market 123 days -- 36 more days than Winston-Salem's current average of 87 days.
For reference, the median list price across 1,619 active listings in Winston-Salem right now is $275,000.

Mortgage calculator

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Est. monthly payment
$2,618/mo
$81,980 down
$327,920 loan
Principal & interest$2,127
Property tax (est.)$342
Home insurance (est.)$150

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Data source: Listing information provided by Triad MLS via Trestle/CoreLogic. Last updated July 29, 2026.

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.