33 properties analyzed · 2–5 bedrooms · Median estimate $335,000
CompCasa analysis of Winston-Salem's housing market
Winston-Salem is a Piedmont North Carolina city that blends deep Southern history with a reinvigorated, creative present. Founded around Moravian settlements, the city still showcases historic districts, restored mills, and tree-lined neighborhoods alongside modern cultural anchors. Its geography of gentle hills and four distinct seasons creates a pleasant backdrop for year-round living, and the city’s compact urban core makes it easier to enjoy cultural attractions, parks, and local businesses without long drives.
As a place to live, Winston-Salem offers a balanced mix of small-city convenience and regional amenities. Local character is strong: you'll find a thriving arts community, longtime family-owned establishments, and neighborhood festivals that reflect a sense of place. Proximity to other Piedmont Triad cities and major highways keeps the region accessible while allowing Winston-Salem to retain a more relaxed pace than larger metros, making it attractive to families, professionals, and retirees alike.
Modern 4-Bed Traditional on .5 Acre with Resort Amenities
$960,000
Mar 11, 2026Renovated Downtown Condo with Skyline Views & Secured Parking
$675,000
Mar 11, 2026Spacious 3BR Ranch on a 0.47-Acre Corner Lot with Updates
$285,000
Mar 8, 2026Spacious 4-Bedroom Home on a .46-Acre Lot in Hanover Park
$325,000
Mar 8, 2026Ardmore Classic: 4-Bed Two-Story with Covered Front Porch
$699,000
Mar 8, 202614+-Acre Equestrian Estate with Pond, Barn, and Wine Cellar
$989,900
Mar 8, 2026Contemporary Single-Story Home in Fishel Village, Winston-Salem
$282,990
Mar 8, 2026Contemporary 3-Bed New Build with Loft in Rosewood Place
$359,000
Mar 8, 2026Updated End-Unit Condo with City Views & Private Patio
$349,999
Mar 8, 2026Historic 1922 Saylor Bungalow with Upper-Level Primary Suite
$587,900
Mar 8, 2026Charming 1946 Ardmore Cottage on a Desirable Corner Lot
$359,000
Mar 8, 2026Half-Acre Corner Lot with Renovated 4-Bed Home
$690,000
Mar 8, 2026Ranch-Style Home on 3.42 Acres with Sunroom & Guest House
$329,900
Mar 8, 2026Sprawling Brick Ranch on a Half-Acre Lot with Basement
$324,900
Mar 8, 2026Prime Corner Lot at Carver School Rd & Lansing Dr — $30K Opportunity
$30,000
Mar 8, 2026Nearly New End-Unit Townhome with Main-Level Primary Suite
$405,000
Mar 8, 2026Spacious 4-Bed Home with New Covered Patio and Pond
$295,000
Mar 8, 2026Remodeled 3BR Manufactured Home on Serene Kingsdale Court
$286,300
Mar 8, 2026Designer 5-Bedroom Home on Quiet Cul-de-Sac in Clemmons
$579,900
Mar 8, 2026Bright New Lennar 2-Story on Corner Homesite — 3 BR, 2.5 BA
$334,999
Mar 8, 2026Renovated 4-Bedroom Home with Finished Basement in Sherwood Forest
$499,900
Mar 8, 2026Renovated One-Level Home with Screened Porch and Deck
$324,900
Mar 8, 2026Cape Cod Charm with Spacious Backyard and Recent Upgrades
$199,500
Mar 8, 2026Private 1.5-Acre Ranch with Covered Deck and Basement Potential
$349,900
Mar 8, 2026Renovated 4-Bed Home with Workshop Garage Near Downtown
$269,000
Mar 8, 20261928 Character Home with Built-Ins and Fenced Yard
$219,000
Mar 8, 2026Spacious Mid‑Century 4-Bed Home with Strong Value in 27103
Spacious New-Build 5BR/4BA — 3,215 Sq Ft in Winston-Salem
Bright New 4-Bed Home with Main-Level Primary Suite
$330,000
Mar 7, 2026Freshly Remodeled 3-Bed Home on Nearly One Acre in Winston-Salem
$349,900
Mar 7, 2026Updated 2-Bed, 2.5-Bath Townhome with Private Enclosed Patio
$185,000
Mar 7, 20261930s Four-Bedroom Home with Historic Character and Yard
$430,600
Mar 6, 2026Sprawling Brick Ranch on 0.61-Acre Lot with Finished Basement
$335,000
Mar 6, 2026